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$1,250,000
5 Beds ⋅ 3 Baths
Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$825,000
4 Beds ⋅ 3 Baths
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 Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida 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. Recent improvements include two new (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. 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. 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
$1,350,000
4 Beds ⋅ 3 Baths
WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

104 Port Ct, Grasonville

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

$499,000
4 Beds ⋅ 3 Baths
Welcome to 336 Timber Lane—a beautifully maintained Colonial offering the space, comfort, and lifestyle today's buyers are looking for, all in a convenient Grasonville location just minutes from Kent Island and the Bay Bridge. With over 2,100 square feet, this move-in ready home features 4 bedrooms, 2.5 baths, hardwood flooring, a cozy fireplace, and a spacious, flowing floor plan designed for everyday living and effortless entertaining. The bright kitchen overlooks the family room, creating the perfect gathering place for holidays, game nights, or simply spending time together. Upstairs, the spacious primary suite offers a peaceful retreat with a walk-in closet and private en-suite bath, while three additional bedrooms provide flexibility for family, guests, a home office, or fitness space. Step outside and enjoy a generous backyard with plenty of room for entertaining, gardening, play, or simply relaxing after a day on the water. One of Grasonville's best-kept secrets is the lifestyle. You'll enjoy quick access to marinas, waterfront restaurants, boating, fishing, shopping, and Route 50—all while experiencing less congestion than many neighboring communities. Best of all, this home offers an incredible opportunity to enjoy the Eastern Shore lifestyle while getting more home for your investment than many comparable properties on Kent Island. Whether you're commuting, raising a family, or looking for a place to enjoy everything the Chesapeake Bay has to offer, 336 Timber Lane delivers the perfect blend of space, value, and location.

336 Timber Ln, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810
$1,470,000
5 Beds ⋅ 5 Baths
Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the Outlets. Just minutes from the Bay Bridge, this beautifully updated home delivers the best of Eastern Shore living with 259' waterfront, community pier, good schools and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water a breeze, while the waterfront backyard soaks up the sun and wildlife on Winchester Creek. This beautiful home features more than 4,400 square feet on three finished levels with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work, creating an everyday space that is upscale yet comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook, and a redesigned island perfect for gathering with family and friends. The first floor also boasts a two-story foyer, formal dining room, and a comfortable living room/study complete with large windows and a 2nd fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel thoughout. Enjoy beautiful water views from the main-level primary suite that features California Closets, a beautifully remodeled spa-inspired bath and a cozy bay window sitting area. The second waterfront ensuite provides ideal accommodations for guests, extended family or single-floor living. The second level features three additional bedrooms and a versatile bonus room ideal for a home office, homework or as a second family room. The third level is designed for entertaining, complete with a wet bar, beverage cooler, full bath and surround sound. It's perfect for game days, movie nights, or extended-stay guests. Set on more than 1.37 acres, the property offers privacy, an expansive lawn, updated landscaping, abundant wildlife and sweeping water views. Enjoy morning coffee as the sun rises over the water and glowing sunsets from the new TimberTech deck and covered porch. The slip at Homeport's 4MLW private pier is almost next-door for an early morning ride or sunset cruise. Whether hosting family and friends, raising children, enjoying pets in the backyard or unwinding by the water after a day on the boat, this setting is thoughtfully designed for comfort and ease. Extensive recent improvements in the dedicated utility room include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system. The home also features smart thermostats on each floor, ceiling fans throughout, a Vector security system, invisible pet fence, professional landscaping, nearly all new lighting inside & out, updated bathrooms and more. Enjoy Chesapeake living with easy access to Annapolis and the Bay Bridge.

109 Starboard Ct, Grasonville

Listing courtesy of Northrop Realty. Contact: 4105310321
$525,000
3 Beds ⋅ 4 Baths
Save up to $320/month with a Lender Paid 1 Point Buy Down with accepted offer by 6/30/26 - Ask Lender for details! Welcome to 114 Bayview—where your boat days get a serious upgrade. This home includes a private boat slip in the community marina with direct access to Kent Narrows, putting you just a 30-minute ride to St. Michaels, Rock Hall, or Cambridge. If you’ve been dreaming about pulling up to waterfront restaurants or spending full days on the water… this is your launch point. Back at home, enjoy front-row views of the 4th of July fireworks, all without leaving your property. Inside, this home is completely turn-key with LVP flooring, fresh paint, and an updated primary bath. Each bedroom features its own private bath, making it ideal for guests, roommates, or weekend hosting. The garage offers the storage every boater needs—perfect for kayaks, paddleboards, bikes, and all your gear. Even better? This home can be sold furnished, making it a true move-in-ready or weekend getaway opportunity. All of this—boat slip, water access, views, updates, garage, and flexibility—offered at just $540,000. If you’ve been waiting for an easy, low-maintenance way to live the Eastern Shore boating lifestyle… this is it.

114 Bayview, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810
$1,215,000
3 Beds ⋅ 4 Baths
Perfectly positioned along the living shoreline of the Chester River, this waterfront residence in the gated community of Narrows Pointe offers breathtaking, million-dollar water views and a lifestyle centered around the beauty of the Eastern Shore. One of the few wide units in the community, the home is thoughtfully designed to maximize its remarkable setting. Three-panel sliding glass doors invite in abundant natural light while framing sweeping water views, and decks on two levels with retractable electric screens create inviting spaces to relax while overlooking the shoreline. A spectacular arrangement of windows throughout the home continually draws your eye to the tranquil river setting. Another plus- Seller has paid the current $10,000 assessment, so the buyer will not be obligated to that. Inside, hardwood flooring, recessed lighting, and a neutral color palette welcome you upon entry. The gourmet kitchen serves as the heart of the home and features granite countertops, a center island with breakfast bar, tile backsplash, wine refrigerator, and 42-inch cabinetry with under-mount lighting and convenient roll-out drawers for easy organization. High-end stainless steel appliances complete the space, and the adjacent dining room provides a bright setting for everyday meals or entertaining. Just off the kitchen, a walk-in pantry and laundry room add everyday convenience and extra storage. Also on the kitchen level is a bedroom suite currently used as an office, enhanced with built-ins that create a comfortable workspace while still offering flexible guest accommodations. The living room showcases a dramatic angled ceiling, a striking stone fireplace, and custom built-ins, creating a warm gathering space while keeping the focus on the surrounding water views. Upstairs, generously sized bedrooms each include en-suite baths with granite-topped vanities. The primary suite offers a peaceful retreat with a walk-in closet featuring built-in organization, a private deck overlooking the river, and a luxurious bath with remote blinds, double vanity, jetted self-cleaning tub, and Toto toilet. Both of the upper-level bedrooms were enhanced with updated hardwood flooring in 2020. The lower-level recreation room adds another versatile living area with a custom bar and cabinetry, making it an ideal space for entertaining. The finished garage features a granite flake floor and storage cabinetry, and the home also includes a whole-house speaker system. Architectural plans are available for the future addition of an elevator. Recent improvements include whole-house interior painting completed in 2020, replacement of the living room sliding glass door, updated electric screens, a 75-gallon water heater, built-ins throughout, professional installation of a TV mount above the fireplace, finished garage upgrades, carpeting and stair runner, water softener, and more. Located near the heart of Kent Narrows, the home offers easy access to a casual waterfront lifestyle with marinas, boating activities, community piers, a kayak launch, and a variety of waterfront restaurants and tiki bars. The Cross Island Trail begins just outside the Narrows Pointe entrance, while shops, hotels, and multiple fitness centers, some with pools, are all within a convenient 10-minute drive. Nearby outdoor destinations such as the local dog park and Terrapin Nature Park add even more ways to enjoy the natural beauty of Maryland’s Eastern Shore.

350 Narrows Pointe Dr, Grasonville

Listing courtesy of Northrop Realty. Contact: 4102956579
$1,375,000
4 Beds ⋅ 5 Baths
BEAUTIFUL 21 ACRE WATERFRONT ESTATE WITH OVER 400' OF WATER FRONTAGE AND SEPARATELY DEEDED DEEP WATER SLIP IS INCLUDED, SLIP #16 AT THE FAR LEFT END OF THE PIER RIGHT ACROSS THE STREET! APPROXIMATELY 6 CLEARED ACRES AND 15 WOODED ACRES. SPECTACULAR 3-STORY HOME WITH 4 LARGE BEDROOMS W/ENSUITE BATHROOMS. RECENT TOP QUALITY GOURMET KITCHEN RENOVATION W/GAS COOKTOP. IT'S AWESOME! ATTACHED 2-CAR GARAGE AND A MONSTROUS DETACHED GARAGE WITH ROOM FOR 6 MORE CARS. PLENTY OF STORAGE. BEAUTIFUL, PRIVATE INGROUND GUNITE POOL. CALL LISTING AGENT FOR MANY MORE AMENITIES. READ HOA DOCS IN DISCLOSURES. TRY TO GIVE 1-2 DAYS SHOWING NOTICE, PLEASE.

105 Port Ct, Grasonville

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690