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$619,900
4 Beds 3 Baths
Discover the perfect blend of modern elegance and comfort in this stunning Colonial-style home located in the desirable Perry's Retreat. Built in 2024, this residence boasts a pristine condition and an array of features designed to enhance your lifestyle. Step inside to find an inviting open floor plan that seamlessly connects the gourmet kitchen, dining area, and family room, creating an ideal space for entertaining and everyday living. The kitchen is a chef's dream, equipped with upgraded countertops, a double oven, built-in microwave, and ample pantry space. With four generous bedrooms and 2.5 baths, this home offers plenty of space for relaxation and privacy. The upper floor laundry adds convenience to your daily routine, while the elegant luxury vinyl plank flooring and tasteful window treatments throughout elevate the aesthetic. Outside, the property features a well-maintained exterior with sidewalks and a concrete driveway leading to a two-car attached garage, ensuring ample parking and easy access. The 0.14-acre lot provides a manageable outdoor space for gardening or leisure activities. This home is not just a place to live; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this exquisite property your own!

242 Perrys Retreat Blvd, Grasonville

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$568,900
4 Beds 3 Baths
Welcome to 329 Union Church Road in Chestertown, located in Queen Anne’s County—a home with plenty of space, useful updates, and room to truly make it your own! Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft—providing plenty of room for storage, hobbies, a workshop, or all the extras. Inside, you’ll find a spacious and functional layout ready for its next owners to settle in and make it feel like home. The kitchen features updated appliances, including a new stove, microwave, oven, and dishwasher in 2026, while new LVP flooring upstairs adds a fresh look. Major mechanical updates include the upstairs HVAC system replaced in 2023 and the downstairs HVAC system replaced in 2026. Outside, the 1.03-acre property gives you room to spread out, enjoy the outdoors, and create a space that fits the way you want to live. The detached pole barn adds even more versatility, while the attached and detached garage spaces provide plenty of options for parking, storage, projects, and more. Additional features include a tankless gas water heater, private well and septic, and an owned water-filtration system. Whether you’re looking for more room inside, space for your hobbies and projects, or simply a place you can put your own stamp on, 329 Union Church Road offers the space and flexibility to make it your own. Come take a look and imagine making this Queen Anne’s County property your next home!

329 Union Church Rd, Chestertown

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

$789,000
3 Beds 3 Baths
Professional Photos Coming Soon! Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A rear-entry two-car garage with a large parking pad provides ample space for residents and guests. Gibson’s Grant is conveniently located near waterfront dining, shopping, and the Cross Island Trail, with easy access to the Bay Bridge for commuting or exploring all that the Eastern Shore has to offer. Experience the perfect blend of waterfront community living, everyday convenience, and the relaxed Shore lifestyle.

402 Macum Creek Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

$529,000
3 Beds 3 Baths
Nestled in the coastal enclave of Kent Island Estates, this exquisite residence, built in 2022, offers a harmonious blend of modern luxury and natural beauty. Spanning a generous 0.25-acre lot, the property is thoughtfully designed to provide both comfort and elegance, making it an ideal retreat for discerning homeowners. As you step inside, you are greeted by an inviting atmosphere enhanced by high-quality finishes and an abundance of natural light. The interior features a seamless flow of luxury vinyl plank and plush carpeting, creating a warm and welcoming ambiance throughout. The spacious living areas are adorned with ceiling fans, ensuring a comfortable environment year-round. The well-appointed kitchen is a culinary enthusiast's dream, equipped with top-of-the-line appliances including a built-in microwave, dishwasher, and refrigerator, complemented by a sleek stove and range. The home boasts three generously sized bedrooms, including a primary suite that serves as a private sanctuary. The primary bath features modern fixtures and finishes, providing a spa-like experience at home. With a total of 2.5 bathrooms, convenience is paramount for both residents and guests. Step outside to discover the enchanting outdoor space that backs to tranquil trees, offering a peaceful retreat for relaxation or outdoor gatherings. The exterior is enhanced by tasteful lighting, creating an inviting atmosphere for evening enjoyment. Kent Island Estates is not just a home; it's a lifestyle. Residents enjoy access to a vibrant community with nearby parks, perfect for leisurely strolls or picnics. The neighborhood is known for its friendly atmosphere and well-maintained surroundings, making it a wonderful place to connect with neighbors. The quiet street is maintained by the County, has new public sewers and is close to the Cross Island Trail, Romancoke Pier, Matapeake Beach and so much more and is served by the Matapeake Elementary and Middle Schools. Just a few minutes to restaurants, shopping, and the Bay Bridge.This property is a rare find, combining modern amenities with the charm of a close-knit community. Experience the best of both worlds in this stunning home, where luxury meets coastal charm.

