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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..

$699,900

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!

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.

$1,110,000

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.

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.

$1,240,000

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.

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:

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!

$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.

$860,000

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.

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.

$800,000

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.

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.

$670,000

Nestled in the serene Prospect Bay community, this charming ranch-style home offers a perfect blend of comfort and convenience. Roof is only 3-4 years old. HVAC 2024-2025 . Hardie Plank Siding and Soffits were installed only a couple of years ago, with Aztec PVC Trim and new gutters and gutter guards, make this pretty much a maintenance free home. With three bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining. The heart of the home features a well-appointed kitchen equipped (redone in 2021) with Viking appliances, including a double wall oven, gas cooktop, and a Bosch dishwasher, making meal preparation a delight. Step into the inviting living area, where a cozy fireplace beckons for quiet evenings or gatherings with loved ones in the Sunroom or relax in the separate Living Room. The thoughtful layout ensures that every corner of this home feels warm and welcoming. The attached garage provides ample space for vehicles and storage. Outside, the community amenities are truly exceptional. Dive into the refreshing outdoor pool, challenge friends on the tennis courts, or enjoy leisurely strolls around the beautifully maintained grounds. For golf enthusiasts, a golf course membership is available, offering endless opportunities for recreation. With a generous one-acre lot and access to navigable waters, this property is perfect for those who appreciate nature and outdoor activities. Experience the tranquility of living in a community that prioritizes leisure and lifestyle. This home is not just a place to live; it's a place to thrive.

3 Beds ⋅ 2 Baths

Nestled in the serene Prospect Bay community, this charming ranch-style home offers a perfect blend of comfort and convenience. Roof is only 3-4 years old. HVAC 2024-2025 . Hardie Plank Siding and Soffits were installed only a couple of years ago, with Aztec PVC Trim and new gutters and gutter guards, make this pretty much a maintenance free home. With three bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining. The heart of the home features a well-appointed kitchen equipped (redone in 2021) with Viking appliances, including a double wall oven, gas cooktop, and a Bosch dishwasher, making meal preparation a delight. Step into the inviting living area, where a cozy fireplace beckons for quiet evenings or gatherings with loved ones in the Sunroom or relax in the separate Living Room. The thoughtful layout ensures that every corner of this home feels warm and welcoming. The attached garage provides ample space for vehicles and storage. Outside, the community amenities are truly exceptional. Dive into the refreshing outdoor pool, challenge friends on the tennis courts, or enjoy leisurely strolls around the beautifully maintained grounds. For golf enthusiasts, a golf course membership is available, offering endless opportunities for recreation. With a generous one-acre lot and access to navigable waters, this property is perfect for those who appreciate nature and outdoor activities. Experience the tranquility of living in a community that prioritizes leisure and lifestyle. This home is not just a place to live; it's a place to thrive.

344 Prospect Bay Dr W, Grasonville

Listing courtesy of Rosendale Realty. Contact:

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

$955,000

Nestled on 1.32 peaceful acres along scenic Little Greenwood Creek, this waterfront residence offers a sense of calm from the moment you arrive. Surrounded by nature and gently bordered by water, this home blends comfort with effortless living. Step inside to rich hardwood floors that flow throughout, setting a warm and inviting tone. The living room, designed with custom ceiling and gas fireplace, feels both elegant and welcoming—an ideal setting for relaxed evenings and lingering conversations. From here, the home unfolds seamlessly into a sunlit kitchen and family room, where expansive windows bring the outdoors in. Designed for both everyday living and entertaining, this bright and spacious kitchen features a five-burner gas stove, Granite counter tops, a pantry, and a breakfast bar that subtly defines the adjoining family area. Crown molding and chair railing grace the separate dining room providing an elegant backdrop for gatherings and special occasions. The versatile main-level office offers flexibility to suit your needs—whether as a productive workspace, cozy den, or guest bedroom. The addition of a new full bath with a walk-in shower enhances both its convenience and functionality. Upstairs, the gracious primary serves as a private retreat that is complemented by an equally gracious primary bath featuring a soaking tub, walk-in shower, double vanities, and a generous walk-in closet. Outdoor living is equally enticing. A Trex deck and screened porch create inviting spaces to relax or entertain while enjoying the peaceful nature views. And just beyond the lawn, a private pier awaits—perfect for quiet mornings on the water, spontaneous kayak adventures, or evenings spent watching the sky change colors. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant—this remarkable property captures the very best of Chesapeake living in a serene, nature filled setting.

