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SPECTACULAR WATERFRONT VIEWS OF A LIFETIME! Luxury and the Coveted "BIG SIX" Rare to Come on the Market * Full Water Access * Deeded 40' Deep Water Boat Slip * Attached Garage * 3 Waterside Decks * Experience the epitome of Luxury Living in this exquisite waterfront townhouse nestled in the prestigious Oyster Cove community. This stunning 3-bedroom, 3.5-bath plus a spacious bonus room with it's own private walk out deck gives you that flexible space for a bedroom suite, a home office, or a game room! An open floor plan on the main level is adorned with rich hickory wood floors, recessed lighting, the ambiance of a wood burning fireplace, and a gourmet kitchen featuring upgraded countertops and new stainless steel appliances. Panoramic Bay Views from your open family room, dining room and waterside deck!! Indulge in the primary suite with Breathtaking Bay Views, a walk-in closet, and a spa-like bathroom complete with a whirlpool tub and walk-in shower. Step outside to your private oasis, where a walk out deck off your bonus room invites you to unwind while overlooking the serene Eastern Bay. Enjoy exclusive access to community amenities, including a saltwater pool, tennis/ pickleball courts, a dog park and a 1 1/2 mile trail that connects to the 38+ mile Cross Island Trail! With a gated entrance and meticulously maintained grounds, this home offers a feeling of both tranquility and security. Located just steps from many local restaurants, coffee shops, tiki bars, and dessert spots! You are just minutes to premier golf courses and designer outlet shopping! Move right in and start enjoying an elevated Waterfront Lifestyle!

3 Beds ⋅ 4 Baths

SPECTACULAR WATERFRONT VIEWS OF A LIFETIME! Luxury and the Coveted "BIG SIX" Rare to Come on the Market * Full Water Access * Deeded 40' Deep Water Boat Slip * Attached Garage * 3 Waterside Decks * Experience the epitome of Luxury Living in this exquisite waterfront townhouse nestled in the prestigious Oyster Cove community. This stunning 3-bedroom, 3.5-bath plus a spacious bonus room with it's own private walk out deck gives you that flexible space for a bedroom suite, a home office, or a game room! An open floor plan on the main level is adorned with rich hickory wood floors, recessed lighting, the ambiance of a wood burning fireplace, and a gourmet kitchen featuring upgraded countertops and new stainless steel appliances. Panoramic Bay Views from your open family room, dining room and waterside deck!! Indulge in the primary suite with Breathtaking Bay Views, a walk-in closet, and a spa-like bathroom complete with a whirlpool tub and walk-in shower. Step outside to your private oasis, where a walk out deck off your bonus room invites you to unwind while overlooking the serene Eastern Bay. Enjoy exclusive access to community amenities, including a saltwater pool, tennis/ pickleball courts, a dog park and a 1 1/2 mile trail that connects to the 38+ mile Cross Island Trail! With a gated entrance and meticulously maintained grounds, this home offers a feeling of both tranquility and security. Located just steps from many local restaurants, coffee shops, tiki bars, and dessert spots! You are just minutes to premier golf courses and designer outlet shopping! Move right in and start enjoying an elevated Waterfront Lifestyle!

1007 Oyster Cove Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

$549,000

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.

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:

$1,400,000

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, all just minutes from the Bay Bridge. This beautifully updated home delivers the best of Eastern Shore living with 259' of waterfront, a community pier, a school district ranked #7 among the Best School Districts in Maryland, and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water effortless. The water views and natural wetlands of Winchester Creek offer sunsets, privacy and abundant birdlife. A mowed path leads to water's edge for kayak and paddleboard launches. This 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's upscale and 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. The first floor also includes a two-story foyer, formal dining room and a comfortable living room/study with large windows and a second fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel throughout. Single-floor living is easy with two first-level bedroom ensuites. The primary suite offers beautiful water views, California Closets, a remodeled spa-inspired bath and a cozy bay window sitting area. The second ensuite has great water views and is ideal for guests, extended family or a second primary. The second level features three additional bedrooms and a large bonus room perfect for a home office, homework, crafting or playroom. The entire third level is built for entertaining with a wet bar, beverage cooler, full bath and surround sound. Set on 1.37 acres, the property offers privacy, an expansive front and back lawn, updated landscaping and sweeping water views bordered by natural wetlands and habitat. Enjoy morning coffee as the sun rises on the water and glowing sunsets from the new TimberTech deck and covered porch. The slip is steps away from the house and Homeport's private pier (4' MLW) is directly adjacent to the Chester River and Chesapeake for day trips or sunset cruises. Recent improvements 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, all housed in a dedicated utility room. Plus, smart thermostats on each floor, Vector security system, invisible pet fence, ceiling fans throughout, professional landscaping, nearly all-new lighting and updated bathrooms. Enjoy Chesapeake living with great views, great schools and easy access to Annapolis and beyond.

