$1,850,000 This stunning waterfront, custom built home sits ideally on a little over an acre fronting Crab Alley Bay in the prestigious Southwind community. Home boast almost 10,000 square feet, between finished living space and additional expansion space. An already large home offers so much more room to grow the perfect, waterfront retreat. This gem features 6 large bedrooms and of those 4 have private baths, and walk-in closets. Original owners designed this home to highlight 8' solid wood doors, Brazilian cherry hardwood floors, high ceilings through-out the first floor, two focal point fireplaces, second floor balcony, come see it all and in vison the possibilities this property offers. This is truly a must-see property. Not to mention its LOCATION. Nestled in the Southwind community that features a clubhouse, basketball court, pickle ball court, tennis court, boat ramp, and plenty of ways to enjoy the nature. 6 Beds ⋅ 6 Baths This stunning waterfront, custom built home sits ideally on a little over an acre fronting Crab Alley Bay in the prestigious Southwind community. Home boast almost 10,000 square feet, between finished living space and additional expansion space. An already large home offers so much more room to grow the perfect, waterfront retreat. This gem features 6 large bedrooms and of those 4 have private baths, and walk-in closets. Original owners designed this home to highlight 8' solid wood doors, Brazilian cherry hardwood floors, high ceilings through-out the first floor, two focal point fireplaces, second floor balcony, come see it all and in vison the possibilities this property offers. This is truly a must-see property. Not to mention its LOCATION. Nestled in the Southwind community that features a clubhouse, basketball court, pickle ball court, tennis court, boat ramp, and plenty of ways to enjoy the nature. 2817 Cox Neck Rd, Chester Listing courtesy of Michael J. Bozek. Contact: Selling Office: Non Subscribing Office.
$1,825,000 Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom and full bath accompany a spacious living area, ideal for extended family or guests. The heart of the home is a stunning, renovated kitchen featuring rich finishes, premium appliances, and an open layout perfect for gathering. Gleaming hardwood floors flow throughout, leading to a mahogany-lined library that exudes warmth and sophistication—a true sanctuary for work or quiet reflection. Outdoor living takes center stage with a screened porch that captures cooling Bay breezes and views of the pool and shimmering water beyond. Whether entertaining or simply savoring the stillness of the shoreline, every space in this home celebrates the beauty of the Chesapeake Bay lifestyle. 4 Beds ⋅ 6 Baths Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom and full bath accompany a spacious living area, ideal for extended family or guests. The heart of the home is a stunning, renovated kitchen featuring rich finishes, premium appliances, and an open layout perfect for gathering. Gleaming hardwood floors flow throughout, leading to a mahogany-lined library that exudes warmth and sophistication—a true sanctuary for work or quiet reflection. Outdoor living takes center stage with a screened porch that captures cooling Bay breezes and views of the pool and shimmering water beyond. Whether entertaining or simply savoring the stillness of the shoreline, every space in this home celebrates the beauty of the Chesapeake Bay lifestyle. 2907 Cox Neck Rd E, Chester Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: RE/MAX Advantage Realty.
$1,750,000 712 Bay Drive isn't simply a waterfront home—it's a turnkey Chesapeake lifestyle, beautifully executed from shore to door. Just two years young, this exceptional waterfront residence combines thoughtful design, elevated finishes and impressive waterfront infrastructure with sweeping views of the Bay. The open-concept main level was designed around the view, with a dramatic wall of windows overlooking the water and a propane fireplace anchoring the living space. The kitchen delivers both beauty and function with an extra-long island, quartz countertops, high-end appliances, crisp white cabinetry, statement hood and walk-in pantry. The main-level primary suite offers a private retreat with a walk-in closet and beautifully finished bath featuring a spacious walk-in shower and shiplap detailing. Upstairs, you'll find three additional bedrooms, a bonus room and abundant walk-in storage, plus a floored, temperature-controlled attic. And then there's the waterfront. A vaulted covered side porch creates another incredible place to take in the views, complete with a hot tub that conveys, while the home's piling construction creates an expansive “Below Deck” entertaining area at ground level—perfect for waterfront gatherings, crab feasts and relaxed summer evenings. The waterfront infrastructure is equally impressive, with a newer bulkhead and pier, 12,500-lb boat lift, electric and water at the pier directly on the Chesapeake Bay. Thoughtful systems include a whole-house water filtration system, tankless water heater, two-year-old roof and HVAC, plus electric HVAC with propane backup for efficiency and peace of mind. Newer construction. Exceptional waterfront infrastructure. Thoughtfully engineered. Turnkey. And a front-row seat to life on the Bay. 4 Beds ⋅ 3 Baths 712 Bay Drive isn't simply a waterfront home—it's a turnkey Chesapeake lifestyle, beautifully executed from shore to door. Just two years young, this exceptional waterfront residence combines thoughtful design, elevated finishes and impressive waterfront infrastructure with sweeping views of the Bay. The open-concept main level was designed around the view, with a dramatic wall of windows overlooking the water and a propane fireplace anchoring the living space. The kitchen delivers both beauty and function with an extra-long island, quartz countertops, high-end appliances, crisp white cabinetry, statement hood and walk-in pantry. The main-level primary suite offers a private retreat with a walk-in closet and beautifully finished bath featuring a spacious walk-in shower and shiplap detailing. Upstairs, you'll find three additional bedrooms, a bonus room and abundant walk-in storage, plus a floored, temperature-controlled attic. And then there's the waterfront. A vaulted covered side porch creates another incredible place to take in the views, complete with a hot tub that conveys, while the home's piling construction creates an expansive “Below Deck” entertaining area at ground level—perfect for waterfront gatherings, crab feasts and relaxed summer evenings. The waterfront infrastructure is equally impressive, with a newer bulkhead and pier, 12,500-lb boat lift, electric and water at the pier directly on the Chesapeake Bay. Thoughtful systems include a whole-house water filtration system, tankless water heater, two-year-old roof and HVAC, plus electric HVAC with propane backup for efficiency and peace of mind. Newer construction. Exceptional waterfront infrastructure. Thoughtfully engineered. Turnkey. And a front-row seat to life on the Bay. 712 Bay Dr, Stevensville Listing courtesy of Samson Properties. Contact: Selling Office: TTR Sotheby's International Realty.
$1,720,000 The waterfront dream home you've been waiting for... the one everyone else will wish they had bought first. This quintessential Kent Island waterfront estate captures everything buyers love about Eastern Shore living. Perfectly positioned on 1.99 private acres just minutes from the Bay Bridge, this exceptional property offers over 3300 SF in main house, and another 450 SF+/- guest space w/ full bath atop detached garage! Designed for effortless waterfront living and entertaining. The main residence features 5 bedrooms and 4 full baths, including a desirable main-level bedroom and full bath, while the detached two-car garage is topped by a private guest suite and full bath—ideal for visitors, extended family, or a private home office retreat. Step outside and discover the lifestyle you've been dreaming about. A private pier, sparkling waterfront pool, expansive covered porch, and beautiful Ipe decking create a resort-like setting where every day feels like a vacation. Southern Eastern Bay views provide the perfect backdrop for boating adventures, summer gatherings, quiet mornings with coffee, and unforgettable sunsets. This is more than a home—it's a waterfront destination. A place where memories are made, boats are launched, friends linger longer, and every season brings a new reason to fall in love with life on the water. Extremely well-maintained with polished updates, to include: Anderson windows (2024 & 2020), refreshed dock & boat lift (8K lb capacity), Additional pilings for guest boat tie-up. Whole-house generator w/1000 Gallon OWNED tank, tankless water heater, fully encapsulated crawlspace, Sub-zero refrigerator & Wolf gas stove, Pool pumps, filter (2020-2023) & new liner (2024). One look and you'll understand why there is nothing like this beauty on market! 5 Beds ⋅ 4 Baths The waterfront dream home you've been waiting for... the one everyone else will wish they had bought first. This quintessential Kent Island waterfront estate captures everything buyers love about Eastern Shore living. Perfectly positioned on 1.99 private acres just minutes from the Bay Bridge, this exceptional property offers over 3300 SF in main house, and another 450 SF+/- guest space w/ full bath atop detached garage! Designed for effortless waterfront living and entertaining. The main residence features 5 bedrooms and 4 full baths, including a desirable main-level bedroom and full bath, while the detached two-car garage is topped by a private guest suite and full bath—ideal for visitors, extended family, or a private home office retreat. Step outside and discover the lifestyle you've been dreaming about. A private pier, sparkling waterfront pool, expansive covered porch, and beautiful Ipe decking create a resort-like setting where every day feels like a vacation. Southern Eastern Bay views provide the perfect backdrop for boating adventures, summer gatherings, quiet mornings with coffee, and unforgettable sunsets. This is more than a home—it's a waterfront destination. A place where memories are made, boats are launched, friends linger longer, and every season brings a new reason to fall in love with life on the water. Extremely well-maintained with polished updates, to include: Anderson windows (2024 & 2020), refreshed dock & boat lift (8K lb capacity), Additional pilings for guest boat tie-up. Whole-house generator w/1000 Gallon OWNED tank, tankless water heater, fully encapsulated crawlspace, Sub-zero refrigerator & Wolf gas stove, Pool pumps, filter (2020-2023) & new liner (2024). One look and you'll understand why there is nothing like this beauty on market! 252 Eareckson Ln, Stevensville Listing courtesy of Chaney Homes, LLC. Contact: Selling Office: Benson & Mangold, LLC.
$1,715,000 Welcome to the pinnacle of waterfront living in Cove Creek Club—one of Kent Island’s most sought-after and low-turnover communities. What truly sets this property apart is what so few homes here can offer: direct navigable waterfront with a private pier. While many homes in the community enjoy water views, only a select few provide the ability to keep your boat right out back with protected, calm waters and easy access to the Chesapeake Bay. Whether it’s sunset cruises, paddleboarding from your backyard, or spending the day on the water, this home delivers the true Eastern Shore boating lifestyle. Extensively renovated and spanning over 4,200 square feet, this one-level residence has been completely reimagined with high-end updates throughout. The renovation included an impressive 1,000-square-foot addition and the addition of a rare 3-car garage, creating exceptional space for both everyday living and waterfront storage needs. The layout features four spacious bedrooms, four full baths, a private study, and a stunning modern addition completed within the last three years. Major improvements include new Hardie Board siding and a high-efficiency three-zone HVAC system for comfort and peace of mind. Outside, your private retreat awaits with an in-ground pool, expansive entertaining decks, and wide-open views overlooking the protected marina basin. The setting is peaceful, private, and designed to embrace waterfront living at every turn. Beyond the home itself, Cove Creek Club is a true lifestyle destination. One of the community’s biggest draws is the unlimited golf included in the HOA, featuring a private 9-hole course played as 18 with multiple tee boxes, along with a driving range and practice areas. Residents also enjoy a marina, boat storage, tennis and pickleball courts, a fitness center and gym, clubhouse, private sandy beach with fire pits, and beautifully maintained grounds surrounded by tidal creeks and the Chesapeake Bay. All of this is tucked away in a quiet waterfront setting while still offering convenient access to Route 50 for easy trips to Annapolis, Washington DC, and the beaches. 4 Beds ⋅ 4 Baths Welcome to the pinnacle of waterfront living in Cove Creek Club—one of Kent Island’s most sought-after and low-turnover communities. What truly sets this property apart is what so few homes here can offer: direct navigable waterfront with a private pier. While many homes in the community enjoy water views, only a select few provide the ability to keep your boat right out back with protected, calm waters and easy access to the Chesapeake Bay. Whether it’s sunset cruises, paddleboarding from your backyard, or spending the day on the water, this home delivers the true Eastern Shore boating lifestyle. Extensively renovated and spanning over 4,200 square feet, this one-level residence has been completely reimagined with high-end updates throughout. The renovation included an impressive 1,000-square-foot addition and the addition of a rare 3-car garage, creating exceptional space for both everyday living and waterfront storage needs. The layout features four spacious bedrooms, four full baths, a private study, and a stunning modern addition completed within the last three years. Major improvements include new Hardie Board siding and a high-efficiency three-zone HVAC system for comfort and peace of mind. Outside, your private retreat awaits with an in-ground pool, expansive entertaining decks, and wide-open views overlooking the protected marina basin. The setting is peaceful, private, and designed to embrace waterfront living at every turn. Beyond the home itself, Cove Creek Club is a true lifestyle destination. One of the community’s biggest draws is the unlimited golf included in the HOA, featuring a private 9-hole course played as 18 with multiple tee boxes, along with a driving range and practice areas. Residents also enjoy a marina, boat storage, tennis and pickleball courts, a fitness center and gym, clubhouse, private sandy beach with fire pits, and beautifully maintained grounds surrounded by tidal creeks and the Chesapeake Bay. All of this is tucked away in a quiet waterfront setting while still offering convenient access to Route 50 for easy trips to Annapolis, Washington DC, and the beaches. 106 N Creek Ct, Stevensville Listing courtesy of RE/MAX Executive. Contact: Selling Office: Real Broker, LLC - Chester.