Nestled on 1.32 peaceful acres along scenic Little Greenwood Creek, this waterfront residence offers a sense of calm from the moment you arrive. Surrounded by nature and gently bordered by water, this home blends comfort with effortless living. Step inside to rich hardwood floors that flow throughout, setting a warm and inviting tone. The living room, designed with custom ceiling and gas fireplace, feels both elegant and welcoming—an ideal setting for relaxed evenings and lingering conversations. From here, the home unfolds seamlessly into a sunlit kitchen and family room, where expansive windows bring the outdoors in. Designed for both everyday living and entertaining, this bright and spacious kitchen features a five-burner gas stove, Granite counter tops, a pantry, and a breakfast bar that subtly defines the adjoining family area. Crown molding and chair railing grace the separate dining room providing an elegant backdrop for gatherings and special occasions. The versatile main-level office offers flexibility to suit your needs—whether as a productive workspace, cozy den, or guest bedroom. The addition of a new full bath with a walk-in shower enhances both its convenience and functionality. Upstairs, the gracious primary serves as a private retreat that is complemented by an equally gracious primary bath featuring a soaking tub, walk-in shower, double vanities, and a generous walk-in closet. Outdoor living is equally enticing. A Trex deck and screened porch create inviting spaces to relax or entertain while enjoying the peaceful nature views. And just beyond the lawn, a private pier awaits—perfect for quiet mornings on the water, spontaneous kayak adventures, or evenings spent watching the sky change colors. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant—this remarkable property captures the very best of Chesapeake living in a serene, nature filled setting.

26 Greenwood Shls, Grasonville

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

Selling Office: Unrepresented.

$890,000

Welcome to this fabulous residence in the coveted Prospect Bay community of Grasonville, where timeless Cape Cod charm meets comfort, space, and an exceptional lifestyle. Thoughtfully designed and beautifully maintained, this picturesque home offers the perfect blend of elegance and functionality. The home features four generously sized bedrooms, including a highly desirable private guest or au pair suite above the garage with its own separate entrance, ideal for visitors, extended family, or flexible living arrangements. The primary suite is a true retreat, complete with a cozy fireplace that adds warmth and character. At the heart of the home is an inviting screened porch designed for effortless entertaining and everyday relaxation, where family and friends will naturally gather while enjoying views of the expansive backyard. The enormous backyard offers exceptional privacy and versatility, featuring an oversized storage shed, play equipment, and double rear gates for convenient access. Storage is abundant throughout the home, with multiple under-eaves storage areas, spacious closets, a 2.5-car garage, and a large storage shed, providing ample room for all your belongings as well as the water toys and equipment needed to fully enjoy life near the Bay. Perfectly positioned just moments from the water’s edge and the renowned Prospect Bay Country Club, residents enjoy a vibrant lifestyle within this premier golf and waterfront community. Centered around the meticulously maintained 18-hole championship golf course and private marina, the community offers year-round resort-style amenities, including dining, tennis, pickleball, a swimming pool, and an active calendar of social and private events. Ideally located just 25 minutes from Annapolis, Easton, and St. Michaels and only an hour from Washington, D.C. and Baltimore, this exceptional home offers the perfect balance of accessibility and serene Eastern Shore living.

Welcome to this fabulous residence in the coveted Prospect Bay community of Grasonville, where timeless Cape Cod charm meets comfort, space, and an exceptional lifestyle. Thoughtfully designed and beautifully maintained, this picturesque home offers the perfect blend of elegance and functionality. The home features four generously sized bedrooms, including a highly desirable private guest or au pair suite above the garage with its own separate entrance, ideal for visitors, extended family, or flexible living arrangements. The primary suite is a true retreat, complete with a cozy fireplace that adds warmth and character. At the heart of the home is an inviting screened porch designed for effortless entertaining and everyday relaxation, where family and friends will naturally gather while enjoying views of the expansive backyard. The enormous backyard offers exceptional privacy and versatility, featuring an oversized storage shed, play equipment, and double rear gates for convenient access. Storage is abundant throughout the home, with multiple under-eaves storage areas, spacious closets, a 2.5-car garage, and a large storage shed, providing ample room for all your belongings as well as the water toys and equipment needed to fully enjoy life near the Bay. Perfectly positioned just moments from the water’s edge and the renowned Prospect Bay Country Club, residents enjoy a vibrant lifestyle within this premier golf and waterfront community. Centered around the meticulously maintained 18-hole championship golf course and private marina, the community offers year-round resort-style amenities, including dining, tennis, pickleball, a swimming pool, and an active calendar of social and private events. Ideally located just 25 minutes from Annapolis, Easton, and St. Michaels and only an hour from Washington, D.C. and Baltimore, this exceptional home offers the perfect balance of accessibility and serene Eastern Shore living.