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, all just minutes from the Bay Bridge. This beautifully updated home delivers the best of Eastern Shore living with 259' of waterfront, a community pier, a school district ranked #7 among the Best School Districts in Maryland, and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water effortless. The water views and natural wetlands of Winchester Creek offer sunsets, privacy and abundant birdlife. A mowed path leads to water's edge for kayak and paddleboard launches. This 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's upscale and 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. The first floor also includes a two-story foyer, formal dining room and a comfortable living room/study with large windows and a second fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel throughout. Single-floor living is easy with two first-level bedroom ensuites. The primary suite offers beautiful water views, California Closets, a remodeled spa-inspired bath and a cozy bay window sitting area. The second ensuite has great water views and is ideal for guests, extended family or a second primary. The second level features three additional bedrooms and a large bonus room perfect for a home office, homework, crafting or playroom. The entire third level is built for entertaining with a wet bar, beverage cooler, full bath and surround sound. Set on 1.37 acres, the property offers privacy, an expansive front and back lawn, updated landscaping and sweeping water views bordered by natural wetlands and habitat. Enjoy morning coffee as the sun rises on the water and glowing sunsets from the new TimberTech deck and covered porch. The slip is steps away from the house and Homeport's private pier (4' MLW) is directly adjacent to the Chester River and Chesapeake for day trips or sunset cruises. Recent improvements 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, all housed in a dedicated utility room. Plus, smart thermostats on each floor, Vector security system, invisible pet fence, ceiling fans throughout, professional landscaping, nearly all-new lighting and updated bathrooms. Enjoy Chesapeake living with great views, great schools and easy access to Annapolis and beyond.

109 Starboard Ct, Grasonville

Listing courtesy of Northrop Realty. Contact:

$405,000

Welcome to 125 Forest Road in Grasonville! This beautifully fully remodeled home is move-in ready and offers modern updates throughout. The brand-new kitchen features fresh finishes and updated amenities, while the newly renovated bathrooms add style and functionality. Major improvements include a new HVAC system, new roof, new well, and refinished floors, providing both peace of mind and lasting value. Tucked away on a quiet cul-de-sac, this home offers a peaceful setting while remaining conveniently located near Route 50 for an easy commute and access to shopping, dining, and recreation. Located in a desirable area with access to good schools, this extensively updated home is an excellent opportunity for buyers looking for comfort, convenience, and a truly turn-key property.

3 Beds ⋅ 2 Baths

Welcome to 125 Forest Road in Grasonville! This beautifully fully remodeled home is move-in ready and offers modern updates throughout. The brand-new kitchen features fresh finishes and updated amenities, while the newly renovated bathrooms add style and functionality. Major improvements include a new HVAC system, new roof, new well, and refinished floors, providing both peace of mind and lasting value. Tucked away on a quiet cul-de-sac, this home offers a peaceful setting while remaining conveniently located near Route 50 for an easy commute and access to shopping, dining, and recreation. Located in a desirable area with access to good schools, this extensively updated home is an excellent opportunity for buyers looking for comfort, convenience, and a truly turn-key property.

125 Forest Rd, Grasonville

Listing courtesy of Homecoin.com. Contact:

$1,199,000

Classic Colonial Overlooking the Golf Course in Prospect Bay. BRAND NEW ROOF! 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. Extra large driveway, fresh paint, all upgraded bathrooms are just some of the upgrades besides the brand new roof. 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.

5 Beds ⋅ 3 Baths

Classic Colonial Overlooking the Golf Course in Prospect Bay. BRAND NEW ROOF! 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. Extra large driveway, fresh paint, all upgraded bathrooms are just some of the upgrades besides the brand new roof. 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:

$489,000

Welcome to this BEST VALUE HOME - 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.

4 Beds ⋅ 3 Baths

Welcome to this BEST VALUE HOME - 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: