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105 State St, Stevensville
$479,500
4 Beds ⋅ 2 Baths
With its charming white picket fence, inviting curb appeal, and timeless character, this delightful 4-bedroom, 2-full-bath Cape Cod feels like something straight out of a storybook! Nestled right in town, this home offers the perfect blend of small-town charm and everyday convenience. Enjoy being just a short stroll from local schools, the library, Love Point Park, the dog park, restaurants, coffee shops, the Kent Island Heritage Society, the Kent Island Federation of Arts, and so much more! Imagine morning coffee at your favorite local spot, afternoon walks through town, and enjoying everything this vibrant community has to offer right outside your door. Inside, you'll find a comfortable and versatile floor plan with two bedrooms and a beautifully appointed full bathroom on the main level, featuring a double vanity and walk-in tiled shower. Upstairs, two generously sized bedrooms and another full bathroom provide plenty of space for family, guests, or a home office. Dual-zone HVAC, replaced within the last five years, adds comfort and efficiency. One of the home's most inviting features is the charming sunporch, complete with brick flooring and a propane stove, creating a cozy retreat to enjoy throughout the seasons. Whether you're sipping your morning coffee, curling up with a good book, or watching the seasons change, this space is sure to become a favorite. Outside, the fully enclosed yard, framed by that quintessential white picket fence, completes the fairy-tale setting. A detached two-car garage offers exceptional functionality, including walk-up stairs to additional storage space, while the paved driveway provides plenty of off-street parking. And the practical perks are just as appealing: public water, public sewer, and NO HOA! Full of character, charm, and convenience, 105 State Street is a rare opportunity to enjoy the lifestyle of historic Stevensville with the space and amenities you've been looking for. Offered at $479,500. Come experience the magic of this storybook home for yourself!

105 State St, Stevensville

Listing courtesy of Samson Properties. Contact:

116 Chesapeake Estates Dr, Stevensville
$384,900
3 Beds ⋅ 1 Baths
Experience Chesapeake Bay living for under $385,000! Ideally located just up the road from the community beach, picnic area, and playground on the Chesapeake Bay, this beautifully updated rancher offers the perfect blend of comfort, value, and location. Thoughtfully updated, this home features new flooring (2026), a new heat pump (2025), a new roof (2024), and newer siding and windows (except bay window), offering added peace of mind for years to come. The spacious 22' x 24' detached garage provides plenty of room for parking, a workshop, hobbies, or additional storage. Outdoor enthusiasts will love being just minutes from the South Island Trail, a scenic 7-mile paved trail stretching from Romancoke Fishing Pier to Matapeake State Park—perfect for walking, running, and biking. Enjoy convenient access to a nearby public boat ramp, waterfront dining, shopping, medical facilities, and everyday amenities. Don't miss this opportunity to own a home in this sought-after Chesapeake Bay waterfront community at an exceptional price! Come discover the lifestyle and make this charming rancher your own. Square Footage based on Public Tax Record, Buyer to verify

116 Chesapeake Estates Dr, Stevensville

Listing courtesy of Rosendale Realty. Contact:

101 Orchestra Pl, Centreville
$589,000
3 Beds ⋅ 3 Baths
Photos coming soon... Welcome to 101 Orchestra Place in Symphony Village at Centreville 55+ Active Adult Community. This beautiful, move in ready Wagner model home is impressive from the moment that you arrive at the home. The stone front on this home is just the beginning of the upgrades on the home. The Wagner is a unique model in the community and you'll be amazed at the open but cozy feeling of the layout. Upgrades in this home include hardwood plank flooring, crown moldings, plantation shutters, granite counters, stainless appliances, gas cooktop, under cabinet lighting, stainless hood, subway tile backsplash, floor to ceiling stone fireplace and much more. As you enter the home, you'll find the front office/bedroom along with a full bath to your right. Just past this area, is the gourmet kitchen with large island and the largest pantry of any model in the community. The oversized laundry room leading to the garage, also features the interior carpeted stairs leading to the fully finished heated and cooled sky basement. The dining and living area off the kitchen leads to the rear screened area and large outdoor paver patio. The master suite with extension and master bath complete the main level of the home. The second level features a oversized sitting area, bedroom and 3rd full bath. Updates on the home include one new HVAC system and a new roof.

101 Orchestra Pl, Centreville

Listing courtesy of RE/MAX Executive. Contact:

215 Alynn Way, Queenstown
$2,795,000
4 Beds ⋅ 6 Baths
Experience exceptional waterfront living on the Wye River in the prestigious Belle Point Farm community. Situated on 2.44 beautifully landscaped acres with approximately 240 feet of waterfrontage, this stunning European-inspired property offers over 6,300 square feet of elegant living space, a private deep-water pier, swimming pool, and a separate 1,300-square-foot carriage house. Designed for both grand entertaining and everyday comfort, the main residence features four spacious bedrooms, four full and two half bathrooms, and an inviting open floor plan with sweeping water views. The gourmet kitchen boasts a generous center island, gas range, double ovens, and ample space for gathering, flowing seamlessly into the family room with a propane fireplace. Refined architectural details, including crown molding and recessed lighting, complement the home’s timeless design. The waterfront primary suite offers a private retreat with a spacious bath and walk-in closet. Outdoor living is equally impressive, with an expansive wraparound deck, multiple balconies, a patio, and a private pool overlooking the picturesque grounds. Boating enthusiasts will appreciate the deep-water pier and direct access to the Wye River, offering endless opportunities to explore the Chesapeake Bay and its surrounding waterways. The separate carriage house provides a second floor apartment/artist studio with an elevator providing exceptional flexibility for guests, recreation, or additional living space with full bath . An attached garage, circular driveway, and backup propane generator add convenience and peace of mind. Offering privacy, expansive waterfront views, and an extraordinary collection of amenities, 215 Alynn Way presents a rare opportunity to enjoy the very best of Maryland’s Eastern Shore waterfront lifestyle.