322 Prospect Bay Dr W, Grasonville

Listing courtesy of EXP Realty, LLC. Contact:

Buyers, get ready... Coveted Prospect Bay has a new beauty that is sure to turn heads! Thoughtful updates include new roof and hvac in 2023, complete kitchen remodel that is stunning (I'm talking removing walls and all!), new fence and deck and more! Backing to the golf course gives you scenic views with wild life on full display which can be enjoyed from the new deck and the modified open air living space (formerly a screened porch). Inside, the new kitchen is the HUB of the home with its generous island that is perfect for gatherings and entertaining. Main living room is anchored by propane fireplace and huge views of the golf course. Home office or sitting room and formal dining room, too. A total of 3 bedrooms (primary suite) and 2 full baths plus 2 car garage with interior access provides ample space to enjoy your 'Shore Life.'

$837,000

3 Beds ⋅ 3 Baths

Buyers, get ready... Coveted Prospect Bay has a new beauty that is sure to turn heads! Thoughtful updates include new roof and hvac in 2023, complete kitchen remodel that is stunning (I'm talking removing walls and all!), new fence and deck and more! Backing to the golf course gives you scenic views with wild life on full display which can be enjoyed from the new deck and the modified open air living space (formerly a screened porch). Inside, the new kitchen is the HUB of the home with its generous island that is perfect for gatherings and entertaining. Main living room is anchored by propane fireplace and huge views of the golf course. Home office or sitting room and formal dining room, too. A total of 3 bedrooms (primary suite) and 2 full baths plus 2 car garage with interior access provides ample space to enjoy your 'Shore Life.'

19 Prospect Bay Dr W, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: RE/MAX United Real Estate.

$1,650,000

This lovely waterfront home is tucked away on a quiet cul-de-sac in desirable Prospect Bay. Thoughtfully designed and built by the original owners, this home offers approximately 2796' of well-planned living space providing 4 bedrooms and 2.5 baths. The open-concept floor plan is enhanced by distinctive architectural details and abundant natural light. A bright kitchen opens to the family room with fireplace—perfect for everyday living and entertaining. The spacious living room features a vaulted ceiling with skylights and opens to a loft area above. The main-level primary bedroom offers water views, a large walk-in closet, and a full bath with soaking tub and walk-in shower. Upstairs, you’ll find three additional bedrooms plus a dedicated office space. Enjoy outdoor living on the wrap-around deck, accessible from the living room, kitchen, and primary bedroom. Additional features include an oversized two-car garage and private pier on a tranquil waterfront setting. Roof is 2 years old and carpet is new. Home is being sold As-Is. Buyer to verify water depth. Prospect Bay amenities include Golf, Pool, Boat Ramp, Tennis Ct, Club House with restaurant/bar/grill plus more.

This lovely waterfront home is tucked away on a quiet cul-de-sac in desirable Prospect Bay. Thoughtfully designed and built by the original owners, this home offers approximately 2796' of well-planned living space providing 4 bedrooms and 2.5 baths. The open-concept floor plan is enhanced by distinctive architectural details and abundant natural light. A bright kitchen opens to the family room with fireplace—perfect for everyday living and entertaining. The spacious living room features a vaulted ceiling with skylights and opens to a loft area above. The main-level primary bedroom offers water views, a large walk-in closet, and a full bath with soaking tub and walk-in shower. Upstairs, you’ll find three additional bedrooms plus a dedicated office space. Enjoy outdoor living on the wrap-around deck, accessible from the living room, kitchen, and primary bedroom. Additional features include an oversized two-car garage and private pier on a tranquil waterfront setting. Roof is 2 years old and carpet is new. Home is being sold As-Is. Buyer to verify water depth. Prospect Bay amenities include Golf, Pool, Boat Ramp, Tennis Ct, Club House with restaurant/bar/grill plus more.