$1,690,000 Positioned along the serene waters of Tanners Creek within the enclave of Cove Creek Club, this exceptional waterfront residence offers a rare opportunity to secure a premier setting while tailoring the interiors to your own vision. Major capital improvements have already been completed—including a new roof, upgraded HVAC system, and the addition of a private pool; providing a strong foundation for the next owner to elevate the home to their exact standards. From nearly every room, sweeping water views create a seamless connection to the surrounding landscape, with sunsets that define the daily experience. The home features a light-filled, open-concept layout designed for both comfortable living and effortless entertaining. The kitchen offers generous cabinetry, a spacious pantry, and a gas cooktop, flowing naturally into the main living and dining areas—all oriented to capture the waterfront backdrop. With four bedrooms and three full baths, there is ample space for family and guests, along with the flexibility to reimagine and enhance over time. Outdoors, the lifestyle is immediate. A private dock provides direct access to kayaking, paddle boarding, crabbing, and fishing just steps from your door, while the protected waters of the creek offer a peaceful, usable setting. For larger vessels, the community marina accommodates boats up to approximately 40 feet and offers water, electric, fuel, and pump-out services which delivers a level of convenience rarely found. The addition of the pool introduces a resort-style element, ideal for relaxing afternoons or entertaining against a waterfront backdrop. The setting, combined with the home’s footprint and improvements, creates a compelling opportunity for a buyer seeking both lifestyle and long-term value. Residents of Cove Creek Club enjoy access to an exceptional amenity package, including a USGA-rated golf course, private beach, marina with boat launch, clubhouse, tennis and basketball courts, and bocce. This is a rare chance to secure a waterfront property with strong fundamentals, significant recent upgrades, and the ability to create a truly custom coastal retreat in one of the Eastern Shore’s most desirable gated communities. 5 Beds ⋅ 3 Baths Positioned along the serene waters of Tanners Creek within the enclave of Cove Creek Club, this exceptional waterfront residence offers a rare opportunity to secure a premier setting while tailoring the interiors to your own vision. Major capital improvements have already been completed—including a new roof, upgraded HVAC system, and the addition of a private pool; providing a strong foundation for the next owner to elevate the home to their exact standards. From nearly every room, sweeping water views create a seamless connection to the surrounding landscape, with sunsets that define the daily experience. The home features a light-filled, open-concept layout designed for both comfortable living and effortless entertaining. The kitchen offers generous cabinetry, a spacious pantry, and a gas cooktop, flowing naturally into the main living and dining areas—all oriented to capture the waterfront backdrop. With four bedrooms and three full baths, there is ample space for family and guests, along with the flexibility to reimagine and enhance over time. Outdoors, the lifestyle is immediate. A private dock provides direct access to kayaking, paddle boarding, crabbing, and fishing just steps from your door, while the protected waters of the creek offer a peaceful, usable setting. For larger vessels, the community marina accommodates boats up to approximately 40 feet and offers water, electric, fuel, and pump-out services which delivers a level of convenience rarely found. The addition of the pool introduces a resort-style element, ideal for relaxing afternoons or entertaining against a waterfront backdrop. The setting, combined with the home’s footprint and improvements, creates a compelling opportunity for a buyer seeking both lifestyle and long-term value. Residents of Cove Creek Club enjoy access to an exceptional amenity package, including a USGA-rated golf course, private beach, marina with boat launch, clubhouse, tennis and basketball courts, and bocce. This is a rare chance to secure a waterfront property with strong fundamentals, significant recent upgrades, and the ability to create a truly custom coastal retreat in one of the Eastern Shore’s most desirable gated communities. 132 Tanners Point Dr, Stevensville Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: Washington Fine Properties, LLC.
$1,650,000 Experience the beauty, privacy, and tranquility of Chesapeake Bay living from this exceptional waterfront retreat set on approximately two private acres. Perfectly positioned to capture sweeping Bay views and spectacular sunsets, 409 Craney Creek Drive offers the rare combination of timeless coastal charm, thoughtful updates, and an unmatched waterfront lifestyle. This beautifully maintained Cape Cod features three bedrooms, a bonus room, dedicated office, and a highly desirable main-level primary suite. Hardwood flooring, fresh paint, updated bathrooms, and new carpeting in the upper-level bedrooms create a move-in-ready home that balances warmth, character, and modern comfort. Designed to embrace its waterfront setting, the home offers multiple living spaces oriented toward the Bay, including a stunning four-season sunroom with its own HVAC system. Whether enjoying your morning coffee, entertaining guests, or unwinding at the end of the day, the ever-changing views and unforgettable sunsets provide the perfect backdrop. The updated kitchen features gas cooking, generous workspace, and seamless flow into the surrounding living and dining areas. Two fireplaces add warmth and ambiance throughout the seasons, creating inviting spaces for gathering with family and friends. Outside, the Shore lifestyle awaits. The private pier with electric boat lift provides direct access to the Chesapeake Bay, while riprap shoreline protection offers both beauty and peace of mind. The expansive two-acre setting provides exceptional privacy, room to roam, and endless opportunities to enjoy the outdoors. Additional highlights include a side-loading two-car garage, abundant storage, and a brand-new septic system scheduled for installation in July 2026. Rarely does a Chesapeake Bay property offer this combination of acreage, privacy, updated living spaces, protected shoreline, boating access, and breathtaking sunset views. Whether you're searching for a full-time residence or an extraordinary waterfront escape, 409 Craney Creek Drive delivers the very best of Eastern Shore living. 3 Beds ⋅ 3 Baths Experience the beauty, privacy, and tranquility of Chesapeake Bay living from this exceptional waterfront retreat set on approximately two private acres. Perfectly positioned to capture sweeping Bay views and spectacular sunsets, 409 Craney Creek Drive offers the rare combination of timeless coastal charm, thoughtful updates, and an unmatched waterfront lifestyle. This beautifully maintained Cape Cod features three bedrooms, a bonus room, dedicated office, and a highly desirable main-level primary suite. Hardwood flooring, fresh paint, updated bathrooms, and new carpeting in the upper-level bedrooms create a move-in-ready home that balances warmth, character, and modern comfort. Designed to embrace its waterfront setting, the home offers multiple living spaces oriented toward the Bay, including a stunning four-season sunroom with its own HVAC system. Whether enjoying your morning coffee, entertaining guests, or unwinding at the end of the day, the ever-changing views and unforgettable sunsets provide the perfect backdrop. The updated kitchen features gas cooking, generous workspace, and seamless flow into the surrounding living and dining areas. Two fireplaces add warmth and ambiance throughout the seasons, creating inviting spaces for gathering with family and friends. Outside, the Shore lifestyle awaits. The private pier with electric boat lift provides direct access to the Chesapeake Bay, while riprap shoreline protection offers both beauty and peace of mind. The expansive two-acre setting provides exceptional privacy, room to roam, and endless opportunities to enjoy the outdoors. Additional highlights include a side-loading two-car garage, abundant storage, and a brand-new septic system scheduled for installation in July 2026. Rarely does a Chesapeake Bay property offer this combination of acreage, privacy, updated living spaces, protected shoreline, boating access, and breathtaking sunset views. Whether you're searching for a full-time residence or an extraordinary waterfront escape, 409 Craney Creek Drive delivers the very best of Eastern Shore living. 409 Craney Creek Rd, Stevensville Listing courtesy of Samson Properties. Contact: Selling Office: Samson Properties.
$1,650,000 Exceptional renovation that offers everything you could want in a waterfront home. 3 Beds ⋅ 2 Baths Exceptional renovation that offers everything you could want in a waterfront home. 114 Chester Vw, Chestertown Listing courtesy of Cross Street Realtors LLC. Contact: Selling Office: Non Subscribing Office.
$1,650,000 This lovely waterfront home is tucked away on a quiet cul-de-sac in desirable Prospect Bay. Thoughtfully designed and built by the original owners, this home offers approximately 2796' of well-planned living space providing 4 bedrooms and 2.5 baths. The open-concept floor plan is enhanced by distinctive architectural details and abundant natural light. A bright kitchen opens to the family room with fireplace—perfect for everyday living and entertaining. The spacious living room features a vaulted ceiling with skylights and opens to a loft area above. The main-level primary bedroom offers water views, a large walk-in closet, and a full bath with soaking tub and walk-in shower. Upstairs, you’ll find three additional bedrooms plus a dedicated office space. Enjoy outdoor living on the wrap-around deck, accessible from the living room, kitchen, and primary bedroom. Additional features include an oversized two-car garage and private pier on a tranquil waterfront setting. Roof is 2 years old and carpet is new. Home is being sold As-Is. Buyer to verify water depth. Prospect Bay amenities include Golf, Pool, Boat Ramp, Tennis Ct, Club House with restaurant/bar/grill plus more. 4 Beds ⋅ 3 Baths This lovely waterfront home is tucked away on a quiet cul-de-sac in desirable Prospect Bay. Thoughtfully designed and built by the original owners, this home offers approximately 2796' of well-planned living space providing 4 bedrooms and 2.5 baths. The open-concept floor plan is enhanced by distinctive architectural details and abundant natural light. A bright kitchen opens to the family room with fireplace—perfect for everyday living and entertaining. The spacious living room features a vaulted ceiling with skylights and opens to a loft area above. The main-level primary bedroom offers water views, a large walk-in closet, and a full bath with soaking tub and walk-in shower. Upstairs, you’ll find three additional bedrooms plus a dedicated office space. Enjoy outdoor living on the wrap-around deck, accessible from the living room, kitchen, and primary bedroom. Additional features include an oversized two-car garage and private pier on a tranquil waterfront setting. Roof is 2 years old and carpet is new. Home is being sold As-Is. Buyer to verify water depth. Prospect Bay amenities include Golf, Pool, Boat Ramp, Tennis Ct, Club House with restaurant/bar/grill plus more. 222 Piney Point Lndg, Grasonville Listing courtesy of Long & Foster Real Estate, Inc.. Contact: Selling Office: TTR Sotheby's International Realty.
