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Detached five-unit multifamily property on Main Street in Grasonville with $1,500 in current monthly rent and three vacant apartments available to lease. Apartment 1 has two bedrooms and one bathroom, and Apartments 2 through 5 each have one bedroom and one bathroom. Apartments 1, 2, and 5 are vacant. Apartments 3 and 4 are occupied by long-term tenants at $750 per month each, with voucher assistance in place for Apartment 3. The three vacancies offer buyers the flexibility to set lease terms and bring additional units into income.

5122 Main St, Grasonville

Listing courtesy of ExecuHome Realty. Contact:

$409,900

Welcome to 451 Timber Lane, Grasonville! Nestled on a desirable corner lot in the sought-after The Woods neighborhood, this beautifully refreshed 3-bedroom, 2-bath rancher offers the perfect combination of comfort, style, and convenient single-level living. From the moment you arrive, the welcoming front porch invites you to sit back, relax, and enjoy the charm of this established neighborhood. Step inside to discover a bright, inviting home featuring a freshly painted interior, updated luxury vinyl plank flooring, and updated ceiling fans and light fixtures. The comfortable, functional floor plan is designed for easy everyday living. The heart of the home is the beautifully updated kitchen, featuring quartz countertops and updated appliances. The inviting living area is enhanced by a cozy electric fireplace, creating the perfect atmosphere for relaxing evenings at home. Three comfortable bedrooms and two full bathrooms provide plenty of flexibility for family, guests, or a home office. Step outside to enjoy the rear deck, an ideal spot for morning coffee, outdoor dining, or simply unwinding after a long day. Location is another standout feature! Conveniently situated in Grasonville, just approximately 15 minutes from the Chesapeake Bay Bridge, this home offers easy access to Route 50, Kent Island, Annapolis, and the surrounding Eastern Shore. Enjoy nearby shopping, dining, marinas, and all the recreational opportunities that make Eastern Shore living so special. Move-in ready, thoughtfully refreshed, and ideally located—451 Timber Lane is ready to welcome you home!

3 Beds ⋅ 2 Baths

Welcome to 451 Timber Lane, Grasonville! Nestled on a desirable corner lot in the sought-after The Woods neighborhood, this beautifully refreshed 3-bedroom, 2-bath rancher offers the perfect combination of comfort, style, and convenient single-level living. From the moment you arrive, the welcoming front porch invites you to sit back, relax, and enjoy the charm of this established neighborhood. Step inside to discover a bright, inviting home featuring a freshly painted interior, updated luxury vinyl plank flooring, and updated ceiling fans and light fixtures. The comfortable, functional floor plan is designed for easy everyday living. The heart of the home is the beautifully updated kitchen, featuring quartz countertops and updated appliances. The inviting living area is enhanced by a cozy electric fireplace, creating the perfect atmosphere for relaxing evenings at home. Three comfortable bedrooms and two full bathrooms provide plenty of flexibility for family, guests, or a home office. Step outside to enjoy the rear deck, an ideal spot for morning coffee, outdoor dining, or simply unwinding after a long day. Location is another standout feature! Conveniently situated in Grasonville, just approximately 15 minutes from the Chesapeake Bay Bridge, this home offers easy access to Route 50, Kent Island, Annapolis, and the surrounding Eastern Shore. Enjoy nearby shopping, dining, marinas, and all the recreational opportunities that make Eastern Shore living so special. Move-in ready, thoughtfully refreshed, and ideally located—451 Timber Lane is ready to welcome you home!

451 Timber Ln, Grasonville

Listing courtesy of Compass. Contact:

$300,000

Renovated and ready to move in! Cathedral ceilings, built-ins, Open Concept kitchen with dining nook, Durable tile flooring and every little available space put to good use during renovation. Come take a look. Some furniture & décor may convey with acceptable offer.

2 Beds ⋅ 2 Baths

Renovated and ready to move in! Cathedral ceilings, built-ins, Open Concept kitchen with dining nook, Durable tile flooring and every little available space put to good use during renovation. Come take a look. Some furniture & décor may convey with acceptable offer.

108 Fox Run, Grasonville

Listing courtesy of Rosendale Realty. Contact:

$1,650,000

Set in a wonderfully private waterfront setting, this elegant traditional home combines timeless charm with impressive renovations and thoughtful modern updates. Offering five bedrooms, the home features a spacious first-floor primary suite with an updated bath and walk-in shower, along with a second-floor waterside bedroom suite. Beautiful hard wood floors flow throughout much of the home, complementing the generously sized rooms and creating an inviting atmosphere for both everyday living and entertainment. The fully renovated kitchen is a standout, featuring upscale appliances, a granite-topped center island, and a striking tile backsplash extending to the ceiling. Formal living and dining rooms, along with a classic library, offer elegant spaces for entertaining, relaxing, and working from home. At the heart of the home, an expansive addition featuring a family room and game room provides exceptional space for gatherings, celebrations, and relaxed waterfront living. Bamboo flooring and vaulted ceilings enhance the bright, open feel of this welcoming retreat. The waterfront setting is truly special, offering privacy, access to the bay, a completely replaced of dock, and a 10,000-pound boat lift. Water depth is approximately four to six feet at medium-low tide. Additional improvements include a painted brick exterior, and an architectural-shingle roof installed just three years ago. A detached, oversized two-car garage with a second floor provides abundant storage and exciting possibilities for a variety of uses. The swimming pool is being sold in as-is condition. Combining classic elegance, extensive living spaces, significant updates, and exceptional waterfront amenities, this distinctive property offers a wonderful opportunity to embrace the privacy and beauty of waterfront living.

5 Beds ⋅ 4 Baths

Set in a wonderfully private waterfront setting, this elegant traditional home combines timeless charm with impressive renovations and thoughtful modern updates. Offering five bedrooms, the home features a spacious first-floor primary suite with an updated bath and walk-in shower, along with a second-floor waterside bedroom suite. Beautiful hard wood floors flow throughout much of the home, complementing the generously sized rooms and creating an inviting atmosphere for both everyday living and entertainment. The fully renovated kitchen is a standout, featuring upscale appliances, a granite-topped center island, and a striking tile backsplash extending to the ceiling. Formal living and dining rooms, along with a classic library, offer elegant spaces for entertaining, relaxing, and working from home. At the heart of the home, an expansive addition featuring a family room and game room provides exceptional space for gatherings, celebrations, and relaxed waterfront living. Bamboo flooring and vaulted ceilings enhance the bright, open feel of this welcoming retreat. The waterfront setting is truly special, offering privacy, access to the bay, a completely replaced of dock, and a 10,000-pound boat lift. Water depth is approximately four to six feet at medium-low tide. Additional improvements include a painted brick exterior, and an architectural-shingle roof installed just three years ago. A detached, oversized two-car garage with a second floor provides abundant storage and exciting possibilities for a variety of uses. The swimming pool is being sold in as-is condition. Combining classic elegance, extensive living spaces, significant updates, and exceptional waterfront amenities, this distinctive property offers a wonderful opportunity to embrace the privacy and beauty of waterfront living.

312 Greenwood Point Rd, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

111 Beach Harbor Dr Unit 85 A, Grasonville

$129,200

Site contains a 2011 DutchPark tiny home style RV with an attached 200sqft sunroom. 2 decks, 8x8 shed, patio, deep shaded lot. The RV is 40ft long, with 2 large bump outs and has cathedral ceilings, a shingle roof and house type siding. Heating is propane forced air and central air conditioning. Has 1 queen br and Sleeps 6 with 2 queen size sleeper sofas. Located in Beach Harbor in Grasonville MD. Membership provides amenities including Clubhouse, Bathhouse, Swimming Pool and Hot Tub, Playground, Multipurpose courts, Boat Launch and Beach. Season runs March 15th through first Monday following Thanksgiving. Limited access during the off season.

1 Beds ⋅ 1 Baths

Site contains a 2011 DutchPark tiny home style RV with an attached 200sqft sunroom. 2 decks, 8x8 shed, patio, deep shaded lot. The RV is 40ft long, with 2 large bump outs and has cathedral ceilings, a shingle roof and house type siding. Heating is propane forced air and central air conditioning. Has 1 queen br and Sleeps 6 with 2 queen size sleeper sofas. Located in Beach Harbor in Grasonville MD. Membership provides amenities including Clubhouse, Bathhouse, Swimming Pool and Hot Tub, Playground, Multipurpose courts, Boat Launch and Beach. Season runs March 15th through first Monday following Thanksgiving. Limited access during the off season.

111 Beach Harbor Dr Unit 85 A, Grasonville

Listing courtesy of Century 21 Downtown. Contact:

$249,000

Grasonville - This 2 Bedroom duplex has been completely remodeled. New stainless-steel appliances, granite counter tops, luxury vinyl floor throughout. Nice back yard fenced with also a shed for storage. One level living with separate laundry room with access to backyard to deck and fenced. Call today for your showing.

2 Beds ⋅ 1 Baths

Grasonville - This 2 Bedroom duplex has been completely remodeled. New stainless-steel appliances, granite counter tops, luxury vinyl floor throughout. Nice back yard fenced with also a shed for storage. One level living with separate laundry room with access to backyard to deck and fenced. Call today for your showing.

116 Watermans Ct, Grasonville

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

$764,500

Custom Home with In-Ground Salt Water Pool, Private Backyard & Detached, Heated and Cooled Studio/Office in Greenwood Community. Discover the distinctive charm of this custom-built home in the sought-after Greenwood Community of Grasonville. Providing four bedrooms, and three-and-a-half- bathrooms, this home combines thoughtful craftsmanship, architectural character, and inviting indoor-outdoor living. Step inside to a light-filled, open layout highlighted by a dramatic two-story family room, soaring ceilings, expansive windows, and an impressive stone fireplace. Hardwood floors, crown molding, decorative leaded-glass windows, rounded wall corners, and distinctive lighting add character throughout. The spacious kitchen features granite counter tops, a generous center island, under-cabinet lighting, and stainless steel appliances, including a double-oven range and beverage cooler. The adjoining dining room overlooks the backyard, creating a welcoming setting for everyday meals and entertaining. A main-level bedroom with a full bathroom offers added flexibility for guests or multi generational living. Upstairs, the spacious primary suite provides a relaxing retreat with a tray ceiling, expansive walk-in closet, and private bath featuring a glass-enclosed shower and jetted soaking tub. Two additional bedrooms and a custom-designed second-floor laundry room with extra storage complete the upper level. The outdoor setting is a standout feature, with an in-ground salt water swimming pool, deck, and backyard designed for relaxing, entertaining. A charming, cottage-inspired studio/office with heating and cooling provides versatile space for hobbies, creative pursuits, a home office, or a personal retreat. Residents of Greenwood Community enjoy amenities including a playground, pavilion, large multipurpose field, designated storage for RVs, boats, and trailers, and a gazebo for community gatherings.

4 Beds ⋅ 4 Baths

Custom Home with In-Ground Salt Water Pool, Private Backyard & Detached, Heated and Cooled Studio/Office in Greenwood Community. Discover the distinctive charm of this custom-built home in the sought-after Greenwood Community of Grasonville. Providing four bedrooms, and three-and-a-half- bathrooms, this home combines thoughtful craftsmanship, architectural character, and inviting indoor-outdoor living. Step inside to a light-filled, open layout highlighted by a dramatic two-story family room, soaring ceilings, expansive windows, and an impressive stone fireplace. Hardwood floors, crown molding, decorative leaded-glass windows, rounded wall corners, and distinctive lighting add character throughout. The spacious kitchen features granite counter tops, a generous center island, under-cabinet lighting, and stainless steel appliances, including a double-oven range and beverage cooler. The adjoining dining room overlooks the backyard, creating a welcoming setting for everyday meals and entertaining. A main-level bedroom with a full bathroom offers added flexibility for guests or multi generational living. Upstairs, the spacious primary suite provides a relaxing retreat with a tray ceiling, expansive walk-in closet, and private bath featuring a glass-enclosed shower and jetted soaking tub. Two additional bedrooms and a custom-designed second-floor laundry room with extra storage complete the upper level. The outdoor setting is a standout feature, with an in-ground salt water swimming pool, deck, and backyard designed for relaxing, entertaining. A charming, cottage-inspired studio/office with heating and cooling provides versatile space for hobbies, creative pursuits, a home office, or a personal retreat. Residents of Greenwood Community enjoy amenities including a playground, pavilion, large multipurpose field, designated storage for RVs, boats, and trailers, and a gazebo for community gatherings.

414 Narnia Dr N, Grasonville

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

$649,000

**Welcome to Perry’s Retreat, where spacious living meets modern comfort and Eastern Shore charm!** Built in 2023, this pristine Ryan Homes Lehigh model offers the **largest floor plan in the community**, featuring over 3,000 square feet of beautifully designed living space, five bedrooms, two-and-a-half bathrooms, and an exceptional open-concept layout. The heart of this home is its expansive main living area, thoughtfully designed for both everyday comfort and effortless entertaining. The open floor plan seamlessly connects the kitchen, dining, and gathering spaces, creating a bright and inviting atmosphere. The spacious kitchen features an oversized center island that serves as the perfect gathering spot for casual meals, entertaining guests, or simply enjoying time together. With generous room to spread out, this main level is truly an entertainer’s dream! Adding to the home's versatility is a main-level bedroom, ideal for guests or multigenerational living, along with a separate flex room that can easily accommodate a home office, exercise room, or hobby space. Upstairs, a spacious additional living area provides the perfect secondary retreat for movie nights, a playroom, or a comfortable place to unwind. The generously sized primary suite features two walk-in closets and a private en-suite bathroom. Three additional bedrooms offer plenty of room and flexibility. Step outside to your own private backyard oasis! A beautifully hardscaped patio provides the ideal setting for outdoor dining, grilling, and entertaining. The fully fenced backyard, complete with attractive vinyl fencing and gated access to the expansive community green space, offers a wonderful combination of privacy and convenience. Perry’s Retreat offers a welcoming neighborhood atmosphere with expansive common grounds, a playground, and a dedicated boat storage area for residents. Additional highlights include a two-car attached garage, public water and sewer, and the peace of mind that comes with owning a nearly new home in pristine condition. **With the largest floor plan in Perry’s Retreat, five bedrooms, multiple living areas, an entertainer-friendly open layout, and beautifully finished outdoor space, this exceptional home truly has it all!** Discover the space, flexibility, and lifestyle you've been looking for!

5 Beds ⋅ 3 Baths

**Welcome to Perry’s Retreat, where spacious living meets modern comfort and Eastern Shore charm!** Built in 2023, this pristine Ryan Homes Lehigh model offers the **largest floor plan in the community**, featuring over 3,000 square feet of beautifully designed living space, five bedrooms, two-and-a-half bathrooms, and an exceptional open-concept layout. The heart of this home is its expansive main living area, thoughtfully designed for both everyday comfort and effortless entertaining. The open floor plan seamlessly connects the kitchen, dining, and gathering spaces, creating a bright and inviting atmosphere. The spacious kitchen features an oversized center island that serves as the perfect gathering spot for casual meals, entertaining guests, or simply enjoying time together. With generous room to spread out, this main level is truly an entertainer’s dream! Adding to the home's versatility is a main-level bedroom, ideal for guests or multigenerational living, along with a separate flex room that can easily accommodate a home office, exercise room, or hobby space. Upstairs, a spacious additional living area provides the perfect secondary retreat for movie nights, a playroom, or a comfortable place to unwind. The generously sized primary suite features two walk-in closets and a private en-suite bathroom. Three additional bedrooms offer plenty of room and flexibility. Step outside to your own private backyard oasis! A beautifully hardscaped patio provides the ideal setting for outdoor dining, grilling, and entertaining. The fully fenced backyard, complete with attractive vinyl fencing and gated access to the expansive community green space, offers a wonderful combination of privacy and convenience. Perry’s Retreat offers a welcoming neighborhood atmosphere with expansive common grounds, a playground, and a dedicated boat storage area for residents. Additional highlights include a two-car attached garage, public water and sewer, and the peace of mind that comes with owning a nearly new home in pristine condition. **With the largest floor plan in Perry’s Retreat, five bedrooms, multiple living areas, an entertainer-friendly open layout, and beautifully finished outdoor space, this exceptional home truly has it all!** Discover the space, flexibility, and lifestyle you've been looking for!

114 Pathfinder Cir, Grasonville

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

$75,000

Waterfront weekends on the Chester River, for a fraction of what a waterfront house costs. Lot 46F on Zuma Beach in Beach Harbor Camper Cooperative comes with a Forest River Silverback fifth-wheel set up under mature shade trees, so your summer afternoons stay cool. Inside: 1 bedroom and 1 bath. Outside: Outside, the setup is already done for you: a brick paver patio with a built-in fire pit, string lights overhead, a privacy screen, built steps to the entry, a storage shed, and a gravel pad for parking, all under mature shade trees. Your co-op membership puts you on Jackson Creek and the Chester River, with a community boat ramp, pier, private beach, pool, hot tub, clubhouse, tennis, basketball, and shuffleboard. Launch the boat in the morning, fish the afternoon, and end the night around your own fire pit. Buy this fall and use the off-season to get it set up, so you're ready the day the season opens. Schedule your private showing now. Since this is a co-op campground financing is not available. See documents section for list of full inclusions

1 Beds ⋅ 1 Baths

Waterfront weekends on the Chester River, for a fraction of what a waterfront house costs. Lot 46F on Zuma Beach in Beach Harbor Camper Cooperative comes with a Forest River Silverback fifth-wheel set up under mature shade trees, so your summer afternoons stay cool. Inside: 1 bedroom and 1 bath. Outside: Outside, the setup is already done for you: a brick paver patio with a built-in fire pit, string lights overhead, a privacy screen, built steps to the entry, a storage shed, and a gravel pad for parking, all under mature shade trees. Your co-op membership puts you on Jackson Creek and the Chester River, with a community boat ramp, pier, private beach, pool, hot tub, clubhouse, tennis, basketball, and shuffleboard. Launch the boat in the morning, fish the afternoon, and end the night around your own fire pit. Buy this fall and use the off-season to get it set up, so you're ready the day the season opens. Schedule your private showing now. Since this is a co-op campground financing is not available. See documents section for list of full inclusions

46 F Zuma Bch, Grasonville

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

$549,900

Seller of 211 Pathfinder is offering up to $18,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 24, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits.Better than new and built in 2025, this beautifully appointed home sits on a quiet premium lot backing to woods and the community pond. Offering nearly 2,000 square feet of living space, three bedrooms, and two full baths, it pairs modern finishes with a peaceful setting. The kitchen features an expansive island, quartz countertops, subway tile backsplash, stainless steel appliances, and a walk-in pantry, with plenty of room for everyday meals and entertaining. Luxury vinyl plank flooring flows throughout the main living spaces. The primary suite offers a tray ceiling, walk-in closet, and spacious en suite bath with a double vanity and walk-in shower. A dedicated laundry room with a high-efficiency washer and dryer and a spacious garage add everyday convenience. Outside, the fully fenced backyard thoughtfully combines vinyl fencing along the sides for privacy with aluminum fencing across the rear to preserve the wooded and pond views. Located in a community across from the Chesapeake Bay Environmental Center, this move-in-ready home offers a beautiful place to settle in and enjoy life on the Shore.

3 Beds ⋅ 2 Baths

Seller of 211 Pathfinder is offering up to $18,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 24, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits.Better than new and built in 2025, this beautifully appointed home sits on a quiet premium lot backing to woods and the community pond. Offering nearly 2,000 square feet of living space, three bedrooms, and two full baths, it pairs modern finishes with a peaceful setting. The kitchen features an expansive island, quartz countertops, subway tile backsplash, stainless steel appliances, and a walk-in pantry, with plenty of room for everyday meals and entertaining. Luxury vinyl plank flooring flows throughout the main living spaces. The primary suite offers a tray ceiling, walk-in closet, and spacious en suite bath with a double vanity and walk-in shower. A dedicated laundry room with a high-efficiency washer and dryer and a spacious garage add everyday convenience. Outside, the fully fenced backyard thoughtfully combines vinyl fencing along the sides for privacy with aluminum fencing across the rear to preserve the wooded and pond views. Located in a community across from the Chesapeake Bay Environmental Center, this move-in-ready home offers a beautiful place to settle in and enjoy life on the Shore.

211 Pathfinder Cir, Grasonville

Listing courtesy of Samson Properties. Contact:

$1,495,000

Some homes are simply places to live. This is a lifestyle. Welcome to 228 Prospect Bay Dr W, an exceptionally maintained and thoughtfully updated home where beautiful water views, resort-style outdoor living, and the coveted Prospect Bay community come together in one unforgettable property. From the moment you arrive, the setting makes an impression. Mature landscaping, a gracious exterior and glimpses of the water create a sense of arrival that feels distinctly Eastern Shore. Step inside and you’ll quickly see that this home has been meticulously cared for and intentionally improved, blending timeless coastal character with sophisticated, modern updates. Hardwood floors extend throughout both levels, while custom trim work, designer wall treatments, updated lighting and carefully selected finishes give each space its own personality. The beautifully updated kitchen is designed for both everyday living and entertaining, featuring new countertops and backsplash, an enhanced island with additional storage, pull-out cabinetry and under-cabinet lighting. Just beyond, the sunroom provides a light-filled retreat overlooking the pool and outdoor living spaces. Formal living and dining areas offer an elevated place to gather, while the family room centers around a striking shiplap accent wall, electric fireplace and quartz hearth. Upstairs, the primary suite feels like a private escape, complete with water views, a masonry fireplace, expanded custom closet and beautifully remodeled spa-like bath with a tiled shower, marble seat, soaking tub and dual vanities. Three additional bedrooms and a well-appointed guest bath provide plenty of room for family and guests, while the bonus space over the garage offers flexibility for an office, studio, additional sleeping space or storage. Outside is where the Prospect Bay lifestyle truly comes alive. The backyard has been transformed into a private resort with a large inground pool, extensive hardscaping, Trex decking, hot tub, pergola and lush landscaping, all surrounded by mature trees for privacy. Steps from the pool, the charming separate guest house creates an incredible space for extended stays, offering its own bedroom, full bath, kitchenette and living area. And while the beauty of this home is immediately apparent, what sets it apart is the level of care behind the scenes. Major improvements include a new roof and gutters in 2024, three high-efficiency heat pumps in 2023, an encapsulated crawlspace in 2023, generator hookup, upgraded electrical service, repaved driveway, updated garage, new washer and dryer in 2026, fresh paint and new landscaping in 2026, along with extensive improvements throughout the kitchen, bathrooms, lighting, flooring, trim and outdoor spaces. All of this is set within Prospect Bay, one of the Eastern Shore’s most sought-after golf course communities, where residents enjoy an 18-hole golf course, clubhouse with restaurant and bar, driving range, tennis and pickleball, community pool, playground, private boat launch and more. Spend summer afternoons by your pool, host friends in the guest house, enjoy quiet mornings overlooking the water, play a round of golf, or launch the boat and spend the day exploring the Eastern Shore. 228 Prospect Bay Dr W isn’t simply a beautifully updated home, it’s the opportunity to live the Prospect Bay lifestyle every single day.

5 Beds ⋅ 4 Baths

Some homes are simply places to live. This is a lifestyle. Welcome to 228 Prospect Bay Dr W, an exceptionally maintained and thoughtfully updated home where beautiful water views, resort-style outdoor living, and the coveted Prospect Bay community come together in one unforgettable property. From the moment you arrive, the setting makes an impression. Mature landscaping, a gracious exterior and glimpses of the water create a sense of arrival that feels distinctly Eastern Shore. Step inside and you’ll quickly see that this home has been meticulously cared for and intentionally improved, blending timeless coastal character with sophisticated, modern updates. Hardwood floors extend throughout both levels, while custom trim work, designer wall treatments, updated lighting and carefully selected finishes give each space its own personality. The beautifully updated kitchen is designed for both everyday living and entertaining, featuring new countertops and backsplash, an enhanced island with additional storage, pull-out cabinetry and under-cabinet lighting. Just beyond, the sunroom provides a light-filled retreat overlooking the pool and outdoor living spaces. Formal living and dining areas offer an elevated place to gather, while the family room centers around a striking shiplap accent wall, electric fireplace and quartz hearth. Upstairs, the primary suite feels like a private escape, complete with water views, a masonry fireplace, expanded custom closet and beautifully remodeled spa-like bath with a tiled shower, marble seat, soaking tub and dual vanities. Three additional bedrooms and a well-appointed guest bath provide plenty of room for family and guests, while the bonus space over the garage offers flexibility for an office, studio, additional sleeping space or storage. Outside is where the Prospect Bay lifestyle truly comes alive. The backyard has been transformed into a private resort with a large inground pool, extensive hardscaping, Trex decking, hot tub, pergola and lush landscaping, all surrounded by mature trees for privacy. Steps from the pool, the charming separate guest house creates an incredible space for extended stays, offering its own bedroom, full bath, kitchenette and living area. And while the beauty of this home is immediately apparent, what sets it apart is the level of care behind the scenes. Major improvements include a new roof and gutters in 2024, three high-efficiency heat pumps in 2023, an encapsulated crawlspace in 2023, generator hookup, upgraded electrical service, repaved driveway, updated garage, new washer and dryer in 2026, fresh paint and new landscaping in 2026, along with extensive improvements throughout the kitchen, bathrooms, lighting, flooring, trim and outdoor spaces. All of this is set within Prospect Bay, one of the Eastern Shore’s most sought-after golf course communities, where residents enjoy an 18-hole golf course, clubhouse with restaurant and bar, driving range, tennis and pickleball, community pool, playground, private boat launch and more. Spend summer afternoons by your pool, host friends in the guest house, enjoy quiet mornings overlooking the water, play a round of golf, or launch the boat and spend the day exploring the Eastern Shore. 228 Prospect Bay Dr W isn’t simply a beautifully updated home, it’s the opportunity to live the Prospect Bay lifestyle every single day.

228 Prospect Bay Dr W, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

$1,199,000

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:

$1,550,000

Enjoy broad water views and spectacular sunsets from this beautifully situated 1.02-acre waterfront property, with water views enjoyed throughout much of the home. Designed for comfortable one-level living, this spacious residence offers 4 bedrooms, 3.5 baths providing 3,137 square feet of living space. The bright kitchen features a skylight, center island with seating, and an open layout connecting seamlessly to the family room with fireplace. The waterfront primary suite takes full advantage of the views and includes a large walk-in closet, private bath with soaking tub, walk-in shower and dual vanities, plus primary has direct access to a semi-private deck. An additional guest bedroom features its own ensuite bath. Oversized 2 Car Garage. Outdoor living is a highlight, with a swimming pool, deck with awning, patio, generous backyard, riprapped shoreline, and a new pier completed in 2026, Roof New in 2021. This property offers an ideal setting for relaxing, entertaining, and enjoying life on the water. The community offers resort-style amenities, including an 18-hole championship golf course, clubhouse with restaurant/bar/grill, swimming pool, tennis and pickleball courts plus. With expansive water views, beautiful sunsets, one-level living, a private pool and pier, this exceptional property offers the Eastern Shore waterfront lifestyle at its best.

4 Beds ⋅ 4 Baths

Enjoy broad water views and spectacular sunsets from this beautifully situated 1.02-acre waterfront property, with water views enjoyed throughout much of the home. Designed for comfortable one-level living, this spacious residence offers 4 bedrooms, 3.5 baths providing 3,137 square feet of living space. The bright kitchen features a skylight, center island with seating, and an open layout connecting seamlessly to the family room with fireplace. The waterfront primary suite takes full advantage of the views and includes a large walk-in closet, private bath with soaking tub, walk-in shower and dual vanities, plus primary has direct access to a semi-private deck. An additional guest bedroom features its own ensuite bath. Oversized 2 Car Garage. Outdoor living is a highlight, with a swimming pool, deck with awning, patio, generous backyard, riprapped shoreline, and a new pier completed in 2026, Roof New in 2021. This property offers an ideal setting for relaxing, entertaining, and enjoying life on the water. The community offers resort-style amenities, including an 18-hole championship golf course, clubhouse with restaurant/bar/grill, swimming pool, tennis and pickleball courts plus. With expansive water views, beautiful sunsets, one-level living, a private pool and pier, this exceptional property offers the Eastern Shore waterfront lifestyle at its best.

251 Prospect Bay Dr W, Grasonville

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

$464,900

Welcome home to this beautifully maintained and fully updated 3-bedroom home, just 8 years young! Featuring like-new systems and roof, this home offers modern comfort and peace of mind. A 4-foot bump-out provides additional living space, while the upgraded kitchen boasts stainless steel appliances and sliding glass doors leading to a spacious 12x20 composite deck—perfect for entertaining. Enjoy outdoor living with an above-ground pool, fully fenced backyard with white vinyl privacy fencing, and a crushed stone patio that leads to a cozy fire pit area. The long gravel driveway and oversized two-car garage offer ample parking and storage. Inside, you’ll find a spacious primary bedroom with a private full bath, plus an additional family room on the lower level with a convenient half bath—ideal for extra living space, guests, or a home office. Perfectly maintained from the front door throughout, this hidden gem is conveniently located near Route 50, making it an excellent choice for commuters. Stairs have recently been painted pictures will be updated soon .No HOA!

3 Beds ⋅ 3 Baths

Welcome home to this beautifully maintained and fully updated 3-bedroom home, just 8 years young! Featuring like-new systems and roof, this home offers modern comfort and peace of mind. A 4-foot bump-out provides additional living space, while the upgraded kitchen boasts stainless steel appliances and sliding glass doors leading to a spacious 12x20 composite deck—perfect for entertaining. Enjoy outdoor living with an above-ground pool, fully fenced backyard with white vinyl privacy fencing, and a crushed stone patio that leads to a cozy fire pit area. The long gravel driveway and oversized two-car garage offer ample parking and storage. Inside, you’ll find a spacious primary bedroom with a private full bath, plus an additional family room on the lower level with a convenient half bath—ideal for extra living space, guests, or a home office. Perfectly maintained from the front door throughout, this hidden gem is conveniently located near Route 50, making it an excellent choice for commuters. Stairs have recently been painted pictures will be updated soon .No HOA!

206 Melvin Ave, Grasonville

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

$719,900

Welcome to Oyster Cove Live the Oyster Cove lifestyle! Welcome to a beautifully maintained townhome in Oyster Cove, a gated waterfront community offering the perfect blend of elegance, convenience, and carefree living. Here, the grounds are maintained for you, giving you more time to enjoy the lifestyle you’ve worked for. Residents can take advantage of the community pool, waterfront surroundings, and peaceful, beautifully landscaped setting. Enjoy the best of Grasonville right outside your door—restaurants, shopping, marinas, entertainment, and everyday conveniences are all just minutes away and easily accessible by car, bike, or even a leisurely walk. Whether you’re looking for a full-time residence, a weekend retreat, or a low-maintenance home where you can simply lock the door and go, Oyster Cove offers an exceptional setting. This is more than a townhome—it’s a lifestyle. Come experience the charm, sophistication, and relaxed waterfront atmosphere of one of the area’s most desirable communities. This beautifully refreshed three-level townhouse is move-in ready and priced to sell at $719,900. Freshly painted throughout, featuring brand-new carpet and freshly refinished hardwood flooring, this home offers a clean, updated feel from the moment you walk in. Enjoy the spacious three-level layout with plenty of room for everyday living and entertaining. A private boat slip is included, adding exceptional value for boating and waterfront enthusiasts. Move right in and enjoy all that Oyster Cove has to offer. Don’t miss this opportunity to own a beautifully refreshed townhouse with a boat slip at an attractive price! Thoughtfully staged (virtual) to highlight the home's spacious rooms, functionality, and potential.

3 Beds ⋅ 4 Baths

Welcome to Oyster Cove Live the Oyster Cove lifestyle! Welcome to a beautifully maintained townhome in Oyster Cove, a gated waterfront community offering the perfect blend of elegance, convenience, and carefree living. Here, the grounds are maintained for you, giving you more time to enjoy the lifestyle you’ve worked for. Residents can take advantage of the community pool, waterfront surroundings, and peaceful, beautifully landscaped setting. Enjoy the best of Grasonville right outside your door—restaurants, shopping, marinas, entertainment, and everyday conveniences are all just minutes away and easily accessible by car, bike, or even a leisurely walk. Whether you’re looking for a full-time residence, a weekend retreat, or a low-maintenance home where you can simply lock the door and go, Oyster Cove offers an exceptional setting. This is more than a townhome—it’s a lifestyle. Come experience the charm, sophistication, and relaxed waterfront atmosphere of one of the area’s most desirable communities. This beautifully refreshed three-level townhouse is move-in ready and priced to sell at $719,900. Freshly painted throughout, featuring brand-new carpet and freshly refinished hardwood flooring, this home offers a clean, updated feel from the moment you walk in. Enjoy the spacious three-level layout with plenty of room for everyday living and entertaining. A private boat slip is included, adding exceptional value for boating and waterfront enthusiasts. Move right in and enjoy all that Oyster Cove has to offer. Don’t miss this opportunity to own a beautifully refreshed townhouse with a boat slip at an attractive price! Thoughtfully staged (virtual) to highlight the home's spacious rooms, functionality, and potential.

1202 Oyster Cove Dr, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$399,000

Grasonville - Property is zoned GVC, this gives you opportunity to own your own home and business. Well maintained property and home located on a corner lot with garage and extra storage sheds. Plenty of room for parking, open floor plan featuring 3 bedrooms 2 baths with luxury vinyl flooring with wonderful kitchen with upgraded commercial size refrigerator/freezer. The decks make it nice for outside entertaining with custom retractable awning and screen/shades.

3 Beds ⋅ 2 Baths

Grasonville - Property is zoned GVC, this gives you opportunity to own your own home and business. Well maintained property and home located on a corner lot with garage and extra storage sheds. Plenty of room for parking, open floor plan featuring 3 bedrooms 2 baths with luxury vinyl flooring with wonderful kitchen with upgraded commercial size refrigerator/freezer. The decks make it nice for outside entertaining with custom retractable awning and screen/shades.

101 King Store Rd, Grasonville

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

$899,000

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and community—all just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 10th green. Situated on a one-acre lot, the home offers over 3,000 square feet, 4–5 bedrooms, a three-car garage, and a comfortable, flexible floor plan designed for everyday living and entertaining. A dramatic two-story foyer leads to bright living spaces accented by tray and vaulted ceilings. The spacious kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, and opens to the family room with bamboo flooring, gas fireplace, custom built-ins, and access to the large deck. A separate dining room and main-level bedroom add versatility. The spacious primary suite offers a large walk-in closet and private bath with soaking tub, dual vanities, and walk-in shower. Enjoy beautiful golf course views from the deck or screened gazebo—perfect for relaxing, entertaining, or an Eastern Shore crab feast.

5 Beds ⋅ 3 Baths

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and community—all just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 10th green. Situated on a one-acre lot, the home offers over 3,000 square feet, 4–5 bedrooms, a three-car garage, and a comfortable, flexible floor plan designed for everyday living and entertaining. A dramatic two-story foyer leads to bright living spaces accented by tray and vaulted ceilings. The spacious kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, and opens to the family room with bamboo flooring, gas fireplace, custom built-ins, and access to the large deck. A separate dining room and main-level bedroom add versatility. The spacious primary suite offers a large walk-in closet and private bath with soaking tub, dual vanities, and walk-in shower. Enjoy beautiful golf course views from the deck or screened gazebo—perfect for relaxing, entertaining, or an Eastern Shore crab feast.