215 Alynn Way, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

412 Chesapeake Ave, Stevensville
$475,000
4 Beds ⋅ 2 Baths
Kentmorr - This home is what you have been looking for! The house offers new roof, windows, doors in 2026. Many other upgrades like new appliances, washer and dryer and AC are 4-year-old. Laundry located on lower and upper levels close to bedrooms. The fenced in backyard offers privacy. The property is located on .45 acre. Kentmorr community offers private beach on the Chesapeake Bay.

412 Chesapeake Ave, Stevensville

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

200 Quail Run Dr, Centreville
$549,000
3 Beds ⋅ 2 Baths
Welcome home to this beautiful Cape Cod located in Corsica Landing Estates, along the Corsica River. This home features three ample sized bedrooms, two full baths, a separate kitchen, dining and living area. While it has plenty of space inside and out, the potential for more living area is yet to be discovered. This home has a fully framed unfinished second floor. While the current septic system is in perfect working order, QAC and a septic company have determined that with an upgrade to a BAT system and extension of the drain fields, you can have an additional one to two bedrooms and another bath. This home just needs you and your design plans! If that isn't enough the home is located just a stone's throw away from the Centreville Wharf where you can launch your boat, fish from the dock or just relax in the park area or let the children roam and enjoy the playground. There are so many other great amenities nearby from restaurants and shops to grocery stores, the YMCA and so much more.

200 Quail Run Dr, Centreville

Listing courtesy of Rosendale Realty. Contact:

108 Griffin Ct, Centreville
$300,000
4 Beds ⋅ 2 Baths
Welcome to 108 Griffin Ct. First time ever on market, same owner since built in 1986. 2.5 acre wooded lot at the end of a cul-de-sac. Home is being sold as is and needs some TLC. If you are looking to buy a home and fix it up or an investor looking for a great priced home in QAC. New primary bath in 2025, well is 5 yrs old, and roof is 15 yrs old. This home has the largest lot in the development. Built in cabinets in dining room, brick fire place in living room, split beds and baths, primary and 4th/office on the right and 2 beds and bath on the left, open living and dining room. Centreville school district.

108 Griffin Ct, Centreville

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

9 Ackerman Ct, Stevensville
$444,000
3 Beds ⋅ 3 Baths
Welcome to 9 Ackerman Court, a charming Cape Cod nestled among mature trees in the sought-after Cloverfields community on Kent Island! Offering the perfect blend of comfort, character, and coastal living, this inviting home features three bedrooms, a versatile bonus room, and the convenience of a main-level primary suite. Step inside to discover a bright and airy living room featuring soaring vaulted ceilings, abundant natural light, and a beautiful brick fireplace that creates a warm and welcoming focal point. The spacious kitchen offers white cabinetry, generous countertop space, and an adjoining dining area with sliding glass doors leading to the expansive rear deck—perfect for everyday living and effortless entertaining. The main-level primary suite offers a comfortable retreat complete with a walk-in closet and private bathroom. Two additional bedrooms and a flexible bonus room provide plenty of options for a home office, playroom, guest space, or whatever best suits your needs. Neutral finishes and attractive flooring throughout create a fresh, inviting atmosphere ready for your personal touch. Outside, enjoy your own private backyard retreat. The expansive deck is ideal for outdoor dining, summer gatherings, or simply relaxing beneath the shade of mature trees. The fully fenced yard offers plenty of room for pets, play, and outdoor activities, while established landscaping and a storage shed add to the property's charm and functionality. Life in Cloverfields is all about embracing the Eastern Shore lifestyle. Residents enjoy access to an impressive collection of community amenities, including a beach along the Chester River, outdoor swimming pool, marina, boat ramp, clubhouse, and playground. Whether you're spending summer days on the water or enjoying the neighborhood amenities, there's something for everyone to love. Conveniently located in Stevensville, just minutes from local shopping, dining, parks, and the Chesapeake Bay Bridge, this home offers easy access to Annapolis and beyond. Discover the charm, convenience, and waterfront lifestyle that make 9 Ackerman Court such a wonderful place to call home. Some photos have been staged and enhanced by AI.