222 Piney Point Lndg, Grasonville

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

Selling Office: TTR Sotheby's International Realty.

$1,350,000

Welcome to this beautifully updated waterfront-view home in Prospect Bay, the premier golf course community on the Eastern Shore! This home tastefully blends coastal charm with modern design and exceptional outdoor living. From the moment you arrive via the paved driveway to the two-car garage, you are greeted by serene water views from the front entrance and porches off the living room and sunroom. Inside, an open entryway with ample storage leads to a formal living room with masonry fireplace that flows seamlessly into a completely remodeled dining room featuring tasteful textured wallpaper, bead and board wall trim. On the opposite side of the entry, a spacious family room boasts a new electric fireplace with shiplap accent wall and quartz hearth. A stylish powder room with statement wallpaper and a new quartz countertop, along with hardwood floors throughout both levels, add to the home’s polished feel. The home offers easy interior access from the two-car garage, with a staircase tucked away down the same hallway that leads to a large room over the garage with dedicated heat pump. Perfect for use as a home office, extra bedroom, additional storage, or craft room. The upgraded kitchen shines with new countertops and backsplash, a remodeled island for added storage, and enhanced carpentry details, flowing into a bright sunroom with pool and water views ideal for an office or hobby space. Just beyond the kitchen, doors open to your private backyard oasis, complete with a deck featuring upgraded Trex materials, extensive hardscaping surrounding a large inground pool, a hot tub installed in 2022, and fresh landscaping framed by mature trees for ultimate privacy. A charming coastal-style guest house with high efficiency mini split units, sits steps from the pool, offering a kitchenette, living area, full bathroom, and bedroom for visitors or extended stays. Upstairs, the primary suite impresses with water views, a masonry fireplace, an expanded walk-in closet outfitted with a custom Elfa system, and a remodeled spa-like bathroom featuring a tiled shower with marble seat, soaking tub, dual vanities, and updated fixtures. Three additional bedrooms share a well-appointed guest bathroom. Recent major upgrades include a new roof and gutters (2024), attic plywood flooring for extra storage, encapsulated crawlspace (2023), three high-efficiency heat pumps (2023), freshly painted and caulked exterior, repaved and resealed driveway, updated garage including flooring, storage cabinets, work bench and door operators. The property also offers a whole-house generator, updated trim work throughout, and so much more, making this home truly move-in ready. Located within the exclusive Prospect Bay Community, 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 water view property offers an unmatched lifestyle in one of Maryland's most prestigious communities.

5 Beds ⋅ 4 Baths

Welcome to this beautifully updated waterfront-view home in Prospect Bay, the premier golf course community on the Eastern Shore! This home tastefully blends coastal charm with modern design and exceptional outdoor living. From the moment you arrive via the paved driveway to the two-car garage, you are greeted by serene water views from the front entrance and porches off the living room and sunroom. Inside, an open entryway with ample storage leads to a formal living room with masonry fireplace that flows seamlessly into a completely remodeled dining room featuring tasteful textured wallpaper, bead and board wall trim. On the opposite side of the entry, a spacious family room boasts a new electric fireplace with shiplap accent wall and quartz hearth. A stylish powder room with statement wallpaper and a new quartz countertop, along with hardwood floors throughout both levels, add to the home’s polished feel. The home offers easy interior access from the two-car garage, with a staircase tucked away down the same hallway that leads to a large room over the garage with dedicated heat pump. Perfect for use as a home office, extra bedroom, additional storage, or craft room. The upgraded kitchen shines with new countertops and backsplash, a remodeled island for added storage, and enhanced carpentry details, flowing into a bright sunroom with pool and water views ideal for an office or hobby space. Just beyond the kitchen, doors open to your private backyard oasis, complete with a deck featuring upgraded Trex materials, extensive hardscaping surrounding a large inground pool, a hot tub installed in 2022, and fresh landscaping framed by mature trees for ultimate privacy. A charming coastal-style guest house with high efficiency mini split units, sits steps from the pool, offering a kitchenette, living area, full bathroom, and bedroom for visitors or extended stays. Upstairs, the primary suite impresses with water views, a masonry fireplace, an expanded walk-in closet outfitted with a custom Elfa system, and a remodeled spa-like bathroom featuring a tiled shower with marble seat, soaking tub, dual vanities, and updated fixtures. Three additional bedrooms share a well-appointed guest bathroom. Recent major upgrades include a new roof and gutters (2024), attic plywood flooring for extra storage, encapsulated crawlspace (2023), three high-efficiency heat pumps (2023), freshly painted and caulked exterior, repaved and resealed driveway, updated garage including flooring, storage cabinets, work bench and door operators. The property also offers a whole-house generator, updated trim work throughout, and so much more, making this home truly move-in ready. Located within the exclusive Prospect Bay Community, 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 water view property offers an unmatched lifestyle in one of Maryland's most prestigious communities.

