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12 Greenwood Shls, Grasonville
$549,000
3 Beds ⋅ 2 Baths
Enjoy easy one-level living in the highly desirable Prospect Bay community at 12 Greenwood Shoals. Set on just over an acre, this inviting three-bedroom, two-bath home offers the convenience of having all of your main living spaces on one level, paired with a peaceful setting in one of Grasonville’s most sought after golf and waterfront communities. Inside, a functional floor plan creates comfortable spaces for everyday living and entertaining with an open concept living room and kitchen that opens up to a large deck overlooking the backyard. The primary suite has a large closet and the two additional bedrooms offer plenty of space for guests or a home office. An oversized two-car garage offers exceptional additional space with room for storage, a golf cart, kayaks, canoes, or other outdoor gear - perfectly suited for the Prospect Bay lifestyle. A newer gutter system adds another thoughtful update to the home. Outside, the spacious fenced backyard is surrounded by mature trees, providing wonderful shade and creating a private, peaceful setting for relaxing, entertaining, pets, or play. Updated landscaping enhances the home’s curb appeal, while shallow water access from the property provides an ideal spot to launch a kayak or canoe and explore the surrounding waterways. Living in Prospect Bay means enjoying a lifestyle centered around recreation and community, with amenities including an 18-hole golf course, swimming pool, tennis and pickleball courts, clubhouse with restaurant and bar, marina, boat ramp, social activities, and more. Owner/Agent.

12 Greenwood Shls, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

330 Prospect Bay Dr W, Grasonville
$849,000
5 Beds ⋅ 3 Baths
NEW PRICE! Won't last long! From the moment you arrive, this exceptional home is sure to impress. Beautifully renovated and impeccably maintained, it feels fresh, modern, and anything but 28 years old. Located in the sought-after Prospect Bay community, this remarkable property offers water access, amenities galore, and the relaxed atmosphere of country-club living on Maryland’s Eastern Shore. A brick walkway and steps lead to the beautiful front porch and an impressive foyer with soaring ceilings, designer paint, and elegant board-and-batten detailing. The dramatic sightline extends through the great room to a wall of windows and two sets of glass French doors opening to the inviting screened porch. The modern eat-in chef’s kitchen is a showstopper, featuring quartz countertops, glass-front cabinetry, abundant storage, and a charming bay-window dining area. Wide-plank, wood-look, porcelain tile flooring flows throughout the main living areas, offering the beauty of wood with exceptional durability. Just off the kitchen, the spacious mudroom includes front-loading laundry machines, a utility sink, cabinetry, generous counter space, and convenient access to the two-car side-load garage. At the heart of the home, the breathtaking great room features soaring ceilings, board-and-batten walls, a wood-burning fireplace, and a dramatic wall of windows overlooking the lush backyard. Glass French doors lead to the expansive screened porch with wood flooring and high ceilings—an idyllic setting for morning coffee, relaxed dinners, and effortless entertaining. Beyond the porch, a spacious paver patio overlooks the peaceful, beautifully landscaped yard, enclosed by a newer white picket fence. The main level also offers an elegant formal dining room and three generously sized bedrooms, including the luxurious primary suite. The primary retreat features a walk-in closet and spa-inspired bath with dual vanities, porcelain tile flooring, a frameless glass walk-in shower with marble walls, and on-trend lighting and hardware. Gorgeous hardwood stairs lead to the upper-level overlook, where wide-plank engineered hardwood flooring continues throughout two additional bedrooms and a beautifully renovated full bath with a glass-enclosed walk-in shower and porcelain tile flooring. The flexible five-bedroom layout provides exceptional space for guests, home offices, hobbies, and/or multigenerational living. Outside, the private and beautifully landscaped lot is equally impressive. A charming backyard shed has been customized with an automatic garage-style door to accommodate a golf cart, while the expansive driveway provides parking for four or more vehicles in addition to the two-car garage. Peaceful, private, and polished from top to bottom, this extraordinary home offers gracious indoor-outdoor living in a community designed for recreation, relaxation, and life near the water. This is more than a home—it is the Eastern Shore lifestyle you have been waiting for.

330 Prospect Bay Dr W, Grasonville

Listing courtesy of Samson Properties. Contact:

Selling Office: Builder Solutions Realty.