9 Ackerman Ct, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

101 Placeks Ln Ln, Stevensville
$659,900
3 Beds ⋅ 2 Baths
The Greystone offers an open floor plan with a modern split bedroom design. Bight and open, with kitchen, breakfast adjoining the family room. Standards included are LVP flooring, tile baths and granite/quartz countertops in kitchen. Plus, a FULL Basement for your future needs. Placek Place offers The Eastern Shore Way of Life. Close by beach, walking trail, pickle ball, marinas plus shopping and resturants. All located in a private enclave with sidewalks, street lights, public water, sewer and full basements. Arare combination on The Island just 1 minute from the bridge. Placek Place is close to walking trails, pickle ball courts,beaches, Blue Heron Golf Course, shopping and causal and formal dining. Enjoy The Eastern Sore Life in your New Home.

101 Placeks Ln Ln, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

2703 Sherman Dr, Chester
$699,000
3 Beds ⋅ 3 Baths
Nestled in the serene Harbor View subdivision, this Colonial-style home offers a perfect blend of luxury and comfort. The interior features elegant bamboo and ceramic tile flooring, enhancing the warm ambiance throughout. The gourmet kitchen is equipped with stainless steel appliances, including a dishwasher, electric oven/range, and refrigerator, making culinary adventures a delight. A charming wood-burning stove adds a touch of warmth to the living space, creating an inviting atmosphere for relaxation. Set on a generous 1.14-acre lot in a peaceful cul-de-sac, the landscaped grounds provide a tranquil retreat. Enjoy stunning water views of Cox Creek, just a short stroll away, where you can indulge in boating and fishing activities. The property includes a private dock with multiple slips, perfect for water enthusiasts. Additional features include an attached garage, off-street parking, and a spacious deck that invites outdoor living. This home is not just a residence; it's a lifestyle, offering the perfect balance of luxury, nature, and community. Experience the exclusive charm of waterfront living in this property.

2703 Sherman Dr, Chester

Listing courtesy of Rosendale Realty. Contact:

102 Queens Colony High Rd, Stevensville
$659,000
5 Beds ⋅ 4 Baths
A flexible layout, select upgrades, and generous outdoor space make this home stand out! The main home offers three bedroom, including a first-floor bedroom currently used as an office, plus two spacious upstairs bedrooms, each with its own private full bathroom, plus a convenient half bath. The converted garage provides an additional suite with two bedrooms, one full bathroom, a kitchenette, and a private entrance. Outside, the large fenced yard offers plenty of room for entertaining, gardening, or simply relaxing. A new Trex deck creates an inviting spot for outdoor dining and gathering, while an outdoor shower with hot water adds extra convenience. With versatile living spaces and appealing outdoor features, this property offers room to make it your own

102 Queens Colony High Rd, Stevensville

Listing courtesy of Douglas Realty LLC. Contact:

101 Jarman Branch Dr, Centreville
$400,000
4 Beds ⋅ 2 Baths
Single-level living with cathedral ceilings, and a 1-acre corner lot surrounded by nature. Life slows down in the best way at this 4-bedroom, 2-bath rambler set on a spacious 1-acre corner lot in the quiet countryside of Ruthsburg. Open fields, towering evergreens, and wide green lawns create a peaceful, laid-back setting. The home is functional and livable as is, while leaving room for you to declutter, update, and truly make it your own. Inside, cathedral ceilings lift the living and family room area, giving the space an open, airy feel with plenty of room to gather. It's the kind of place where you can breathe easy and enjoy the view from your own front porch. The kitchen is generously sized with abundant cabinetry, ample counter space, and a breakfast bar. All 4 bedrooms are on one level, giving you flexibility for guests, a home office, or a hobby room. Two full baths keep daily routines running smoothly. There’s also the attic for extra storage space. Outdoors, your acre of yard gives you room to garden, play, or simply relax. You're located on Ruthsburg Road (Route 304) near Mason Branch Road, with Route 481 just down the road for easy connections to nearby towns and main routes. Local farms like Wagner Farm dot the landscape, and you'll be surrounded by the quiet charm of rural Queen Anne's County. With space, privacy, and potential in a peaceful country setting, this home is ready for your vision. Schedule your showing today and picture the possibilities!

101 Jarman Branch Dr, Centreville

Listing courtesy of EXP Realty, LLC. Contact:

104 Mariners Cir, Stevensville
$1,825,000
4 Beds ⋅ 4 Baths
Set on more than three acres, this distinctive waterfront residence offers over 3,400 square feet of living space, sweeping water views and beautiful sunrises. From the moment you enter, the view draws you through the home to the spacious family room, where a soaring cathedral ceiling and dramatic Palladian window frame the water like a work of art. Beautiful random-width white oak hardwood floors, crown molding and thoughtful architectural details add warmth and character throughout. The bright gourmet kitchen is designed for both everyday living and entertaining, with two ovens, stainless steel appliances, quartz countertops, abundant cabinetry and workspace, a pantry, and generous table space. Nearby, the separate dining room is accented by a gorgeous crystal chandelier, creating an elegant setting for holiday dinners and larger gatherings. The main-level primary suite is a private retreat overlooking the water, complete with an expansive dressing room and luxurious bath featuring a walk-in shower, soaking tub, heated floors and rich cabinetry. Bedroom four offers its own private ensuite bath, captivating views and direct access to a waterside deck—an ideal retreat for family or overnight guests. Outdoor living is equally appealing, with an in-ground swimming pool, patio, waterside deck and private pier providing numerous ways to enjoy the setting. Significant improvements include two HVAC systems installed in 2016, a new roof in 2018, a new septic system in 2021, and a new well in 2023. With more than three acres of privacy, generous gathering spaces inside and out, and the water as its backdrop, this remarkable property captures the essence of Eastern Shore waterfront living.

