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$749,900

Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the primary bath offers a private retreat with sophisticated fixtures. Enjoy the tranquility of river views from your porch, where you can unwind and soak in the picturesque surroundings. The property boasts deeded private 40 foot boat slip, ideal for boating enthusiasts, and a community pool for leisurely afternoons. Additional amenities include a gated entrance, ensuring privacy and security, along with beautifully maintained common grounds and walking paths. With three generously sized bedrooms and a cozy electric fireplace, this home is designed for both relaxation and entertaining. The community offers a wealth of recreational options, including tennis courts, pickle ball and picnic areas, enhancing the luxurious lifestyle that Oyster Cove provides. Experience the ultimate in waterfront living, where every detail has been thoughtfully curated for your enjoyment.

3 Beds ⋅ 2 Baths

Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the primary bath offers a private retreat with sophisticated fixtures. Enjoy the tranquility of river views from your porch, where you can unwind and soak in the picturesque surroundings. The property boasts deeded private 40 foot boat slip, ideal for boating enthusiasts, and a community pool for leisurely afternoons. Additional amenities include a gated entrance, ensuring privacy and security, along with beautifully maintained common grounds and walking paths. With three generously sized bedrooms and a cozy electric fireplace, this home is designed for both relaxation and entertaining. The community offers a wealth of recreational options, including tennis courts, pickle ball and picnic areas, enhancing the luxurious lifestyle that Oyster Cove provides. Experience the ultimate in waterfront living, where every detail has been thoughtfully curated for your enjoyment.

130 Oyster Cove Dr Unit #130, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$209,000

Welcome to the water privileged community of Chester River Beach where you will find this water view lot just waiting to have a new home built on it. Enjoy the added bonus of having a large existing garage or stroll down to the beautiful waterfront park and boat ramp. This lot has public sewer access. Embrace the lifestyle you've always wanted on MDs beautiful eastern shore. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Great investment opportunity.

903 Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$599,000

Enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community! Offering 3 bedrooms and 2 full bathrooms, this light-filled, one-level residence features an open floor plan designed for easy living and entertaining! Stunning wide plank wood flooring flows throughout the main living areas, complemented by newer stone countertops, fresh interior custom paint throughout and NEW carpet in the bedrooms. The spacious living and dining areas open to a Waterfront Deck where you can relax and enjoy breathtaking Sunsets over Eastern Bay and The Narrows. The thoughtfully designed layout offers generous bedroom sizes and two updated baths. Recent exterior improvements include new siding and new windows. Oyster Cove residents enjoy an exceptional Waterfront lifestyle with access to two Marinas, Swimming Pool, two Tennis Courts, a walking/jogging path and a Clubhouse with a fitness room. Conveniently located within walking distance to many restaurants, coffee spots, ice cream parlors, shops and popular dock bars!! Hop on the Kent Island Cross Trail for a bike ride throughout the Island! Just minutes from the Chesapeake Bay Bridge, this is Eastern Shore living at its finest!

3 Beds ⋅ 2 Baths

Enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community! Offering 3 bedrooms and 2 full bathrooms, this light-filled, one-level residence features an open floor plan designed for easy living and entertaining! Stunning wide plank wood flooring flows throughout the main living areas, complemented by newer stone countertops, fresh interior custom paint throughout and NEW carpet in the bedrooms. The spacious living and dining areas open to a Waterfront Deck where you can relax and enjoy breathtaking Sunsets over Eastern Bay and The Narrows. The thoughtfully designed layout offers generous bedroom sizes and two updated baths. Recent exterior improvements include new siding and new windows. Oyster Cove residents enjoy an exceptional Waterfront lifestyle with access to two Marinas, Swimming Pool, two Tennis Courts, a walking/jogging path and a Clubhouse with a fitness room. Conveniently located within walking distance to many restaurants, coffee spots, ice cream parlors, shops and popular dock bars!! Hop on the Kent Island Cross Trail for a bike ride throughout the Island! Just minutes from the Chesapeake Bay Bridge, this is Eastern Shore living at its finest!