14 Fairway Is, Grasonville

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

$759,000

Nestled in the serene enclave of Oyster Cove, this stunning bayfront townhouse offers a harmonious blend of contemporary design and luxurious living. With three spacious bedrooms and three and a half bathrooms, this residence is perfect for those seeking comfort and style. The moment you step inside, you are greeted by an open floor plan that seamlessly connects the living and dining areas, enhanced by beautiful wood floors and abundant natural light. The living space features a cozy fireplace with glass doors, creating an inviting atmosphere for gatherings or quiet evenings at home. The heart of the home is the country-style kitchen, equipped with upgraded countertops and a suite of modern appliances, including a self-cleaning oven, dishwasher, and refrigerator. Enjoy casual meals in the eat-in kitchen or host dinner parties in the elegant dining area. The primary bedroom is a true retreat, boasting bayfront views, a walk-in closet, and a luxurious en-suite bathroom complete with a jetted tub and walk-in shower. Step outside to discover the community's exceptional amenities. Enjoy leisurely afternoons by the saltwater pool, take a stroll along the scenic jog/walk paths, or engage in friendly matches on the tennis and pickleball courts. The gated community ensures peace of mind, while the clubhouse and party room provide perfect venues for social gatherings. For those who love the outdoors, the nearby marina offers water access to the beautiful Eastern Bay, ideal for boating and fishing enthusiasts. Oyster Cove is not just a home; it's a lifestyle. The neighborhood is rich with common grounds, picnic areas, and a dog park, making it perfect for outdoor activities. With easy access to local shopping, dining, and entertainment, everything you need is just a short drive away. This property is not just a place to live; it's a sanctuary where you can unwind and enjoy the beauty of waterfront living. Don't miss the opportunity to make this exquisite townhouse your new home in Oyster Cove, where every day feels like a vacation. Experience the perfect blend of luxury, comfort, and community in this exceptional property.

3 Beds ⋅ 4 Baths

Nestled in the serene enclave of Oyster Cove, this stunning bayfront townhouse offers a harmonious blend of contemporary design and luxurious living. With three spacious bedrooms and three and a half bathrooms, this residence is perfect for those seeking comfort and style. The moment you step inside, you are greeted by an open floor plan that seamlessly connects the living and dining areas, enhanced by beautiful wood floors and abundant natural light. The living space features a cozy fireplace with glass doors, creating an inviting atmosphere for gatherings or quiet evenings at home. The heart of the home is the country-style kitchen, equipped with upgraded countertops and a suite of modern appliances, including a self-cleaning oven, dishwasher, and refrigerator. Enjoy casual meals in the eat-in kitchen or host dinner parties in the elegant dining area. The primary bedroom is a true retreat, boasting bayfront views, a walk-in closet, and a luxurious en-suite bathroom complete with a jetted tub and walk-in shower. Step outside to discover the community's exceptional amenities. Enjoy leisurely afternoons by the saltwater pool, take a stroll along the scenic jog/walk paths, or engage in friendly matches on the tennis and pickleball courts. The gated community ensures peace of mind, while the clubhouse and party room provide perfect venues for social gatherings. For those who love the outdoors, the nearby marina offers water access to the beautiful Eastern Bay, ideal for boating and fishing enthusiasts. Oyster Cove is not just a home; it's a lifestyle. The neighborhood is rich with common grounds, picnic areas, and a dog park, making it perfect for outdoor activities. With easy access to local shopping, dining, and entertainment, everything you need is just a short drive away. This property is not just a place to live; it's a sanctuary where you can unwind and enjoy the beauty of waterfront living. Don't miss the opportunity to make this exquisite townhouse your new home in Oyster Cove, where every day feels like a vacation. Experience the perfect blend of luxury, comfort, and community in this exceptional property.

1107 Oyster Cove Dr, Grasonville

Listing courtesy of Star Realty. Contact:

$579,900

Please remove shoes or use shoe covers provided! Welcome to the rarely-available upgraded Hudson model at Perry's Retreat located at 106 Pixie Court. This beautiful unit offers the perfect blend of space, comfort, and modern design on a PREMIUM LOT. This home presents a rare opportunity to own one of the community's most desirable models in a cud-de-sac. The main level features an open concept design that seamlessly connects the kitchen, dining, and living areas, creating an ideal layout for both everyday living and entertaining. A private office with French doors provides the perfect work from home space, while an additional ensuite bedroom on this level offers endless possibilities as a guest room, or hobby space. The upgraded kitchen serves as the heart of the home, showcasing quartz countertops, stainless steel appliances, upgraded backsplash, additional wall oven, and a large island overlooking the spacious living room. Luxury vinyl plank flooring in most of the main level adds both style and durability. Upstairs, the spacious primary suite offers a relaxing retreat with a tray ceiling, two oversized walk-in closets, and a beautifully appointed en-suite bathroom featuring dual vanities, private water closet, and linen closet. Three additional bedrooms, a full bathroom with double sinks, and a convenient upper-level laundry room complete the second floor. Outside, enjoy a backyard that creates a setting for relaxation and entertaining. Community amenities include a playground, open green space for neighborhood events. Conveniently located just minutes from Route 50, residents enjoy easy access to Kent Island, Annapolis, Easton, St. Michaels, Oxford, Tilghman Island, Baltimore, and Washington, D.C. Directly across from the community, the Chesapeake Bay Environmental Center offers hiking trails, kayaking, wildlife viewing, educational programs, and summer camps, allowing you to fully embrace the Eastern Shore lifestyle. Professional photos coming soon!

5 Beds ⋅ 3 Baths

Please remove shoes or use shoe covers provided! Welcome to the rarely-available upgraded Hudson model at Perry's Retreat located at 106 Pixie Court. This beautiful unit offers the perfect blend of space, comfort, and modern design on a PREMIUM LOT. This home presents a rare opportunity to own one of the community's most desirable models in a cud-de-sac. The main level features an open concept design that seamlessly connects the kitchen, dining, and living areas, creating an ideal layout for both everyday living and entertaining. A private office with French doors provides the perfect work from home space, while an additional ensuite bedroom on this level offers endless possibilities as a guest room, or hobby space. The upgraded kitchen serves as the heart of the home, showcasing quartz countertops, stainless steel appliances, upgraded backsplash, additional wall oven, and a large island overlooking the spacious living room. Luxury vinyl plank flooring in most of the main level adds both style and durability. Upstairs, the spacious primary suite offers a relaxing retreat with a tray ceiling, two oversized walk-in closets, and a beautifully appointed en-suite bathroom featuring dual vanities, private water closet, and linen closet. Three additional bedrooms, a full bathroom with double sinks, and a convenient upper-level laundry room complete the second floor. Outside, enjoy a backyard that creates a setting for relaxation and entertaining. Community amenities include a playground, open green space for neighborhood events. Conveniently located just minutes from Route 50, residents enjoy easy access to Kent Island, Annapolis, Easton, St. Michaels, Oxford, Tilghman Island, Baltimore, and Washington, D.C. Directly across from the community, the Chesapeake Bay Environmental Center offers hiking trails, kayaking, wildlife viewing, educational programs, and summer camps, allowing you to fully embrace the Eastern Shore lifestyle. Professional photos coming soon!