104 Mariners Cir, Stevensville

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

211 Pathfinder Cir, Grasonville
$550,000
3 Beds ⋅ 2 Baths
Open Sunday 11-1pm! Better than new and built in 2025, this beautifully appointed home sits on a quiet premium lot backing to woods and the community pond. Offering nearly 2,000 square feet of living space, three bedrooms, and two full baths, it pairs modern finishes with a peaceful setting. The kitchen features an expansive island, quartz countertops, subway tile backsplash, stainless steel appliances, and a walk-in pantry, with plenty of room for everyday meals and entertaining. Luxury vinyl plank flooring flows throughout the main living spaces. The primary suite offers a tray ceiling, walk-in closet, and spacious en suite bath with a double vanity and walk-in shower. A dedicated laundry room with a high-efficiency washer and dryer and a spacious garage add everyday convenience. Outside, the fully fenced backyard thoughtfully combines vinyl fencing along the sides for privacy with aluminum fencing across the rear to preserve the wooded and pond views. Located in a community across from the Chesapeake Bay Environmental Center, this move-in-ready home offers a beautiful place to settle in and enjoy life on the Shore.

211 Pathfinder Cir, Grasonville

Listing courtesy of Samson Properties. Contact:

117 River Run, Queenstown
$1,300,000
4 Beds ⋅ 3 Baths
Wye River Waterfront Living at Its Best! If you love boating, fishing, crabbing, and being on the water, this Cape Cod-style home on the Wye River may be just what you have been waiting for. Situated on 1.46 private acres with more than 250 feet of waterfront, this property offers a peaceful setting surrounded by mature trees, beautiful landscaping, and plenty of privacy. The Wye River is well known for its excellent boating, fishing, and crabbing, along with its deep water that makes it especially appealing to boaters. Whether you are looking for a full-time residence, a second home, or an investment opportunity, this property offers tremendous possibilities. Enjoy the outdoors from the private screened porch, the perfect place to relax, entertain, and take in the peaceful surroundings. Inside, the home offers four bedrooms and two and a half baths, with generously sized rooms throughout. The first-floor primary suite provides the convenience of one-level living and makes the home well suited for those looking to remain in the home long term. Upstairs are three spacious bedrooms and a full bath, providing plenty of room for family and guests. The light-filled family room features a beautiful fireplace and offers a comfortable space for both relaxing and entertaining. A separate game room provides even more flexibility for gatherings, hobbies, or recreation. Recent improvements include new flooring, a new septic system, and a new roof, giving you a great foundation to add your own personal touches. The property also offers excellent versatility. It could potentially be used as a second home or rental property, and the layout lends itself to possibilities such as an in-law suite or caretaker accommodations, depending on your needs and applicable approvals. With its private setting, mature trees, extensive waterfront, deep-water boating potential, and flexible floor plan, this four-bedroom Cape Cod with a two-car-plus garage is a rare opportunity to enjoy the Wye River lifestyle. Bring your boat, fishing gear, crab pots, and your vision—and make this special waterfront property your own!

117 River Run, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

153 White Tail Ct, Centreville
$725,000
5 Beds ⋅ 3 Baths
Welcome home to this sanctuary that beautifully blends modern comfort with warm Eastern Shore charm. Nestled at the end of a quiet cul-de-sac in the desirable Willow Branch East community, this property offers a sprawling 1.61-acre lot with * 5 BEDROOMS * A welcoming front porch leads into a dramatic two-story open foyer featuring an elegant staircase. The main level boasts a bright, flexible formal dining room or home office and a spacious living room. At the heart of the home is a spacious kitchen fully equipped with Silestone countertops, 42" Maple Toffee cabinetry, and brand-new stainless steel appliances, plus a generous keeping room perfect for large gatherings. Transition effortlessly through the cozy sunroom—complete with a stylish barn door—to the rear stone paver patio for seamless indoor-outdoor entertaining. Upstairs, the private primary suite serves as a true sanctuary, showcasing a spacious sitting room and a spa-like en-suite bath with a jetted soaking tub. Four additional bedrooms and a full hall bath provide ample space for family and guests. Premium Andersen windows flood the home with natural light, while upgrades like a Rinnai tankless water heater, reverse osmosis, a water softener, and recent two-zone heat pumps (2023 & 2025) ensure modern comfort. With the holidays around the corner an added feature...conveniently located inside.... HOLIDAY LIGHT SWITCH FOR THE FRONT ELEVATION! Located just minutes from historic Centreville, enjoy peaceful, private living with convenient commuter access to Route 301, Annapolis, Easton, and the Chesapeake Bay Bridge.