350 Prospect Bay Dr W, Grasonville
$849,000
5 Beds ⋅ 4 Baths
Make your dream lifestyle a reality! MOTIVATED SELLERS HAVE FOUND THEIR HOME OF CHOICE! Bring your offer! With two primary suites, a renovated in-ground pool, more than an acre of privacy, and extensive updates throughout, 350 Prospect Bay Drive offers one of the best opportunities in its price range. Schedule your showing and bring your offer! Welcome to 350 Prospect Bay Drive, where resort-style living meets everyday comfort on a private 1.02-acre lot in the sought-after community of Prospect Bay. This beautifully updated 5-bedroom, 3.5-bath home offers over 2,700 square feet of thoughtfully designed living space, including two spacious primary suites—a rare feature ideal for multigenerational living, extended guests, or private owner retreats. Inside, soaring cathedral ceilings and an open, light-filled floor plan create an inviting atmosphere. The updated kitchen features refreshed cabinetry, granite countertops, GE refrigerator, double wall ovens, Bosch dishwasher, range hood, and luxury vinyl plank flooring throughout the main living areas. A renovated bonus room provides the perfect home office, hobby room, or flex space for today's lifestyle. Recent improvements offer peace of mind, including a new HVAC system, updated electrical, renovated hall bath, newer chimney liner, updated gutters and downspouts, fresh exterior paint, new garage door, storm doors, lighting, front walkway, fencing, and an architectural shingle roof approximately 10 years old. Step outside to your own private backyard oasis featuring a recently renovated Sylvan concrete in-ground pool, expansive paver patio, mature trees, professional landscaping, and plenty of space to entertain, relax, or simply enjoy the peaceful Eastern Shore setting. Prospect Bay offers exceptional amenities, including a marina, golf course, clubhouse, swimming pool, tennis courts, and more—all just minutes from the Bay Bridge for an easy commute to Annapolis, Baltimore, and Washington, D.C. Move in before summer ends and start enjoying your own private pool! This is a rare opportunity to own one of Prospect Bay's best values with space, privacy, and an incredible lifestyle! Very well maintained and one-year home waranty for added peace of mind.

350 Prospect Bay Dr W, Grasonville

Listing courtesy of CENTURY 21 New Millennium. Contact:

Selling Office: Gunther-McClary Real Estate.

5 Prospect Bay Dr W, Grasonville
$820,000
4 Beds ⋅ 3 Baths
This charming ranch-style home in the desirable Prospect Bay community offers a perfect blend of comfort and elegance. With 4 spacious bedrooms and 3 full baths, the traditional floor plan features a cozy family room off the gourmet kitchen, ideal for gatherings. Enjoy upgraded countertops and a pantry, complemented by modern stainless steel appliances and huge center island. The large 3 Season room offers great flex space and views of the course. Enjoy the benefits of a tankless hot water, too! Step outside to a serene 1.01-acre lot with a rear yard, perfect for outdoor activities. The expansive deck invites you to relax while taking in stunning views of the nearby golf course. Community amenities include a refreshing pool and easy access to Prospect Bay, where you can enjoy canoeing, kayaking, and fishing. Conveniently located less than 10 miles from the airport, this home also boasts an oversized attached garage and ample driveway parking. Experience the warmth of this inviting residence, where every detail is designed for comfort and enjoyment.

5 Prospect Bay Dr W, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

12 Fairway Is, Grasonville
$699,900
4 Beds ⋅ 3 Baths
Back on the market at no fault of the seller. The previous contract was contingent upon the buyer's home sale, and the buyer was unable to secure a contract on their current home within the 60-day contingency period. Inspections and appraisal had been completed. This stunning 4-bedroom, 2.5-bath home sits directly on the golf course, overlooking the 10th hole in the prestigious Prospect Bay community. Hardwood floors flow throughout, with refinished flooring in the kitchen and living area, while large windows fill every room with natural light. The updated kitchen boasts granite countertops, stainless steel appliances, and new lighting above the island, opening to a spacious living area with high ceilings and an open floor plan perfect for entertaining. The first-floor primary suite includes a sitting room or private office, offering comfort and flexibility. Step outside to enjoy the screened-in porch, large pool with hot tub, privacy fence, and beautifully landscaped backyard, all with direct access to the golf course. A new compressor has been installed in one of the HVAC units, new skylights and the home has been freshly painted. Experience the ultimate lifestyle within this vibrant waterfront community—golf, boating, dining, and social events are just steps from your door. The community features a welcoming clubhouse with a restaurant and event space, a pool, and courts for pickleball and tennis. Enjoy a pro shop and driving range, plus a private marina and boat ramp providing direct access to Prospect Bay!

12 Fairway Is, Grasonville

Listing courtesy of RE/MAX Advantage Realty. Contact:

Selling Office: Unrepresented.

40 Greenwood Shls, Grasonville
$1,110,000
4 Beds ⋅ 3 Baths
MAJOR PRICE IMPROVEMENT! Just in time to enjoy your Prospect Bay waterfront home this summer! Welcome home to this waterfront property in the Eastern Shore’s premier golf course community of Prospect Bay. Set on just over an acre overlooking Little Greenwood Creek, this home offers peaceful views, spacious living areas, and direct water access. From the moment you enter, the welcoming foyer with coat closet opens to a bright living room with large windows plus a stone fireplace, and a dining area that overlooks the backyard and water, creating a light-filled space ideal for everyday living and entertaining. The remodeled eat-in kitchen features abundant natural light, granite countertops, and direct access to the deck, where you can enjoy relaxing water views or dine outdoors. The home’s thoughtful layout continues on the lower level with an additional living area, half bathroom, laundry room, and convenient access to the spacious three-car garage. Sliding doors off the lower living area lead directly to the backyard and patio, seamlessly connecting indoor and outdoor living. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with beautiful water views, a walk-in closet, double vanity, and an electric fireplace that adds a cozy touch to the space. Situated on a large lot, the backyard provides plenty of room for outdoor entertaining and offers the potential for a pool overlooking the water. The recently redone pier allows for easy access to Little Greenwood Creek and the Chesapeake Bay, making this an excellent opportunity for those who enjoy waterfront living and boat rides to the Narrows, Saint Michaels, Annapolis, and beyond. Prospect Bay community offers an array of amenities, including an 18-hole golf course, a clubhouse with a members-only restaurant and bar, a marina with a launch, a pool, tennis and pickleball courts, a playground, and year-round social activities. Here, every day feels like a vacation.

40 Greenwood Shls, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

43 Greenwood Shls, Grasonville
$1,240,000
3 Beds ⋅ 3 Baths
Tucked behind mature trees on a private 1.02-acre lot with a creek glimpse from the home, this 4,000+ sq ft coastal home sits inside Prospect Bay, Grasonville's premier golf communities — and it lives every bit as well as it looks. The kitchen is the showpiece. Built for the cook who loves to entertain, it's outfitted with high-end commercial-grade appliances, including a commercial range, anchored by a center island and a walk-in pantry — ready for everything from weeknight dinners to holidays with a full house. Rich hardwood floors run throughout, framed by 9'+ ceilings, crown molding, and recessed lighting that give every room a warm, finished feel. There's room to spread out and room to unwind. A spacious living room addition and a screened-in porch extend the everyday living space, while out back the deck, fenced in-ground saltwater pool, and dedicated pool house turn the private yard into a true retreat. The primary suite is its own escape, with an attached bathroom that features double sinks and luxury shower, walk-in closet, and private deck access. Three bedrooms, 3.5 baths, a formal dining room, a dedicated office, and a side-entry two-car garage complete the floor plan — all behind a classic hardiplank exterior built to last. Then there's the lifestyle. Prospect Bay is a resort-style community wrapped around an 18-hole golf course, with access to a community pool, tennis and pickleball courts, and a clubhouse with casual and fine dining. A private community waterfront adds a marina, boat ramp, pier, and kayak launch with available storage. You're roughly ten minutes from the Bay Bridge, 25 minutes from Annapolis, Easton, and St. Michael's, and about an hour from Baltimore and D.C. Homes of this size rarely come available here. If you've been waiting for the right home on the Shore — this is it.

43 Greenwood Shls, Grasonville

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

Selling Office: Coldwell Banker Realty.

4 Bunkers Ct, Grasonville
$800,000
3 Beds ⋅ 4 Baths
Enjoy a waterfront country club lifestyle with the privacy of wooded views at 4 Bunkers Court! This beautifully updated and private creek front home is tucked away on a wooded 1.53 acre cul-de-sac lot at the top of Little Greenwood Creek in the sought after waterfront golf course community of Prospect Bay. From soaring vaulted ceilings and over $100k of recent thoughtful upgrades throughout, this home combines comfort, style, and space indoors and out. Step inside to a welcoming foyer and formal dining room with updated lighting. The showstopper of the home is the stunning family room featuring vaulted wood planked ceilings and a striking stone fireplace, an architectural focal point that adds warmth and character. The updated kitchen is a chef's delight with new stainless steel Frigidaire Gallery appliances, granite countertops, freshly installed tile backsplash, new flooring, and a sleek hood vent. A cozy breakfast nook with custom built-ins offers extra storage and bar countertop seating. Just off the kitchen, you’ll find a new mudroom and laundry area with two additional storage closets and a newly added powder room, all connecting to the oversized two-car garage for everyday convenience. The main level offers three bedrooms and two full bathrooms, including a serene primary suite with private patio access, two closets, and a fully updated en suite featuring a walk-in glass enclosed shower with overhead and wall mounted shower heads, and a double vanity with modern finishes. Upstairs, a spiral staircase leads to a spacious and versatile loft ideal as a fourth bedroom, office, or entertaining space. This grand loft includes a game and TV area, pool table, full bathroom with designer tile and a glass shower door, and a custom-built bar area with a beverage fridge, microwave, sink, cabinetry, and backsplash perfect for hosting guests in style. Outside, step onto your private bluestone patio and hot tub, surrounded by the natural beauty of your wooded lot. The sellers have explored the potential of building a boardwalk to the creek with a floating dock buyers to verify offering exciting possibilities for enjoying the waterfront setting. Living in Prospect Bay means more than just a beautiful home, it’s a lifestyle. Enjoy first class amenities including a championship 18 hole golf course, tennis and pickleball courts, outdoor pool, clubhouse with dining, social events, boat basin, and more. Whether you're hosting in the open concept living spaces, relaxing in your upstairs retreat, or soaking in the serenity of your private wooded backyard, 4 Bunkers Court is the perfect place to call home!

4 Bunkers Ct, Grasonville

Listing courtesy of Washington Fine Properties. Contact:

Selling Office: Real Broker, LLC - Annapolis.

167 Masters Way, Grasonville
$860,000
4 Beds ⋅ 4 Baths
Welcome to this beautifully upgraded home at the Enclave in Prospect Bay, the Eastern Shore’s premier golf course community, offering main-level living, thoughtful design, and premium finishes throughout. Perfectly situated on a premium lot, this home blends comfort, style, and functionality both inside and out. Located on a private lot next to the golf cart path with access to Prospect Bay’s 18-hole golf course, you are greeted by a welcoming covered front porch as you arrive. The main level features a spacious primary suite along with two additional bedrooms and two full baths, providing convenient single-level living. The primary suite showcases elegant tray ceilings and a luxurious ensuite bath with a frameless glass shower. Upstairs, a versatile loft with LVP flooring and surround sound offers flexible living space and includes a third full bath, giving it the potential to serve as an office, guest suite, or recreation room. The upgraded kitchen is a standout, featuring enhanced cabinetry, KitchenAid appliances, under-cabinet lighting, and a stand-alone ice machine, making it as functional as it is beautiful. The kitchen opens to the living room and a dining area overlooking the paver patio and the 11th hole of Prospect Bay’s golf course. Also located on this level is a spacious office with barn doors. With direct access to the garage, the conveniently located laundry room continues the upscale finishes with upgraded cabinetry and granite countertops. Designed with both style and entertaining in mind, the home features luxury vinyl plank flooring throughout the main living areas and primary bedroom, tray ceilings in the primary bedroom, dining room, kitchen, and living room, and crown molding in all main-level bedrooms and living spaces. Stylish board and batten molding and a custom wall mural in the main hallway and main-level office add distinctive character. Smart and modern touches include motorized blinds and a surround sound system in both the living room and loft. The two car garage is fully finished and thoughtfully upgraded, featuring complete interior painting, custom epoxy flooring, a bump-out for your golf car and built-in shelving for additional storage. Above the garage, extended pull-down stairs provide convenient access to additional storage space. Outdoor living is just as impressive, with a sealed and coated front porch and a paver patio with a gas-lit fire pit, perfect for relaxing evenings or entertaining guests. The community maintains the gardens and lawn, offering a true turn-key experience. Located within the exclusive Enclave at Prospect Bay, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this golf course-view property offers an unmatched lifestyle in one of Maryland’s most prestigious communities.

167 Masters Way, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

115 Masters Way, Grasonville
$800,000
4 Beds ⋅ 4 Baths
Great price improvement! Welcome to The Enclave at Prospect Bay, where this former model home showcases the sought-after “Pebble Beach” floor plan with thoughtful upgrades and timeless details, backing directly to the 18-hole golf course. Designed for both everyday living and entertaining, the home features three first floor bedrooms, three and a half bathrooms, and a spacious walk-up “sky basement” with a full bath—ideal as a fourth bedroom, office, or media room. The chef’s kitchen offers Quartz countertops, wall oven, cooktop, ceramic tile backsplash, pantry, and a large island that opens to the dining area and family room.  There is a bonus coffee or wine bar with mini fridge, stylish glass cabinets, and additional storage located off the kitchen. In the living room, a custom fireplace with built-ins creates a warm focal point, while expansive windows and plantation shutters throughout the home invite natural light. The main-level primary suite includes a spa-like bath with dual vanities, a walk-in shower, and private water closet. Two additional bedrooms and a versatile bonus room provide flexible living space. Step outside to a spacious patio overlooking the 11th hole—perfect for entertaining or simply enjoying the views. The fenced yard is beautifully landscaped with flourishing gardens and an in-ground sprinkler system, while the HOA maintains the yard for a low-maintenance lifestyle. Additional highlights include a mudroom/laundry room off the two-car garage and efficient upgrades such as the Rinnai tankless water heater. Living in Prospect Bay means access to an array of community amenities including an 18-hole golf course, clubhouse with dining, marina, pool, tennis and pickleball courts, and year-round social activities. Here, every day feels like a vacation.

115 Masters Way, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

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