228 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: RE/MAX Executive.

$889,000

Welcome to this beautifully remodeled one-story home in the highly sought-after Prospect Bay community. From the moment you step inside, you’ll be impressed by the open floor plan, vaulted ceilings with skylights, and a stunning gourmet kitchen designed for both everyday living and entertaining. The upgraded kitchen features a gas cooktop, double oven with warming drawer, granite countertops, abundant cabinetry, a walk-in pantry, and a stylish wine bar. Natural hickory hardwood flooring flows throughout the home, complemented by a four-season sunroom overlooking the spacious backyard and golf course. Outdoor living is a dream with a large deck, hot tub, fire pit, and heated saltwater pool—perfect for relaxing or hosting guests year-round. The home offers four generously sized bedrooms and three full bathrooms. The primary suite includes a walk-in closet and spa-like bath with heated tile floors, walk-in shower, and soaking tub. A second primary bedroom on the opposite side of the home provides added privacy with its own full bath and walk-in closet. Meticulously maintained and beautifully landscaped, this property also offers access to all the amenities of Prospect Bay Golf & Country Club, including an 18-hole golf course, pool, tennis and pickleball courts, and a clubhouse with restaurant, bar, and grill. A rare opportunity—this home truly has it all.

Welcome to this beautifully remodeled one-story home in the highly sought-after Prospect Bay community. From the moment you step inside, you’ll be impressed by the open floor plan, vaulted ceilings with skylights, and a stunning gourmet kitchen designed for both everyday living and entertaining. The upgraded kitchen features a gas cooktop, double oven with warming drawer, granite countertops, abundant cabinetry, a walk-in pantry, and a stylish wine bar. Natural hickory hardwood flooring flows throughout the home, complemented by a four-season sunroom overlooking the spacious backyard and golf course. Outdoor living is a dream with a large deck, hot tub, fire pit, and heated saltwater pool—perfect for relaxing or hosting guests year-round. The home offers four generously sized bedrooms and three full bathrooms. The primary suite includes a walk-in closet and spa-like bath with heated tile floors, walk-in shower, and soaking tub. A second primary bedroom on the opposite side of the home provides added privacy with its own full bath and walk-in closet. Meticulously maintained and beautifully landscaped, this property also offers access to all the amenities of Prospect Bay Golf & Country Club, including an 18-hole golf course, pool, tennis and pickleball courts, and a clubhouse with restaurant, bar, and grill. A rare opportunity—this home truly has it all.