153 White Tail Ct, Centreville

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

223 Evelyne St, Chester
$799,000
3 Beds ⋅ 3 Baths
Welcome to 223 Evelyne Street in Gibson’s Grant! Built by Koch Homes, this expanded Ashford model combines the convenience of a main-level primary bedroom with spacious living areas and an oversized garage with an enlarged family room above. Hardwood floors, plantation shutters throughout the home, and a beautiful stone-surround fireplace add warmth and timeless style. The spacious living room, kitchen, and dining area offer a welcoming setting for everyday living and entertaining, while a separate office provides a dedicated space for work or study. A beautiful Andersen sliding door opens to the deck and hardscaped patio, creating an inviting outdoor space for dining, relaxing, and gathering. Two additional bedrooms and a full bathroom are located upstairs. A standout feature is the expanded family room over the garage, known as the FROG. The oversized garage option provides additional space for parking and storage below and a larger recreation room above—perfect for a media room, game room, or additional living space. Plumbing is already in place in the garage so it would be easily accessible to run it above the garage for a potential future full bathroom, offering added flexibility to make the space your own. Gibson’s Grant offers a waterfront community setting with an outdoor pool, clubhouse, fitness center, and fishing and crabbing pier. Enjoy direct access to the Cross Island Trail and easy access to Route 50, the Bay Bridge, waterfront restaurants, shopping, and everyday conveniences. Discover the space, versatility, and coastal lifestyle that make this home a special opportunity on Kent Island.

223 Evelyne St, Chester

Listing courtesy of Samson Properties. Contact:

2011 Stevens Dr, Chester
$489,900
3 Beds ⋅ 2 Baths
Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

2011 Stevens Dr, Chester

Listing courtesy of Samson Properties. Contact:

109 Autumn Ln, Centreville
$539,000
4 Beds ⋅ 3 Baths
Welcome to 109 Autumn Lane in Centreville, MD, where beautiful updates meet exceptional outdoor living! Step inside and discover a home designed for both comfort and entertaining, featuring an inviting open floor plan and a beautifully renovated primary bathroom that offers a spa-like retreat. Additional bonus storage space above the garage provides extra room to keep everything organized. A new roof adds even more value and peace of mind! Outside, the new composite deck and stunning stone patio with fire pit create the perfect setting for relaxing evenings, weekend gatherings, and making memories. The spacious backyard offers plenty of room to play, entertain, or simply enjoy the outdoors. With thoughtful upgrades, inviting spaces, and an incredible backyard oasis, this Centreville home is one you won’t want to miss!

109 Autumn Ln, Centreville

Listing courtesy of RE/MAX Executive. Contact:

228 Prospect Bay Dr W, Grasonville
$1,495,000
5 Beds ⋅ 4 Baths
Some homes are simply places to live. This is a lifestyle. Welcome to 228 Prospect Bay Dr W, an exceptionally maintained and thoughtfully updated home where beautiful water views, resort-style outdoor living, and the coveted Prospect Bay community come together in one unforgettable property. From the moment you arrive, the setting makes an impression. Mature landscaping, a gracious exterior and glimpses of the water create a sense of arrival that feels distinctly Eastern Shore. Step inside and you’ll quickly see that this home has been meticulously cared for and intentionally improved, blending timeless coastal character with sophisticated, modern updates. Hardwood floors extend throughout both levels, while custom trim work, designer wall treatments, updated lighting and carefully selected finishes give each space its own personality. The beautifully updated kitchen is designed for both everyday living and entertaining, featuring new countertops and backsplash, an enhanced island with additional storage, pull-out cabinetry and under-cabinet lighting. Just beyond, the sunroom provides a light-filled retreat overlooking the pool and outdoor living spaces. Formal living and dining areas offer an elevated place to gather, while the family room centers around a striking shiplap accent wall, electric fireplace and quartz hearth. Upstairs, the primary suite feels like a private escape, complete with water views, a masonry fireplace, expanded custom closet and beautifully remodeled spa-like bath with a tiled shower, marble seat, soaking tub and dual vanities. Three additional bedrooms and a well-appointed guest bath provide plenty of room for family and guests, while the bonus space over the garage offers flexibility for an office, studio, additional sleeping space or storage. Outside is where the Prospect Bay lifestyle truly comes alive. The backyard has been transformed into a private resort with a large inground pool, extensive hardscaping, Trex decking, hot tub, pergola and lush landscaping, all surrounded by mature trees for privacy. Steps from the pool, the charming separate guest house creates an incredible space for extended stays, offering its own bedroom, full bath, kitchenette and living area. And while the beauty of this home is immediately apparent, what sets it apart is the level of care behind the scenes. Major improvements include a new roof and gutters in 2024, three high-efficiency heat pumps in 2023, an encapsulated crawlspace in 2023, generator hookup, upgraded electrical service, repaved driveway, updated garage, new washer and dryer in 2026, fresh paint and new landscaping in 2026, along with extensive improvements throughout the kitchen, bathrooms, lighting, flooring, trim and outdoor spaces. All of this is set within Prospect Bay, one of the Eastern Shore’s most sought-after golf course communities, where residents enjoy an 18-hole golf course, clubhouse with restaurant and bar, driving range, tennis and pickleball, community pool, playground, private boat launch and more. Spend summer afternoons by your pool, host friends in the guest house, enjoy quiet mornings overlooking the water, play a round of golf, or launch the boat and spend the day exploring the Eastern Shore. 228 Prospect Bay Dr W isn’t simply a beautifully updated home, it’s the opportunity to live the Prospect Bay lifestyle every single day.

