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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.

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.

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:

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.

$1,361,000

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

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:

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.

$1,340,000

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.

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.

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:

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:

Your Maryland Eastern Shore Country Retreat on 65± Acres Presenting a rare opportunity in the Centreville area of Queen Anne’s County, this distinctive 65± acre property combines exceptional privacy, remarkable versatility, and a thriving collection of fruit trees—including peaches, pears, persimmons, paw paws, figs, raspberries, blackberries, and blueberries. This country estate is a true outdoorsman’s paradise for deer, turkey, and waterfowl, featuring a move‑in ready main home, a fully independent guest house, and a scenic pond that anchors the property’s natural beauty. It’s an ideal blend of rural charm and modern comfort—perfect as a private retreat, multi‑generational compound, or working hobby farm. The main residence offers nearly 3,000± sq ft of inviting living space with 3 bedrooms, 2 full baths, and an open, comfortable layout designed for everyday living. A spacious kitchen, bright living areas, and multiple gathering spaces including a Great Room with cathedral ceiling and stone hearth fireplace—make it easy to entertain or unwind while taking in panoramic views of the land. Large windows and easy deck access bring the outside in—perfect for sunrise coffee, golden‑hour sunsets, and overlooking your fruit trees, open space, and private pond. The separate 3‑bedroom, 2‑bath guest house (approx. 1,400± sq ft) is fully self‑contained with its own well, septic, and electric. This second dwelling offers flexible possibilities, including in‑law or guest quarters, rental income, or a private workspace. (Buyers should confirm any accessory dwelling or rental approvals with Queen Anne’s County.) Outside, wide‑open areas, wooded edges, producing fruit trees, a private food plot, and the picture‑perfect pond create endless opportunities for recreation, wildlife watching, gardening, and outdoor living or adventure. Whether your vision includes hunting, fishing, horses, an expanded orchard or berry patch, or peaceful waterfront views, this property provides room to breathe and space to grow. Ideally located minutes from Centreville, local schools, and commuter routes to Annapolis and the Bay Bridge, this Spaniard Neck Road property delivers the best of both worlds—quiet Eastern Shore living with convenient access to everything you need. If you’ve been waiting for a truly one‑of‑a‑kind country estate with two homes, exceptional acreage, abundant wildlife, and established fruit trees, this Eastern Shore retreat is ready to welcome you home. ***Seller makes no representations or warranties beyond the contract of sale. All square footage, lot size, and year built are approximate—buyer to verify. Potential income, rental, agricultural, or subdivision uses are not guaranteed and must be confirmed with Queen Anne’s County or other authorities. Info deemed reliable but not guaranteed; buyer to verify all details.***

6 Beds ⋅ 4 Baths

Your Maryland Eastern Shore Country Retreat on 65± Acres Presenting a rare opportunity in the Centreville area of Queen Anne’s County, this distinctive 65± acre property combines exceptional privacy, remarkable versatility, and a thriving collection of fruit trees—including peaches, pears, persimmons, paw paws, figs, raspberries, blackberries, and blueberries. This country estate is a true outdoorsman’s paradise for deer, turkey, and waterfowl, featuring a move‑in ready main home, a fully independent guest house, and a scenic pond that anchors the property’s natural beauty. It’s an ideal blend of rural charm and modern comfort—perfect as a private retreat, multi‑generational compound, or working hobby farm. The main residence offers nearly 3,000± sq ft of inviting living space with 3 bedrooms, 2 full baths, and an open, comfortable layout designed for everyday living. A spacious kitchen, bright living areas, and multiple gathering spaces including a Great Room with cathedral ceiling and stone hearth fireplace—make it easy to entertain or unwind while taking in panoramic views of the land. Large windows and easy deck access bring the outside in—perfect for sunrise coffee, golden‑hour sunsets, and overlooking your fruit trees, open space, and private pond. The separate 3‑bedroom, 2‑bath guest house (approx. 1,400± sq ft) is fully self‑contained with its own well, septic, and electric. This second dwelling offers flexible possibilities, including in‑law or guest quarters, rental income, or a private workspace. (Buyers should confirm any accessory dwelling or rental approvals with Queen Anne’s County.) Outside, wide‑open areas, wooded edges, producing fruit trees, a private food plot, and the picture‑perfect pond create endless opportunities for recreation, wildlife watching, gardening, and outdoor living or adventure. Whether your vision includes hunting, fishing, horses, an expanded orchard or berry patch, or peaceful waterfront views, this property provides room to breathe and space to grow. Ideally located minutes from Centreville, local schools, and commuter routes to Annapolis and the Bay Bridge, this Spaniard Neck Road property delivers the best of both worlds—quiet Eastern Shore living with convenient access to everything you need. If you’ve been waiting for a truly one‑of‑a‑kind country estate with two homes, exceptional acreage, abundant wildlife, and established fruit trees, this Eastern Shore retreat is ready to welcome you home. ***Seller makes no representations or warranties beyond the contract of sale. All square footage, lot size, and year built are approximate—buyer to verify. Potential income, rental, agricultural, or subdivision uses are not guaranteed and must be confirmed with Queen Anne’s County or other authorities. Info deemed reliable but not guaranteed; buyer to verify all details.***

930 Spaniard Neck Rd, Centreville

Listing courtesy of Bayside Realty. Contact:

Selling Office: Patterson-Schwartz Real Estate.