116 Oyster Cove Dr Unit #1D, Grasonville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$994,000

Welcome to this stunning custom home overlooking the 10th green in the prestigious Prospect Bay community. Situated on a beautiful one-acre lot, this residence offers over 3,000 square feet of living space with 4-5 bedrooms and an ideal floor plan for everyday living and entertaining. The dramatic two-story foyer welcomes you into a thoughtfully designed home featuring elegant architectural details, including tray and vaulted ceilings. The bright kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, plus a separate formal dining room. Open to the kitchen, the inviting family room offers bamboo flooring, a gas fireplace, custom built-ins, and access to the expansive deck overlooking the backyard and golf course. The spacious primary bedroom includes a large walk-in closet and private bath with a soaking tub, dual vanities, and a walk-in shower. Four additional bedrooms provide flexibility for guests, a home office, or multigenerational living, including one bedroom conveniently located on the main level. Enjoy the best of Eastern Shore living with outdoor spaces designed for relaxing and entertaining. Barbecue on the large deck or gather with family and friends for a traditional Maryland crab feast in the screened gazebo while taking in peaceful golf course views. Additional highlights include a three-car garage, oversized parking pad, main level heat pump replaced in 2021, and crawl space encapsulated in 2025. Prospect Bay residents enjoy outstanding resort-style amenities, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, boat ramp, pro shop, and an active social calendar. Ideally located just minutes from the Chesapeake Bay Bridge, this lovely home offers the perfect combination of golf, boating, and relaxed coastal living.

5 Beds ⋅ 3 Baths

Welcome to this stunning custom home overlooking the 10th green in the prestigious Prospect Bay community. Situated on a beautiful one-acre lot, this residence offers over 3,000 square feet of living space with 4-5 bedrooms and an ideal floor plan for everyday living and entertaining. The dramatic two-story foyer welcomes you into a thoughtfully designed home featuring elegant architectural details, including tray and vaulted ceilings. The bright kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, plus a separate formal dining room. Open to the kitchen, the inviting family room offers bamboo flooring, a gas fireplace, custom built-ins, and access to the expansive deck overlooking the backyard and golf course. The spacious primary bedroom includes a large walk-in closet and private bath with a soaking tub, dual vanities, and a walk-in shower. Four additional bedrooms provide flexibility for guests, a home office, or multigenerational living, including one bedroom conveniently located on the main level. Enjoy the best of Eastern Shore living with outdoor spaces designed for relaxing and entertaining. Barbecue on the large deck or gather with family and friends for a traditional Maryland crab feast in the screened gazebo while taking in peaceful golf course views. Additional highlights include a three-car garage, oversized parking pad, main level heat pump replaced in 2021, and crawl space encapsulated in 2025. Prospect Bay residents enjoy outstanding resort-style amenities, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, boat ramp, pro shop, and an active social calendar. Ideally located just minutes from the Chesapeake Bay Bridge, this lovely home offers the perfect combination of golf, boating, and relaxed coastal living.

14 Fairway Is, Grasonville

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

$525,000

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

3 Beds ⋅ 4 Baths

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

114 Bayview, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810

$70,000

HUGE PRICE DROP! Now is your time to buy that sweet summer spot! Welcome to your waterfront paradise in the highly sought-after Beach Harbor Camper Cooperative Inc. of Grasonville, MD! This Town and Country Park model ranch-style home is the perfect blend of comfort, convenience, and offers some inspiring views, making it the ultimate 3-season go to for the water and beach lovers! This incredible home boasts 1.5 bedrooms and one bathroom, perfect for weekend or monthly summer getaways. New vinyl flooring and fresh paint. Beautiful water views of the Jackson Creek and the majestic Chester River. Shed provides ample storage. Step outside onto the deck and enjoy your morning coffee or entertain for breakfast, lunch or dinner. Picture yourself lounging on the beach or embarking on thrilling adventures in your kayak or boat through the sprawling waterways of the area. If you're a paddle-boarder, the protected waters of the creek and river are an absolute dream! Indoors cool off with window air conditioners for personalized climate control. The "half bedroom" features 2 bunk beds and a window, while the primary bedroom offers ample space for a queen bed and includes a closet. Conveniently located just steps from the community beach, this community offers immediate access to a host of outdoor activities, from swimming and fishing to kayaking, paddleboarding, shuffleboard, basketball and tennis. The delightful community pool, hot tub and clubhouse provide the perfect place for social gatherings and community events. Don't let this opportunity slip away! Take the first step towards owning your slice of paradise in the Beach Harbor Camper Cooperative. Schedule a viewing today and prepare to experience the very best of waterfront living, all at an incredibly affordable price! Enjoy! (Monthly fee $350/Monthly or $4,200/Yearly