228 Prospect Bay Dr W, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

515 Baxter Rd, Sudlersville
$465,000
3 Beds ⋅ 2 Baths
Welcome home to this 3-bedroom, 2-bath home situated on .75 acres along a peaceful road backing to mature trees and farmland. Inside, you'll find an inviting open kitchen and living area featuring a charming brick wood-burning fireplace, creating a warm and comfortable gathering space. Step outside to the oversized back deck, perfect for entertaining, relaxing, or enjoying the private country setting. The backyard is ready for summer with a fenced 18' x 36' in-ground saltwater pool, offering plenty of space for outdoor fun and gatherings. Adding even more versatility to the property is the 30' x 40' detached garage, approximately five years old, complete with a half bath and 220V electrical service for electric vehicle charging—ideal for vehicles, hobbies, a workshop, or additional storage. Recent updates include a new heat pump in 2026, new furnace in 2025 and roof 5 years old. With plenty of outdoor space, a pool, an impressive detached garage, and peaceful views, this property offers a great combination of comfort, functionality, and country living.

515 Baxter Rd, Sudlersville

Listing courtesy of Benson & Mangold, LLC. Contact:

107 Lee Rd, Chester
$330,000
3 Beds ⋅ 1 Baths
107 Lee Rd is a one-story Chester home with a streamlined layout and a fully fenced backyard. The kitchen provides ample counter space, white cabinetry, a refrigerator, a range, and a nearby utility nook. The main living area has windows and an open connection to the kitchen, creating flexible space for dining and everyday use. The primary bedroom includes two windows and closet storage, while the bathroom has a vanity and a tub-shower combination. A dedicated laundry area includes a washer and dryer. The broad backyard contains a storage shed, completing this residence with practical interior organization and useful outdoor storage.

107 Lee Rd, Chester

Listing courtesy of Open Door Brokerage, LLC. Contact:

419 Craney Creek Rd, Stevensville
$3,495,000
4 Beds ⋅ 6 Baths
Set on nearly **3 private acres with more than 300 feet of Chesapeake Bay waterfront**, 419 Craney Creek is a custom-built home designed to embrace its remarkable setting. Over 6,000 square feet of living space offers 4 bedrooms, 4.5 baths, a first-floor primary suite, private office, bonus room and a 3-car side-loading garage. Inside, hardwood floors and abundant natural light carry throughout the home, while the dramatic two-story living room—with its fireplace and expansive windows—captures sweeping Bay views. The spacious kitchen is equally suited for entertaining and everyday living with custom cabinetry, granite countertops, a generous island, abundant workspace and a butler’s pantry. The first-floor primary suite is a retreat of its own, complete with a fireplace and direct access to the waterfront patio. Outdoor spaces unfold across the back of the home, from the covered porch and deck to the paver patio with 10 person hot tub and second-level porch—each offering a front-row seat to the **Chesapeake Bay and unforgettable sunsets**. A private pier with boat lifts and riprapped shoreline complete the waterfront experience, while the expansive grounds offer plenty of room for a future pool. An unfinished basement with rough-in and spacious unfinished attic provide even more opportunity to create additional living, entertaining or recreation space. **Beautifully established yet filled with possibility, 419 Craney Creek offers the space, privacy and waterfront lifestyle that make a Chesapeake Bay property truly special.**

419 Craney Creek Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

129 Anna Carol Dr, Stevensville
$700,000
4 Beds ⋅ 3 Baths
Coastal charm, exceptional living spaces, and a coveted main-level primary suite come together beautifully in this standout Ellendale at Kent Island home. Mature landscaping and an expansive covered front porch create an inviting first impression, while inside, hardwood floors, crown molding, chair rail, and thoughtful architectural details give the home warmth and character from the moment you enter. At the heart of the home, the kitchen and family room form a spacious, open gathering area designed for both everyday living and entertaining. The beautifully appointed kitchen features granite countertops, stainless steel appliances, gas cooking, recessed lighting, and pendant lighting above a generous center island with breakfast bar seating. Open to the kitchen, the family room is enhanced by a soaring cathedral ceiling and offers plenty of space to gather, while direct access to the screened porch extends the living area outdoors, creating an easy flow for entertaining. A separate open dining area provides a dedicated setting for meals and gatherings, while a phenomenal butler’s pantry is equally accessible from both the dining area and kitchen. More than simply additional storage, this thoughtfully designed space features granite countertops, a wine refrigerator, and a double-door pantry, allowing it to function beautifully as a beverage station, serving area, additional prep space, and pantry, all while providing a natural connection between the kitchen and dining area. Privately positioned away from the main gathering spaces, the main-level primary suite offers an inviting retreat with an oversized walk-in closet and a spacious en suite bath featuring dual vanities and a tiled walk-in shower. A powder room and conveniently located laundry room complete the main level. Upstairs, an exceptionally spacious open landing overlooks the family room and leads to three bright bedrooms and a well-appointed full hall bath with ceramic tile flooring and a tiled shower. One bedroom connects to a separate finished sitting room or study, creating an especially versatile suite with space for a private office, reading room or hobby space. Large windows fill the upper level with natural light, while charming coved ceilings and wide baseboard molding add another layer of architectural character. Storage is another standout feature. An interior staircase provides convenient walk-down access to an expansive, storage area beneath the home, offering an unusually generous place for seasonal décor and household items. At the rear, an alley leads to the driveway and two-car garage, discreetly positioning parking away from the front of the home and preserving its charming streetscape. Adding to the home’s everyday efficiency, the solar panels are owned outright, providing the opportunity for substantial savings on electricity with no solar lease to assume. Ellendale at Kent Island completes the package with a clubhouse, community pool, tot lot, and recreational amenities in a setting that combines the relaxed character of Maryland’s Eastern Shore with exceptional accessibility. Located approximately one mile from the Chesapeake Bay Bridge, the community is convenient to historic Stevensville, Kent Narrows, Terrapin Nature Park, and public water access at Thompson Creek. Boating, waterfront dining, walking and biking trails, and the natural beauty of Kent Island are close at hand, while Annapolis and destinations throughout the greater Washington-Baltimore region remain within easy reach—a remarkable combination of coastal living and everyday convenience.

