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$1,250,000

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

5 Beds ⋅ 3 Baths

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

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$825,000

Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful golf course views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Recent improvements include two new (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

4 Beds ⋅ 3 Baths

Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful golf course views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Recent improvements include two new (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

116 Prospect Bay Dr W, Grasonville

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

$650,000

Contemporary home in Prospect Bay offering approximately 2,850 square feet of living space and available for the first time since 1999. Features 3 bedrooms, including 2 on the main level, and 2.5 baths. The family room includes a fireplace and triple sliders leading to the deck. Spacious primary suite. Loft overlooking the family room, ideal for a home office, sitting area, or additional living space. Separate dining room and dedicated mudroom with laundry. Complete with a 2-car garage and deck overlooking the backyard. Located in Prospect Bay Golf and Country Club. Club amenities include: golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant.

3 Beds ⋅ 3 Baths

Contemporary home in Prospect Bay offering approximately 2,850 square feet of living space and available for the first time since 1999. Features 3 bedrooms, including 2 on the main level, and 2.5 baths. The family room includes a fireplace and triple sliders leading to the deck. Spacious primary suite. Loft overlooking the family room, ideal for a home office, sitting area, or additional living space. Separate dining room and dedicated mudroom with laundry. Complete with a 2-car garage and deck overlooking the backyard. Located in Prospect Bay Golf and Country Club. Club amenities include: golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant.

24 Fairway Is, Grasonville

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

$875,000

Much loved home sited on 1.03 acres offering sunset views over the water on one side and golf course views on the other. This spacious home features quality 2x6 construction, hardwood flooring, and Andersen windows that provide abundant natural light throughout. The kitchen measures approximately 19’ x 14’ and includes maple cabinetry, a center island, table space, and an open layout connecting directly to the family room. The family room features a fireplace with an efficient wood-burning insert and a wall mounted 77 inch LG OLED TV, about one year old. Separate living and dining rooms, both with bow windows, frame the beautiful water views. The main-level fourth bedroom includes built-in shelving and currently serves as a home office. The gracious primary suite features water views from a bow window, a large bath, and huge walk-in closet. Two additional good sized bedrooms and a full bath complete the upper level. The oversized two-car garage offers approximately 600 square feet with workshop space, pegboard walls, and extensive shelving. The blacktop driveway includes a large parking pad with room for up to six vehicles. Outdoor features include a screened porch overlooking the golf course and a 16’ x 12’ Amish-built shed designed to complement the home, complete with interior shelving. Additional features include a walk-in attic with shelving and extensive storage space, recently upgraded lighting, a built-in ironing board in the laundry area, and a Bruno stairlift on the wide staircase between the first and second floors, which can be removed if desired. Recent upgrades include new washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps that are less than two years old. 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.

4 Beds ⋅ 3 Baths

Much loved home sited on 1.03 acres offering sunset views over the water on one side and golf course views on the other. This spacious home features quality 2x6 construction, hardwood flooring, and Andersen windows that provide abundant natural light throughout. The kitchen measures approximately 19’ x 14’ and includes maple cabinetry, a center island, table space, and an open layout connecting directly to the family room. The family room features a fireplace with an efficient wood-burning insert and a wall mounted 77 inch LG OLED TV, about one year old. Separate living and dining rooms, both with bow windows, frame the beautiful water views. The main-level fourth bedroom includes built-in shelving and currently serves as a home office. The gracious primary suite features water views from a bow window, a large bath, and huge walk-in closet. Two additional good sized bedrooms and a full bath complete the upper level. The oversized two-car garage offers approximately 600 square feet with workshop space, pegboard walls, and extensive shelving. The blacktop driveway includes a large parking pad with room for up to six vehicles. Outdoor features include a screened porch overlooking the golf course and a 16’ x 12’ Amish-built shed designed to complement the home, complete with interior shelving. Additional features include a walk-in attic with shelving and extensive storage space, recently upgraded lighting, a built-in ironing board in the laundry area, and a Bruno stairlift on the wide staircase between the first and second floors, which can be removed if desired. Recent upgrades include new washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps that are less than two years old. 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.

108 Prospect Bay Dr W, Grasonville

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

$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:

$769,000

Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fishing enthusiasts. Located in a friendly community with excellent schools and nearby parks, this home is perfect for those seeking comfort and convenience. BONUS: Outdoor Office with private entrance on back right corner of house. PLUS: Community has a few boat slips available for rent!

4 Beds ⋅ 3 Baths

Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fishing enthusiasts. Located in a friendly community with excellent schools and nearby parks, this home is perfect for those seeking comfort and convenience. BONUS: Outdoor Office with private entrance on back right corner of house. PLUS: Community has a few boat slips available for rent!

1 Bunker, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250