Expansive views stretch along Jackson Creek to the Chester River, creating a waterfront setting that is truly exceptional. For anyone who loves life on the water, this property offers a rare opportunity, complete with a sandy beach and impressive waterfront frontage. The outdoor amenities are designed for both relaxation and recreation, including a pier with boat lift and electric, a beach house cabana, pool, pergola, hardscape, and plenty of space for poolside entertaining. Natural light fills the home from sunrise over the Chester River throughout the day as the sun moves west. The main house is in excellent condition and offers multiple living spaces, including three sitting areas, a breakfast room, and a formal dining room. Beautiful finishes include hardwood floors, cherry kitchen cabinetry, stainless steel appliances, and a beverage bar. A stone fireplace adds warmth and ambiance to the open living areas. The home features five bedrooms, three full baths, and one-half bath, with hardwood flooring throughout both levels. A first-floor bedroom with a full bath provides flexibility for guests or multigenerational living. The primary suite is ideally positioned on the waterside and includes a private balcony. An indoor porch, outdoor porches, and a game room make this home especially well-suited for entertaining. Surrounded by mature trees, the property also offers a spacious yard with fencing already in place for children and pets.

Expansive views stretch along Jackson Creek to the Chester River, creating a waterfront setting that is truly exceptional. For anyone who loves life on the water, this property offers a rare opportunity, complete with a sandy beach and impressive waterfront frontage. The outdoor amenities are designed for both relaxation and recreation, including a pier with boat lift and electric, a beach house cabana, pool, pergola, hardscape, and plenty of space for poolside entertaining. Natural light fills the home from sunrise over the Chester River throughout the day as the sun moves west. The main house is in excellent condition and offers multiple living spaces, including three sitting areas, a breakfast room, and a formal dining room. Beautiful finishes include hardwood floors, cherry kitchen cabinetry, stainless steel appliances, and a beverage bar. A stone fireplace adds warmth and ambiance to the open living areas. The home features five bedrooms, three full baths, and one-half bath, with hardwood flooring throughout both levels. A first-floor bedroom with a full bath provides flexibility for guests or multigenerational living. The primary suite is ideally positioned on the waterside and includes a private balcony. An indoor porch, outdoor porches, and a game room make this home especially well-suited for entertaining. Surrounded by mature trees, the property also offers a spacious yard with fencing already in place for children and pets.

110 Perrys Rd, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Tucked behind mature trees on a private 1.02-acre lot with a creek glimpse from the home, this 4,000+ sq ft coastal home sits inside Prospect Bay, Grasonville's premier golf communities — and it lives every bit as well as it looks. The kitchen is the showpiece. Built for the cook who loves to entertain, it's outfitted with high-end commercial-grade appliances, including a commercial range, anchored by a center island and a walk-in pantry — ready for everything from weeknight dinners to holidays with a full house. Rich hardwood floors run throughout, framed by 9'+ ceilings, crown molding, and recessed lighting that give every room a warm, finished feel. There's room to spread out and room to unwind. A spacious living room addition and a screened-in porch extend the everyday living space, while out back the deck, fenced in-ground saltwater pool, and dedicated pool house turn the private yard into a true retreat. The primary suite is its own escape, with an attached bathroom that features double sinks and luxury shower, walk-in closet, and private deck access. Three bedrooms, 3.5 baths, a formal dining room, a dedicated office, and a side-entry two-car garage complete the floor plan — all behind a classic hardiplank exterior built to last. Then there's the lifestyle. Prospect Bay is a resort-style community wrapped around an 18-hole golf course, with access to a community pool, tennis and pickleball courts, and a clubhouse with casual and fine dining. A private community waterfront adds a marina, boat ramp, pier, and kayak launch with available storage. You're roughly ten minutes from the Bay Bridge, 25 minutes from Annapolis, Easton, and St. Michael's, and about an hour from Baltimore and D.C. Homes of this size rarely come available here. If you've been waiting for the right home on the Shore — this is it.

$1,240,000

Tucked behind mature trees on a private 1.02-acre lot with a creek glimpse from the home, this 4,000+ sq ft coastal home sits inside Prospect Bay, Grasonville's premier golf communities — and it lives every bit as well as it looks. The kitchen is the showpiece. Built for the cook who loves to entertain, it's outfitted with high-end commercial-grade appliances, including a commercial range, anchored by a center island and a walk-in pantry — ready for everything from weeknight dinners to holidays with a full house. Rich hardwood floors run throughout, framed by 9'+ ceilings, crown molding, and recessed lighting that give every room a warm, finished feel. There's room to spread out and room to unwind. A spacious living room addition and a screened-in porch extend the everyday living space, while out back the deck, fenced in-ground saltwater pool, and dedicated pool house turn the private yard into a true retreat. The primary suite is its own escape, with an attached bathroom that features double sinks and luxury shower, walk-in closet, and private deck access. Three bedrooms, 3.5 baths, a formal dining room, a dedicated office, and a side-entry two-car garage complete the floor plan — all behind a classic hardiplank exterior built to last. Then there's the lifestyle. Prospect Bay is a resort-style community wrapped around an 18-hole golf course, with access to a community pool, tennis and pickleball courts, and a clubhouse with casual and fine dining. A private community waterfront adds a marina, boat ramp, pier, and kayak launch with available storage. You're roughly ten minutes from the Bay Bridge, 25 minutes from Annapolis, Easton, and St. Michael's, and about an hour from Baltimore and D.C. Homes of this size rarely come available here. If you've been waiting for the right home on the Shore — this is it.