19 Greenwood Shls, Grasonville

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

Seller to pay the $5000 initiation fee for the Buyers! Welcome to your move-in ready retreat in Prospect Bay, the Eastern Shore's premier golf community! This beautifully maintained home offers a wooded setting that backs to the 12th hole. It combines timeless design with extensive updates and thoughtful spaces for everyday living and entertaining. All located in one of the most popular golf communities on the Eastern Shore, offering resort style amenities for members. As you walk towards the front entrance, you'll be greeted by a welcoming front porch that overlooks your front yard at the quiet end of Fairway Island. A separate office or formal living room is tucked just off the main entrance, with a convenient coat closet and powder room located on the other side. The main level features a spacious primary suite with a bonus sitting room that opens to the rear deck and a completely remodeled primary bathroom. The heart of the home is the family room with soaring two-story ceilings, a wood fireplace, and abundant natural light, flowing seamlessly into the oversized screened porch — perfect for morning coffee, outdoor dining, or unwinding in the evenings. The kitchen was remodeled in 2023 and features a large window overlooking the private backyard, granite counters, updated lighting and appliances, and a walk-in pantry with custom built-ins. Off the kitchen, you’ll find a formal dining room that could easily be converted to a bonus office or room. The garage has direct access to the laundry room that is tucked away by the kitchen. Upstairs, there are three generously sized bedrooms with walk-in closets, one offering access to a partially finished attic space—ideal for storage or creating an additional room. The full bathroom upstairs has also been updated. Outdoor living is easy with a rear paver patio and pathway connecting to the paved driveway, mature landscaping, and private backyard. The oversized screened porch and new primary bedroom deck provide multiple ways to enjoy the setting. Extensive updates ensure peace of mind: oversized screened porch, French drains, sump pumps, irrigation system, and roof (2013); HVAC (2014); kitchen and bath renovations, new appliances, custom pantry, alarm system, and garage/laundry doors (2023); and a full suite of 2025 improvements including new windows, doors, flooring, paint, gutters, lighting, driveway sealing, landscaping, garage systems, and more. Every detail—inside and out—has been thoughtfully maintained or upgraded, making this home truly turnkey and ready for its next chapter. Schedule your tour today! Prospect Bay is the premier golf community on the Eastern Shore offering 18-hole course, pickle ball, tennis, private clubhouse with restaurant and bar, driving range, pool, and more!

$860,000

Seller to pay the $5000 initiation fee for the Buyers! Welcome to your move-in ready retreat in Prospect Bay, the Eastern Shore's premier golf community! This beautifully maintained home offers a wooded setting that backs to the 12th hole. It combines timeless design with extensive updates and thoughtful spaces for everyday living and entertaining. All located in one of the most popular golf communities on the Eastern Shore, offering resort style amenities for members. As you walk towards the front entrance, you'll be greeted by a welcoming front porch that overlooks your front yard at the quiet end of Fairway Island. A separate office or formal living room is tucked just off the main entrance, with a convenient coat closet and powder room located on the other side. The main level features a spacious primary suite with a bonus sitting room that opens to the rear deck and a completely remodeled primary bathroom. The heart of the home is the family room with soaring two-story ceilings, a wood fireplace, and abundant natural light, flowing seamlessly into the oversized screened porch — perfect for morning coffee, outdoor dining, or unwinding in the evenings. The kitchen was remodeled in 2023 and features a large window overlooking the private backyard, granite counters, updated lighting and appliances, and a walk-in pantry with custom built-ins. Off the kitchen, you’ll find a formal dining room that could easily be converted to a bonus office or room. The garage has direct access to the laundry room that is tucked away by the kitchen. Upstairs, there are three generously sized bedrooms with walk-in closets, one offering access to a partially finished attic space—ideal for storage or creating an additional room. The full bathroom upstairs has also been updated. Outdoor living is easy with a rear paver patio and pathway connecting to the paved driveway, mature landscaping, and private backyard. The oversized screened porch and new primary bedroom deck provide multiple ways to enjoy the setting. Extensive updates ensure peace of mind: oversized screened porch, French drains, sump pumps, irrigation system, and roof (2013); HVAC (2014); kitchen and bath renovations, new appliances, custom pantry, alarm system, and garage/laundry doors (2023); and a full suite of 2025 improvements including new windows, doors, flooring, paint, gutters, lighting, driveway sealing, landscaping, garage systems, and more. Every detail—inside and out—has been thoughtfully maintained or upgraded, making this home truly turnkey and ready for its next chapter. Schedule your tour today! Prospect Bay is the premier golf community on the Eastern Shore offering 18-hole course, pickle ball, tennis, private clubhouse with restaurant and bar, driving range, pool, and more!