123 Tennessee Rd, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$479,900
3 Beds 3 Baths
Coming soon! WELCOME TO KENT ISLAND! Built in 2021, this attractive 3-bedroom, 2.5-bath home offers nearly 1,700 sq. ft. of comfortable living space with a bright, open floor plan and thoughtful upgrades throughout. The main level features durable LVP flooring and an open kitchen with granite countertops, tile backsplash, stainless steel appliances and plenty of space for gathering and entertaining. Upstairs, the spacious primary suite offers a walk-in closet and a generously sized private bath with double vanity, soaking tub and separate stand-up shower. Two additional bedrooms, another full bath and conveniently located upstairs laundry complete the second level. Additional features include a whole-house water filtration system with softener and chemical feeder, an encapsulated crawl space, attached garage and a fenced backyard with white vinyl fencing and a patio for outdoor relaxing, grilling or play. Located in Kent Island Estates, this home offers the laid-back Eastern Shore lifestyle with optional access to community waterfront recreation and Chesapeake Bay beach areas for a low voluntary annual fee. Enjoy nearby parks, marinas, restaurants, boating and all that Kent Island has to offer, while still being within easy reach of the Bay Bridge. Only five years young, well cared for and move-in ready, 125 Harford Road offers a wonderful opportunity to own a newer home on Kent Island.

125 Harford Rd, Stevensville

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact: (800) 383-3535

$640,000
4 Beds 3 Baths
Welcome to 422 John Patrick Drive, a beautifully updated home situated on a corner lot in the sought-after Ellendale community on Kent Island. Offering over 2,200 square feet of thoughtfully designed living space, this move-in-ready home features an open, functional floor plan with inviting spaces for everyday living and entertaining. The updated kitchen showcases quartz countertops, a stylish backsplash, a center island with pendant lighting, and newer KitchenAid and Bosch appliances. The kitchen opens seamlessly to the living room, where custom built-ins add character and storage while creating a welcoming gathering space. Just off the kitchen, a light-filled dining area overlooks the front yard, while an additional playroom offers flexibility as a formal dining room, home office, or other space to suit your needs. Recessed lighting throughout the kitchen, living room, and hallway enhances the home’s bright, polished feel. Upstairs, the oversized primary suite offers a relaxing retreat with a walk-in closet featuring a built-in organization system. The beautifully remodeled primary bath includes quartz countertops, Moen fixtures, a soaking tub, separate shower, and space-saving pocket door. Three additional bedrooms, another full bath, and a conveniently located laundry area with an LG washer and dryer complete the upper level. Outside, enjoy a fully fenced backyard overlooking the peaceful neighboring farm, complete with a patio, storage shed, and a newer play set (2025). Major recent improvements provide added peace of mind, including a Rinnai tankless gas water heater and a complete Rheem HVAC replacement featuring electric air conditioning and gas heat. Ellendale residents enjoy access to a community pool, clubhouse, walking trails, playground, fishing pier, kayak launch and storage, and boat storage. Conveniently located near shopping, dining, schools, the Bay Bridge, and commuter routes to Washington DC and Baltimore, this thoughtfully updated home offers comfort, convenience, and the best of the Kent Island lifestyle.

422 John Patrick Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$597,000
3 Beds 3 Baths
Beautifully renovated historic home in the heart of charming Queenstown, a water-oriented Eastern Shore town rich in history and small-town appeal. Approaching 150 years old, this distinctive residence offers approximately 1,920 square feet of thoughtfully updated living space while preserving its original character. Featuring 3 bedrooms, 2.5 updated tile baths, hardwood floors, period details throughout, a gourmet kitchen, newer dual-zone air conditioning, forced-air and baseboard heat, and a re-lined fireplace in the living room, this home seamlessly blends historic charm with modern comfort. Step outside to enjoy beautifully established gardens, the result of generations of owners' passion for flowers, nature, butterflies, and birdsong. Relax on the patio within the fenced backyard overlooking a tranquil pond, stroll to the water, or launch a kayak, canoe, or paddleboard from one of Queenstown's convenient public access points to Queenstown Creek. The town also offers a marina for boating enthusiasts. Golf lovers will appreciate nearby Queenstown Harbor's 36 championship holes set amidst stunning natural surroundings. Rich in history, Queenstown is home to the nation's oldest standing courthouse and offers a vibrant sense of community with concerts in the park, holiday celebrations, and other events throughout the year. Conveniently located for commuting to Annapolis, Baltimore, and Washington, D.C. Zoned to allow a home office or small business. A rare opportunity to own a piece of Queenstown history while enjoying the best of Eastern Shore living.