43 Greenwood Shls, Grasonville

Listing courtesy of Real Broker, LLC - Chester. Contact:

Selling Office: Coldwell Banker Realty.

$1,200,000

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural charm to the main living area. Step outside to the screened patio, where you can relax and take in peaceful waterfront views, creating the perfect setting for morning coffee or evening gatherings. The kitchen is equipped with a full suite of appliances, and a washer and dryer are also included, allowing you to move in with ease and enjoy modern convenience from day one. The primary bath features a spacious walk-in shower, offering a comfortable and spa-inspired retreat to unwind at the end of the day. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

2 Beds ⋅ 3 Baths

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural charm to the main living area. Step outside to the screened patio, where you can relax and take in peaceful waterfront views, creating the perfect setting for morning coffee or evening gatherings. The kitchen is equipped with a full suite of appliances, and a washer and dryer are also included, allowing you to move in with ease and enjoy modern convenience from day one. The primary bath features a spacious walk-in shower, offering a comfortable and spa-inspired retreat to unwind at the end of the day. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

216 Kingfisher Ln, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living. Unlike many waterfront properties, the level lot provides easy access from the home to the water and private pier—no steep banks or long flights of stairs to navigate. Whether you enjoy boating, kayaking, fishing, crabbing, or simply relaxing by the water, this property makes it easy to embrace the Eastern Shore lifestyle. Inside, you'll find more than 2,200 square feet of comfortable living space designed to capture the stunning river views. A charming four-season room with brick flooring and panoramic water views is the perfect place to enjoy your morning coffee year-round, while the screened porch is ideal for summer crab feasts and outdoor entertaining. At the heart of the home, a wood-burning brick fireplace that creates a warm and inviting atmosphere. The flexible floor plan includes a main-level bedroom and full bath, ideal for guests or one-level living. Upstairs, the primary suite serves as a peaceful retreat, featuring breathtaking river views, abundant natural light, and a private ensuite bath with double vanities and a tiled shower. Two additional generously sized bedrooms and another full bath provide ample space for family and visitors. Recent improvements include a new roof in 2020 and an electric vehicle charger installed in the attached garage in 2025. An irrigation system serves both the front and rear yards, and the property is located outside the flood plain, so flood insurance is not required. Tucked away near the end of a private road, this serene setting feels calm and peaceful while remaining just minutes from Chestertown's shops, restaurants, marina, and popular farmers market. Enjoy daily visits from eagles, ospreys, herons, owls, deer, and other wildlife, all from your own backyard. Whether you're searching for a full-time waterfront residence or the perfect weekend escape, this rare Chester River property offers the beauty, tranquility, and lifestyle that makes Maryland's Eastern Shore so special.

$1,200,000

Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living. Unlike many waterfront properties, the level lot provides easy access from the home to the water and private pier—no steep banks or long flights of stairs to navigate. Whether you enjoy boating, kayaking, fishing, crabbing, or simply relaxing by the water, this property makes it easy to embrace the Eastern Shore lifestyle. Inside, you'll find more than 2,200 square feet of comfortable living space designed to capture the stunning river views. A charming four-season room with brick flooring and panoramic water views is the perfect place to enjoy your morning coffee year-round, while the screened porch is ideal for summer crab feasts and outdoor entertaining. At the heart of the home, a wood-burning brick fireplace that creates a warm and inviting atmosphere. The flexible floor plan includes a main-level bedroom and full bath, ideal for guests or one-level living. Upstairs, the primary suite serves as a peaceful retreat, featuring breathtaking river views, abundant natural light, and a private ensuite bath with double vanities and a tiled shower. Two additional generously sized bedrooms and another full bath provide ample space for family and visitors. Recent improvements include a new roof in 2020 and an electric vehicle charger installed in the attached garage in 2025. An irrigation system serves both the front and rear yards, and the property is located outside the flood plain, so flood insurance is not required. Tucked away near the end of a private road, this serene setting feels calm and peaceful while remaining just minutes from Chestertown's shops, restaurants, marina, and popular farmers market. Enjoy daily visits from eagles, ospreys, herons, owls, deer, and other wildlife, all from your own backyard. Whether you're searching for a full-time waterfront residence or the perfect weekend escape, this rare Chester River property offers the beauty, tranquility, and lifestyle that makes Maryland's Eastern Shore so special.

202 Royston Shores Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$1,200,000

Finally, one of the highly sought-after “Big Six” Waterfront Townhomes is available—complete with an attached garage and deeded boat slip (M1-PB-11) in the protected North Marina. This exceptional property truly represents the best of Waterfront Living. Fully renovated just four years ago with top-of-the-line finishes and beautiful coastal design throughout. Features include ¾" luxury vinyl plank flooring, a bright designer kitchen with commercial-grade Thermador stainless steel appliances. At the center of the space is a stunning custom “River Table” island that serves as an unforgettable showpiece.. Floor-to-ceiling glass captures breathtaking Eastern Bay views and fills the home with natural light. Each level offers its own deck - perfect for entertaining or simply enjoying spectacular Water Views and sunsets just steps from your door. The first level offers a versatile bonus room ideal for a recreation room or additional primary suite, complete with a beautifully designed bath and modern fireplace. The open-concept kitchen, dining, and family room feature another fireplace (gas burning) and sweeping WATER VIEWS. The spacious primary suite offers incredible waterfront views ,vaulted ceiling, and nothing less than a magazine-worthy bath. Two additional guest rooms and a beautifully appointed hall bath complete the upper level. Even the garage is decorated "Retro Flair" including a kitchenette , extra storage, and still room for your car! This is the perfect get away or better yet, live here year around! It's the perfect one of a kind coastal retreat! Residents enjoy a beautiful clubhouse with party room, fitness center, and saltwater pool, along with tennis/pickleball courts and a basketball court. A scenic 1.5-mile waterfront path connects to the Cross Island Trail, a 38-mile award-winning trail linking beaches, parks, marinas, shops, restaurants, coffee spots, and ice cream shops. Just 7 minutes to Queenstown Harbor Golf and Prime Outlets, 20 minutes to Annapolis and Easton, and under an hour to Washington, DC and Baltimore. It’s not just a home—it’s a lifestyle. 🌅🏡