29 Fairway Is, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Taylor Properties.

$739,000

Prestigious Prospect Bay – Golf Course and Waterfront Living at Its Finest! This stunning Colonial sits directly on the golf course with breathtaking views of the 18th tee, a rare opportunity to own in one of the Eastern Shore’s most sought-after waterfront communities. Inside, you’ll find 4 spacious bedrooms and 2.5 beautifully appointed baths with over 2300 sq ft!! . The gourmet kitchen is a showstopper! Gorgeous granite countertops, under-cabinet lighting, and a farmhouse sink perfectly positioned to overlook the lush backyard and fairway. A cozy sitting area with a fireplace creates the perfect spot for morning coffee, while the large eat-in dining space offers panoramic golf course views. The main level bedroom provides flexibility for guests, an office, or a den. The family room boasts custom trim work, adding charm and character. Upstairs, hardwood floors run throughout. The primary suite is bright and spacious with a walk-in closet and a renovated spa-like bathroom featuring tile floors and a custom vanity. Bedrooms two and three are equally impressive, both oversized with huge closets. The backyard is an entertainer’s dream! Screened-in porch, expansive deck, and wide-open yard all facing the golf course. The property also includes a detached 2-car garage, providing extra storage and parking space. Living in Prospect Bay means enjoying an unmatched resort lifestyle with a private clubhouse featuring a restaurant and party room, a sparkling community pool with a snack shack, pickleball and tennis courts, a pro shop and driving range, plus a private marina and boat ramp with water access to Prospect Bay and the area’s best waterfront restaurants. Here, you’ll have golf, boating, dining, and social events right at your doorstep. You’ll never want to leave!

Prestigious Prospect Bay – Golf Course and Waterfront Living at Its Finest! This stunning Colonial sits directly on the golf course with breathtaking views of the 18th tee, a rare opportunity to own in one of the Eastern Shore’s most sought-after waterfront communities. Inside, you’ll find 4 spacious bedrooms and 2.5 beautifully appointed baths with over 2300 sq ft!! . The gourmet kitchen is a showstopper! Gorgeous granite countertops, under-cabinet lighting, and a farmhouse sink perfectly positioned to overlook the lush backyard and fairway. A cozy sitting area with a fireplace creates the perfect spot for morning coffee, while the large eat-in dining space offers panoramic golf course views. The main level bedroom provides flexibility for guests, an office, or a den. The family room boasts custom trim work, adding charm and character. Upstairs, hardwood floors run throughout. The primary suite is bright and spacious with a walk-in closet and a renovated spa-like bathroom featuring tile floors and a custom vanity. Bedrooms two and three are equally impressive, both oversized with huge closets. The backyard is an entertainer’s dream! Screened-in porch, expansive deck, and wide-open yard all facing the golf course. The property also includes a detached 2-car garage, providing extra storage and parking space. Living in Prospect Bay means enjoying an unmatched resort lifestyle with a private clubhouse featuring a restaurant and party room, a sparkling community pool with a snack shack, pickleball and tennis courts, a pro shop and driving range, plus a private marina and boat ramp with water access to Prospect Bay and the area’s best waterfront restaurants. Here, you’ll have golf, boating, dining, and social events right at your doorstep. You’ll never want to leave!

20 Prospect Bay Dr W, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Taylor Properties.

$1,450,000

HIGHEST AND BEST DUE SUNDAY 10/19 6PM----Welcome to 16 Fairway Island, a 5,100 sq. ft. coastal-inspired estate designed for both everyday luxury and effortless entertaining. With a main-level primary suite, spacious office, and four oversized bedrooms upstairs, this home offers the perfect balance of comfort, style, and functionality. Step inside to soaring spaces wrapped in fresh paint, new luxury vinyl plank flooring , and upgraded lighting that bring a crisp, modern feel. The chef’s kitchen features a new cooktop, two dishwashers, a wine fridge, and professionally refinished cabinets — ideal for preparing family meals or hosting on a grand scale. A generous family room anchors the main level, while formal and casual dining spaces provide versatility for gatherings. The main-level primary suite is a private retreat, complete with spacious layout and spa-like finishes. Upstairs, four large bedrooms offer room for family, guests, or flexible use. A dedicated main-level office ensures work-from-home convenience without sacrificing style. Outside, enjoy your own private resort: a saltwater pool with recently upgraded motorized cover, outdoor shower, built-in umbrella, gas hookup, hot tub, built in fire pit, and a newly fenced yard framed by lush landscaping. And as a bonus — the property includes a pool house with a wood-burning fireplace, mini-split system, and water hookup, creating an additional entertaining space for summer pool parties or cozy fall evenings. Practical features include a 3-car garage with workbench and second-level storage, laundry located both upstairs and downstairs, interior crawlspace access, propane service, and annual HVAC maintenance for peace of mind. Located in the sought after golf course community of Prospect Bay, this award winning neighborhood offers the best of both worlds-- a premier 18 hole golf course and access to the Chesapeake Bay. Perfect for golf enthusiasts but it's not just about golf...residents enjoy full club amenities including fine and casual dining, tennis, pickleball, a marina, and a vibrant social calendar Prospect Bay combines resort-style amenities with an unbeatable Eastern Shore location This isn’t just a home — it’s lifestyle on Maryland’s Eastern Shore. https://unbranded.youriguide.com/1l8pu_16_fairway_island_grasonville_md/ **3DTour**