7108 Maryland Ave, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$639,900
4 Beds 3 Baths
Nestled along the shores of Shipping Creek in Kent Island Estates, this exquisite new construction home embodies the essence of luxury living. In a contemporary Farmhouse architectural style, this brand new home offers a perfect blend of elegance and comfort and is set on a generous lot of nearly a half acre surrounded by mature trees. Step inside to discover a thoughtfully designed layout featuring contemporary black steel finishes and fixtures along with crisp whites and warm wide plank flooring. A Bright and open foyer invites you into a formal Dining room with windows looking out to the front and water views beyond. The Kitchen is the heart of the home with its central location in this updated open plan layout. A Breakfast area leads into the generous Family room with sleek sliding doors that open to a large composite deck for outdoor entertaining and leisure activities. Upstairs you will find four spacious bedrooms and two and a half beautifully appointed bathrooms. Laundry is conveniently located in the upper hall. The oversize Owners suite provides privacy and purpose with a very generous walk-in closet and a gleaming bathroom suite. Feel the tranquil effect of the morning sun rising over the water views of Shipping Creek when you arise each day. There are three more bedrooms providing ample space and a hall bath as well. The property boasts high-end finishes and meticulous craftsmanship, ensuring a lifestyle of sophistication and ease. The excellent construction of the home reflects a commitment to quality and attention to detail. Kent Island Estates is located close to the Romancoke fishing pier and the South Kent Island Trail. Perfect for enjoying leisurely strolls through the picturesque surroundings and observing local wildlife. The property is designed for those who appreciate the finer things in life, offering a peaceful retreat from the hustle and bustle of urban living. Convenience is paramount with an attached two-car garage and ample driveway space, ensuring easy access and plenty of room for guests. This home is not just a residence; it's a lifestyle choice, inviting you to experience the beauty of water-oriented living while enjoying the comforts of modern amenities. Indulge in the exclusive lifestyle that Kent Island Estates offers, where luxury meets nature, and every day feels like a getaway. This is more than a home; it's a sanctuary waiting for you to create lasting memories.

506 Talbot Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$489,900
4 Beds 4 Baths
Why wait for new construction when you can move right in? Welcome to 205 Jessica Lyn Ave #F20, a nearly new 4-bedroom, 3.5-bath townhome offering approximately 2,280 square feet of thoughtfully designed living space in Stevensville. Built in 2024, this home delivers the modern finishes, and open layout buyers are looking for without the wait or the price tag of competing new construction. The main level features a bright, open-concept layout with 9-foot ceilings, abundant natural light, luxury vinyl plank flooring, and a spacious kitchen that opens seamlessly to the dining and living areas. The kitchen offers generous cabinetry, stainless steel appliances, a large island with seating, and plenty of space for both everyday living and entertaining. Upstairs you'll find a spacious primary suite along with additional bedrooms and flexible living space. The other level provides even more versatility with a bedroom and full bath, ideal for guests, a home office, multigenerational living, or anyone looking for additional privacy. Located on Kent Island with convenient access to Route 50/301 and the Bay Bridge, this home puts Annapolis and the Western Shore within easy reach while still offering the Eastern Shore lifestyle. With newer construction nearby competing at significantly higher prices, 205 Jessica Lyn Ave represents an opportunity that's hard to ignore. Schedule your showing and see the value for yourself.

205 Jessica Lyn Ave Unit #F20, Stevensville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$550,000
5 Beds 4 Baths
Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this residence is designed for comfort and functionality. Enjoy cozy evenings by one of the two fireplaces. With new windows, the natural light floods the traditional floor plan, enhanced by recessed lighting and wood floors throughout. The entry-level bedroom offers convenience, while the walk-in closets provide ample storage. Step outside to your personal oasis with an in-ground pool (new pool pump), ideal for summer relaxation and entertaining. With a generous 0.39-acre lot and side-entry garage, this home combines space and style.