$1,650,000 Experience waterfront living at its absolute finest in this breathtaking, fully renovated Chester River estate, where shimmering water views unfold from nearly every window and the lifestyle is nothing short of extraordinary. With 125 feet of pristine shoreline and sweeping panoramic river vistas, this remarkable property is equally suited as a luxurious primary residence or an unforgettable vacation retreat. The recent addition expanded the main level footprint and added the second story over the main part of the home. The welcoming family room impresses with soaring vaulted ceilings and a cozy fireplace framed by a refined panel-molding accent wall, creating an inviting yet elegant gathering space. Just beyond, the sun-drenched main-level sunroom offers vaulted ceilings, ceramic tile flooring, a ceiling fan, and dramatic picture windows that frame the water like living art. At the heart of the home is a magazine-worthy kitchen renovation featuring custom cabinetry, granite countertops, pull-out drawers, gas cooking, and upgraded GE appliances, all anchored by a statement center island with pendant lighting. A stylish dry bar with display cabinetry adds a sophisticated touch, while the open-concept design flows effortlessly into the dining and family rooms. Perfectly positioned to capture the ever-changing river scenery, hardwood floors and recessed lighting grace the common areas, while walls of windows and sliding glass doors invite the outdoors in and open directly to the expansive waterfront deck. The main-level primary suite is a serene sanctuary with tranquil water views, a walk-in closet with custom organization, and a spa-inspired ensuite bath highlighted by a large tiled stall shower. Two additional main-level bedrooms, each appointed with ceiling fans and plush carpeting, are thoughtfully served by a beautifully finished hall bath, providing comfort and privacy for family and guests alike. Upstairs a charming loft creates a peaceful reading nook or relaxation space. Two additional bedrooms with plush carpeting and ceiling fans share access to an upstairs hall bath, while a cozy flex room, ideal for a home office, features carpeting and a delightful round window. Adding to the home’s versatility is a private second upper-level suite located above the two-car garage, offering an expansive bedroom with an architecturally striking half-wall separating a sitting or office area, along with a spacious en-suite bath, perfect for guests or multi-generational living. Outdoors, the property truly becomes unforgettable. 125 feet of unobstructed Chester River frontage provides direct access to the water, complemented by a deep-water dock with a boat lift and two jet ski lifts, all conveyed as-is. An enormous IPE wood deck creates an exceptional setting for entertaining, complete with a hot tub and a covered outdoor kitchen featuring a bar, grill, sink, ice maker, and even a full bath, delivering a true resort-style experience at home. A graceful circular driveway enhances both curb appeal and convenience, offering ample parking for guests. Recent improvements include a new roof and siding (2023), a replaced well and pump (2017), and the added luxury of a water softener and whole-house reverse osmosis system. This extraordinary waterfront residence seamlessly blends refined renovations, exceptional indoor and outdoor amenities, and an unparalleled riverfront setting, presenting a rare opportunity to own a true Chester River masterpiece. 6 Beds ⋅ 5 Baths Experience waterfront living at its absolute finest in this breathtaking, fully renovated Chester River estate, where shimmering water views unfold from nearly every window and the lifestyle is nothing short of extraordinary. With 125 feet of pristine shoreline and sweeping panoramic river vistas, this remarkable property is equally suited as a luxurious primary residence or an unforgettable vacation retreat. The recent addition expanded the main level footprint and added the second story over the main part of the home. The welcoming family room impresses with soaring vaulted ceilings and a cozy fireplace framed by a refined panel-molding accent wall, creating an inviting yet elegant gathering space. Just beyond, the sun-drenched main-level sunroom offers vaulted ceilings, ceramic tile flooring, a ceiling fan, and dramatic picture windows that frame the water like living art. At the heart of the home is a magazine-worthy kitchen renovation featuring custom cabinetry, granite countertops, pull-out drawers, gas cooking, and upgraded GE appliances, all anchored by a statement center island with pendant lighting. A stylish dry bar with display cabinetry adds a sophisticated touch, while the open-concept design flows effortlessly into the dining and family rooms. Perfectly positioned to capture the ever-changing river scenery, hardwood floors and recessed lighting grace the common areas, while walls of windows and sliding glass doors invite the outdoors in and open directly to the expansive waterfront deck. The main-level primary suite is a serene sanctuary with tranquil water views, a walk-in closet with custom organization, and a spa-inspired ensuite bath highlighted by a large tiled stall shower. Two additional main-level bedrooms, each appointed with ceiling fans and plush carpeting, are thoughtfully served by a beautifully finished hall bath, providing comfort and privacy for family and guests alike. Upstairs a charming loft creates a peaceful reading nook or relaxation space. Two additional bedrooms with plush carpeting and ceiling fans share access to an upstairs hall bath, while a cozy flex room, ideal for a home office, features carpeting and a delightful round window. Adding to the home’s versatility is a private second upper-level suite located above the two-car garage, offering an expansive bedroom with an architecturally striking half-wall separating a sitting or office area, along with a spacious en-suite bath, perfect for guests or multi-generational living. Outdoors, the property truly becomes unforgettable. 125 feet of unobstructed Chester River frontage provides direct access to the water, complemented by a deep-water dock with a boat lift and two jet ski lifts, all conveyed as-is. An enormous IPE wood deck creates an exceptional setting for entertaining, complete with a hot tub and a covered outdoor kitchen featuring a bar, grill, sink, ice maker, and even a full bath, delivering a true resort-style experience at home. A graceful circular driveway enhances both curb appeal and convenience, offering ample parking for guests. Recent improvements include a new roof and siding (2023), a replaced well and pump (2017), and the added luxury of a water softener and whole-house reverse osmosis system. This extraordinary waterfront residence seamlessly blends refined renovations, exceptional indoor and outdoor amenities, and an unparalleled riverfront setting, presenting a rare opportunity to own a true Chester River masterpiece. 1017 Long Point Rd, Grasonville Listing courtesy of Northrop Realty. Contact: Selling Office: Benson & Mangold, LLC.
$1,600,000 Set on more than six private acres in one of Kent Island’s most desirable locations, this exceptional estate offers a rare blend of luxury, scale, and refined livability. Encompassing approximately 5,995 square feet, the residence has been thoughtfully elevated through extensive improvements, resulting in a truly turnkey offering in a setting defined by privacy, presence, and the freedom of no HOA restrictions, including the ability to keep livestock. At the heart of the home, a spectacular chef’s kitchen sets the tone for both everyday living and elevated entertaining. Custom cabinetry frames a suite of premium Viking and Miele appliances, complemented by an oversized refrigerator and freezer, multiple ovens, dual dishwashers, beverage refrigeration, a dedicated ice maker, and a walk-in pantry. This is a space designed to perform just as well for quiet evenings as it does for large gatherings. A soaring two-story family room anchors the main level, filled with natural light and centered around a newly installed pellet stove insert. The main-level primary suite serves as a private retreat, featuring a fully reimagined spa-inspired bath with a steam shower, soaking tub, and bespoke cabinetry. Across three finished levels, five bedrooms provide exceptional flexibility for family, guests, and multi-generational living. In addition, a spacious home office featuring a large closet and custom built-in shelving offers an ideal workspace or library, while the finished third level includes a generous loft and recreation room that provide endless possibilities for a media room, game room, fitness space, hobby area, or additional gathering space. Throughout the home, refreshed interiors, custom built-ins, and thoughtful updates contribute to a cohesive sense of comfort and refinement. Outdoors, the property unfolds like a private resort. An expansive patio, gazebo, curated landscaping, and swimming pool create an effortless setting for entertaining or quiet relaxation. The surrounding acreage enhances the sense of seclusion, with space for recreation, gardening, livestock, or simply enjoying the quiet rhythm of estate living. The detached two-story garage extends the property's versatility, with a dedicated fitness studio above and generous space below for vehicles, equipment, hobbies, or future expansion. What truly distinguishes the property is the quiet confidence of what has already been accomplished. Comprehensive improvements to core systems and infrastructure ensure a level of reliability and peace of mind rarely found in homes of this scale, allowing the next owner to simply arrive and enjoy. Despite its private and pastoral setting, the estate remains just minutes from Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Eastern Shore. Positioned near the highly regarded Matapeake school campus, it offers a rare combination of seclusion, accessibility, and everyday convenience. Rarely does a property combine acreage, scale, and refinement in such a complete way. This is more than a home. It is a private Kent Island estate designed for living well, entertaining effortlessly, and enjoying space without compromise. 5 Beds ⋅ 6 Baths Set on more than six private acres in one of Kent Island’s most desirable locations, this exceptional estate offers a rare blend of luxury, scale, and refined livability. Encompassing approximately 5,995 square feet, the residence has been thoughtfully elevated through extensive improvements, resulting in a truly turnkey offering in a setting defined by privacy, presence, and the freedom of no HOA restrictions, including the ability to keep livestock. At the heart of the home, a spectacular chef’s kitchen sets the tone for both everyday living and elevated entertaining. Custom cabinetry frames a suite of premium Viking and Miele appliances, complemented by an oversized refrigerator and freezer, multiple ovens, dual dishwashers, beverage refrigeration, a dedicated ice maker, and a walk-in pantry. This is a space designed to perform just as well for quiet evenings as it does for large gatherings. A soaring two-story family room anchors the main level, filled with natural light and centered around a newly installed pellet stove insert. The main-level primary suite serves as a private retreat, featuring a fully reimagined spa-inspired bath with a steam shower, soaking tub, and bespoke cabinetry. Across three finished levels, five bedrooms provide exceptional flexibility for family, guests, and multi-generational living. In addition, a spacious home office featuring a large closet and custom built-in shelving offers an ideal workspace or library, while the finished third level includes a generous loft and recreation room that provide endless possibilities for a media room, game room, fitness space, hobby area, or additional gathering space. Throughout the home, refreshed interiors, custom built-ins, and thoughtful updates contribute to a cohesive sense of comfort and refinement. Outdoors, the property unfolds like a private resort. An expansive patio, gazebo, curated landscaping, and swimming pool create an effortless setting for entertaining or quiet relaxation. The surrounding acreage enhances the sense of seclusion, with space for recreation, gardening, livestock, or simply enjoying the quiet rhythm of estate living. The detached two-story garage extends the property's versatility, with a dedicated fitness studio above and generous space below for vehicles, equipment, hobbies, or future expansion. What truly distinguishes the property is the quiet confidence of what has already been accomplished. Comprehensive improvements to core systems and infrastructure ensure a level of reliability and peace of mind rarely found in homes of this scale, allowing the next owner to simply arrive and enjoy. Despite its private and pastoral setting, the estate remains just minutes from Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Eastern Shore. Positioned near the highly regarded Matapeake school campus, it offers a rare combination of seclusion, accessibility, and everyday convenience. Rarely does a property combine acreage, scale, and refinement in such a complete way. This is more than a home. It is a private Kent Island estate designed for living well, entertaining effortlessly, and enjoying space without compromise. 102 Little Neck Rd, Stevensville Listing courtesy of HomeSource Pro Real Estate. Contact: Selling Office: Berkshire Hathaway HomeServices PenFed Realty.