2 Beds ⋅ 1 Baths

HUGE PRICE DROP! Now is your time to buy that sweet summer spot! Welcome to your waterfront paradise in the highly sought-after Beach Harbor Camper Cooperative Inc. of Grasonville, MD! This Town and Country Park model ranch-style home is the perfect blend of comfort, convenience, and offers some inspiring views, making it the ultimate 3-season go to for the water and beach lovers! This incredible home boasts 1.5 bedrooms and one bathroom, perfect for weekend or monthly summer getaways. New vinyl flooring and fresh paint. Beautiful water views of the Jackson Creek and the majestic Chester River. Shed provides ample storage. Step outside onto the deck and enjoy your morning coffee or entertain for breakfast, lunch or dinner. Picture yourself lounging on the beach or embarking on thrilling adventures in your kayak or boat through the sprawling waterways of the area. If you're a paddle-boarder, the protected waters of the creek and river are an absolute dream! Indoors cool off with window air conditioners for personalized climate control. The "half bedroom" features 2 bunk beds and a window, while the primary bedroom offers ample space for a queen bed and includes a closet. Conveniently located just steps from the community beach, this community offers immediate access to a host of outdoor activities, from swimming and fishing to kayaking, paddleboarding, shuffleboard, basketball and tennis. The delightful community pool, hot tub and clubhouse provide the perfect place for social gatherings and community events. Don't let this opportunity slip away! Take the first step towards owning your slice of paradise in the Beach Harbor Camper Cooperative. Schedule a viewing today and prepare to experience the very best of waterfront living, all at an incredibly affordable price! Enjoy! (Monthly fee $350/Monthly or $4,200/Yearly

111 Beach Harbor F, Grasonville

Listing courtesy of HSA By The Bay. Contact: 4432504707

$1,275,000

REDUCED PRICE ! Experience Exceptional Waterfront Living on the Chester River! A stunning 3000 sq ft townhome featuring 3 bedrooms, 3.5 bathrooms, a dedicated office AND a large bonus room - offering the perfect combination of comfort and flexibility. This was also one of the few "stretch" units- built wider to accommodate setbacks. The result was a wider Dining Room adding more natural light, wider decks, and more WATERVIEWS! Inside you'll find an open floor plan that's perfect for entertaining! It has hardwood floors, a dramatic floor to ceiling stone fireplace, a gourmet kitchen with high end newer stainless steel appliances & finishes, granite countertops, and ensuite bathrooms in all the bedrooms! Enjoy Beautiful Water Views from nearly every room thanks to thoughtfully designed architectural windows. Two covered decks with remote controlled screens invite you to relax and take in the breathtaking views over the Chester River. You also have a 2 car attached garage! Located in an exclusive gated community on a private peninsula, this home backs up to the renowned Safe Harbor Marina that offers a pool, fitness center, and over 600 slips, making it a boaters dream! Narrows Pointe is just around the corner from many great ( docking) restaurants, tiki bars, coffee and dessert spots! Golf enthusiasts will love being just 5 minutes from Queenstown Golf Links, close to other courses too! Outlet shopping is nearby for convenience. Only 20 minutes from Annapolis and Easton, 45 minutes from BWI Airport, 55 minutes from Washington, DC & Baltimore, and 1 1/2 hours away from Ocean City ! Whether you're looking for a year-round residence or a weekend retreat, this home offers the ultimate Chesapeake Bay lifestyle !

3 Beds ⋅ 4 Baths

REDUCED PRICE ! Experience Exceptional Waterfront Living on the Chester River! A stunning 3000 sq ft townhome featuring 3 bedrooms, 3.5 bathrooms, a dedicated office AND a large bonus room - offering the perfect combination of comfort and flexibility. This was also one of the few "stretch" units- built wider to accommodate setbacks. The result was a wider Dining Room adding more natural light, wider decks, and more WATERVIEWS! Inside you'll find an open floor plan that's perfect for entertaining! It has hardwood floors, a dramatic floor to ceiling stone fireplace, a gourmet kitchen with high end newer stainless steel appliances & finishes, granite countertops, and ensuite bathrooms in all the bedrooms! Enjoy Beautiful Water Views from nearly every room thanks to thoughtfully designed architectural windows. Two covered decks with remote controlled screens invite you to relax and take in the breathtaking views over the Chester River. You also have a 2 car attached garage! Located in an exclusive gated community on a private peninsula, this home backs up to the renowned Safe Harbor Marina that offers a pool, fitness center, and over 600 slips, making it a boaters dream! Narrows Pointe is just around the corner from many great ( docking) restaurants, tiki bars, coffee and dessert spots! Golf enthusiasts will love being just 5 minutes from Queenstown Golf Links, close to other courses too! Outlet shopping is nearby for convenience. Only 20 minutes from Annapolis and Easton, 45 minutes from BWI Airport, 55 minutes from Washington, DC & Baltimore, and 1 1/2 hours away from Ocean City ! Whether you're looking for a year-round residence or a weekend retreat, this home offers the ultimate Chesapeake Bay lifestyle !

346 Narrows Pointe Dr, Grasonville

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