5 Beds ⋅ 4 Baths

HIGHEST AND BEST DUE SUNDAY 10/19 6PM----Welcome to 16 Fairway Island, a 5,100 sq. ft. coastal-inspired estate designed for both everyday luxury and effortless entertaining. With a main-level primary suite, spacious office, and four oversized bedrooms upstairs, this home offers the perfect balance of comfort, style, and functionality. Step inside to soaring spaces wrapped in fresh paint, new luxury vinyl plank flooring , and upgraded lighting that bring a crisp, modern feel. The chef’s kitchen features a new cooktop, two dishwashers, a wine fridge, and professionally refinished cabinets — ideal for preparing family meals or hosting on a grand scale. A generous family room anchors the main level, while formal and casual dining spaces provide versatility for gatherings. The main-level primary suite is a private retreat, complete with spacious layout and spa-like finishes. Upstairs, four large bedrooms offer room for family, guests, or flexible use. A dedicated main-level office ensures work-from-home convenience without sacrificing style. Outside, enjoy your own private resort: a saltwater pool with recently upgraded motorized cover, outdoor shower, built-in umbrella, gas hookup, hot tub, built in fire pit, and a newly fenced yard framed by lush landscaping. And as a bonus — the property includes a pool house with a wood-burning fireplace, mini-split system, and water hookup, creating an additional entertaining space for summer pool parties or cozy fall evenings. Practical features include a 3-car garage with workbench and second-level storage, laundry located both upstairs and downstairs, interior crawlspace access, propane service, and annual HVAC maintenance for peace of mind. Located in the sought after golf course community of Prospect Bay, this award winning neighborhood offers the best of both worlds-- a premier 18 hole golf course and access to the Chesapeake Bay. Perfect for golf enthusiasts but it's not just about golf...residents enjoy full club amenities including fine and casual dining, tennis, pickleball, a marina, and a vibrant social calendar Prospect Bay combines resort-style amenities with an unbeatable Eastern Shore location This isn’t just a home — it’s lifestyle on Maryland’s Eastern Shore. https://unbranded.youriguide.com/1l8pu_16_fairway_island_grasonville_md/ **3DTour**

16 Fairway Is, Grasonville

Listing courtesy of Douglas Realty LLC. Contact:

This meticulously renovated and maintained home checks all the boxes - inside and outside! Enjoy an oversized saltwater heated pool [20x44] with custom waterfalls and new liner. Entertain year-round in the expansive screened gazebo complete with a kitchen, firepit, and projector home theater with surround sound. Additional family-friendly features include adjustable basketball hoop (glass backboard), adorable custom-built treehouse with zip line, and a second screened gazebo with hot tub and seating and hammocks. Inside, the main level has an open-concept gourmet kitchen and great room space with cedar plank vaulted ceiling and skylights. There’s also a game room, complete with claw-foot billiard table that conveys. Upstairs, the large primary suite features a transom for extra daylight as well as an ensuite bath with dedicated makeup vanity, bubbler tub, and walk-in closet with custom shelving system. Three additional bedrooms share a well-appointed hall bath. This home has been lovingly maintained and upgraded by the current owners for 22 years including: Hybrid high-efficiency hot water tank (2023) Dual-zone HVAC systems replaced (2021) Fiber optic WiFi upgrade (2024) Crawl space encapsulation with dehumidifier ($25k investment) Whole house water filtration system (2025) Notable exterior upgrades include updated siding, windows, exterior doors, plus a composite front porch and custom garage door. Backing to the 10th fairway, this home is close enough to the community clubhouse for walks to your next pickleball match, round of golf, swim team practice/meets for the kids, or dinner at the restaurant. Just a bit farther, you’ll find the amazing marina providing direct access to the Eastern Bay. Don’t wait to enjoy this rare slice of Eastern Shore paradise - book your showing now!

$980,000