3 Beds ⋅ 4 Baths

Finally, one of the highly sought-after “Big Six” Waterfront Townhomes is available—complete with an attached garage and deeded boat slip (M1-PB-11) in the protected North Marina. This exceptional property truly represents the best of Waterfront Living. Fully renovated just four years ago with top-of-the-line finishes and beautiful coastal design throughout. Features include ¾" luxury vinyl plank flooring, a bright designer kitchen with commercial-grade Thermador stainless steel appliances. At the center of the space is a stunning custom “River Table” island that serves as an unforgettable showpiece.. Floor-to-ceiling glass captures breathtaking Eastern Bay views and fills the home with natural light. Each level offers its own deck - perfect for entertaining or simply enjoying spectacular Water Views and sunsets just steps from your door. The first level offers a versatile bonus room ideal for a recreation room or additional primary suite, complete with a beautifully designed bath and modern fireplace. The open-concept kitchen, dining, and family room feature another fireplace (gas burning) and sweeping WATER VIEWS. The spacious primary suite offers incredible waterfront views ,vaulted ceiling, and nothing less than a magazine-worthy bath. Two additional guest rooms and a beautifully appointed hall bath complete the upper level. Even the garage is decorated "Retro Flair" including a kitchenette , extra storage, and still room for your car! This is the perfect get away or better yet, live here year around! It's the perfect one of a kind coastal retreat! Residents enjoy a beautiful clubhouse with party room, fitness center, and saltwater pool, along with tennis/pickleball courts and a basketball court. A scenic 1.5-mile waterfront path connects to the Cross Island Trail, a 38-mile award-winning trail linking beaches, parks, marinas, shops, restaurants, coffee spots, and ice cream shops. Just 7 minutes to Queenstown Harbor Golf and Prime Outlets, 20 minutes to Annapolis and Easton, and under an hour to Washington, DC and Baltimore. It’s not just a home—it’s a lifestyle. 🌅🏡

1009 Oyster Cove Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

Selling Office: Compass.

$1,198,526

Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red oak Properties, LLC, one of the Eastern Shore Premier builders. One lot remains with this builder. Call for additional details.

Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red oak Properties, LLC, one of the Eastern Shore Premier builders. One lot remains with this builder. Call for additional details.

Lot 4 Finley Creek, Centreville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Douglas Realty LLC.

$1,160,000

Luxury Waterfront Living in a Gated Community Enjoy the best of waterfront living in this beautiful gated community, perfectly situated between the Chester River and Safe Harbor Marina. This stunning home offers breathtaking water views and an open, airy floor plan designed for both relaxing and entertaining. Inside, you'll find rich hardwood floors and spacious bedrooms, each featuring its own private bath and walk-in closet, offering comfort and privacy for everyone. The upgraded kitchen boasts high-end appliances, including a wine fridge, making it perfect for hosting. Step outside to the two rear decks, both equipped with remote-controlled screens, allowing you to enjoy the incredible views in comfort any time of day. Neighborhood has a living shore line and 3 piers. Additional highlights include: • Cozy fireplace for chilly evenings • Jetted soaking tub for spa-like relaxation • Condo association will be putting a fresh coat of paint on the exterior in May • New roof • 2 car garage • Tankless water heater * New washer and dryer • Located just 20 minutes from Annapolis This exceptional home combines luxury, comfort, and unbeatable waterfront scenery—truly a must-see! And so much more!

3 Beds ⋅ 4 Baths

Luxury Waterfront Living in a Gated Community Enjoy the best of waterfront living in this beautiful gated community, perfectly situated between the Chester River and Safe Harbor Marina. This stunning home offers breathtaking water views and an open, airy floor plan designed for both relaxing and entertaining. Inside, you'll find rich hardwood floors and spacious bedrooms, each featuring its own private bath and walk-in closet, offering comfort and privacy for everyone. The upgraded kitchen boasts high-end appliances, including a wine fridge, making it perfect for hosting. Step outside to the two rear decks, both equipped with remote-controlled screens, allowing you to enjoy the incredible views in comfort any time of day. Neighborhood has a living shore line and 3 piers. Additional highlights include: • Cozy fireplace for chilly evenings • Jetted soaking tub for spa-like relaxation • Condo association will be putting a fresh coat of paint on the exterior in May • New roof • 2 car garage • Tankless water heater * New washer and dryer • Located just 20 minutes from Annapolis This exceptional home combines luxury, comfort, and unbeatable waterfront scenery—truly a must-see! And so much more!

430 Narrows Pointe Dr, Grasonville

Listing courtesy of RE/MAX United Real Estate. Contact:

Selling Office: RE/MAX Leading Edge.