326 Castle Marina Rd, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$539,990
4 Beds 3 Baths
Discover the charm of this new construction home in Kent Island Estates, where coastal elegance meets modern comfort. With 4 spacious bedrooms and 2.5 baths, this residence features an inviting open floor plan, perfect for gatherings. The heart of the home is the kitchen, complete with a stylish island and energy-efficient stainless steel appliances, making meal prep a delight. Enjoy the luxury of partially carpeted and luxury vinyl plank flooring throughout, enhancing both warmth and durability. The family room, conveniently located off the kitchen, creates a cozy atmosphere for relaxation. Set on a generous 0.24-acre lot, this home offers ample outdoor space for future landscaping or entertaining. The community is enriched by nearby parks, excellent schools, and convenient public services, fostering a vibrant neighborhood spirit. With an attached garage and driveway parking, convenience is at your fingertips. Embrace the opportunity to make this beautiful house your home! Seller is offering $10,000 towards options or closing assistance through preferred lender and title company!

101 Oak St, Stevensville

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

$350,000
2 Beds 2 Baths
Your Island Getaway Is Waiting! Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bedroom Island home may be just what you’ve been waiting for! Start your mornings—or wind down your evenings—on the inviting front porch, where you can swing with the little ones, rock to your favorite playlist, and enjoy the laid-back Island lifestyle. Inside the spacious living room features a wood stove, creating the perfect spot for cozy winter nights. The bright, well-appointed kitchen offers a center island, granite countertops, stainless steel appliances, abundant cabinetry, and a pantry—plenty of room for preparing family meals or entertaining friends. Just off the kitchen, the screened porch is ready for three-season enjoyment. Imagine crab feasts with family and friends, relaxing evenings, or cheering on your favorite team while enjoying the crisp fall air! Outside, the huge, privately fenced rear yard offers plenty of space for the kids to play, pets to roam, or everyone to gather. Multiple sheds provide convenient storage for all your crabbing, fishing, boating, and outdoor gear. Upstairs, you’ll find two spacious bedrooms plus a walk-up attic with endless possibilities. Use it for additional storage, a home office, hobby space—or transform it into an additional bedroom to suit your needs. Whether you’re looking for a year-round home, a weekend retreat, or your own slice of Island living, this one offers comfort, space, charm, and plenty of potential at a great price. PLUS...the boat ramp is just 2 mins away which means fresh seafood is what's for dinner! Come see it for yourself—this Island gem won’t last long!

200 Church St, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$400,000
5 Beds 4 Baths
List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the Chesapeake Bay Bridge, this property combines generous proportions with a layout designed for comfortable everyday living and entertaining. The main level makes an immediate impression with 12-foot ceilings and oversized 6-foot windows, creating bright, open living spaces throughout. The floor plan includes a spacious family room, vaulted morning room, sunroom, and an eat-in kitchen that serves as the heart of the home. The kitchen is equipped with granite countertops, a large center island, pantry, and ample cabinet and workspace. The home’s 5-bedroom, 3.5-bath configuration provides plenty of flexibility. The primary suite features a tray ceiling and private bath with a custom-tiled shower and double vanity. Four additional bedrooms are complemented by two Jack-and-Jill-style bathrooms, offering a functional arrangement for family, guests, home offices, or additional flex space. Outdoor living is another highlight, with an impressive 800± square-foot wraparound deck providing plenty of room for grilling, dining, entertaining, and relaxing. Additional features include: • Hardwood and tile flooring • Roman blinds and wood shutters • New HVAC system • Finished garage • Dedicated laundry room with New washer and dryer • Approximately 4-foot crawl-space ceiling height • Numerous custom builder upgrades • No HOA With its impressive bedroom count, expansive living areas, oversized deck, substantial storage, and convenient Chester location, 1868 Roberta Drive offers bidders a unique opportunity to purchase a custom Eastern Shore home and make it their own. Don’t miss your opportunity to bid!