106 Pixie Ct, Grasonville

Listing courtesy of HomeSmart. Contact:

$379,000

Charming Cape Cod home offering both residential comfort and commercial potential, beautifully updated with modern finishes while maintaining its classic character. This move-in-ready property features 2 bedrooms, 1 full bathroom, an inviting sunroom entry, and luxury vinyl plank flooring throughout. The updated kitchen showcases stainless steel appliances, an induction range, new refrigerator, granite countertops, and refreshed cabinetry. Recent improvements include the bathroom, double-pane windows, roof, siding, HVAC system, well system, electrical panel, and front entry door. The property also features an oversized detached garage with side entry and a spacious asphalt driveway for added convenience. Minutes to Kent Island, close to major hwy. A rare opportunity to own a versatile property with endless possibilities!

2 Beds ⋅ 1 Baths

Charming Cape Cod home offering both residential comfort and commercial potential, beautifully updated with modern finishes while maintaining its classic character. This move-in-ready property features 2 bedrooms, 1 full bathroom, an inviting sunroom entry, and luxury vinyl plank flooring throughout. The updated kitchen showcases stainless steel appliances, an induction range, new refrigerator, granite countertops, and refreshed cabinetry. Recent improvements include the bathroom, double-pane windows, roof, siding, HVAC system, well system, electrical panel, and front entry door. The property also features an oversized detached garage with side entry and a spacious asphalt driveway for added convenience. Minutes to Kent Island, close to major hwy. A rare opportunity to own a versatile property with endless possibilities!

3801 Main St, Grasonville

Listing courtesy of Fairfax Realty Select. Contact:

$299,999

Tenant occupied, income producing two unit property in downtown Grasonville now available! The front house (B) rents for $1200 per month to a month to month tenant. The house (B) has 3 bedrooms and 2 baths. The 2 bed 1 bath second floor garage apt rents for $1378 per month to month to month tenants. All tenant spay their own utilities.

106 Phyllis Ct, Grasonville

Listing courtesy of Alberti Realty, LLC. Contact:

$1,299,000

Sellers of 952 Chester River are offering up to $39,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 24, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits. Experience the best of Waterfront living at 952 Chester River Drive, where panoramic water views, spectacular sunsets, and thoughtful custom design come together to create an exceptional waterfront retreat. Offering over 3,500 square feet of living space, this custom-built home is perfectly positioned to capture endless water views from nearly every room. High ceilings and expansive windows fill the home with natural light while framing the ever-changing waterfront backdrop. Designed for both everyday living and effortless entertaining, the main level features an open floor plan that seamlessly connects the living, dining, and kitchen spaces. The gourmet kitchen is equipped with gas cooking, abundant cabinetry, and generous workspace, allowing you to prepare meals while enjoying stunning views of the water. With five bedrooms and three-and-a-half baths, there is plenty of room for family and guests. Thoughtful design elements throughout the home maximize both functionality and comfort while keeping the focus on the incredible waterfront setting. Step outside and discover a boater's dream. The private pier is equipped with electric, water, three boat lifts, including a 20,000-pound lift, 10,000-pound lift, and 2,500-pound lift, offering exceptional flexibility for multiple vessels and watercraft. Spend your days on the water and return home to breathtaking sunsets over the Chester. Additional features include a NEW roof, 2 - 1 year old HVAC systems, tankless hot water heater, attached two-car garage with excellent storage, 50 amp RV hook up, and the quality craftsmanship expected in a custom-built waterfront residence. Whether you're searching for a year-round residence or the ultimate waterfront getaway, 952 Chester Beach Road offers a rare opportunity to enjoy unmatched views, premier boating access, and the relaxed lifestyle that makes Maryland's Eastern Shore so special.

5 Beds ⋅ 4 Baths

Sellers of 952 Chester River are offering up to $39,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 24, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits. Experience the best of Waterfront living at 952 Chester River Drive, where panoramic water views, spectacular sunsets, and thoughtful custom design come together to create an exceptional waterfront retreat. Offering over 3,500 square feet of living space, this custom-built home is perfectly positioned to capture endless water views from nearly every room. High ceilings and expansive windows fill the home with natural light while framing the ever-changing waterfront backdrop. Designed for both everyday living and effortless entertaining, the main level features an open floor plan that seamlessly connects the living, dining, and kitchen spaces. The gourmet kitchen is equipped with gas cooking, abundant cabinetry, and generous workspace, allowing you to prepare meals while enjoying stunning views of the water. With five bedrooms and three-and-a-half baths, there is plenty of room for family and guests. Thoughtful design elements throughout the home maximize both functionality and comfort while keeping the focus on the incredible waterfront setting. Step outside and discover a boater's dream. The private pier is equipped with electric, water, three boat lifts, including a 20,000-pound lift, 10,000-pound lift, and 2,500-pound lift, offering exceptional flexibility for multiple vessels and watercraft. Spend your days on the water and return home to breathtaking sunsets over the Chester. Additional features include a NEW roof, 2 - 1 year old HVAC systems, tankless hot water heater, attached two-car garage with excellent storage, 50 amp RV hook up, and the quality craftsmanship expected in a custom-built waterfront residence. Whether you're searching for a year-round residence or the ultimate waterfront getaway, 952 Chester Beach Road offers a rare opportunity to enjoy unmatched views, premier boating access, and the relaxed lifestyle that makes Maryland's Eastern Shore so special.

952 Chester River Dr, Grasonville

Listing courtesy of Samson Properties. Contact:

$579,900

REDUCED $20,000 and Sellers will pay ONE YEAR of CONDO/HOA fees! Come and enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community at the KENT NARROWS! 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! Qualified buyers may receive a 5.875% interest rate or the first year at no cost through our preferred lender! Come enjoy Sunsets over the Bay from your own home!!

3 Beds ⋅ 2 Baths

REDUCED $20,000 and Sellers will pay ONE YEAR of CONDO/HOA fees! Come and enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community at the KENT NARROWS! 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! Qualified buyers may receive a 5.875% interest rate or the first year at no cost through our preferred lender! Come enjoy Sunsets over the Bay from your own home!!

116 Oyster Cove Dr Unit 1D, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

$819,000

Located in the waterfront community of Prospect Bay, residents enjoy golf, swimming pool, boat ramp, tennis courts, and a clubhouse with restaurant. Welcome to this much-loved home, beautifully situated on 1.03 acres with sunset water views on one side and golf course views on the other. Quality built with 2x6 construction, the home features hardwood flooring, Andersen windows, and abundant natural light. The kitchen offers maple cabinetry, a center island, table space, and an open layout connecting to the family room with fireplace and efficient wood-burning insert. Separate living and dining rooms feature bow windows showcasing the water views. A main-level fourth bedroom with built-ins currently serves as a home office. Upstairs, the spacious primary suite features water views, a large bath, and generous walk-in closet, along with two additional bedrooms and a full bath. Enjoy a screened porch overlooking the golf course, a 16' x 12' Amish-built shed, and an oversized two-car garage with workshop space and extensive storage. The large driveway and parking pad accommodate up to six vehicles. Additional storage is available in the walk-in attic. Recent updates include a washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps less than two years old.

4 Beds ⋅ 3 Baths

Located in the waterfront community of Prospect Bay, residents enjoy golf, swimming pool, boat ramp, tennis courts, and a clubhouse with restaurant. Welcome to this much-loved home, beautifully situated on 1.03 acres with sunset water views on one side and golf course views on the other. Quality built with 2x6 construction, the home features hardwood flooring, Andersen windows, and abundant natural light. The kitchen offers maple cabinetry, a center island, table space, and an open layout connecting to the family room with fireplace and efficient wood-burning insert. Separate living and dining rooms feature bow windows showcasing the water views. A main-level fourth bedroom with built-ins currently serves as a home office. Upstairs, the spacious primary suite features water views, a large bath, and generous walk-in closet, along with two additional bedrooms and a full bath. Enjoy a screened porch overlooking the golf course, a 16' x 12' Amish-built shed, and an oversized two-car garage with workshop space and extensive storage. The large driveway and parking pad accommodate up to six vehicles. Additional storage is available in the walk-in attic. Recent updates include a washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps less than two years old.

108 Prospect Bay Dr W, Grasonville

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

$150,000

Zoned for commercial/residential, public sewer, no water currently availability. Trailer is not livable. Great opportunity to build your new home in the heart of Grasonville and on 1/2 acre lot with lots of mature trees.

110 James Ln, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

$572,999

Tucked away in a peaceful community on the Chesapeake Bay, this 2 bedroom, 2.5 bathroom townhouse with a loft offers the perfect mix of comfort, charm, and bay living. Situated on a desirable corner lot, the home features beautiful hardwood floors, a spacious kitchen with plenty of room to cook and gather, and a cozy fireplace that makes the living space feel warm and inviting on a winter day. **Boat Slip Included & Dredging has been started!** Step outside onto the large deck and take in the views — the perfect spot for morning coffee or relaxing evenings by the Bay. The loft adds extra flexible space for a home office, guest area, or additional lounge space. Residents also enjoy access to a private community pool, making it easy to enjoy everything this lifestyle has to offer.

2 Beds ⋅ 3 Baths

Tucked away in a peaceful community on the Chesapeake Bay, this 2 bedroom, 2.5 bathroom townhouse with a loft offers the perfect mix of comfort, charm, and bay living. Situated on a desirable corner lot, the home features beautiful hardwood floors, a spacious kitchen with plenty of room to cook and gather, and a cozy fireplace that makes the living space feel warm and inviting on a winter day. **Boat Slip Included & Dredging has been started!** Step outside onto the large deck and take in the views — the perfect spot for morning coffee or relaxing evenings by the Bay. The loft adds extra flexible space for a home office, guest area, or additional lounge space. Residents also enjoy access to a private community pool, making it easy to enjoy everything this lifestyle has to offer.

118 Bayview, Grasonville

Listing courtesy of LPT Realty, LLC. Contact:

$725,000

2 Lots, 2 tax parcels 3.38 acres facing US Route 50/301 on Hess Frontage Road. Quasi Private Drive shared with Delmarva Power Company right of way, Whaler Boat Sales, Furniture Sales, Zoned Urban Commercial with most uses permitted. Has a private rear right of way to County Wilson Road for possible sewer hook-up currently has existing single family residence with 1 bath, kitchen living room and 2 bedrooms, covert it to office and add your workshop, storage buildings.

144 Hess Frontage Rd, Grasonville

Listing courtesy of Tidewater Properties. Contact:

$155,000

Come build your dream home or invest for later. This hard to find 1 acre in Grasonville sits off Forest Rd and has a public sewer hookup available. Owner is putting in the culvert pipe/driveway entrance and some of the driveway. Beautiful mostly wooded lot that can't wait to meet its new owners. So close to everything yet in a country residential area on MDs Eastern Shore. No HOA or covenants/restrictions - WOW! Owner will consider all reasonable offers.

Forest Road, Grasonville

Listing courtesy of Taylor Properties. Contact:

$699,000

Highly motived sellers enjoyed Prospect Bay and want you to as well--they just reduced again making it super attractive. 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

Highly motived sellers enjoyed Prospect Bay and want you to as well--they just reduced again making it super attractive. 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:

$410,000

SELLER WILL CONSIDER OWNER FINANCING! Waterfront Lifestyle with Included Boat Slip – some Bayview at Kent Narrows Experience the best of Eastern Shore living in this beautifully renovated 3-bedroom, 3.5-bath contemporary townhouse with garage, ideally located just over the Kent Narrows Bridge in the sought-after Bayview waterfront community. Waterview's from second and third floor bedrooms. This move-in-ready home features a stunning new kitchen with stylish gray shaker cabinetry, granite countertops, and stainless-steel appliances. The open-concept living and dining areas are enhanced by new luxury vinyl plank flooring, creating a modern, inviting space perfect for everyday living and entertaining. The spacious primary suite offers vaulted ceilings, abundant natural light, a ceiling fan, double closet plus walk-in closet, and a dressing area. The completely renovated spa-inspired primary bath is a true showstopper, featuring a luxurious oversized double shower with dual shower heads, built-in benches, niches, and sleek glass doors. Two additional generously sized bedrooms provide excellent flexibility, including one with a private en-suite bath, plus a third full bathroom for guests. Step outside and embrace the water-privileged lifestyle this community offers. Your assigned boat slip is in the private community marina, complete with water and electricity, and included in the monthly condo fee. Launch directly into Muddy Creek, which leads straight to the Chester River—putting you just minutes by boat from Red Eye Dock Bar, Harris’ Crab House, and The Dock House Restaurant.

3 Beds ⋅ 4 Baths

SELLER WILL CONSIDER OWNER FINANCING! Waterfront Lifestyle with Included Boat Slip – some Bayview at Kent Narrows Experience the best of Eastern Shore living in this beautifully renovated 3-bedroom, 3.5-bath contemporary townhouse with garage, ideally located just over the Kent Narrows Bridge in the sought-after Bayview waterfront community. Waterview's from second and third floor bedrooms. This move-in-ready home features a stunning new kitchen with stylish gray shaker cabinetry, granite countertops, and stainless-steel appliances. The open-concept living and dining areas are enhanced by new luxury vinyl plank flooring, creating a modern, inviting space perfect for everyday living and entertaining. The spacious primary suite offers vaulted ceilings, abundant natural light, a ceiling fan, double closet plus walk-in closet, and a dressing area. The completely renovated spa-inspired primary bath is a true showstopper, featuring a luxurious oversized double shower with dual shower heads, built-in benches, niches, and sleek glass doors. Two additional generously sized bedrooms provide excellent flexibility, including one with a private en-suite bath, plus a third full bathroom for guests. Step outside and embrace the water-privileged lifestyle this community offers. Your assigned boat slip is in the private community marina, complete with water and electricity, and included in the monthly condo fee. Launch directly into Muddy Creek, which leads straight to the Chester River—putting you just minutes by boat from Red Eye Dock Bar, Harris’ Crab House, and The Dock House Restaurant.

109 Bayview, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

How much is your home worth?

How much is your home worth?