$1,150,000

Sellers have identified their home of choice. A rare opportunity to own one of the largest and most beautiful homes in Gibson's Grant! Welcome to this exceptional coastal retreat in the sought-after community of Gibson’s Grant on Kent Island, offering expansive views of the community pond and Macum Creek. Blending timeless architectural details with modern updates, this beautifully appointed home delivers luxury waterfront living in one of Kent Island’s most desirable neighborhoods. At the heart of the home, the open-concept living and kitchen spaces are thoughtfully designed for both everyday living and entertaining. The light-filled gourmet kitchen features an oversized center island with ample seating, custom built-in banquette dining with additional storage, stainless steel appliances, and seamless flow into the spacious family room. A striking coffered ceiling and extensive custom built-in cabinetry add warmth, character, and functionality to the main living area. The main-level primary suite offers newly installed engineered hardwood flooring, elegant French doors, and sweeping views of the water and expansive backyard. Throughout the home, fresh interior paint, plantation shutters, and custom window treatments create a clean and refined aesthetic. The second level features generously sized bedrooms along with a large bonus living area perfect for recreation, media space, or additional lounge seating. Step outside onto the covered upper-level porch to enjoy peaceful elevated water views. Above the garage, a private apartment with full bath provides exceptional flexibility as a fifth bedroom, guest suite, or home office and is equipped with two new high-efficiency mini-split systems for personalized comfort. Outdoor living is equally impressive with a spacious rear deck overlooking the fully fenced backyard, professionally manicured landscaping, and protected natural surroundings. A wide driveway offers ample parking, a rare feature within Gibson’s Grant. Ideally situated on a quiet street just steps from the scenic Cross Island Trail, residents enjoy access to resort style community amenities including a pool, fitness center, fishing pier, playground, bocce ball court, kayak launch and storage, clubhouse with fitness center and meeting room, nature trails, and waterfront pavilion and grills. Experience the best of Eastern Shore living in this thoughtfully designed coastal home surrounded by the natural beauty of the Chesapeake Bay. Just a short drive to Route 50, providing easy access to local dining, shopping, and commuter routes to Annapolis, Baltimore, and Washington DC. Schedule your tour today!

Sellers have identified their home of choice. A rare opportunity to own one of the largest and most beautiful homes in Gibson's Grant! Welcome to this exceptional coastal retreat in the sought-after community of Gibson’s Grant on Kent Island, offering expansive views of the community pond and Macum Creek. Blending timeless architectural details with modern updates, this beautifully appointed home delivers luxury waterfront living in one of Kent Island’s most desirable neighborhoods. At the heart of the home, the open-concept living and kitchen spaces are thoughtfully designed for both everyday living and entertaining. The light-filled gourmet kitchen features an oversized center island with ample seating, custom built-in banquette dining with additional storage, stainless steel appliances, and seamless flow into the spacious family room. A striking coffered ceiling and extensive custom built-in cabinetry add warmth, character, and functionality to the main living area. The main-level primary suite offers newly installed engineered hardwood flooring, elegant French doors, and sweeping views of the water and expansive backyard. Throughout the home, fresh interior paint, plantation shutters, and custom window treatments create a clean and refined aesthetic. The second level features generously sized bedrooms along with a large bonus living area perfect for recreation, media space, or additional lounge seating. Step outside onto the covered upper-level porch to enjoy peaceful elevated water views. Above the garage, a private apartment with full bath provides exceptional flexibility as a fifth bedroom, guest suite, or home office and is equipped with two new high-efficiency mini-split systems for personalized comfort. Outdoor living is equally impressive with a spacious rear deck overlooking the fully fenced backyard, professionally manicured landscaping, and protected natural surroundings. A wide driveway offers ample parking, a rare feature within Gibson’s Grant. Ideally situated on a quiet street just steps from the scenic Cross Island Trail, residents enjoy access to resort style community amenities including a pool, fitness center, fishing pier, playground, bocce ball court, kayak launch and storage, clubhouse with fitness center and meeting room, nature trails, and waterfront pavilion and grills. Experience the best of Eastern Shore living in this thoughtfully designed coastal home surrounded by the natural beauty of the Chesapeake Bay. Just a short drive to Route 50, providing easy access to local dining, shopping, and commuter routes to Annapolis, Baltimore, and Washington DC. Schedule your tour today!

108 Carriage Heath, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: RE/MAX Leading Edge.

$1,150,000

Stevensville - Location! Location! Location! Professional Office Building completely redone in 2017. Everything was replaced including wall studs, complete renovation of entire building inside. All new plumbing fixtures (toilets, sinks, faucets etc.) All new electrical wiring for electric and internet (CAT 6 lines) All new subflooring on 2nd floor (under wood floor) 3 out of 4 AC units have been replaced with new AC units; 1 unit in 2022; 2 units in 2017) All new paint, blinds, doors, flooring, countertops, trim, cabinetry, etc. New water tank in tenant side (2024) and law side (2016) Currently used as three separate suites, with private bathrooms, kitchenettes, conference rooms. Many possible opinions for the use of the large space. Elevator makes it easy for your client's access to the second floor. Extra store in attic area as well.

