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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:

$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:

$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:

$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:

$1,550,000

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:

$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:

$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:

$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:

$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:

$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:

Grasonville Cemetery Rd Unit LOT 2, Grasonville

$662,550

Welcome to The Corsica, a beautifully designed two-story home offering 1,664 square feet of well-planned living space. With 4 bedrooms and 2.5 bathrooms, this layout is ideal for anyone seeking both functionality and modern style. Step inside to an inviting open-concept Kitchen, Eating, & Great Room, perfect for entertaining or relaxing with loved ones. The kitchen features an attached large island overlooking the spacious living area, ensuring you’re always part of the conversation. Natural light fills the space, creating a warm and welcoming atmosphere for everyday living. Convenience meets practicality with the Mud/Laundry Room located just off the garage, providing a seamless transition from outdoor activity to the home’s main living areas which is perfect for busy mornings or returning from weekend adventures. Upstairs, you’ll find four comfortable bedrooms, including a private primary suite with a full bath and walk-in closet. Three additional bedrooms share a second full bathroom, offering flexibility for guests, family, or a home office. An optional 16' x 12' rear deck expands your living space outdoors and is ideal for dining or enjoying quiet evenings surrounded by nature. Charming curb appeal, efficient design, and thoughtful flow make The Corsica the perfect place to call home. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, an open concept floor plan, and a convenient mud room. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

4 Beds ⋅ 3 Baths

Welcome to The Corsica, a beautifully designed two-story home offering 1,664 square feet of well-planned living space. With 4 bedrooms and 2.5 bathrooms, this layout is ideal for anyone seeking both functionality and modern style. Step inside to an inviting open-concept Kitchen, Eating, & Great Room, perfect for entertaining or relaxing with loved ones. The kitchen features an attached large island overlooking the spacious living area, ensuring you’re always part of the conversation. Natural light fills the space, creating a warm and welcoming atmosphere for everyday living. Convenience meets practicality with the Mud/Laundry Room located just off the garage, providing a seamless transition from outdoor activity to the home’s main living areas which is perfect for busy mornings or returning from weekend adventures. Upstairs, you’ll find four comfortable bedrooms, including a private primary suite with a full bath and walk-in closet. Three additional bedrooms share a second full bathroom, offering flexibility for guests, family, or a home office. An optional 16' x 12' rear deck expands your living space outdoors and is ideal for dining or enjoying quiet evenings surrounded by nature. Charming curb appeal, efficient design, and thoughtful flow make The Corsica the perfect place to call home. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, an open concept floor plan, and a convenient mud room. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

Grasonville Cemetery Rd Unit LOT 2, Grasonville

Listing courtesy of EXP Realty, LLC. Contact:

Grasonville Cemetery Rd Unit LOT 1, Grasonville

$664,650

Welcome to the Syberry, a thoughtfully designed single-story home offering 1,710 square feet of modern comfort and convenience. This 4-bedroom, 2-bathroom layout blends open-concept living with functional flow, perfect for today’s lifestyle. At the heart of the home, the spacious Kitchen, Eating, & Great Room create an inviting open area ideal for entertaining and family gatherings. Large windows fill the space with natural light, while the kitchen’s central island provides plenty of prep and seating space to keep everyone connected. The private primary suite offers a peaceful retreat, complete with a generous walk-in closet and en-suite bath. Three additional bedrooms provide flexible options for family, guests, or a home office. From the one car garage, a convenient Mud/Laundry Room connects directly to the main living area, keeping daily routines organized and tidy. An optional 16' x 12' rear deck expands your living space outdoors, perfect for morning coffee or evening relaxation. With its timeless exterior, open interior design, and practical layout, the Syberry delivers the ideal balance of comfort, efficiency, and charm all in a single-level home built for the way you live. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, open concept floor plan, garage with shop/storage, convenient Mud Room, and a covered front porch. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

4 Beds ⋅ 2 Baths

Welcome to the Syberry, a thoughtfully designed single-story home offering 1,710 square feet of modern comfort and convenience. This 4-bedroom, 2-bathroom layout blends open-concept living with functional flow, perfect for today’s lifestyle. At the heart of the home, the spacious Kitchen, Eating, & Great Room create an inviting open area ideal for entertaining and family gatherings. Large windows fill the space with natural light, while the kitchen’s central island provides plenty of prep and seating space to keep everyone connected. The private primary suite offers a peaceful retreat, complete with a generous walk-in closet and en-suite bath. Three additional bedrooms provide flexible options for family, guests, or a home office. From the one car garage, a convenient Mud/Laundry Room connects directly to the main living area, keeping daily routines organized and tidy. An optional 16' x 12' rear deck expands your living space outdoors, perfect for morning coffee or evening relaxation. With its timeless exterior, open interior design, and practical layout, the Syberry delivers the ideal balance of comfort, efficiency, and charm all in a single-level home built for the way you live. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, open concept floor plan, garage with shop/storage, convenient Mud Room, and a covered front porch. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

Grasonville Cemetery Rd Unit LOT 1, Grasonville

Listing courtesy of EXP Realty, LLC. Contact:

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