$1,600,000 Experience a true “wow” moment the instant you arrive at this meticulously maintained estate in the exclusive Bennett Point community, set on a private street with views of the renowned Wye River. Step into the grand foyer and be greeted by soaring ceilings, elegant columns, lighted niches, graceful arches, and a stunning curved staircase. The home opens into a formal dining room perfect for entertaining, flowing seamlessly into a dramatic two-story family room with a wall of windows overlooking the patio, saltwater Gunite pool, fenced backyard, and barn. A floor-to-ceiling stone gas fireplace anchors the space—ideal for cozy winter nights or gathering for the big game. The open-concept layout continues into a chef’s dream kitchen, featuring granite countertops, abundant Merillat Masterpiece solid cherry cabinetry, and premium appliances including a Sub-Zero refrigerator/freezer, commercial-grade Viking cooktop with hood and pot filler, double wall ovens, built-in microwave, beverage cooler, dishwasher, and ice maker. A spacious island, built-in desk, appliance cabinet, hidden cutting board, and corner pantry make this kitchen as functional as it is beautiful. The main level offers two luxurious owner’s suites. The primary suite includes a wet bar, private sitting area, dual walk-in closets, and a spa-inspired bath with heated soaking tub, dual-head shower, travertine floors, and marble countertops. The second suite features a gas fireplace, built-in desk, and an accessible ensuite bath with roll-in shower and elegant finishes—ideal for multi-generational living or guests. A main-level laundry room adds everyday convenience. Throughout the home, you’ll find rich teak flooring, tray ceilings, and abundant recessed lighting. Upstairs, three spacious bedrooms each feature private ensuite baths, along with a large game room. A generous unfinished third level offers endless possibilities for expansion, including an au pair suite or additional bedrooms. Outdoor living is equally impressive. Enjoy the fenced saltwater pool with water feature, a screened porch with Easy-Breeze windows for year-round use, and a beautifully maintained yard with underground irrigation, vegetable garden, and whole-house generator. The conditioned crawl space adds efficiency and peace of mind. Equestrian enthusiasts will appreciate the adjacent horse training facility with covered arena. The property includes a 3-stall barn with heat sensor, two pastures, dry lot, heated water, electric, and vinyl fencing—perfect for year-round care and riding. This exceptional property offers luxury, functionality, and lifestyle—all in one remarkable setting. 5 Beds ⋅ 6 Baths Experience a true “wow” moment the instant you arrive at this meticulously maintained estate in the exclusive Bennett Point community, set on a private street with views of the renowned Wye River. Step into the grand foyer and be greeted by soaring ceilings, elegant columns, lighted niches, graceful arches, and a stunning curved staircase. The home opens into a formal dining room perfect for entertaining, flowing seamlessly into a dramatic two-story family room with a wall of windows overlooking the patio, saltwater Gunite pool, fenced backyard, and barn. A floor-to-ceiling stone gas fireplace anchors the space—ideal for cozy winter nights or gathering for the big game. The open-concept layout continues into a chef’s dream kitchen, featuring granite countertops, abundant Merillat Masterpiece solid cherry cabinetry, and premium appliances including a Sub-Zero refrigerator/freezer, commercial-grade Viking cooktop with hood and pot filler, double wall ovens, built-in microwave, beverage cooler, dishwasher, and ice maker. A spacious island, built-in desk, appliance cabinet, hidden cutting board, and corner pantry make this kitchen as functional as it is beautiful. The main level offers two luxurious owner’s suites. The primary suite includes a wet bar, private sitting area, dual walk-in closets, and a spa-inspired bath with heated soaking tub, dual-head shower, travertine floors, and marble countertops. The second suite features a gas fireplace, built-in desk, and an accessible ensuite bath with roll-in shower and elegant finishes—ideal for multi-generational living or guests. A main-level laundry room adds everyday convenience. Throughout the home, you’ll find rich teak flooring, tray ceilings, and abundant recessed lighting. Upstairs, three spacious bedrooms each feature private ensuite baths, along with a large game room. A generous unfinished third level offers endless possibilities for expansion, including an au pair suite or additional bedrooms. Outdoor living is equally impressive. Enjoy the fenced saltwater pool with water feature, a screened porch with Easy-Breeze windows for year-round use, and a beautifully maintained yard with underground irrigation, vegetable garden, and whole-house generator. The conditioned crawl space adds efficiency and peace of mind. Equestrian enthusiasts will appreciate the adjacent horse training facility with covered arena. The property includes a 3-stall barn with heat sensor, two pastures, dry lot, heated water, electric, and vinyl fencing—perfect for year-round care and riding. This exceptional property offers luxury, functionality, and lifestyle—all in one remarkable setting. 313 Wye Rd, Queenstown Listing courtesy of Long & Foster Real Estate, Inc.. Contact: Selling Office: Coldwell Banker Realty.
$1,600,000 STUNNING waterfront private oasis just minutes from the Bay Bridge, where coastal luxury meets effortless Chesapeake Bay living. Nearly 3100 sf, , this gorgeous retreat features four spacious bedrooms and three beautifully updated baths, designed for comfort, style & unforgettable gatherings. Main level bedroom & full bath offer flexibility! The heart of the home? A magazine-worthy coastal kitchen with new custom cabinetry, gleaming white quartz countertops, & shiny stainless steel appliances. Wide-plank white oak flooring that carries warmth and sophistication. Open, airy, and filled with natural light — every space feels intentional and elevated. Primary suite emulates the finest of hotels with cozy gas fireplace, catwalk to waterfront balcony, bonus room/office & STUNNING spa bath with sunken tub, walk-in-shower & vanity for two, heated floors & spacious closet for ample storage. Step outside to your own resort setting — with private in-ground pool, expansive entertaining areas, maintenance-free deck with cable rails for nautical feel. and a private pier with boat lift & two jet ski lifts - just three lots from direct Chesapeake Bay access. With 4' MLW, boating enthusiasts will appreciate effortless access to open water in minutes. This is more than a home — it’s a lifestyle, waterfront living re-defined. Opportunities like this don't float by twice- your boat belongs here! 4 Beds ⋅ 3 Baths STUNNING waterfront private oasis just minutes from the Bay Bridge, where coastal luxury meets effortless Chesapeake Bay living. Nearly 3100 sf, , this gorgeous retreat features four spacious bedrooms and three beautifully updated baths, designed for comfort, style & unforgettable gatherings. Main level bedroom & full bath offer flexibility! The heart of the home? A magazine-worthy coastal kitchen with new custom cabinetry, gleaming white quartz countertops, & shiny stainless steel appliances. Wide-plank white oak flooring that carries warmth and sophistication. Open, airy, and filled with natural light — every space feels intentional and elevated. Primary suite emulates the finest of hotels with cozy gas fireplace, catwalk to waterfront balcony, bonus room/office & STUNNING spa bath with sunken tub, walk-in-shower & vanity for two, heated floors & spacious closet for ample storage. Step outside to your own resort setting — with private in-ground pool, expansive entertaining areas, maintenance-free deck with cable rails for nautical feel. and a private pier with boat lift & two jet ski lifts - just three lots from direct Chesapeake Bay access. With 4' MLW, boating enthusiasts will appreciate effortless access to open water in minutes. This is more than a home — it’s a lifestyle, waterfront living re-defined. Opportunities like this don't float by twice- your boat belongs here! 802 Broadcreek Dr, Stevensville Listing courtesy of Chaney Homes, LLC. Contact: Selling Office: TTR Sotheby's International Realty.
$1,600,000 Welcome to 1026 Long Point Road, Grasonville, MD — a waterfront retreat on the Chester River with sunrise out back and sunset out front. Completely renovated inside and out in 2017, this 6-bedroom, 5.5-bath home combines timeless coastal charm with modern updates, offering water views from every room. The renovation included a new roof, siding, windows, HVAC, hardwood floors, carpet, doors, appliances, bulkhead, pier, boat lift, and decks — truly turn-key and ready for years of enjoyment. Designed for entertaining, the main level features expansive living and family rooms, a large dining area plus breakfast nook, and multiple sliders leading to the waterside deck with sleek cable railing. The spacious kitchen opens seamlessly to the deck—ideal for gatherings that flow from indoors to out. There are two bedrooms and 3 full bathrooms on the main level. A large laundry room and a versatile office (or additional bedroom) complete the first floor. Upstairs, two primary suites each offer en-suite baths and water views, separated by a comfortable sitting area. The main primary suite includes a private balcony overlooking the river. An additional guest bedroom upstairs with a half bath provides even more space for family or visitors. Outside, the private pier with an 8,000 lb. boat lift and 4–5 ft. MLW invites effortless boating, crabbing, and fishing right from your backyard. A shed provides extra storage for gear and equipment. Located near the end of the Long Point peninsula, where homes rarely come available, this property offers privacy and proximity to everything you love about the Eastern Shore—walk or bike the Cross Island Trail, easily boat to Kent Narrows, Rock Hall, Chestertown, and St. Michaels, and enjoy quick access to Route 50/301, shopping, restaurants, and nightlife. Whether you’re looking for a primary residence, weekend escape, or vacation rental investment, 1026 Long Point Road delivers the perfect blend of comfort, convenience, and Chesapeake charm. 6 Beds ⋅ 6 Baths Welcome to 1026 Long Point Road, Grasonville, MD — a waterfront retreat on the Chester River with sunrise out back and sunset out front. Completely renovated inside and out in 2017, this 6-bedroom, 5.5-bath home combines timeless coastal charm with modern updates, offering water views from every room. The renovation included a new roof, siding, windows, HVAC, hardwood floors, carpet, doors, appliances, bulkhead, pier, boat lift, and decks — truly turn-key and ready for years of enjoyment. Designed for entertaining, the main level features expansive living and family rooms, a large dining area plus breakfast nook, and multiple sliders leading to the waterside deck with sleek cable railing. The spacious kitchen opens seamlessly to the deck—ideal for gatherings that flow from indoors to out. There are two bedrooms and 3 full bathrooms on the main level. A large laundry room and a versatile office (or additional bedroom) complete the first floor. Upstairs, two primary suites each offer en-suite baths and water views, separated by a comfortable sitting area. The main primary suite includes a private balcony overlooking the river. An additional guest bedroom upstairs with a half bath provides even more space for family or visitors. Outside, the private pier with an 8,000 lb. boat lift and 4–5 ft. MLW invites effortless boating, crabbing, and fishing right from your backyard. A shed provides extra storage for gear and equipment. Located near the end of the Long Point peninsula, where homes rarely come available, this property offers privacy and proximity to everything you love about the Eastern Shore—walk or bike the Cross Island Trail, easily boat to Kent Narrows, Rock Hall, Chestertown, and St. Michaels, and enjoy quick access to Route 50/301, shopping, restaurants, and nightlife. Whether you’re looking for a primary residence, weekend escape, or vacation rental investment, 1026 Long Point Road delivers the perfect blend of comfort, convenience, and Chesapeake charm. 1026 Long Point Rd, Grasonville Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: Engel & Volkers Annapolis.
$1,566,000 Commanding an exceptional waterfront setting, this timeless historic property offers an increasingly rare opportunity to own a generational retreat defined by land, water, and view. Encompassing 35 acres and approximately 599 feet of shoreline, the property unfolds to a private beach and panoramic vistas across the Bay, where dramatic sunsets and iconic views of the Bay Bridge create a daily backdrop of natural beauty and quiet spectacle. With ample frontage and the potential for a private pier, the setting invites a true waterfront lifestyle. Enjoy boating, paddleboarding, lounging at the waterfront, and relishing evenings spent watching the light change across the water. Much of the acreage is designated agricultural, offering meaningful tax advantages while preserving the open, pastoral character of the land. This combination of expansive waterfrontage, open fields, and protected views creates a sense of scale, privacy, and long-term value that is rarely found. The historic residence, lovingly maintained by multiple generations, serves as a gracious complement to the land rather than its focus. An authentic, well-preserved home that anchors the property without overshadowing its extraordinary setting. 3 bedrooms, 2 baths, hardwood floors, original architectural details, and generously sized rooms reflect a quieter era of craftsmanship and care, while multiple windows throughout capture water views from nearly every vantage point. This is a property of substance and legacy—where expansive shoreline, agricultural land benefits, and one of the Bay’s most recognizable views converge to create an unparalleled waterfront offering. Welcome Home! 3 Beds ⋅ 3 Baths Commanding an exceptional waterfront setting, this timeless historic property offers an increasingly rare opportunity to own a generational retreat defined by land, water, and view. Encompassing 35 acres and approximately 599 feet of shoreline, the property unfolds to a private beach and panoramic vistas across the Bay, where dramatic sunsets and iconic views of the Bay Bridge create a daily backdrop of natural beauty and quiet spectacle. With ample frontage and the potential for a private pier, the setting invites a true waterfront lifestyle. Enjoy boating, paddleboarding, lounging at the waterfront, and relishing evenings spent watching the light change across the water. Much of the acreage is designated agricultural, offering meaningful tax advantages while preserving the open, pastoral character of the land. This combination of expansive waterfrontage, open fields, and protected views creates a sense of scale, privacy, and long-term value that is rarely found. The historic residence, lovingly maintained by multiple generations, serves as a gracious complement to the land rather than its focus. An authentic, well-preserved home that anchors the property without overshadowing its extraordinary setting. 3 bedrooms, 2 baths, hardwood floors, original architectural details, and generously sized rooms reflect a quieter era of craftsmanship and care, while multiple windows throughout capture water views from nearly every vantage point. This is a property of substance and legacy—where expansive shoreline, agricultural land benefits, and one of the Bay’s most recognizable views converge to create an unparalleled waterfront offering. Welcome Home! 301 John Kallis Ln, Stevensville Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: TTR Sotheby's International Realty.
$1,500,000 Waterfront on the Corsica River—opportunities like this don't come along every day! Proudly positioned on a spectacular 2-acre lot with approximately 540 feet of shoreline, this exceptional 4-bedroom, 3-bath home offers breathtaking panoramic views and an unmatched waterfront lifestyle. Located at the end of a quiet cul-de-sac in the established community of Corsica Landing Estates, just outside Centreville town limits, you'll enjoy the benefits of no town taxes or HOA fees. Mature landscaping and thoughtfully designed hardscaping create a private setting that perfectly complements the expansive river views. Designed for entertaining, the backyard is truly a waterfront oasis. Enjoy the in-ground concrete pool with diving board, a spacious hot tub housed in its own versatile room for year-round enjoyment, and a 145-foot private dock with approximately 6 feet of mean low water, complete with electric, water, two boat lifts, and a floating dock. Whether you prefer relaxing in the sun or unwinding in the shade, the beautifully landscaped outdoor living spaces have something for everyone, including an expansive 47.5' x 18' Trex deck with two pergola-like covered cooking and dining areas and a spacious waterside patio. Inside, the home offers comfortable living with generous spaces throughout. The eat-in kitchen features granite countertops, stainless steel appliances, including a new oversized refrigerator, and a separate wet bar with wine refrigerator and wine rack. The main level also includes a spacious living room with a wood-burning fireplace, an oversized formal dining room, a home office with custom built-ins and a large bay window, a full bath, and a convenient laundry/mudroom. One of the home's standout features is the incredible waterside sunroom, filled with natural light from walls of windows and offering spectacular views of the pool and river. Complete with a beautiful stone propane fireplace and ceiling fans, it's the perfect place to relax in every season. The spacious primary suite includes hardwood flooring, a walk-in closet, dual vanities, a walk-in shower, and direct access to a large 18.5' x 24' bonus room above the garage. With its own private staircase from the attached two-car garage, this flexible space is ideal for a guest suite, recreation room, fitness area, studio, or additional home office. Next to the garage is an attached exterior storage/utility room which provides even more convenience. THE FINISHED LIVING AREA SQUARE FOOTAGE FOR THIS HOME IS LARGER THAN THE ASSESSMENT OFFICE REPRESENTS AND THE GOOGLE SATELLITE IMAGE MAP DOES NOT REFLECT ALL OF THE PROPERTY. PLEASE SEE DEEDS AND MAPS ATTACHED IN THE DOCUMENTS. Numerous updates have been completed over the years, including the HVAC system and ductwork, roof, triple-pane windows and sunroom doors with a lifetime warranty. The pool was renovated in 2016, with a new pool pump and skimmer pipe installed in 2023 and a new pool motor in 2026. The well pump was replaced and lowered in 2007, offering additional peace of mind. Whether you're searching for a full-time waterfront residence, the ultimate family gathering place, or a home designed for entertaining, this remarkable property delivers. With boating, fishing, kayaking, swimming, and unforgettable sunsets right from your backyard—and a county boat ramp, playground, and pavilion just minutes away—there's still plenty of summer left to enjoy. Schedule your private tour today and experience everything this extraordinary Corsica River property has to offer. Located within an hour to Baltimore, Washington, DC or Delaware. Stay Tuned For Professional Photos Coming Soon ! 4 Beds ⋅ 3 Baths Waterfront on the Corsica River—opportunities like this don't come along every day! Proudly positioned on a spectacular 2-acre lot with approximately 540 feet of shoreline, this exceptional 4-bedroom, 3-bath home offers breathtaking panoramic views and an unmatched waterfront lifestyle. Located at the end of a quiet cul-de-sac in the established community of Corsica Landing Estates, just outside Centreville town limits, you'll enjoy the benefits of no town taxes or HOA fees. Mature landscaping and thoughtfully designed hardscaping create a private setting that perfectly complements the expansive river views. Designed for entertaining, the backyard is truly a waterfront oasis. Enjoy the in-ground concrete pool with diving board, a spacious hot tub housed in its own versatile room for year-round enjoyment, and a 145-foot private dock with approximately 6 feet of mean low water, complete with electric, water, two boat lifts, and a floating dock. Whether you prefer relaxing in the sun or unwinding in the shade, the beautifully landscaped outdoor living spaces have something for everyone, including an expansive 47.5' x 18' Trex deck with two pergola-like covered cooking and dining areas and a spacious waterside patio. Inside, the home offers comfortable living with generous spaces throughout. The eat-in kitchen features granite countertops, stainless steel appliances, including a new oversized refrigerator, and a separate wet bar with wine refrigerator and wine rack. The main level also includes a spacious living room with a wood-burning fireplace, an oversized formal dining room, a home office with custom built-ins and a large bay window, a full bath, and a convenient laundry/mudroom. One of the home's standout features is the incredible waterside sunroom, filled with natural light from walls of windows and offering spectacular views of the pool and river. Complete with a beautiful stone propane fireplace and ceiling fans, it's the perfect place to relax in every season. The spacious primary suite includes hardwood flooring, a walk-in closet, dual vanities, a walk-in shower, and direct access to a large 18.5' x 24' bonus room above the garage. With its own private staircase from the attached two-car garage, this flexible space is ideal for a guest suite, recreation room, fitness area, studio, or additional home office. Next to the garage is an attached exterior storage/utility room which provides even more convenience. THE FINISHED LIVING AREA SQUARE FOOTAGE FOR THIS HOME IS LARGER THAN THE ASSESSMENT OFFICE REPRESENTS AND THE GOOGLE SATELLITE IMAGE MAP DOES NOT REFLECT ALL OF THE PROPERTY. PLEASE SEE DEEDS AND MAPS ATTACHED IN THE DOCUMENTS. Numerous updates have been completed over the years, including the HVAC system and ductwork, roof, triple-pane windows and sunroom doors with a lifetime warranty. The pool was renovated in 2016, with a new pool pump and skimmer pipe installed in 2023 and a new pool motor in 2026. The well pump was replaced and lowered in 2007, offering additional peace of mind. Whether you're searching for a full-time waterfront residence, the ultimate family gathering place, or a home designed for entertaining, this remarkable property delivers. With boating, fishing, kayaking, swimming, and unforgettable sunsets right from your backyard—and a county boat ramp, playground, and pavilion just minutes away—there's still plenty of summer left to enjoy. Schedule your private tour today and experience everything this extraordinary Corsica River property has to offer. Located within an hour to Baltimore, Washington, DC or Delaware. Stay Tuned For Professional Photos Coming Soon ! 405 Quail Run Dr, Centreville Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Benson & Mangold, LLC.
$1,450,000 HIGHEST AND BEST DUE SUNDAY 10/19 6PM----Welcome to 16 Fairway Island, a 5,100 sq. ft. coastal-inspired estate designed for both everyday luxury and effortless entertaining. With a main-level primary suite, spacious office, and four oversized bedrooms upstairs, this home offers the perfect balance of comfort, style, and functionality. Step inside to soaring spaces wrapped in fresh paint, new luxury vinyl plank flooring , and upgraded lighting that bring a crisp, modern feel. The chef’s kitchen features a new cooktop, two dishwashers, a wine fridge, and professionally refinished cabinets — ideal for preparing family meals or hosting on a grand scale. A generous family room anchors the main level, while formal and casual dining spaces provide versatility for gatherings. The main-level primary suite is a private retreat, complete with spacious layout and spa-like finishes. Upstairs, four large bedrooms offer room for family, guests, or flexible use. A dedicated main-level office ensures work-from-home convenience without sacrificing style. Outside, enjoy your own private resort: a saltwater pool with recently upgraded motorized cover, outdoor shower, built-in umbrella, gas hookup, hot tub, built in fire pit, and a newly fenced yard framed by lush landscaping. And as a bonus — the property includes a pool house with a wood-burning fireplace, mini-split system, and water hookup, creating an additional entertaining space for summer pool parties or cozy fall evenings. Practical features include a 3-car garage with workbench and second-level storage, laundry located both upstairs and downstairs, interior crawlspace access, propane service, and annual HVAC maintenance for peace of mind. Located in the sought after golf course community of Prospect Bay, this award winning neighborhood offers the best of both worlds-- a premier 18 hole golf course and access to the Chesapeake Bay. Perfect for golf enthusiasts but it's not just about golf...residents enjoy full club amenities including fine and casual dining, tennis, pickleball, a marina, and a vibrant social calendar Prospect Bay combines resort-style amenities with an unbeatable Eastern Shore location This isn’t just a home — it’s lifestyle on Maryland’s Eastern Shore. https://unbranded.youriguide.com/1l8pu_16_fairway_island_grasonville_md/ **3DTour** 5 Beds ⋅ 4 Baths HIGHEST AND BEST DUE SUNDAY 10/19 6PM----Welcome to 16 Fairway Island, a 5,100 sq. ft. coastal-inspired estate designed for both everyday luxury and effortless entertaining. With a main-level primary suite, spacious office, and four oversized bedrooms upstairs, this home offers the perfect balance of comfort, style, and functionality. Step inside to soaring spaces wrapped in fresh paint, new luxury vinyl plank flooring , and upgraded lighting that bring a crisp, modern feel. The chef’s kitchen features a new cooktop, two dishwashers, a wine fridge, and professionally refinished cabinets — ideal for preparing family meals or hosting on a grand scale. A generous family room anchors the main level, while formal and casual dining spaces provide versatility for gatherings. The main-level primary suite is a private retreat, complete with spacious layout and spa-like finishes. Upstairs, four large bedrooms offer room for family, guests, or flexible use. A dedicated main-level office ensures work-from-home convenience without sacrificing style. Outside, enjoy your own private resort: a saltwater pool with recently upgraded motorized cover, outdoor shower, built-in umbrella, gas hookup, hot tub, built in fire pit, and a newly fenced yard framed by lush landscaping. And as a bonus — the property includes a pool house with a wood-burning fireplace, mini-split system, and water hookup, creating an additional entertaining space for summer pool parties or cozy fall evenings. Practical features include a 3-car garage with workbench and second-level storage, laundry located both upstairs and downstairs, interior crawlspace access, propane service, and annual HVAC maintenance for peace of mind. Located in the sought after golf course community of Prospect Bay, this award winning neighborhood offers the best of both worlds-- a premier 18 hole golf course and access to the Chesapeake Bay. Perfect for golf enthusiasts but it's not just about golf...residents enjoy full club amenities including fine and casual dining, tennis, pickleball, a marina, and a vibrant social calendar Prospect Bay combines resort-style amenities with an unbeatable Eastern Shore location This isn’t just a home — it’s lifestyle on Maryland’s Eastern Shore. https://unbranded.youriguide.com/1l8pu_16_fairway_island_grasonville_md/ **3DTour** 16 Fairway Is, Grasonville Listing courtesy of Douglas Realty LLC. Contact: Selling Office: Coldwell Banker Realty.
$1,400,000 This is the quintessential Eastern Shore Waterfront Estate to turn into your legacy property. Sitting on over 12 acres just minutes from the Bay Bridge, this substantial craftsman built in 1914 once served as the primary residence for one of the lead engineers for the Pentagon, Jefferson Memorial, and other DC marvels due to its balance of proximity to the city and quality of life. Lifestyle amenities have improved since then with nationally renowned Queenstown Harbor Golf Resort and the marinas/dining options in Kent Narrows all minutes away. Privacy is paramount here with a wooded and gated entry lane but without sacrificing access due to the exit on Route 50 still less than a mile away. The sweeping views here are unmatched with the protected lands of Eastern Neck Wildlife Refuge across the Chester from the residence also guaranteeing this peace and tranquility for years to come. The home itself is a historic masterpiece with hardwood floors, hand blown glass windows, and grand center hall staircase. The connection with the water is celebrated here with multiple sunrooms boasting big water views for those special moments. A rough cut timber 2 car garage and workshop provides old Eastern Shore charm. Wildlife here is abundant for the outdoorsman and nature lover due to it being one of the first large parcels after crossing through the hustle and bustle of Kent Island. Invest wisely while improving your quality of life with your own waterfront sanctuary to create those special memories for generations. 5 Beds ⋅ 5 Baths This is the quintessential Eastern Shore Waterfront Estate to turn into your legacy property. Sitting on over 12 acres just minutes from the Bay Bridge, this substantial craftsman built in 1914 once served as the primary residence for one of the lead engineers for the Pentagon, Jefferson Memorial, and other DC marvels due to its balance of proximity to the city and quality of life. Lifestyle amenities have improved since then with nationally renowned Queenstown Harbor Golf Resort and the marinas/dining options in Kent Narrows all minutes away. Privacy is paramount here with a wooded and gated entry lane but without sacrificing access due to the exit on Route 50 still less than a mile away. The sweeping views here are unmatched with the protected lands of Eastern Neck Wildlife Refuge across the Chester from the residence also guaranteeing this peace and tranquility for years to come. The home itself is a historic masterpiece with hardwood floors, hand blown glass windows, and grand center hall staircase. The connection with the water is celebrated here with multiple sunrooms boasting big water views for those special moments. A rough cut timber 2 car garage and workshop provides old Eastern Shore charm. Wildlife here is abundant for the outdoorsman and nature lover due to it being one of the first large parcels after crossing through the hustle and bustle of Kent Island. Invest wisely while improving your quality of life with your own waterfront sanctuary to create those special memories for generations. 500 Nesbit Rd, Queenstown Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact: Selling Office: Potomac Country Real Estate.