102 Saint Claire Pl, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan is filled with natural light and highlighted by gleaming hardwood floors and exceptional upgrades throughout this 4 bedroom, 3 full bath estate. The stunning designer kitchen is truly the heart of the home, featuring crisp white cabinetry, granite countertops, an oversized center island, a premium Wolf 5-burner gas cooktop flanked by custom spice cabinets, a wall convection oven, and built-in microwave...crafted for both everyday living and effortless entertaining. Just beyond the main living areas, the inviting three-season sun porch with white tile flooring overlooks your own private backyard retreat. Step outside onto the expansive maintenance-free decking and new patio surrounding the spectacular heated gunite pool, complete with a waterfall feature and dual stair entrances, creating the ultimate outdoor oasis. The professionally designed landscaping continues throughout the property, accented with colorful plantings, mature greenery, and thoughtfully designed outdoor spaces. A custom-built shed, designed to perfectly complement the home, offers electric service and a gated outdoor storage area. Additional premium features include an oversized two-car garage with air conditioning, two-zone gas heat and central air, a whole-house generator, tankless water heater, updated crawlspace with dehumidifier, and energy-saving foil-wrapped attic insulation. The roof is only two years young, offering peace of mind for years to come. Perfectly positioned to capture serene open-space and water views, this exceptional property also includes access to South Wind’s sought-after amenities, including a community beach, boat ramp, pier, tennis courts, dry dock, and more. This is more than a home...it’s a private Kent Island retreat designed for exceptional living.

$1,125,000

Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan is filled with natural light and highlighted by gleaming hardwood floors and exceptional upgrades throughout this 4 bedroom, 3 full bath estate. The stunning designer kitchen is truly the heart of the home, featuring crisp white cabinetry, granite countertops, an oversized center island, a premium Wolf 5-burner gas cooktop flanked by custom spice cabinets, a wall convection oven, and built-in microwave...crafted for both everyday living and effortless entertaining. Just beyond the main living areas, the inviting three-season sun porch with white tile flooring overlooks your own private backyard retreat. Step outside onto the expansive maintenance-free decking and new patio surrounding the spectacular heated gunite pool, complete with a waterfall feature and dual stair entrances, creating the ultimate outdoor oasis. The professionally designed landscaping continues throughout the property, accented with colorful plantings, mature greenery, and thoughtfully designed outdoor spaces. A custom-built shed, designed to perfectly complement the home, offers electric service and a gated outdoor storage area. Additional premium features include an oversized two-car garage with air conditioning, two-zone gas heat and central air, a whole-house generator, tankless water heater, updated crawlspace with dehumidifier, and energy-saving foil-wrapped attic insulation. The roof is only two years young, offering peace of mind for years to come. Perfectly positioned to capture serene open-space and water views, this exceptional property also includes access to South Wind’s sought-after amenities, including a community beach, boat ramp, pier, tennis courts, dry dock, and more. This is more than a home...it’s a private Kent Island retreat designed for exceptional living.

2812 Harvest Ct, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,110,000

MAJOR PRICE IMPROVEMENT! Just in time to enjoy your Prospect Bay waterfront home this summer! Welcome home to this waterfront property in the Eastern Shore’s premier golf course community of Prospect Bay. Set on just over an acre overlooking Little Greenwood Creek, this home offers peaceful views, spacious living areas, and direct water access. From the moment you enter, the welcoming foyer with coat closet opens to a bright living room with large windows plus a stone fireplace, and a dining area that overlooks the backyard and water, creating a light-filled space ideal for everyday living and entertaining. The remodeled eat-in kitchen features abundant natural light, granite countertops, and direct access to the deck, where you can enjoy relaxing water views or dine outdoors. The home’s thoughtful layout continues on the lower level with an additional living area, half bathroom, laundry room, and convenient access to the spacious three-car garage. Sliding doors off the lower living area lead directly to the backyard and patio, seamlessly connecting indoor and outdoor living. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with beautiful water views, a walk-in closet, double vanity, and an electric fireplace that adds a cozy touch to the space. Situated on a large lot, the backyard provides plenty of room for outdoor entertaining and offers the potential for a pool overlooking the water. The recently redone pier allows for easy access to Little Greenwood Creek and the Chesapeake Bay, making this an excellent opportunity for those who enjoy waterfront living and boat rides to the Narrows, Saint Michaels, Annapolis, and beyond. Prospect Bay community offers an array of amenities, including an 18-hole golf course, a clubhouse with a members-only restaurant and bar, a marina with a launch, a pool, tennis and pickleball courts, a playground, and year-round social activities. Here, every day feels like a vacation.

MAJOR PRICE IMPROVEMENT! Just in time to enjoy your Prospect Bay waterfront home this summer! Welcome home to this waterfront property in the Eastern Shore’s premier golf course community of Prospect Bay. Set on just over an acre overlooking Little Greenwood Creek, this home offers peaceful views, spacious living areas, and direct water access. From the moment you enter, the welcoming foyer with coat closet opens to a bright living room with large windows plus a stone fireplace, and a dining area that overlooks the backyard and water, creating a light-filled space ideal for everyday living and entertaining. The remodeled eat-in kitchen features abundant natural light, granite countertops, and direct access to the deck, where you can enjoy relaxing water views or dine outdoors. The home’s thoughtful layout continues on the lower level with an additional living area, half bathroom, laundry room, and convenient access to the spacious three-car garage. Sliding doors off the lower living area lead directly to the backyard and patio, seamlessly connecting indoor and outdoor living. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with beautiful water views, a walk-in closet, double vanity, and an electric fireplace that adds a cozy touch to the space. Situated on a large lot, the backyard provides plenty of room for outdoor entertaining and offers the potential for a pool overlooking the water. The recently redone pier allows for easy access to Little Greenwood Creek and the Chesapeake Bay, making this an excellent opportunity for those who enjoy waterfront living and boat rides to the Narrows, Saint Michaels, Annapolis, and beyond. Prospect Bay community offers an array of amenities, including an 18-hole golf course, a clubhouse with a members-only restaurant and bar, a marina with a launch, a pool, tennis and pickleball courts, a playground, and year-round social activities. Here, every day feels like a vacation.