1868 Roberta Dr, Chester

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

$674,900
4 Beds 3 Baths
NEW CONSTRUCTION IN QUEENSTOWN – PRIVATE WOODED SETTING! Welcome to this thoughtfully designed new construction home on beautiful John Brown Road.  This home offers nearly 2,300 square feet of high quality living space in a peaceful, private setting surrounded by towering hardwood trees and backing to the wooded portion of a 1,000+ acre farm. Step inside this bright and inviting home offering super nice kitchen, large great room with gas fireplace, large first floor laundry, and plenty of space for both everyday living and entertaining. The really spacious first-floor primary suite offers convenience and privacy with granite vanity, large tiled shower, and huge closet! Upstairs, you'll find three big bedrooms, providing plenty of room for family, guests, home offices, or additional flex space. Additional highlights include granite counters, oversized trim, LVP flooring, insulated and finished 2 car garage, with stamped concrete walks, porch, and patio really dress this home up!  Secondary driveway is perfect for parking that large RV or boat! Everyone loves that peace of mind that comes with owning a brand-new home. Quality goes well beyond what you can see – spray foam sealed crawlspace walls and concrete floor make the conditioned crawl space a dry and energy efficient feature.   The home is equipped with a whole-house water treatment system designed to address arsenic, iron, and other common well-water contaminants. All exterior walls are flash coated with closed cell insulation for maximum efficiency. If you've been searching for the perfect combination of new construction, space, privacy, and Eastern Shore living, this home deserves a look. More photos and additional details coming soon!

1306 John Brown Rd, Queenstown

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$569,900
4 Beds 3 Baths
Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and architectural details throughout including crown molding, chair rail, and wainscoting. The gourmet kitchen is the heart of the home, showcasing silestone countertops, stainless steel appliances, under-cabinet lighting, ceramic tile backsplash, a spacious island, and additional cabinetry and countertop space adjacent to the pantry. The separate breakfast area features a new sliding glass door (2025) leading to the private fenced backyard, complete with a Trex/Vinyl deck (2015), shed, extensive hardscape, and beautifully landscaped grounds. The inviting family room features a floor-to-ceiling stone gas/propane fireplace (2018) and adjacent office/storage area. Renovated main-level powder room with updated vanity and lighting (2020), laundry room with Closet America cabinetry and access to attached two-car garage with epoxy flooring (2024) and insulated, finished walls (2025). OWNER IS WILLING TO REMOVE STAIR LIFT TO UPPER LEVEL AND REPLACE WITH CARPET ON STAIRCASE. On the upper level, you'll find four generously sized bedrooms, including a spacious primary suite with a walk-in closet and private en-suite bathroom featuring dual granite vanities and a large walk-in shower. The renovated hall bathroom offers updated ceramic tile, a quartz vanity, and tub/shower combination. The second floor and stairway have also been freshly painted. Additional highlights include updated hallway, foyer, and kitchen lighting, brushed nickel door hardware and hinges throughout. The home also features 6" gutters and downspouts with gutter guards (2023), asphalt roof replaced in (2018), and driveway torn out and replaced/sealed (2024/2026). Clayborne Woods is a private neighborhood that offers a jog/walk path, community management, and trash service. Enjoy the best of Kent Island living with a location just minutes from the Chesapeake Bay Bridge, beaches, parks, boat ramps, marinas, waterfront dining, shopping, restaurants, and schools. This exceptional home combines comfort, convenience, thoughtful updates, and coastal charm. Come see for yourself what Kent Island living is all about!

233 Cross Creek Ct, Chester

Listing courtesy of Rory S. Coakley Realty, Inc.. Contact:

$540,500
4 Beds 4 Baths
Discover an exceptional opportunity in the desirable Church Hill Hunt subdivision. This stunning Colonial-style residence, built in 2007, offers a spacious 3,720 square feet of thoughtfully designed living space. Featuring four generously sized bedrooms and three and a half bathrooms, this home is perfect for both entertaining and everyday living. The heart of the home boasts a cozy gas fireplace with glass doors, creating an inviting atmosphere for gatherings. The partially finished basement provides additional space for recreation or storage, with both interior access and a convenient outside entrance. Enjoy the ease of upper-floor laundry and the comfort of an attached two-car garage with front entry. Set on a generous 0.86-acre lot, this property offers ample outdoor space for relaxation and activities. With no pool to maintain, you can focus on enjoying your surroundings. This residence combines modern convenience with classic charm, making it an ideal choice for discerning buyers seeking a blend of comfort and style.

151 Fox Den Rd, Church Hill

Listing courtesy of Real Estate Professionals, Inc.. Contact:

$464,900
4 Beds 3 Baths
Built in 2024 and tucked away on a quiet, private street in the heart of Centreville, 306 Windsor Ave gives you the best of both worlds, peace and privacy at home with everything downtown just a short walk away. Inside, you'll find a bright, modern interior featuring LVP flooring, granite countertops, gorgeous bathrooms, and generously sized bedrooms with plenty of space to spread out. Step outside to a fully fenced backyard and composite deck, perfect for entertaining, pets, grilling, or relaxing at the end of the day. And the location is hard to beat! Hop on the Millstream Trail and walk to Millstream Park and the Centreville Wharf, or stroll into town for restaurants, shops, coffee, and local favorites. When Centreville's parades, festivals, and community events take over downtown, forget about finding parking, you’re already home. Nearly new. Quiet street. Walkable downtown lifestyle. If you've been waiting for newer construction without giving up the charm and convenience of living in Centreville, 306 Windsor Ave is the one to see.

306 Windsor Ave, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$595,000
4 Beds 4 Baths
This charming 4-bedroom, 4-bathroom townhouse in the desirable Ellendale community offers a perfect blend of modern comfort and inviting warmth. Built in 2023, this Baldwin built home features an open floor plan with luxury vinyl plank flooring and carpet in the bedrooms, ideal for both relaxation and entertaining. The spacious kitchen features a large center island and high-quality appliances, including a built-in microwave and dishwasher, making meal prep a delight. Large Deck off dining/kitchen area, too! Enjoy evenings by the fireplace or step out onto the balcony and deck to soak in the serene views of the garden and open common area. Nearby parks and walking paths invite outdoor adventures, while excellent schools and convenient access to commuter lots and the airport ensure a seamless daily routine. With an attached garage and driveway parking, this home is a true gem in a vibrant neighborhood, ready to welcome you home.

314 Allison Jane Dr Unit #H-2, Stevensville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250

$339,900
2 Beds 3 Baths
NEW PRICE | FEE-SIMPLE CREEKSIDE LIVING ON KENT ISLAND — $339,900! Welcome to 346 Creekside Commons, a rare opportunity to enjoy life along Thompson Creek without the higher condo fees found in many neighboring waterfront communities. This fee-simple, 2-bedroom, 2.5-bath townhome offers approximately 1,240 square feet and an easy two-level layout, but it's the setting that makes this home special. Step through the living room to the rear deck and you'll immediately understand why. Start the morning with coffee overlooking the creek, launch a kayak or paddleboard for an afternoon on the water, watch the wildlife pass by, or simply come home and unwind with the peaceful backdrop of Thompson Creek. Inside, natural light fills the main level, featuring a spacious living room, dining area, kitchen and convenient half bath. Upstairs you'll find two generously sized bedrooms, including a spacious primary suite with its own private bath, plus an additional full hall bath. One of Creekside Commons' biggest advantages is its combination of fee-simple ownership and approximately $160/month HOA dues. Compare that with many neighboring waterfront condo communities with substantially higher monthly fees. Here, you can spend less on community amenities and more time enjoying the amenity that brought you to Kent Island in the first place, the water. Located in Stevensville with convenient access to Route 50, the Bay Bridge, shopping, restaurants and everything Kent Island and the Eastern Shore have to offer. Fee simple. Lower monthly fees. Thompson Creek outside your back door. Bring the kayak. Bring the paddleboard. Choose your paint color and make 346 Creekside Commons home.

346 Creekside Commons Ct, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$899,000
3 Beds 3 Baths
Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add modern convenience throughout. The kitchen has been refreshed with new KitchenAid appliances, backsplash, under-cabinet lighting, updated fixtures and hardware, a new exhaust fan and disposal, instant hot water, and an enhanced pantry with pull-out storage. Just beyond, the mudroom adds both charm and function with brick flooring and Pottery Barn built-ins. The primary suite feels like a private retreat, featuring a completely renovated bath with a custom vanity, Kohler fixtures, and a luxurious BainUltra spa tub with chromatherapy lighting, along with added built-in closet storage. The guest bath and powder room have also been beautifully updated, while the laundry room features new cabinetry, luxury vinyl flooring, and a new GE washer and dryer. Outside, enjoy a private setting backing to trees and a quiet rear alley. Extensive professional landscaping, a drip irrigation system, landscape lighting, new pergola, and added deck railing create an inviting outdoor space for relaxing or entertaining. Even the garage has been thoughtfully upgraded with an EV charger, Elfa shelving, motion-detected lighting, fresh paint, and a GE refrigerator. Located in Gibson’s Grant, one of Kent Island’s most desirable waterfront communities, residents enjoy picturesque streets, walking trails, a community pool and clubhouse, waterfront pavilion, fishing pier, kayak launch, and beautiful views of Macum Creek and the Chester River. With its extensive 2025 renovation, private setting, and coveted Gibson’s Grant location, 148 Elinor Street offers the rare opportunity to enjoy an established coastal community with the feel and finish of a newly designed home.

148 Elinor St, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

$565,000
2 Beds 2 Baths
Experience the relaxed coastal lifestyle you've been dreaming of at 902 Moorings Circle in the highly sought-after 55+ community of Bay Bridge Cove! This beautifully maintained Oxford Model villa offers the perfect blend of comfort, convenience, and resort-style amenities on Maryland's Eastern Shore. Designed for easy, one-level living, this 2-bedroom, 2-bath home features a bright, open floor plan filled with natural light. The spacious kitchen boasts granite countertops, modern appliances, and abundant cabinetry, flowing seamlessly into the living room with a cozy gas fireplace. A separate formal dining room provides the perfect setting for holiday gatherings and entertaining. The private primary suite offers a tray ceiling, generous walk-in shower with low entry, dual vanities, and a linen closet. A second bedroom provides flexible space for guests, a home office, or hobbies. New carpet has been installed in both bedrooms for the next owner. Enjoy your morning coffee or evening glass of wine from the screened porch, host summer crab feasts, or fire up the grill on the adjoining paver patio. A spacious crawlspace provides exceptional storage, while the attached two-car garage adds everyday convenience. Bay Bridge Cove offers more than a home—it's a lifestyle. Residents enjoy a beautifully appointed clubhouse with a fitness center, yoga studio, game room, gathering spaces, and an outdoor pool. Walking trails, scenic ponds, and a full calendar of clubs and social events make it easy to stay active and connected. Located on Kent Island just minutes from the Chesapeake Bay Bridge, you'll enjoy quick access to Annapolis, Baltimore, Washington, D.C., Ocean City, and Delaware beaches while coming home to the peaceful charm of the Eastern Shore. Whether you're boating, fishing, dining on the waterfront, or simply enjoying the slower pace of life, this home offers the perfect place to embrace your next chapter.

902 Moorings Cir Unit #10, Stevensville

Listing courtesy of Samson Properties. Contact: 3018500255

$1,675,000
3 Beds 4 Baths
105 Night Heron is a substantially expanded and renovated home offering more than 4400 square feet of finished living space plus an additional 850 square feet of finished, conditioned, multi-purpose garage space. The property features expansive water views and numerous high end finishes including custom Omega cabinetry, granite and black walnut countertops, extensive built-ins, premium Miele, Viking and Sharp appliances, hardwood and limestone flooring, Kohler fixtures, a custom coffered bar-room ceiling, a 500-bottle wine storage room, and extensive recess lighting. The main floor boasts a dream kitchen with breakfast area and fireplace and a formal dining room off the foyer with designer lighting that is included in the sale. A bar and billiards room has custom cabinetry, a pool table and seating area with fireplace, and views of Eastern Bay. Also on this floor is a formal living room with fireplace, a home office with Bay views, and a large mud-laundry room with adjoining powder room. The large primary suite has 3 closets in the bedroom area as well as a walk in closet and dressing room with custom cabinetry and natural light. The large primary bath has custom cabinetry with lots of storage, a separate tub and shower, dual sinks, limestone floors and a separate water closet. The second floor loft opens to two more bedrooms and a shared bath. One of the bedrooms leads to a veranda with stone fireplace and sweeping views of Eastern Bay. Appliances include a Miele refrigerator and freezer, Viking gas range, dishwasher, microwave, warming drawer, beverage and wine coolers, washer and dryer, garage refrigerator and beverage station and a Napoleon outdoor grill. Televisions and sound bars located in the bar area, club room, second floor loft and kitchen are included in the sale. The garage includes two Lift Master garage door openers, two SunPro motorized screens and RaceDeck flooring. Cove Creek Club is situated on 334 acres of large home sites with beautiful landscaping and views of Eastern Bay. Amenities include a USGA rated golf course, a private marina with direct access to Eastern Bay, boat ramp and storage yard, a private sandy beach, tennis, basketball and bocce ball courts, a club house and event facility, pro shop, walking and biking trails, and an exercise facility. It is conveniently located to Annapolis, Baltimore, Washington DC and Philadelphia.

105 Night Heron Ct, Stevensville

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

$559,999
4 Beds 3 Baths
Welcome to 120 Meadowcroft Drive, where space, style, and your own backyard retreat come together! Offering over 3,100 square feet, this beautifully updated home is designed for both everyday living and entertaining. Step inside to find LVP flooring throughout the main level, fresh finishes, and a spacious, functional layout. The kitchen features quartz countertops, generous workspace, and plenty of room to gather. A main-level office provides the perfect space for working from home. Upstairs, you’ll find four generously sized bedrooms, including a primary suite you won’t want to leave, a spacious retreat designed for relaxing at the end of the day. Upper-level laundry adds everyday convenience, while new carpet in 2026 gives the entire level a fresh, move-in-ready feel. Outside is where this home really shines. Enjoy your own private backyard escape with a saltwater in-ground pool, new pool pump, and a pool liner just 3 years old. Two decks provide plenty of room for grilling, outdoor dining, entertaining, or simply relaxing poolside. Major updates include a NEW ROOF in 2024 offering added peace of mind for the next owner. With 4 large bedrooms, over 3,100 square feet, a main-level office, upper-level laundry, updated finishes, multiple outdoor living spaces, and a saltwater pool, 120 Meadowcroft Drive offers the space and lifestyle you’ve been waiting for!

120 Meadowcroft Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$619,900
5 Beds 3 Baths
New Construction, Ready September, this new home features 4 bedrooms, 2.5 bathrooms, and the builder’s highly sought-after 3rd Floor Sky-Basement. This home combines comfort, style, and versatility. The main level boasts an open floor plan with luxury vinyl plank flooring and crown molding throughout. A flex room off the foyer is ideal for a home office or formal living area. The gourmet kitchen features granite countertops, white shaker cabinets, stainless steel appliances, and a large breakfast bar, seamlessly connecting to a bright and airy sunroom—perfect for casual dining and entertaining. The spacious family room offers a cozy retreat for relaxing evenings. A stylish mudroom with a barn door and built-in bench leads to the attached 2-car garage. Upstairs, the owner’s suite includes a spacious walk-in closet and a spa-inspired bath with double vanities. Three additional bedrooms and a full hall bath offer plenty of room for family or guests. The third-floor Sky-Basement is fully finished with its own HVAC system—ideal for a rec room, gym, media space, or extra storage. Located in a quiet, neighbor-friendly community with convenient access to commuter routes, including US-50, this home is a perfect blend of luxury and accessibility. Sales price reflects builder promotion with the use of a preferred lender and title company. See the sales agent for details. Photos are for illustrative purposes and may show optional features. Home is under construction.

157 Fawn Ln, Grasonville

Listing courtesy of Island Realty, LLC. Contact:

$575,000
4 Beds 4 Baths
Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access to nearby trails, shopping, dining and everything Kent Island has to offer. Coming soon — stay tuned for your opportunity to see this spacious, updated Cloverfields home!

624 Davol Rd, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$649,500
4 Beds 3 Baths
LIKE NEW HOME located in the Romancoke on the Bay community featuring 4 bedrooms, 2.5 baths & 2-car side-entry garage situated on a 0.67 acre lot backing to TREES. Walking up to the home the Walk is Stamped Concrete which leads to the Stamped Concrete COVERED Front Porch & Upgraded Front Door. Upon Entering the Home the MAIN Level Features: Primary Bedroom w/ large walk in closet & En-suite Bath w/ Tiled Stall Shower & oversized White Vanity * Luxury vinyl plank flooring throughout the Foyer, Kitchen, Dining & Family Rooms * Gourmet Kitchen w/ White soft-close cabinets, Stainless Appliances, MARBLE countertops & step up counter overlooking Spacious Family Room complete w/ Propane Fireplace * Laundry Room w/ Washer/Dryer included + additional cabinetry w/ Marble countertops * Separate Dining Room w/ pass- thru to Kitchen * Upgraded baseboards & Handrails * Slider off Family Room to 16x20 Stamped Concrete Patio. Upstairs you'll find 3 Spacious bedrooms, all w/ AMPLE Closet space, Additional linen closets in the Hallway & Full Bath w/ Luxury Vinyl Floors, White Vanity & Tub/Shower. Boasting just over 2100sq ft, this home has Elegant features & is Waiting for YOU to Call it HOME! Recent Improvements include: Paved Asphalt Driveway, Kohler Whole House Generator, OWNED 250 gallon Propane Tank, Direct Propane Connection for 2 Grills on the Patio, Gutter Guard system, Custom Hunter Douglas Blinds Throughout the Home, Whole House Water Filtration System + RO system at Kitchen Sink & Exterior Landscaping! Lot has been expanded in size since the original sale providing potential for Pole Barn or other uses! County has approved Olive Branch Rd for paving to be completed approx. Q4 2026/Q1 2027. Home can possibly become active sooner with suitable rent back option for sellers.

136 Olive Branch Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$799,900
4 Beds 3 Baths
Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, Chester

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848