$1,400,000 Wake up every day to breathtaking views of the Chesapeake Bay and the iconic Bay Bridge at this exceptional waterfront-inspired home in Stevensville! 702 Bayside Drive is truly one-of-a-kind, offering stunning water views from nearly every room and an incredible setting that captures the beauty of Maryland’s Eastern Shore lifestyle! This beautifully maintained home combines comfort, elegance, and unforgettable scenery. Enjoy relaxing mornings watching the sunrise over the bay, entertaining with panoramic water views, and peaceful evenings with the Bay Bridge glowing in the distance. The open and airy layout was designed to maximize the views, creating a seamless connection between indoor living and the surrounding waterfront beauty. ✨ Spectacular Chesapeake Bay & Bay Bridge views ✨ Water views from throughout the home ✨ Desirable Bayside location ✨ Bright, open-concept living spaces ✨ Perfect for entertaining or relaxing ✨ Minutes to shopping, dining, marinas, and the Bay Bridge Homes with views like this rarely come available — this is your chance to own a special piece of the Eastern Shore! 4 Beds ⋅ 4 Baths Wake up every day to breathtaking views of the Chesapeake Bay and the iconic Bay Bridge at this exceptional waterfront-inspired home in Stevensville! 702 Bayside Drive is truly one-of-a-kind, offering stunning water views from nearly every room and an incredible setting that captures the beauty of Maryland’s Eastern Shore lifestyle! This beautifully maintained home combines comfort, elegance, and unforgettable scenery. Enjoy relaxing mornings watching the sunrise over the bay, entertaining with panoramic water views, and peaceful evenings with the Bay Bridge glowing in the distance. The open and airy layout was designed to maximize the views, creating a seamless connection between indoor living and the surrounding waterfront beauty. ✨ Spectacular Chesapeake Bay & Bay Bridge views ✨ Water views from throughout the home ✨ Desirable Bayside location ✨ Bright, open-concept living spaces ✨ Perfect for entertaining or relaxing ✨ Minutes to shopping, dining, marinas, and the Bay Bridge Homes with views like this rarely come available — this is your chance to own a special piece of the Eastern Shore! 702 Bayside Dr, Stevensville Listing courtesy of Long & Foster Real Estate, Inc.. Contact: Selling Office: Coldwell Banker Realty.
$1,391,000 Experience elevated waterfront living in one of Kent Narrows' most desirable marina communities. Perfectly positioned as an end-unit in prestigious Wells Cove Townhomes & Marina, this extensively renovated four-level residence captures sweeping Chesapeake Bay and marina views while offering the rare combination of refined finishes, deep-water boating, and a true lock-and-leave lifestyle. Ready for immediate occupancy, this is the turnkey waterfront home you've been waiting for. Spanning approximately 3,500 square feet, the thoughtfully designed floor plan features four bedrooms, four full baths, one half bath, and a private elevator servicing all four levels. Crafted to satisfy even the most discerning buyer, the home reflects an uncompromising commitment to quality, comfort, and timeless design. Rich hardwood flooring, custom millwork, designer lighting, soaring 9-foot ceilings, abundant natural light, and beautifully renovated interiors create an atmosphere that is both sophisticated and inviting. At the heart of the home is a stunning chef's kitchen, completely redesigned in 2019 with custom cabinetry, premium appliances, stone countertops, an oversized center island, and exceptional workspace. Multiple living and entertaining areas, two spacious owner suites, a loft, and a generous recreation room with a wet bar provide remarkable flexibility for family and guests alike. Four private covered waterfront decks seamlessly extend the living space outdoors, creating the perfect setting to enjoy morning coffee, watch boats glide through the marina, or unwind with spectacular Chesapeake Bay sunsets. From nearly every level, the ever-changing waterfront views become part of everyday life. For boating enthusiasts, the deeded deep-water boat slip is one of the marina's most desirable, offering approximately 4 feet of mean low water and the ability to accommodate a substantial vessel. Ideally positioned for convenient access to the Chesapeake Bay, it provides an exceptional home port for everything from an afternoon cruise to a weekend on the water. An oversized two-car garage offers generous storage for vehicles, bicycles, paddleboards, fishing gear, and all the essentials for an active waterfront lifestyle. Located in the heart of Kent Narrows, you're just moments from waterfront restaurants, marinas, boutique shopping, the Cross Island Trail, golf, and Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches. Beautifully renovated, impeccably maintained, and completely turnkey, this extraordinary residence presents a rare opportunity to own one of Wells Cove's premier waterfront homes. Simply arrive, settle in, and begin enjoying the Chesapeake Bay lifestyle from day one. 4 Beds ⋅ 5 Baths Experience elevated waterfront living in one of Kent Narrows' most desirable marina communities. Perfectly positioned as an end-unit in prestigious Wells Cove Townhomes & Marina, this extensively renovated four-level residence captures sweeping Chesapeake Bay and marina views while offering the rare combination of refined finishes, deep-water boating, and a true lock-and-leave lifestyle. Ready for immediate occupancy, this is the turnkey waterfront home you've been waiting for. Spanning approximately 3,500 square feet, the thoughtfully designed floor plan features four bedrooms, four full baths, one half bath, and a private elevator servicing all four levels. Crafted to satisfy even the most discerning buyer, the home reflects an uncompromising commitment to quality, comfort, and timeless design. Rich hardwood flooring, custom millwork, designer lighting, soaring 9-foot ceilings, abundant natural light, and beautifully renovated interiors create an atmosphere that is both sophisticated and inviting. At the heart of the home is a stunning chef's kitchen, completely redesigned in 2019 with custom cabinetry, premium appliances, stone countertops, an oversized center island, and exceptional workspace. Multiple living and entertaining areas, two spacious owner suites, a loft, and a generous recreation room with a wet bar provide remarkable flexibility for family and guests alike. Four private covered waterfront decks seamlessly extend the living space outdoors, creating the perfect setting to enjoy morning coffee, watch boats glide through the marina, or unwind with spectacular Chesapeake Bay sunsets. From nearly every level, the ever-changing waterfront views become part of everyday life. For boating enthusiasts, the deeded deep-water boat slip is one of the marina's most desirable, offering approximately 4 feet of mean low water and the ability to accommodate a substantial vessel. Ideally positioned for convenient access to the Chesapeake Bay, it provides an exceptional home port for everything from an afternoon cruise to a weekend on the water. An oversized two-car garage offers generous storage for vehicles, bicycles, paddleboards, fishing gear, and all the essentials for an active waterfront lifestyle. Located in the heart of Kent Narrows, you're just moments from waterfront restaurants, marinas, boutique shopping, the Cross Island Trail, golf, and Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches. Beautifully renovated, impeccably maintained, and completely turnkey, this extraordinary residence presents a rare opportunity to own one of Wells Cove's premier waterfront homes. Simply arrive, settle in, and begin enjoying the Chesapeake Bay lifestyle from day one. 314 Channel Marker Way, Grasonville Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Keller Williams Realty Centre.
$1,390,000 This waterfront home rests on the banks of Price Creek, a protected waterway leading to the Chesapeake Bay. Offering 4 bedrooms and 3 full bathrooms, the home features two spacious primary suites, each with en-suite baths and walk-in closets. The open-concept floor plan is filled with natural light and showcases stunning water and pool views throughout. Step outside to the screened porch and enjoy gentle breezes and the peaceful sounds of nature. Take advantage of the upgraded saltwater pool, a private boat lift, and the peace of mind provided by a new roof installed in 2024, along with a home generator. Inside, unwind in comfortable living spaces designed for both relaxation and entertaining, with seamless indoor-outdoor flow that makes the most of this exceptional waterfront setting. Enjoy the protected waters of Price Creek for kayaking, canoeing, or paddleboarding, or venture out to the Chesapeake Bay for a day on the water—all just steps from your back door. Located in Queen Anne Colony, the community also boasts a marina and playground and the home is just minutes from a public walking trail and golf course. 4 Beds ⋅ 3 Baths This waterfront home rests on the banks of Price Creek, a protected waterway leading to the Chesapeake Bay. Offering 4 bedrooms and 3 full bathrooms, the home features two spacious primary suites, each with en-suite baths and walk-in closets. The open-concept floor plan is filled with natural light and showcases stunning water and pool views throughout. Step outside to the screened porch and enjoy gentle breezes and the peaceful sounds of nature. Take advantage of the upgraded saltwater pool, a private boat lift, and the peace of mind provided by a new roof installed in 2024, along with a home generator. Inside, unwind in comfortable living spaces designed for both relaxation and entertaining, with seamless indoor-outdoor flow that makes the most of this exceptional waterfront setting. Enjoy the protected waters of Price Creek for kayaking, canoeing, or paddleboarding, or venture out to the Chesapeake Bay for a day on the water—all just steps from your back door. Located in Queen Anne Colony, the community also boasts a marina and playground and the home is just minutes from a public walking trail and golf course. 115 Congressional Dr, Stevensville Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact: Selling Office: Realty Navigator.
$1,375,000 Set along the peaceful shores of Chews Creek, this beautifully renovated waterfront home delivers the quintessential Eastern Shore lifestyle, where spectacular sunsets, endless water views, and effortless indoor-outdoor living take center stage. Thoughtfully updated throughout, the home offers five bedrooms and four full baths with a layout designed for both comfortable everyday living and exceptional entertaining. Hardwood floors flow throughout the main level, while abundant natural light and an open floor plan create a bright, inviting atmosphere. At the heart of the home, the gourmet kitchen features a large center island, Silestone countertops, Sub-Zero refrigerator, Viking gas cooktop, Miele built-in espresso maker, beverage refrigerator, nugget ice maker, stainless steel appliances, and ample space for gathering with all your guests. The kitchen opens seamlessly to the living and entertaining spaces, all oriented to capture beautiful water views. The main level offers tremendous versatility with a first-floor bedroom, dedicated office space, formal dining room accented by designer wallpaper, and an elegant living room with fireplace. A spacious waterside family room provides the perfect setting to relax, entertain, and enjoy the ever-changing waterfront scenery. Upstairs, the waterside primary suite serves as a private retreat overlooking the creek. Additional guest accommodations include generously sized bedrooms and a large bunk room ideal for hosting family and friends. Beautifully renovated baths feature custom tile work, dual vanities, and oversized walk-in showers. Outdoor living is equally impressive. A large waterside deck overlooks the heated and cooled salt-water swimming pool, creating a resort-like setting for summer gatherings. The outdoor amenities also feature a private outdoor spa/hot tub for year-round enjoyment. Professionally landscaped grounds, mature plantings, and multiple outdoor entertaining areas enhance the property’s relaxed waterfront lifestyle. Additional highlights include a detached two-car garage with an additional office space/bonus room,, roof less than ten years old, updated finishes throughout, and a setting that showcases some of the most breathtaking sunset views on Maryland’s Eastern Shore. Whether enjoying a quiet evening by the pool, entertaining guests on the deck, or watching the sun disappear over the water, this exceptional waterfront property offers a rare opportunity to experience Kent Island living at its finest. 5 Beds ⋅ 4 Baths Set along the peaceful shores of Chews Creek, this beautifully renovated waterfront home delivers the quintessential Eastern Shore lifestyle, where spectacular sunsets, endless water views, and effortless indoor-outdoor living take center stage. Thoughtfully updated throughout, the home offers five bedrooms and four full baths with a layout designed for both comfortable everyday living and exceptional entertaining. Hardwood floors flow throughout the main level, while abundant natural light and an open floor plan create a bright, inviting atmosphere. At the heart of the home, the gourmet kitchen features a large center island, Silestone countertops, Sub-Zero refrigerator, Viking gas cooktop, Miele built-in espresso maker, beverage refrigerator, nugget ice maker, stainless steel appliances, and ample space for gathering with all your guests. The kitchen opens seamlessly to the living and entertaining spaces, all oriented to capture beautiful water views. The main level offers tremendous versatility with a first-floor bedroom, dedicated office space, formal dining room accented by designer wallpaper, and an elegant living room with fireplace. A spacious waterside family room provides the perfect setting to relax, entertain, and enjoy the ever-changing waterfront scenery. Upstairs, the waterside primary suite serves as a private retreat overlooking the creek. Additional guest accommodations include generously sized bedrooms and a large bunk room ideal for hosting family and friends. Beautifully renovated baths feature custom tile work, dual vanities, and oversized walk-in showers. Outdoor living is equally impressive. A large waterside deck overlooks the heated and cooled salt-water swimming pool, creating a resort-like setting for summer gatherings. The outdoor amenities also feature a private outdoor spa/hot tub for year-round enjoyment. Professionally landscaped grounds, mature plantings, and multiple outdoor entertaining areas enhance the property’s relaxed waterfront lifestyle. Additional highlights include a detached two-car garage with an additional office space/bonus room,, roof less than ten years old, updated finishes throughout, and a setting that showcases some of the most breathtaking sunset views on Maryland’s Eastern Shore. Whether enjoying a quiet evening by the pool, entertaining guests on the deck, or watching the sun disappear over the water, this exceptional waterfront property offers a rare opportunity to experience Kent Island living at its finest. 115 Nw Creek Dr, Stevensville Listing courtesy of TTR Sotheby's International Realty. Contact: Selling Office: Redfin Corp.
$1,375,000 Waterfront, living on Kent Island! This waterfront home is in a great location, Queen Anne Colony community and sits nearly an acre at the end of a quiet cul-de-sac. With over 180 feet of waterfront on Price Creek, you’ll enjoy protected deep water and quick access to the Chesapeake Bay, making it a true boater’s paradise. The home is in excellent condition and features 4 bedrooms and 3 full baths. The open-concept main living area is perfect for entertaining while taking in the beautiful water views. Additional living space includes a cozy den for quiet relaxation. The primary suite offers water views, a spacious walk-in closet, and a private bath with double vanities. In addition to the location and condition this home is all one level living, so this could be your home forever, age in place. Beautiful new exterior finishings provide great curb appeal. Fish and crab right from your private pier with a deep-water slip or spend the afternoon relaxing by the pool after a day on the water. Entertain family and friends on the screened porch, launch kayaks from your private ramp, or simply enjoy the peaceful waterfront views. Conveniently located just minutes from the Bay Bridge, this property is ideal for a weekend getaway or full-time residence with easy commutes to DC, and Annapolis. Enjoy nearby Blue Heron Golf Course and the Cross Island Trail located just outside the community. 4 Beds ⋅ 3 Baths Waterfront, living on Kent Island! This waterfront home is in a great location, Queen Anne Colony community and sits nearly an acre at the end of a quiet cul-de-sac. With over 180 feet of waterfront on Price Creek, you’ll enjoy protected deep water and quick access to the Chesapeake Bay, making it a true boater’s paradise. The home is in excellent condition and features 4 bedrooms and 3 full baths. The open-concept main living area is perfect for entertaining while taking in the beautiful water views. Additional living space includes a cozy den for quiet relaxation. The primary suite offers water views, a spacious walk-in closet, and a private bath with double vanities. In addition to the location and condition this home is all one level living, so this could be your home forever, age in place. Beautiful new exterior finishings provide great curb appeal. Fish and crab right from your private pier with a deep-water slip or spend the afternoon relaxing by the pool after a day on the water. Entertain family and friends on the screened porch, launch kayaks from your private ramp, or simply enjoy the peaceful waterfront views. Conveniently located just minutes from the Bay Bridge, this property is ideal for a weekend getaway or full-time residence with easy commutes to DC, and Annapolis. Enjoy nearby Blue Heron Golf Course and the Cross Island Trail located just outside the community. 108 Holly Ct, Stevensville Listing courtesy of Coldwell Banker Realty. Contact: Selling Office: Unrepresented.
$1,375,000 Welcome to your new waterfront home! Nestled on over 2 acres of prime waterfront on Shipping Creek. This property offers so much. Mature landscaping with sprinkler system to keep your lawn and landscaping lush. Beautifully appointed home with gourmet kitchen with open floor plan make this a prime area for entertaining. Did I mention the double-sided fireplace in the living/ dining area, with a wet bar that offers a wine fridge and icemaker. The primary suite offers a gorgeous primary bath with walk in shower and soaking tub with endless views of the creek. The primary suite also has huge walk-in closet and private screened in porch to take in your morning coffee. Two additional bedrooms offer a shared bath and separate entrances and their own screened in porch! Not enough room in the main house? Take the breezeway from the main house to the heated and cooled 3 car garage, then wander up the stairs to the private deck and enjoy more views of the creek. Located over the 3-car garage are separate guest quarters with a full gourmet kitchen, open floor plan, full bath and bedroom. With so many great features to this property how could there be more? How about over 200 ft of waterfrontage fully rip-rapped, pier with water, electric and ride on boat and jet ski lifts. Don't blink and miss this one in sought after Goose Point Estates. 4 Beds ⋅ 4 Baths Welcome to your new waterfront home! Nestled on over 2 acres of prime waterfront on Shipping Creek. This property offers so much. Mature landscaping with sprinkler system to keep your lawn and landscaping lush. Beautifully appointed home with gourmet kitchen with open floor plan make this a prime area for entertaining. Did I mention the double-sided fireplace in the living/ dining area, with a wet bar that offers a wine fridge and icemaker. The primary suite offers a gorgeous primary bath with walk in shower and soaking tub with endless views of the creek. The primary suite also has huge walk-in closet and private screened in porch to take in your morning coffee. Two additional bedrooms offer a shared bath and separate entrances and their own screened in porch! Not enough room in the main house? Take the breezeway from the main house to the heated and cooled 3 car garage, then wander up the stairs to the private deck and enjoy more views of the creek. Located over the 3-car garage are separate guest quarters with a full gourmet kitchen, open floor plan, full bath and bedroom. With so many great features to this property how could there be more? How about over 200 ft of waterfrontage fully rip-rapped, pier with water, electric and ride on boat and jet ski lifts. Don't blink and miss this one in sought after Goose Point Estates. 124 Eareckson Ln, Stevensville Listing courtesy of Rosendale Realty. Contact: Selling Office: Real Broker, LLC.
$1,361,000 OFFER DEADLINE is Sunday 5/3 at 3:00. Manor House is an extraordinary 18th century residence where the light from the home's windows once guided ships along the Chesapeake Bay. This is a rare opportunity to own a piece of Kent Island history reimagined for today's lifestyle. The house sits on 1.81 acres and has been masterfully restored for modern living while preserving its original charm. This stunning brick home offers timeless architecture , beautifully updated interiors, and seemless indoor-outdoor living. The private backyard oasis features a pool, hot tub, expansive patio, gazebo and original wishing well...creating the perfect setting for entertaining or a quiet retreat. The lovely updated farm-style kitchen exposes the original wood beams and brick fireplace, creating a warm and inviting space. The french doors which open invitingly to the pool and patio offer effortless indoor/outdoor living. A private, deeded slip awaits at Price Creek, which is just around the corner, and offers a sheltered berth with easy access to the Chesapeake Bay. Imagine during the summer a swim in the pool or playing golf at the public course abutting the neighborhood. Zip out to the Chesapeake Bay to fish, tube, or take a jaunt across the bay to Annapolis for dinner. Kayak along the peaceful shoreline to see blue herons, nesting osprey, and bald eagles soaring overhead. A private marina is just down the street beckoning larger boats. Queen Anne Colony offers multiple water access and scenic viewing points to the Bay. Grab your morning coffee or evening cocktails and watch the sun rise or set to your heart's desire. Queen Anne Marina located in the neighborhood gives you easy access to your boat and the Blue Heron golf course abuts the front of the neighborhood. What more could you ask for?? Located at the first exit off the Bay Bridge with easy access to Annapolis, DC, Baltimore, and points north. 4 Beds ⋅ 5 Baths OFFER DEADLINE is Sunday 5/3 at 3:00. Manor House is an extraordinary 18th century residence where the light from the home's windows once guided ships along the Chesapeake Bay. This is a rare opportunity to own a piece of Kent Island history reimagined for today's lifestyle. The house sits on 1.81 acres and has been masterfully restored for modern living while preserving its original charm. This stunning brick home offers timeless architecture , beautifully updated interiors, and seemless indoor-outdoor living. The private backyard oasis features a pool, hot tub, expansive patio, gazebo and original wishing well...creating the perfect setting for entertaining or a quiet retreat. The lovely updated farm-style kitchen exposes the original wood beams and brick fireplace, creating a warm and inviting space. The french doors which open invitingly to the pool and patio offer effortless indoor/outdoor living. A private, deeded slip awaits at Price Creek, which is just around the corner, and offers a sheltered berth with easy access to the Chesapeake Bay. Imagine during the summer a swim in the pool or playing golf at the public course abutting the neighborhood. Zip out to the Chesapeake Bay to fish, tube, or take a jaunt across the bay to Annapolis for dinner. Kayak along the peaceful shoreline to see blue herons, nesting osprey, and bald eagles soaring overhead. A private marina is just down the street beckoning larger boats. Queen Anne Colony offers multiple water access and scenic viewing points to the Bay. Grab your morning coffee or evening cocktails and watch the sun rise or set to your heart's desire. Queen Anne Marina located in the neighborhood gives you easy access to your boat and the Blue Heron golf course abuts the front of the neighborhood. What more could you ask for?? Located at the first exit off the Bay Bridge with easy access to Annapolis, DC, Baltimore, and points north. 213 Columbia Ln, Stevensville Listing courtesy of Long & Foster Real Estate, Inc.. Contact: Selling Office: TTR Sotheby's International Realty.
$1,350,000 Welcome to this beautifully updated waterfront-view home in Prospect Bay, the premier golf course community on the Eastern Shore! This home tastefully blends coastal charm with modern design and exceptional outdoor living. From the moment you arrive via the paved driveway to the two-car garage, you are greeted by serene water views from the front entrance and porches off the living room and sunroom. Inside, an open entryway with ample storage leads to a formal living room with masonry fireplace that flows seamlessly into a completely remodeled dining room featuring tasteful textured wallpaper, bead and board wall trim. On the opposite side of the entry, a spacious family room boasts a new electric fireplace with shiplap accent wall and quartz hearth. A stylish powder room with statement wallpaper and a new quartz countertop, along with hardwood floors throughout both levels, add to the home’s polished feel. The home offers easy interior access from the two-car garage, with a staircase tucked away down the same hallway that leads to a large room over the garage with dedicated heat pump. Perfect for use as a home office, extra bedroom, additional storage, or craft room. The upgraded kitchen shines with new countertops and backsplash, a remodeled island for added storage, and enhanced carpentry details, flowing into a bright sunroom with pool and water views ideal for an office or hobby space. Just beyond the kitchen, doors open to your private backyard oasis, complete with a deck featuring upgraded Trex materials, extensive hardscaping surrounding a large inground pool, a hot tub installed in 2022, and fresh landscaping framed by mature trees for ultimate privacy. A charming coastal-style guest house with high efficiency mini split units, sits steps from the pool, offering a kitchenette, living area, full bathroom, and bedroom for visitors or extended stays. Upstairs, the primary suite impresses with water views, a masonry fireplace, an expanded walk-in closet outfitted with a custom Elfa system, and a remodeled spa-like bathroom featuring a tiled shower with marble seat, soaking tub, dual vanities, and updated fixtures. Three additional bedrooms share a well-appointed guest bathroom. Recent major upgrades include a new roof and gutters (2024), attic plywood flooring for extra storage, encapsulated crawlspace (2023), three high-efficiency heat pumps (2023), freshly painted and caulked exterior, repaved and resealed driveway, updated garage including flooring, storage cabinets, work bench and door operators. The property also offers a whole-house generator, updated trim work throughout, and so much more, making this home truly move-in ready. Located within the exclusive Prospect Bay Community, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this water view property offers an unmatched lifestyle in one of Maryland's most prestigious communities. 5 Beds ⋅ 4 Baths Welcome to this beautifully updated waterfront-view home in Prospect Bay, the premier golf course community on the Eastern Shore! This home tastefully blends coastal charm with modern design and exceptional outdoor living. From the moment you arrive via the paved driveway to the two-car garage, you are greeted by serene water views from the front entrance and porches off the living room and sunroom. Inside, an open entryway with ample storage leads to a formal living room with masonry fireplace that flows seamlessly into a completely remodeled dining room featuring tasteful textured wallpaper, bead and board wall trim. On the opposite side of the entry, a spacious family room boasts a new electric fireplace with shiplap accent wall and quartz hearth. A stylish powder room with statement wallpaper and a new quartz countertop, along with hardwood floors throughout both levels, add to the home’s polished feel. The home offers easy interior access from the two-car garage, with a staircase tucked away down the same hallway that leads to a large room over the garage with dedicated heat pump. Perfect for use as a home office, extra bedroom, additional storage, or craft room. The upgraded kitchen shines with new countertops and backsplash, a remodeled island for added storage, and enhanced carpentry details, flowing into a bright sunroom with pool and water views ideal for an office or hobby space. Just beyond the kitchen, doors open to your private backyard oasis, complete with a deck featuring upgraded Trex materials, extensive hardscaping surrounding a large inground pool, a hot tub installed in 2022, and fresh landscaping framed by mature trees for ultimate privacy. A charming coastal-style guest house with high efficiency mini split units, sits steps from the pool, offering a kitchenette, living area, full bathroom, and bedroom for visitors or extended stays. Upstairs, the primary suite impresses with water views, a masonry fireplace, an expanded walk-in closet outfitted with a custom Elfa system, and a remodeled spa-like bathroom featuring a tiled shower with marble seat, soaking tub, dual vanities, and updated fixtures. Three additional bedrooms share a well-appointed guest bathroom. Recent major upgrades include a new roof and gutters (2024), attic plywood flooring for extra storage, encapsulated crawlspace (2023), three high-efficiency heat pumps (2023), freshly painted and caulked exterior, repaved and resealed driveway, updated garage including flooring, storage cabinets, work bench and door operators. The property also offers a whole-house generator, updated trim work throughout, and so much more, making this home truly move-in ready. Located within the exclusive Prospect Bay Community, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this water view property offers an unmatched lifestyle in one of Maryland's most prestigious communities. 228 Prospect Bay Dr W, Grasonville Listing courtesy of Coldwell Banker Realty. Contact: Selling Office: RE/MAX Executive.
$1,350,000 This stunning 4,500+ sq ft home with 5 bedrooms and 4.5 baths is set on a private 1.25-acre lot in the sought-after water-privileged Tower Gardens community—just minutes from the Bay Bridge. Ideal for generational living, the home features primary suites on both the first and second floors, offering flexibility for a variety of lifestyles. At the heart of the home, the gourmet kitchen boasts a massive island, custom cabinetry, a hidden walk-in pantry, and a Viking appliance package—all accented with designer finishes. The open-concept layout flows seamlessly into multiple living areas, anchored by indoor and outdoor fireplaces that create inviting spaces to gather year-round. The second-floor primary suite includes a private balcony, with expansive windows throughout filling the home with natural light. Thoughtful upgrades like a high-efficiency 2-stage HVAC, Anderson 400 series casement windows, Hardie siding, and a tankless water heater ensure lasting quality and comfort. Tower Gardens residents enjoy a private community beach and pier with sweeping sunset views over the Chesapeake Bay, plus a boat ramp just around the corner for easy access to the water. From this tranquil setting, you’re only minutes from Annapolis or St. Michaels and just 45 minutes to Washington, D.C. or BWI Airport. 5 Beds ⋅ 5 Baths This stunning 4,500+ sq ft home with 5 bedrooms and 4.5 baths is set on a private 1.25-acre lot in the sought-after water-privileged Tower Gardens community—just minutes from the Bay Bridge. Ideal for generational living, the home features primary suites on both the first and second floors, offering flexibility for a variety of lifestyles. At the heart of the home, the gourmet kitchen boasts a massive island, custom cabinetry, a hidden walk-in pantry, and a Viking appliance package—all accented with designer finishes. The open-concept layout flows seamlessly into multiple living areas, anchored by indoor and outdoor fireplaces that create inviting spaces to gather year-round. The second-floor primary suite includes a private balcony, with expansive windows throughout filling the home with natural light. Thoughtful upgrades like a high-efficiency 2-stage HVAC, Anderson 400 series casement windows, Hardie siding, and a tankless water heater ensure lasting quality and comfort. Tower Gardens residents enjoy a private community beach and pier with sweeping sunset views over the Chesapeake Bay, plus a boat ramp just around the corner for easy access to the water. From this tranquil setting, you’re only minutes from Annapolis or St. Michaels and just 45 minutes to Washington, D.C. or BWI Airport. 208 Tower Dr, Stevensville Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Unrepresented.
$1,340,000 Welcome to Storybook charm meets waterfront living at 212 Dutcher Rd in Queenstown… and this one is something truly special 🌊🏡 Nestled on a stunning 1.34-acre waterfront lot, this Cape Cod offers the kind of Eastern Shore lifestyle people dream about—complete with a updated private pier, electric boat lift, and even your own sandy beach. Days on the water, evenings by the shoreline… this is what it’s all about.The main home (2,425 sq ft.) features 4 bedrooms and 3 full baths, filled with warmth, character, and timeless design. And just when you think it couldn’t get better—there’s a separate 1 bedroom, 1 bath guest house, perfect for visitors, extended family, or a private retreat. With nearly 3,000 sq ft of total living space and located in the desirable Belle Point community (low HOA!), this property offers both privacy and connection—just minutes to the Bay Bridge, marinas, and everything the Shore has to offer. 4 Beds ⋅ 4 Baths Welcome to Storybook charm meets waterfront living at 212 Dutcher Rd in Queenstown… and this one is something truly special 🌊🏡 Nestled on a stunning 1.34-acre waterfront lot, this Cape Cod offers the kind of Eastern Shore lifestyle people dream about—complete with a updated private pier, electric boat lift, and even your own sandy beach. Days on the water, evenings by the shoreline… this is what it’s all about.The main home (2,425 sq ft.) features 4 bedrooms and 3 full baths, filled with warmth, character, and timeless design. And just when you think it couldn’t get better—there’s a separate 1 bedroom, 1 bath guest house, perfect for visitors, extended family, or a private retreat. With nearly 3,000 sq ft of total living space and located in the desirable Belle Point community (low HOA!), this property offers both privacy and connection—just minutes to the Bay Bridge, marinas, and everything the Shore has to offer. 212 Dutcher Rd, Queenstown Listing courtesy of Samson Properties. Contact: Selling Office: Samson Properties.
$1,300,000 Coming soon to Kent Island Estates — a rare opportunity to own directly on the Eastern Bay. This 5-bedroom, 3.5-bath Coastal-style home offers 2,704 square feet of finished living space across three levels, with soaring high ceilings, rich hardwood floors, and crown molding and wainscotting carrying throughout. The gourmet kitchen features upgraded countertops and premium appliances, with a breakfast area perfect for casual mornings, plus a fireplace in the main living area for cooler evenings. Professional Photos to come. Multiple bedrooms open directly onto a screened-in porch and private balconies, framing sweeping views of the Chesapeake Bay from nearly every angle. Step outside to your own private pier and dock, putting boating, fishing, and bay access just steps from the back door — while an in-ground pool adds resort-style living to your own backyard. Pella double-pane windows fill the home with natural light while keeping energy costs in check. Set on a 0.32-acre lot with no HOA, this home sits in the sought-after Kent Island Estates community, with access to a neighborhood park, the South Kent Island Trail, and quick proximity to local restaurants, grocery stores, and the Bay Bridge for an easy commute to Annapolis. Waterfront opportunities like this on the Eastern Bay are rare — don't miss your chance. 5 Beds ⋅ 4 Baths Coming soon to Kent Island Estates — a rare opportunity to own directly on the Eastern Bay. This 5-bedroom, 3.5-bath Coastal-style home offers 2,704 square feet of finished living space across three levels, with soaring high ceilings, rich hardwood floors, and crown molding and wainscotting carrying throughout. The gourmet kitchen features upgraded countertops and premium appliances, with a breakfast area perfect for casual mornings, plus a fireplace in the main living area for cooler evenings. Professional Photos to come. Multiple bedrooms open directly onto a screened-in porch and private balconies, framing sweeping views of the Chesapeake Bay from nearly every angle. Step outside to your own private pier and dock, putting boating, fishing, and bay access just steps from the back door — while an in-ground pool adds resort-style living to your own backyard. Pella double-pane windows fill the home with natural light while keeping energy costs in check. Set on a 0.32-acre lot with no HOA, this home sits in the sought-after Kent Island Estates community, with access to a neighborhood park, the South Kent Island Trail, and quick proximity to local restaurants, grocery stores, and the Bay Bridge for an easy commute to Annapolis. Waterfront opportunities like this on the Eastern Bay are rare — don't miss your chance. 366 Queen Anne Rd, Stevensville Listing courtesy of Real Broker, LLC - Chester. Contact: Selling Office: Long & Foster Real Estate, Inc..
$1,300,000 Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout. The ground-level "Party Zone" is a showstopper, featuring a full bar and lounge with dual garage doors that open directly to a private oasis complete with a pool, hot tub, and patio. Just steps away, your private dock awaits, equipped with two boat lifts, water, and electric. Inside, the craftsmanship shines through extensive custom built-ins and exquisite trim work. The heart of the home is the chef’s kitchen, recently remodeled with stunning Taj Mahal Quartzite, marble backsplash, and a hidden wine cellar. The top-floor primary retreat is a destination of its own, boasting a private viewing deck, a spa-like bath with a rain shower/jetted tub, a massive custom closet, and a dedicated morning bar (fridge/microwave/laundry) for ultimate convenience. With two additional ensuite guest suites and a flexible loft space, this home offers luxury at every turn. Live the life you’ve imagined—schedule your private tour today. 3 Beds ⋅ 5 Baths Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout. The ground-level "Party Zone" is a showstopper, featuring a full bar and lounge with dual garage doors that open directly to a private oasis complete with a pool, hot tub, and patio. Just steps away, your private dock awaits, equipped with two boat lifts, water, and electric. Inside, the craftsmanship shines through extensive custom built-ins and exquisite trim work. The heart of the home is the chef’s kitchen, recently remodeled with stunning Taj Mahal Quartzite, marble backsplash, and a hidden wine cellar. The top-floor primary retreat is a destination of its own, boasting a private viewing deck, a spa-like bath with a rain shower/jetted tub, a massive custom closet, and a dedicated morning bar (fridge/microwave/laundry) for ultimate convenience. With two additional ensuite guest suites and a flexible loft space, this home offers luxury at every turn. Live the life you’ve imagined—schedule your private tour today. 1719 Harbor Dr, Chester Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact: Selling Office: Long & Foster Real Estate, Inc..