40 Greenwood Shls, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,054,000

A Peaceful Waterfront Retreat Set along the quiet shores of Northwest Creek, this beautifully maintained single-story brick home offers sweeping 180-degree water views and a sense of calm from the moment you arrive. The back deck offers an escape to bird watch for eagles, osprey, blue heron, egrets and more during the day and stargaze at night. A gently winding walkway leads through lush, thoughtfully landscaped gardens filled with colorful blooms throughout the year. A Warm Welcome Step inside the foyer and the view immediately takes center stage. Straight ahead, past the living room is the sunlit three-season room. The sparkling water creates a stunning backdrop that draws you through the home. Living Areas & Kitchen The formal dining room and spacious living area feature warm wood floors, large windows, and plenty of natural light, all designed to showcase the peaceful waterfront setting. The kitchen is both functional and inviting, with upgraded appliances, Corian countertops, under-cabinet lighting, a tile backsplash, and generous cabinet space. Whether preparing meals or enjoying your morning coffee, the uninterrupted creek views make this space especially enjoyable. Private Bedroom Layout The split-bedroom floor plan provides privacy and comfort for both owners and guests. The primary suite is tucked away on the left side of the home and offers beautiful water views through oversized windows, along with rich wood flooring and a relaxing atmosphere. The spacious en-suite bath includes dual vanities, two walk-in closets, a walk-in shower, and a soaking tub. On the opposite side of the home, a separate hallway leads to two spacious guest bedrooms filled with natural light, a full guest bathroom with a shower, a convenient half bath and laundry room, and direct access to the oversized two-car garage. Additional Living Space Just beyond the kitchen, the home opens into a cozy den and library area. Built-in bookcases and a gas fireplace create the perfect setting for relaxing evenings, reading, or gathering with family and friends. The Three-Season Room French doors off the kitchen, Living room, or primary bed room lead into a large three-season room stretching across the back of the home. This room has both heat and a/c provided by a mini split. Surrounded by natural light and panoramic water views, this versatile space is ideal for morning coffee, casual dining, yoga, entertaining, or simply enjoying the peaceful scenery year-round. The roof was replaced in 2024 with 50 Year architectural shingles, and a transferrable warranty. Blending indoor comfort with the beauty of the outdoors, this waterfront home offers a quiet retreat designed for everyday living and relaxing. This home is close to many recreational amenities including parks, with bike trails, pickleball courts, fishing piers and a public golf course.

A Peaceful Waterfront Retreat Set along the quiet shores of Northwest Creek, this beautifully maintained single-story brick home offers sweeping 180-degree water views and a sense of calm from the moment you arrive. The back deck offers an escape to bird watch for eagles, osprey, blue heron, egrets and more during the day and stargaze at night. A gently winding walkway leads through lush, thoughtfully landscaped gardens filled with colorful blooms throughout the year. A Warm Welcome Step inside the foyer and the view immediately takes center stage. Straight ahead, past the living room is the sunlit three-season room. The sparkling water creates a stunning backdrop that draws you through the home. Living Areas & Kitchen The formal dining room and spacious living area feature warm wood floors, large windows, and plenty of natural light, all designed to showcase the peaceful waterfront setting. The kitchen is both functional and inviting, with upgraded appliances, Corian countertops, under-cabinet lighting, a tile backsplash, and generous cabinet space. Whether preparing meals or enjoying your morning coffee, the uninterrupted creek views make this space especially enjoyable. Private Bedroom Layout The split-bedroom floor plan provides privacy and comfort for both owners and guests. The primary suite is tucked away on the left side of the home and offers beautiful water views through oversized windows, along with rich wood flooring and a relaxing atmosphere. The spacious en-suite bath includes dual vanities, two walk-in closets, a walk-in shower, and a soaking tub. On the opposite side of the home, a separate hallway leads to two spacious guest bedrooms filled with natural light, a full guest bathroom with a shower, a convenient half bath and laundry room, and direct access to the oversized two-car garage. Additional Living Space Just beyond the kitchen, the home opens into a cozy den and library area. Built-in bookcases and a gas fireplace create the perfect setting for relaxing evenings, reading, or gathering with family and friends. The Three-Season Room French doors off the kitchen, Living room, or primary bed room lead into a large three-season room stretching across the back of the home. This room has both heat and a/c provided by a mini split. Surrounded by natural light and panoramic water views, this versatile space is ideal for morning coffee, casual dining, yoga, entertaining, or simply enjoying the peaceful scenery year-round. The roof was replaced in 2024 with 50 Year architectural shingles, and a transferrable warranty. Blending indoor comfort with the beauty of the outdoors, this waterfront home offers a quiet retreat designed for everyday living and relaxing. This home is close to many recreational amenities including parks, with bike trails, pickleball courts, fishing piers and a public golf course.

110 Carville Ct, Stevensville

Listing courtesy of Compass. Contact:

Selling Office: Berkshire Hathaway HomeServices Homesale Realty.

$999,000

Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautifully renovated 3-bedroom, 2.5 bath home offers an open-concept layout design to capture breathing taking water views that stretch endless across the horizon. Each evening brings magnificent, direct sunset views-- the kind that make you stop, breathe, and take it all in. New pier in 2020! Step inside to luxury plank flooring that flows throughout the home, complementing a bright, modern kitchen outfitted with brilliant white quartz countertops, all new stainless steel appliances, abundant white cabinetry, and generous workspace ideal for cooking and entertaining. The refined design continues into each bathroom, where matching quartz countertops and coordinated cabinetry create a polished, cohesive aesthetic. With its expansive lot, serene waterfront setting, and elegant interior updates, this is a rare opportunity to own a home that blends comfort, beauty, and unforgettable views.

Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautifully renovated 3-bedroom, 2.5 bath home offers an open-concept layout design to capture breathing taking water views that stretch endless across the horizon. Each evening brings magnificent, direct sunset views-- the kind that make you stop, breathe, and take it all in. New pier in 2020! Step inside to luxury plank flooring that flows throughout the home, complementing a bright, modern kitchen outfitted with brilliant white quartz countertops, all new stainless steel appliances, abundant white cabinetry, and generous workspace ideal for cooking and entertaining. The refined design continues into each bathroom, where matching quartz countertops and coordinated cabinetry create a polished, cohesive aesthetic. With its expansive lot, serene waterfront setting, and elegant interior updates, this is a rare opportunity to own a home that blends comfort, beauty, and unforgettable views.

1704 Bayside Dr, Chester

Listing courtesy of Cottage Street Realty LLC. Contact:

Selling Office: RE/MAX Leading Edge.

$985,000

Stevensville - The Ye Olde Church house is listed for sale. This unique property is being sold with 2 additional lots. A total of 1.74 acres of prime location in downtown Stevensville. The property has been previously used as an antique store but has many other uses under the zoning of SHVC. This is opportunity knocking for your new business. The property is located in the enterprise zone, that will offer business discounts or credits when bringing your business to Stevensville. The property has just been surveyed and stacked with corner markers. Additional tax #1804057503 and 1804112385 convey with sale.

426 Love Point Rd, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

This charming Colonial home in the desirable Bay City community offers a perfect blend of comfort and convenience. With 1,716 sq. ft. of well-designed space, the open floor plan features a cozy living area with a propane fireplace, a bright breakfast area, and a kitchen island ideal for gatherings. Enjoy the luxury of a primary bath with a jetted tub and stand alone shower. Step outside to a beautifully landscaped 0.44-acre lot, complete with a hardscaped patio for outdoor relaxation. The property boasts 80 feet of waterfront along Broad Creek, perfect for kayaking or enjoying serene water views. Bay City offers fantastic amenities, including a beach, playgrounds, and common grounds, fostering a vibrant community spirit. Nearby parks and excellent schools enhance the neighborhood's appeal, while convenient access to commuter lots and the airport ensures easy travel. Experience the warmth of home in this inviting setting! Whether you are looking for a weekend home or looking for the island life 365 days a year, 604 Broadcreek is exactly what you have been waiting for! Pier Permit in process with county.

$980,000

This charming Colonial home in the desirable Bay City community offers a perfect blend of comfort and convenience. With 1,716 sq. ft. of well-designed space, the open floor plan features a cozy living area with a propane fireplace, a bright breakfast area, and a kitchen island ideal for gatherings. Enjoy the luxury of a primary bath with a jetted tub and stand alone shower. Step outside to a beautifully landscaped 0.44-acre lot, complete with a hardscaped patio for outdoor relaxation. The property boasts 80 feet of waterfront along Broad Creek, perfect for kayaking or enjoying serene water views. Bay City offers fantastic amenities, including a beach, playgrounds, and common grounds, fostering a vibrant community spirit. Nearby parks and excellent schools enhance the neighborhood's appeal, while convenient access to commuter lots and the airport ensures easy travel. Experience the warmth of home in this inviting setting! Whether you are looking for a weekend home or looking for the island life 365 days a year, 604 Broadcreek is exactly what you have been waiting for! Pier Permit in process with county.

604 Broadcreek Dr, Stevensville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: Real Estate Depot.

$979,990

The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry bar for entertaining, a cozy electric fireplace, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and a polished finish. The kitchen is well equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath serves as a relaxing retreat with a shower featuring a built-in seat, handheld shower wand, double sinks, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

2 Beds ⋅ 3 Baths

The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry bar for entertaining, a cozy electric fireplace, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and a polished finish. The kitchen is well equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath serves as a relaxing retreat with a shower featuring a built-in seat, handheld shower wand, double sinks, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2443, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$965,000

Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in the community's newer sections, this exceptional home combines thoughtful design with upscale finishes throughout. A spacious foyer welcomes you into an open and inviting layout that is perfect for both everyday living and entertaining. At the heart of the home is a stunning gourmet kitchen featuring an oversized center island that naturally becomes the gathering place for family and friends. Whether hosting indoors or enjoying the outdoors, you'll appreciate the seamless flow to the screened porch and beautifully designed patio complete with a built-in fire pit. The private primary suite is a true retreat, highlighted by an elegant tray ceiling, an impressive custom walk-in closet system, and a luxurious en-suite bath featuring a spacious walk-in shower, dual vanities, and a dedicated built-in makeup vanity. The main level also offers a second bedroom, full bath, private home office, and convenient laundry room, providing the ease of one-level living. Upstairs, guests will enjoy their own private space with an additional living area, bedroom, and full bath and access to the conditioned sky garage which is great for storage. Attached two car garage with epoxy flooring and inside access. Beyond the home, enjoy the award-winning lifestyle Four Seasons at Kent Island is known for. Residents have access to an impressive 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, dog parks, walking trails, and an active calendar of social events—all designed for exceptional 55+ living.