129 Anna Carol Dr, Stevensville

Listing courtesy of Northrop Realty. Contact:

325 Rings End Rd, Millington
$589,000
5 Beds ⋅ 3 Baths
Discover an exceptional investment opportunity with this stunning Colonial-style residence operating as a guest favorite on Airbnb. Perfectly positioned just 16 feet from the serene Chester River. Step inside to find an inviting open floor plan that seamlessly connects the family room to the kitchen, creating a warm and welcoming atmosphere. The home is adorned with built-ins and window treatments that enhance its charm, while the cozy carpet and wood floors add a touch of elegance throughout. The property features two fireplaces, providing a cozy ambiance during cooler months, and an attic for additional storage or potential expansion. The upper-floor laundry adds convenience, making this home not only beautiful but functional as well. Outside, the allure continues with a personal in-ground pool, perfect for relaxation and recreation. The expansive 1.43-acre lot offers ample space for outdoor activities, while the breathtaking water views create a tranquil backdrop for your daily life. With water access just steps away, you can enjoy kayaking, fishing, or simply soaking in the natural beauty of the Chester River. From an investment perspective, this property stands out with its excellent condition and desirable features. The combination of spacious living areas, modern amenities, and proximity to water activities makes it highly attractive for potential renters or future buyers. The growing demand for waterfront properties ensures that your investment will appreciate over time, providing both immediate enjoyment and long-term financial benefits. This residence is not just a home; it's a lifestyle choice that offers the perfect blend of comfort, luxury, and investment potential. Don't miss your chance to own a piece of paradise that promises both personal enjoyment and financial growth. Seize this opportunity today!

325 Rings End Rd, Millington

Listing courtesy of Hostetter Realty. Contact:

510 Talbot Rd, Stevensville
$599,900
3 Beds ⋅ 3 Baths
Nestled in the serene enclave of Kent Island Estates, this exquisite new construction home, soon to be completed in 2026, embodies the perfect blend of luxury and comfort. With a stunning Craftsman architectural style, this detached residence offers a warm and inviting atmosphere, ideal for those seeking an exclusive lifestyle. Step inside to discover a thoughtfully designed open floor plan that seamlessly connects the living, dining, and kitchen areas. The large gourmet kitchen is a chef's dream, featuring upgraded quartz countertops, a spacious island, and stainless-steel appliances, including a sleek oven/range with hood and French door refrigerator with water and ice dispenser. There is abundant cabinet and counter space here, this kitchen is sure to meet your every need. Upstairs this home boasts three generously sized bedrooms, including a primary suite complete with a luxurious bathroom featuring a large double vanity and tiled stall shower ensuring a spa-like experience at home. The primary suite features a huge walk in closet complete with wire shelving. The Primary suite looks out over Eastern Bay and Shipping Creek, a vista that is sure to instill relaxation and peace. Each bedroom is designed with comfort in mind, offering ample closet spaces that provide both functionality and style. Bedroom floors are carpeted for comfort, and ceiling fans ensure temperature control. The upper-level hall bath is also equipped with a large double vanity for convenience and a generous tub shower combination. The main interior is adorned with luxury vinyl plank flooring and wainscoted walls, enhancing the home's aesthetic while ensuring durability. The upper floor laundry adds convenience to your daily routine, making chores a breeze. Outside, the property is graced with a level water oriented front yard and a level lot that backs to trees, providing a tranquil backdrop for outdoor gatherings. Enjoy the fresh air on the expansive deck, perfect for entertaining or simply unwinding after a long day. The paved driveway leads to an attached garage, offering both convenience and security. Located just one block from the picturesque Shipping Creek, this home offers a unique opportunity to embrace a water-oriented lifestyle. The views of the bay and creek create a serene environment, perfect for nature lovers and those seeking a peaceful retreat. Kent Island Estates is a suburban haven, providing easy access to local amenities while maintaining a sense of privacy and tranquility. This property is not just a home; it's a lifestyle choice that promises comfort, elegance, and a connection to nature. Experience the luxury of new construction and the joy of creating lasting memories in this exceptional residence.

510 Talbot Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

101 Chestnut Rd, Stevensville
$455,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained and thoughtfully designed home, ideally situated on a desirable corner lot with a fully fenced backyard. Offering an excellent combination of comfort, functionality, and style, this property is an ideal opportunity for a first-time buyer, growing family, or anyone looking for a move-in-ready home. Step inside and you’ll immediately appreciate the inviting traditional floor plan, enhanced by beautiful new wood flooring, recessed lighting, upgraded countertops, and an abundance of natural light. The spacious family room flows seamlessly from the kitchen, creating a comfortable and welcoming space for everyday living and entertaining. The well-appointed kitchen offers an abundance of workspace and storage, featuring a center island, pantry, eat-in area, table space, upgraded countertops, built-in microwave, built-in range, self-cleaning oven, dishwasher, and exhaust fan. Whether you’re preparing a quick breakfast or hosting family and friends, this kitchen provides the convenience and functionality today’s homeowners desire. The home offers two full bathrooms, including one with a convenient walk-in shower. Generously sized bedrooms provide comfortable living spaces, while walk-in closets offer excellent storage. Ceiling fans and window treatments throughout the home add comfort and convenience. The main-level laundry area makes everyday living simple and efficient, with a washer and electric dryer included. Additional features include storm doors, double-hung windows, an electric alarm system, an owned water-conditioning system, a water-treatment system, and a water heater. The crawl space has also received important improvements. All cavities and walls have been fully insulated and sealed, and a dedicated dehumidifier system has been installed to help maintain a cleaner, drier, and more controlled environment beneath the home. Outside, the spacious corner-lot setting and fully fenced backyard provide plenty of room for outdoor enjoyment, entertaining, gardening, play, or simply relaxing. The backyard offers the privacy, flexibility, and functionality many buyers are looking for, making it an ideal space for families and outdoor activities. With its comfortable living spaces, practical upgrades, excellent storage, and inviting outdoor setting, this home offers an exceptional opportunity to establish roots and enjoy years of comfortable living. Whether you’re purchasing your first home, looking for additional space for your family, or simply searching for a well-maintained property in a desirable setting, this home is one you won’t want to miss.

101 Chestnut Rd, Stevensville

Listing courtesy of EXP Realty, LLC. Contact:

205 Dominion Ln, Chester
$300,000
3 Beds ⋅ 2 Baths
COMING SOON on Kent Island! Opportunity awaits at 205 Dominion Ln in Chester. Currently used as a rental, this detached home offers the chance to bring your vision and make it your own. The property could use some TLC, but for the right buyer, that’s exactly where the potential begins. Whether you’re looking for a home you can update over time and turn into your own Eastern Shore retreat, or you’re an investor searching for your next project or rental opportunity, this property offers plenty of possibilities. Located on sought-after Kent Island with convenient access to everything the area has to offer. Bring your ideas and imagine what this home could become. More details and photos coming soon!

205 Dominion Ln, Chester

Listing courtesy of EXP Realty, LLC. Contact:

1509 Calvert Rd, Chester
$1,350,000
4 Beds ⋅ 3 Baths
Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

1509 Calvert Rd, Chester

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

225 Hickory Ridge Dr, Queenstown
$1,195,000
4 Beds ⋅ 3 Baths
A Private Wye River Sanctuary! Some properties offer a home. Others offer a lifestyle. This exceptional Wye River retreat offers both.Set along one of the Eastern Shore’s most beautiful waterways, this beautifully updated ranch home is an invitation to slow down, entertain effortlessly, and enjoy waterfront living at its finest. From morning coffee on the screened porch to sunset swims in the Gunite pool, every day here feels like a getaway.The light-filled, open interior provides an inviting backdrop for relaxed gatherings and everyday living, while a versatile additional living area offers the flexibility for an in-law suite, private home office, game room, or guest retreat. The serene primary bedroom enjoys direct access to the screened porch, creating a private connection to the tranquil waterfront setting.The extensive improvements provide peace of mind while enhancing the home's appeal, including an architectural roof, vinyl siding, gutters, sophisticated hybrid heat pump/propane HVAC system, select updated flooring, and an updated BAT septic system.Outside is where this property truly shines. The Gunite pool features strategically placed bench seating, creating the perfect vantage point for unforgettable Wye River sunsets. The screened porch captures the river breezes and provides an ideal setting for morning coffee, afternoon cocktails, or long evenings with friends and family.For the boating enthusiast, the private dock features two electric boat lifts—8,000 and 12,000 pounds—and 2+ feet of mean low water, providing excellent access for boating and watersports. Spend the day on the river, catch crabs from the dock, or simply let the water set the pace.This is more than a waterfront home—it is a place to create traditions, host unforgettable gatherings, escape the ordinary, and experience the Wye River in a deeply personal way.Private waterfront. Private dock. Gunite pool. Sunset views. Exceptional outdoor living. A rare opportunity to make the Wye River your everyday retreat.

225 Hickory Ridge Dr, Queenstown

Listing courtesy of Pearson Smith Realty, LLC. Contact: