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$595,000
6 Beds 7 Baths
Professional Photos Coming Soon - PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the Eastern Shore lifestyle! Beautiful hardwood floors flow throughout the main level, where the kitchen, dining room and family room all take advantage of the spectacular water views. The modern kitchen opens to the living areas, while built-in bookcases and a gas fireplace add character and function to the family room. Step outside to one of two waterside decks and enjoy the ever-changing river views, passing boats and beautiful scenery. Upstairs, wake up each morning to endless WATER VIEWS from the Primary Suite, then step directly onto your private waterside deck with your morning coffee. Bedrooms feature the privacy and convenience of ensuite baths. A large upper-level Bonus Room with its own full bath provides wonderful flexibility—create a 3rd bedroom, spacious home office, a guest suite, den or whatever best fits your lifestyle. The views are even better from up here! Freshly painted and truly MOVE-IN READY, this light-filled end unit offers the combination everyone is looking for—beautiful interiors, flexible living space, two waterside decks and an exceptional location overlooking the Chester River. Bayside offers wonderful community amenities, including a swimming pool, party room, fitness center, tennis/pickleball courts and volleyball. The 38+ mile Cross Island Trail is just around the corner for walking, jogging and biking. You’re also conveniently located near restaurants, grocery shopping, outlet shopping and golf courses. Love boating? The marina bordering the community offers boat slips that may be available for rent or purchase, making it easy to enjoy everything the Chesapeake Bay and Eastern Shore have to offer. Come experience the Kent Island waterfront lifestyle—beautiful views, boating, recreation and convenience, all right outside your door!

1010 Auckland Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535

$659,950
4 Beds 4 Baths
Welcome home to 120 Pathfinder Circle in Perry's Retreat! Built in 2023 and meticulously maintained, this 4 -bedroom , 3.5 bath home offers approximately 3,010 sf of beautify designed living space, where thoughtful upgrades,custom touches,and everyday functionality come together. From the moment you walk in, the attention to detail is impossible to miss. The main level showcases a stunning three-sided fireplace topped with a custom walnut mantel - an eye catching centerpiece that makes the living space feel warm, inviting, and distinctly your own. The kitchen is made for gathering, cooking and entertaining, featuring two ovens and custom -made pendant lighting that adds both function and personality. Throughout the home, an upgraded Craftsman trim package recessed lighting , luxury vinyl plank flooring, and ceiling fans in every room create a polished, comfortable feel. With Ethernet wiring throughout , this home is ready for everything from work from home days to movie nights and streaming marathons. Upstairs, the spacious primary suite feels like a retreat, complete with two walk in closets and a generous shower with dual showerheads. A secondary bedroom with its own ensuite bath offers a private space for guests or family. Two additional flex spaces give you the freedom to create dedicated offices, home gym, playroom or whatever your lifestyle demands. A separate loft adds even additional room to spread out. The back yard is where this property really shines. The 16x40 patio provides an incredible outdoor living and entertaining space, while the privacy fence creates a comfortable, secluded setting. The meticulously maintained landscaping and lush lawn are true standouts and add exceptional curb appeal. With a three car garage, there's plenty of room for vehicles and storage. This is more than a newer home - it's a home that has been thoughtfully enhanced and lovingly maintained. The custom details and flexible spaces truly make it feel special. Come see why 120 Pathfinder Circle is the home you have been looking for.

120 Pathfinder Cir, Grasonville

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

$560,000
4 Beds 3 Baths
Welcome to 135 Crossgate Drive, a beautifully maintained 4-bedroom, 2.5-bath home in Church Hill. Freshly painted throughout and truly move-in ready, this home offers a spacious, functional layout with plenty of room to settle in and make it your own. Step inside to an open, welcoming foyer framed by a graceful staircase, with a dedicated home office on one side and a formal dining room on the other. The kitchen is designed for everyday living and entertaining, featuring a large island, abundant cabinetry, and a sunny eat-in area that flows naturally into the living room, where a cozy fireplace anchors the space. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite with a private bath and walk-in closet. The unfinished basement offers even more possibilities—create a second living space, home gym, playroom, workshop, or simply enjoy the additional storage. An attached two-car garage provides even more space for vehicles, tools, and gear (the walk-in cooler can be negotiated in the sale of the house). Enjoy the charm and quieter pace of Church Hill while remaining conveniently located to Centreville, Chestertown, Route 301, and all that Queen Anne's County and the Eastern Shore have to offer. Thoughtfully cared for, freshly updated, and offering room to grow, 135 Crossgate Drive is ready to welcome its next owners home.

135 Crossgate Dr, Church Hill

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$869,000
4 Beds 4 Baths
Welcome to 128 Lynch Court in the Brand New Starfield Farms Community. To be built with estimated completion Spring 2027 by the reputable craftsmanship of Mike's Custom Homes. This stunning 4 bedroom, 3.5 bathroom residence offers 3400 square feet of thoughtfully designed living space, with an additional 1700 sq feet of unfinished walkout basement, on a 1.4 acre lot. Get in now and customize your selections. Build your dream home with Mike's Custom Homes! Nestled in a serene setting with spacious lots, high-quality craftsmanship, and modern finishes, these homes offer the best of Eastern Shore living. Don’t miss this opportunity to build in a prime location with easy access to local amenities, schools, and major routes. Secure your lot today—contact us for more details! *Photos are of a previously sold model and may feature options that are upgrades.

128 Lynch Ct, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$639,990
2 Beds 2 Baths
Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area offers a spacious and functional space for lounging. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

641 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$574,900
4 Beds 4 Baths
Luxury homes rarely become available. This stunning end unit townhome offering 4 bedrooms, 3.5 bathrooms, and an impressive list of high end upgrades is available in sought after Ellendale Community. Filled with natural light, the open floor plan features hardwood floors, custom plantation shutters, elegant trim, and a built-in Bose surround sound system. The gourmet kitchen is equipped with stainless steel appliances, 42" soft close maple cabinetry, under cabinet & pendant lighting, and backsplash. Escape to the spacious primary suite with a tray ceiling and spa bath or unwind on the composite deck overlooking spectacular sunset views. Remodeled bathrooms, LED lighting throughout, central vacuum and an oversized 2 car garage with custom storage. Located just minutes from the Bay Bridge, you will also enjoy resort style community amenities including a pool, clubhouse, fishing pier, boat storage, and walking trails.

118 Amanda Frances Ln, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$550,000
4 Beds 4 Baths
Room to Breathe. Space to Dream. There is something special about coming home to a place where life feels just a little slower and a bit quieter. Set on a fabulous one-acre parcel surrounded by farms and open countryside, this well-loved home offers a sense of privacy and breathing room that can be hard to find—yet it is still just minutes from the places and conveniences you need. Here, mornings can begin with coffee overlooking your own piece of land, weekends can be spent in the garden, and evenings feel removed from the noise and pace of the day. And with an acre of your own, there is room to imagine what comes next. Create the vegetable and flower gardens you have always wanted. Add an outbuilding, workshop, or hobby space. Spread out, entertain, play, plant, tinker—or simply enjoy having open space around you. The home itself has a wonderful sense of history and has clearly been loved over the years. Inside, you'll find an updated kitchen with granite countertops, warm wood floors, four full baths, a huge mudroom, and generous living spaces that offer flexibility for everyday life, guests, hobbies, or working from home. Then there is the unfinished basement—a whole additional level waiting for the next owner's vision. Perhaps a recreation room, home gym, workshop, studio, additional living space, or simply incredible storage. It is another reminder that this is a property with room not only for how you live today, but for the ideas you may have for tomorrow. Outside, an oversized garage, paved driveway, and expansive parking area provide plenty of space for vehicles, equipment, projects, and gatherings. And while this home has plenty of character and history, many of the less glamorous—but very important—systems have received significant attention in recent years, including the roof, water-conditioning system, French drains, septic system, and more. Some homes are defined by finishes and square footage. This one feels defined by something more: space, privacy, possibility, and the freedom to make it your own. A place with a past, plenty of room for the present, and so many possibilities for what comes next.

746 Hope Rd, Centreville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$439,000
3 Beds 4 Baths
Set along scenic Lake Amletto in the waterfront resort-style community of Queen’s Landing, this three-level garage townhome pairs updated interiors with relaxing water views and an impressive collection of community amenities. Neutral paint, wide-plank luxury vinyl plank flooring, new carpeting, and updates to the kitchen and bathrooms create a fresh, cohesive feel throughout. Step inside to a spacious living and dining room combination designed for easy everyday living and entertaining. The dining area flows into the updated kitchen, with a breakfast bar providing a natural transition between the spaces. Quartz countertops, stainless steel appliances, and a subway tile backsplash give the kitchen a polished look, while its open connection to the adjacent family room keeps the layout inviting and functional. A sliding glass door leads from the family room to the deck, where views of Lake Amletto create a peaceful backdrop for dining or unwinding outdoors. Upstairs, all three bedrooms feature vaulted ceilings that enhance the sense of space. The primary bedroom includes two closets and a stylish vanity area, along with a private water closet featuring a tiled tub and shower surround with a soaking tub. Two additional bedrooms share the hall bath, where a vaulted ceiling and statement light fixture lend an elevated feel. The lower level adds valuable flexibility with a recreation room and sliding glass door opening to the backyard. A separate laundry room is also located on this level, along with interior access to the attached one-car garage. Just inside the garage, a convenient drop zone helps keep everyday essentials organized, while the painted garage offers additional storage space. Beyond the home, Queen’s Landing delivers a true waterfront lifestyle along the Chester River on Kent Island. Residents enjoy a heated waterfront pool, clubhouse, fitness center, indoor racquetball court, tennis and pickleball courts, walking paths, kayak storage and launch areas, and a resident-only 62-slip marina. With Lake Amletto just outside and access to Kent Narrows, Eastern Bay, and the Chesapeake Bay nearby, this inviting home offers an ideal blend of updated comfort, water views, and resort-style living. Please note: photos depicting furniture have utilized virtual staging.

41 Queen Catherine Ct, Chester

Listing courtesy of Northrop Realty. Contact: 4104651770

$819,900
3 Beds 3 Baths
Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedroom enhanced by a three-foot extension. A first-floor study offers flexible space for a home office, den, or possible fourth bedroom. Thoughtfully designed and exceptionally well-maintained, the home offers numerous updates and features, including a new roof installed in 2026 with a transferable manufacturer’s warranty and a new kitchen completed in 2022 featuring GE Café appliances, including a professional 36” six-burner range with convection oven, an additional oven in the island, and an Advantium speed-cook microwave. The kitchen appliances are under warranty through February 2028. The Primary Bathroom was renovated in 2019 and features heated floors, an oversized shower, and a customized makeup vanity. A Rinnai tankless hot water system provides efficient, on-demand hot water. The main level features beautiful hardwood floors, a convenient half bath, motorized window blinds in the Family Room, and a Ring security system. The home also offers a spacious basement crawl space with convenient interior access, providing valuable additional storage for seasonal items and household belongings, as well as a water-powered backup sump pump for added peace of mind. Outdoor spaces are equally inviting, with a welcoming front porch, spacious rear deck, rear patio, fenced yard, and a propane quick-connect hookup on the deck for a grill, making outdoor cooking and entertaining easy and convenient. A rear-entry two-car garage with a three-car parking pad provides ample parking. The garage includes a refrigerator, a freezer with a warranty through October 2027, a storage system, and electric bike lift with an HDTV antenna mounted on the garage roof. Upstairs are two additional bedrooms and a full bathroom, while the finished room above the garage offers flexible living, office, hobby, or recreation space and features a split-system HVAC for year-round comfort. Enjoy all that Gibson’s Grant has to offer, including water access to Macum Creek and the Chester River, a community pool, clubhouse, fitness center, kayak launch, walking trails, playgrounds, and scenic open spaces. Ideally located just minutes from the Bay Bridge, shopping, dining, and everything Kent Island has to offer, this exceptional home provides the perfect combination of quality construction, thoughtful updates, flexible living spaces, and a wonderful waterfront community lifestyle.

207 Thomas White Blvd, Chester

Listing courtesy of RE/MAX Components. Contact: 4433535281

$749,990
2 Beds 3 Baths
Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

536 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$400,000
3 Beds 2 Baths
Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend retreat, full-time residence, recreational getaway, or potential future waterfront homesite, this property offers plenty of possibilities. Convenient access to US Route 301 provides easy travel to Delaware and surrounding Eastern Shore communities. Enjoy 7.19± acres of Chester River waterfront with hunting, fishing, and boating opportunities on Maryland’s Eastern Shore.

405 Rings End Rd, Millington

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$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:

$1,100,000
3 Beds 4 Baths
The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

117 Flycatcher Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$868,000
4 Beds 3 Baths
OPEN SUNDAY SEPT 20, 11;30;AM-1:30 PM--A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$998,000
3 Beds 3 Baths
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

111 Marshgrass Way Unit #41, Chester

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

$374,900
3 Beds 2 Baths
ALL NEW Carpet & flooring, fresh custom paint, Granite countertops and Newer Appliances! Welcome to one of the most desirable homes in the Bridgepointe community! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after amenities... an ATTACHED GARAGE with interior access! This exceptional home also offers a MAIN LEVEL Primary bedroom & full bath, first floor laundry, making it ideal for guests, multigenerational living, a home office, or anyone seeking the convenience of main level living. Step inside to discover bright, inviting living spaces enhanced by the additional windows that only an end unit can provide. The open concept layout creates an effortless flow for both everyday living and entertaining. The well-appointed kitchen opens to the main living areas while the spacious bedrooms provide flexibility for family, guests, or work-from-home needs. Enjoy the best of low maintenance living in the highly desirable Bridgepointe community, with easy access to shopping, dining, parks, schools, marinas, and the Chesapeake Bay. Commuters will appreciate the close proximity to the Bay Bridge, Route 50, Annapolis and Maryland's Eastern Shore. Whether you are searching for a full-time residence or a weekend retreat, this exceptional home offers the perfect combination of location, lifestyle, and value.

2004 Bridgepointe Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$899,990
3 Beds 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

532 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$929,990
3 Beds 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

540 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$749,000
4 Beds 3 Baths
PRICED TO SELL - RARE OPPORTUNITY - Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful Golf Course Views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Brookhaven cabinets, Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida ( or four seasons) room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Select spaces have been refreshed with new interior paint and elegant crown molding (2025), adding a touch of sophistication and style. Recent improvements include Dual-Zone Hybrid HVAC (2024/2026): Customized upstairs/downstairs comfort with two brand-new 2026 Lennox HVAC units with heat pumps and smart thermostats, backed by a Navien tankless combi-boiler Installed in 2024 for ultra-efficient, multi-zone hydronic heating. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026). Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. The monthly HOA Fees INCLUDE Golf Membership and Greens Fees. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

116 Prospect Bay Dr W, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535

$595,000
2 Beds 3 Baths
Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$599,900
3 Beds 3 Baths
Recently Reduced and Ready for Its New Owner! Experience the best of Eastern Shore living at 1024 Avalon Court, where spacious design, natural light, and a peaceful setting come together beautifully. Perfectly positioned on a desirable lot with views of the community pond area and protected woodlands, this exceptional residence offers a wonderful blend of privacy, comfort, and everyday convenience. From the inviting exterior with stone accents and a two car garage to the open interior layout and exceptional outdoor living spaces, this home is designed for easy living and effortless entertaining. Step inside to a welcoming foyer with neutral paint and a bright, airy feel that continues throughout the main level. The thoughtfully designed floor plan offers excellent flexibility with formal living and dining areas, generous open gathering spaces, and seamless flow between rooms. Expansive windows bring in beautiful natural light while framing peaceful rear views, creating a warm and inviting atmosphere throughout the home. The heart of the home is the open concept kitchen and family room area, ideal for both everyday living and entertaining. The kitchen features abundant cabinetry, granite counters, stainless steel appliances, recessed lighting, a center island cooktop, and direct connection to the surrounding living spaces. The spacious family room offers a cozy fireplace and easy access to the private screened porch and large raised concrete patio, two standout features rarely found in this community. Both outdoor spaces overlook the community pond area and protected woodlands, creating a private and peaceful backdrop for relaxing, dining, and entertaining. The home continues with spacious bedrooms, including a large main level owner’s suite with generous closet space and a private bath featuring dual vanities, a soaking tub, and separate shower. This main level suite offers excellent flexibility for multigenerational living, guests, or those seeking everyday convenience. Additional bedrooms on the upper level provide comfortable space for family, guests, home office needs, hobbies, or recreation. Outdoor living is truly a highlight, with multiple areas to enjoy the serene wooded setting. The private screened porch is perfect for morning coffee, quiet evenings, or relaxing without the elements, while the oversized raised concrete patio offers wonderful space for grilling, entertaining, or simply enjoying the peaceful rear views. Additional highlights include flexible living spaces, a heated and air conditioned two car garage with amazing storage, and a peaceful rear setting rarely found in such a convenient location. Ideally positioned with easy access to major commuter routes including Routes 50 and 301, this exceptional residence offers convenient access to Downtown Annapolis, Washington, D.C., Baltimore, Kent Island, the Bay Bridge, Middletown, Dover, NSA, Fort Meade and Dover Air Force Base. Enjoy great local amenities including restaurants, shopping, recreation, and all the lifestyle conveniences that make the Eastern Shore so desirable. Don’t miss out on this incredible opportunity!

1024 Avalon Ct, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$825,000
4 Beds 4 Baths
Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

232 Evelyne St, Chester

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

$679,900
3 Beds 2 Baths
Welcome to Meadow Creek. Estate homes on acre plus homesites with plenty of room for a pool and a separate garage.. In the country but close to downtown Centreville. Centreville offers restaurants, grocery stores, parks and schools. This one level home features a formal dining area flanked by columns as well as three nicely sized bedrooms and a large living area with gourmet-appointed island kitchen, breakfast room and optional morning room on one level. Your owner’s bath includes a separate soaking tub and shower or you may choose to install the large enclosed spa shower and closet for linens. Plan features a main level washer/dryer laundry/mud room and a lower level which can be customized to meet your needs. **Special offer Construction financing** Models shown with options

319 Twin Meadows Farm Ln, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$969,000
4 Beds 3 Baths
STUNNING NEW CONSTRUCTION – Experience the pinnacle of modern luxury in this exquisite "Farmhouse Chic" masterpiece, perfectly situated in a highly coveted Kent Island community near the shores of the Chesapeake Bay. Offering over 2,600 square feet of meticulously crafted living space, this residence features 4 spacious bedrooms, 2.5 designer baths, and a versatile retreat living space tailored for contemporary life, with optional 5th and 6th bedrooms. Covell Signature Homes provides well-crafted homes specified to fit YOUR needs! Act soon and you can DESIGN YOUR DREAM HOME the way YOU want it, with all the finishes, options and features that work for YOUR life. The home’s striking exterior sets the stage for the upscale finishes found within. Step inside to an expansive open-concept Great Room and a gourmet kitchen designed for the culinary enthusiast, complete with high-end stainless-steel appliances, premium countertops, and a massive island perfect for entertaining. Durable, luxury vinyl plank flooring flows seamlessly throughout the main areas, leading to a dedicated private study—the ideal sanctuary for a home office or library - or an optional 5th bedroom. Retreat to the upper level where the additional living area provides a second gathering spot, while the primary suite offers a spa-like escape. The retreat living space can also convert to a 5th or 6th bedroom. Every inch of this home reflects a commitment to quality and style, blending rustic farmhouse charm with sophisticated, high-end details. The lifestyle is equally unmatched. Located in a premier water-access community, you can keep your boat at the Queen Anne Marina, enjoy a round of golf at the adjacent Blue Heron Golf Course, or explore the island’s famous waterfront dining just minutes away. This is more than a home; it is an incredible opportunity to own a piece of the Kent Island dream!

416 5 Farms Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$995,000
5 Beds 5 Baths
Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

215 Kingfisher Ln, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$949,000
4 Beds 3 Baths
STUNNING NEW CONSTRUCTION located within the highly sought-after water-access community of Queen Anne’s Colony. Welcome to the Talbot, a beautifully designed, single-level residence offering over 2,000 square feet of thoughtfully designed living space, complete with 4 bedrooms and 2.5 baths. This exceptional coastal Craftsman-style home on Kent Island blends modern luxury, elegant design, and upscale finishes. The exterior showcases HardiePlank lap siding, signature Craftsman-style double columns, and a full-length front porch that creates inviting curb appeal, along with upgraded front and garage doors that enhance the home’s character and charm. Inside, the open-concept kitchen is beautifully designed, featuring upgraded cabinetry with dovetail construction and soft-close doors and drawers, quartz countertops, and a high-end GE Café appliance package. Additional highlights include a custom trim package that includes a brick-surround fireplace flanked by custom built-in shelving units, a soaring cathedral ceiling in the Great Room with white painted beams and shiplap trim, durable luxury vinyl plank flooring throughout the main living areas, and beautifully tiled shower surrounds, offering both style and functionality at every turn. Enjoy an unbeatable location with stunning water views, peaceful streets, and a true sense of community. Keep your boat at Queen Anne Marina within the neighborhood, take a leisurely stroll to the adjacent Blue Heron Golf Course and enjoy being just minutes from a variety of exceptional waterfront dining and local restaurants. Incredible opportunity you won't want to miss!

410 5 Farms Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$425,000
3 Beds 4 Baths
THIS TOWNHOME IS NOT ONLY A VALUE FROM A PRICE PER SQUARE FOOT, THE SELLER IS OFFERING TO PAY ONE YEAR OF HOA FEES $8,040. SO YOU WILL NOT HAVETO PAY FEES FOR A YEAR PERIOD! Waterfront Lifestyle with Included Boat Slip – Bayview at Kent Narrows Experience the best of Eastern Shore living in this beautifully renovated 3-bedroom, 3.5-bath contemporary townhouse with garage, ideally located just over the Kent Narrows Bridge in the sought-after Bayview waterfront community. Waterview's from second and third floor bedrooms. This move-in-ready home features a stunning new kitchen with stylish gray shaker cabinetry, granite countertops, and stainless-steel appliances. The open-concept living and dining areas are enhanced by new luxury vinyl plank flooring, creating a modern, inviting space perfect for everyday living and entertaining. The spacious primary suite offers vaulted ceilings, abundant natural light, a ceiling fan, double closet plus walk-in closet, and a dressing area. The completely renovated spa-inspired primary bath is a true showstopper, featuring a luxurious oversized double shower with dual shower heads, built-in benches, niches, and sleek glass doors. Two additional generously sized bedrooms provide excellent flexibility, including one with a private en-suite bath, plus a third full bathroom for guests. Step outside and embrace the water-privileged lifestyle this community offers. Your assigned boat slip is in the private community marina, complete with water and electricity, and included in the monthly condo fee. Launch directly into Muddy Creek, which leads straight to the Chester River—putting you just minutes by boat from Red Eye Dock Bar, Harris’ Crab House, and The Dock House Restaurant.

109 Bayview, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$529,000
4 Beds 4 Baths
NEW PRICE ....Welcome to 142 Harmony and this beautiful Beethoven model home featuring 4 bedrooms and 3 and one half bath. Situated on a lot that is just a short walk to the community club house, pools and all amenities, this home is designed with a beautiful brick front. As you enter, the floor inviting floor plan welcomes you with the living and dining area on the front of the home and stairs to the side to the upper level. Moving through you'll enter the very large family room with fireplace and the oversized gourmet kitchen with additional cabinets. The breakfast area off of the kitchen allows for relaxing views of the rear patio. The master suite is also located on the main level with master bath featuring a walk-in shower and a walk-in jetted tub. This suite also has two walk-in closets and additional stairs to the upper level. To complete the main level of the home is a half bath and laundry room with access to the garage which includes a sky basement for storage above. The second level of the home offers a very large additional area that can be utilized in many ways along with a carpeted walk-in storage area that can be utilized as a closet or utility room. To complete the upper level is a sitting room overlooking the family room below along with another bedroom and full bath. This home is move in ready and available for a quick settlement.

142 Harmony Way, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900