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Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The amenities here are a major plus with Franklin pond and community access directly to Churn Creek. The home has had a transformation in the last 2 years with updated bathrooms, floors, kitchen, landscaping, and a new HVAC unit. The main floor master suite allows you to live in luxury with two walk in closets, hardwood double doors, and brand new bathroom with soaking tub and walk in steam shower. Upstairs is a blend of spacious bedrooms and bathrooms galore with an office nook to look out at nature. Storage is no issue with a full basement ready to take on as many holiday decorations as your heart desires. The property is sprawling on over 4 acres that abut the community pond and green space. Outdoor living is celebrated here with a massive deck out back for entertaining and covered front porch for birdwatching. The abundance of our Eastern Shore is just a short ride away with local staples such as Red Acres Hydroponics and Lockbriar Farms for your produce right in Worton and the Chestertown Farmer's Market for the rest. Invest wisely while improving your quality of life.

24274 Waterview Dr, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Benson & Mangold, LLC.

118 Little Harbor Way Unit 202, Chestertown

$660,000

Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the studs and thoughtfully rebuilt, the condo feels brand new from top to bottom. The open floor plan is filled with soft, natural light and showcases wide-plank wood flooring, a cozy gas fireplace, and uninterrupted river views from the main living areas. The stunning kitchen features white quartz countertops and backsplash, stainless steel appliances, and a seamless flow for both everyday living and entertaining. The primary suite is a true retreat, complete with a walk-in closet and a spa-like tiled shower with multiple shower heads, including a rainfall feature. Both bathrooms are finished with timeless, high-quality materials, creating a clean, classic, and calming feel throughout. Step out onto the private balcony and take in peaceful, north-facing river views with soft, consistent light throughout the day. It is ideal for relaxing, reading, or simply watching boats drift by without the glare of direct sun. This is waterfront living at its most comfortable and serene. Additional features include elevator access to the second floor, a one-car garage, and a deeded boat slip, approximately 4 feet MLW. The community offers a pool, fishing pier, and marina with floating docks, along with beautifully maintained grounds featuring oyster shell walking paths and a firepit. The marina area also includes a community grill and multiple tables, perfect for outdoor dining and gathering. Flood insurance is not currently required for this second-floor unit, contributing to overall affordability. Buyers are encouraged to perform their own due diligence and verify any insurance requirements. Ideally located within walking distance to historic downtown Chestertown, and just a short drive to golf, dining, and the yacht club at Chester River Yacht and Country Club, this condo is perfectly suited for those looking to downsize, simplify, or secure a refined second home on the water. Move in ready, thoughtfully updated, and designed for relaxed coastal living, this is Eastern Shore living at its finest.

Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the studs and thoughtfully rebuilt, the condo feels brand new from top to bottom. The open floor plan is filled with soft, natural light and showcases wide-plank wood flooring, a cozy gas fireplace, and uninterrupted river views from the main living areas. The stunning kitchen features white quartz countertops and backsplash, stainless steel appliances, and a seamless flow for both everyday living and entertaining. The primary suite is a true retreat, complete with a walk-in closet and a spa-like tiled shower with multiple shower heads, including a rainfall feature. Both bathrooms are finished with timeless, high-quality materials, creating a clean, classic, and calming feel throughout. Step out onto the private balcony and take in peaceful, north-facing river views with soft, consistent light throughout the day. It is ideal for relaxing, reading, or simply watching boats drift by without the glare of direct sun. This is waterfront living at its most comfortable and serene. Additional features include elevator access to the second floor, a one-car garage, and a deeded boat slip, approximately 4 feet MLW. The community offers a pool, fishing pier, and marina with floating docks, along with beautifully maintained grounds featuring oyster shell walking paths and a firepit. The marina area also includes a community grill and multiple tables, perfect for outdoor dining and gathering. Flood insurance is not currently required for this second-floor unit, contributing to overall affordability. Buyers are encouraged to perform their own due diligence and verify any insurance requirements. Ideally located within walking distance to historic downtown Chestertown, and just a short drive to golf, dining, and the yacht club at Chester River Yacht and Country Club, this condo is perfectly suited for those looking to downsize, simplify, or secure a refined second home on the water. Move in ready, thoughtfully updated, and designed for relaxed coastal living, this is Eastern Shore living at its finest.

118 Little Harbor Way Unit 202, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$650,000

Classic Rock Hall craftsman home expanded and updated with luxury amenities. This is one of the largest homes on south Hawthorne, on almost an acre of land. One of the first homes built on Hawthorne, the home and property has been lovingly cared for and expanded by previous and current owners. Three bedrooms plus two full renovated baths offer plenty of room to relax. The large detached garage is a workshop paradise. All this is just steps from Rock Hall harbor and close to marinas and restaurants.

Classic Rock Hall craftsman home expanded and updated with luxury amenities. This is one of the largest homes on south Hawthorne, on almost an acre of land. One of the first homes built on Hawthorne, the home and property has been lovingly cared for and expanded by previous and current owners. Three bedrooms plus two full renovated baths offer plenty of room to relax. The large detached garage is a workshop paradise. All this is just steps from Rock Hall harbor and close to marinas and restaurants.

5786 S Hawthorne Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: TTR Sotheby's International Realty.

$650,000

109 South Water, along with the historic Custom House, is a bookend to a small, but iconic, cluster of historic (c1900) townhouses that give pause to every passer-by, especially those equipped with a lens. Beautifully designed and maintained block-wide landscaping, individually maintained, provides exceptional street appeal. The smallest (2064 square feet) of the four clapboard houses, all with engaging front porches, has the benefit of additional light from its' six southern facing windows overlooking the waterside lawn, with sculpture, of the historic residence of the President of Washington College. Two quaint river side porches, one screened, guarantee that calm, cool, collected vibe. In 2024, a substantial restoration effort focused on new mechanical systems (including electrical) kitchen and laundry appliances, rebuilt front porch and roof, and the opening up of the two third-floor bedrooms into a beautiful street to riverside space, currently a tech-heavy creative office space but could be earmarked for an amazing primary suite. For the future-minded, well-funded buyer(s), a flawless expansion plan, with HDC approvals, by architect John Hutchinson, are available for use.

4 Beds ⋅ 2 Baths

109 South Water, along with the historic Custom House, is a bookend to a small, but iconic, cluster of historic (c1900) townhouses that give pause to every passer-by, especially those equipped with a lens. Beautifully designed and maintained block-wide landscaping, individually maintained, provides exceptional street appeal. The smallest (2064 square feet) of the four clapboard houses, all with engaging front porches, has the benefit of additional light from its' six southern facing windows overlooking the waterside lawn, with sculpture, of the historic residence of the President of Washington College. Two quaint river side porches, one screened, guarantee that calm, cool, collected vibe. In 2024, a substantial restoration effort focused on new mechanical systems (including electrical) kitchen and laundry appliances, rebuilt front porch and roof, and the opening up of the two third-floor bedrooms into a beautiful street to riverside space, currently a tech-heavy creative office space but could be earmarked for an amazing primary suite. For the future-minded, well-funded buyer(s), a flawless expansion plan, with HDC approvals, by architect John Hutchinson, are available for use.

109 Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$650,000

Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first floor, with discreet powder room and comfortable kitchen with radiant floor heating, the abundance of windows throughout, and more make this corner brick home, with wrap-around porch, tended landscape and white picket fence an exceptional offering. Four bedrooms, three baths, and a separate laundry room are approached by the original 3-level oak staircase. Off-street parking and charming two-car garage with curve-track doors is the envy of many downtown residents. Tucked behind the residence and garage is a super-comfortable and cozy slate patio for entertaining, grilling, reading or just chilling. An authentic Widow's Walk tops the house, for the adventurers yearning to view the fireworks or hide-away for a brief escape.

Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first floor, with discreet powder room and comfortable kitchen with radiant floor heating, the abundance of windows throughout, and more make this corner brick home, with wrap-around porch, tended landscape and white picket fence an exceptional offering. Four bedrooms, three baths, and a separate laundry room are approached by the original 3-level oak staircase. Off-street parking and charming two-car garage with curve-track doors is the envy of many downtown residents. Tucked behind the residence and garage is a super-comfortable and cozy slate patio for entertaining, grilling, reading or just chilling. An authentic Widow's Walk tops the house, for the adventurers yearning to view the fireworks or hide-away for a brief escape.

200 Washington Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$640,000

Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree. The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming atmosphere throughout. The large primary suite offers comfort and convenience, and there is the option for a second bedroom on the main level. Current owners have opted to make that room a large office, and it features two closets. The kitchen is a dream — spacious enough for a large island and a generous breakfast area that easily fits a full-sized table. There is a mural border that shows scenes of historic Chestertown. Pantry and plenty of storage. Upstairs, you’ll find two large bedrooms and a full hall bath, ideal for guests or loved ones. Each bedroom offers walk-in storage — no attic ladders needed! Solar operated fans keep the attic spaces cool. Additional highlights include leased solar panels which have been paid out, a large garage with ample storage, additional storage shed with electric and water. , and a fantastic location just minutes from the Chester River and the Chester River Yacht and Country Club. Two zone for heating and cooling. Come see this charming home for yourself — it’s the perfect blend of beauty, comfort, and thoughtful design!

Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree. The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming atmosphere throughout. The large primary suite offers comfort and convenience, and there is the option for a second bedroom on the main level. Current owners have opted to make that room a large office, and it features two closets. The kitchen is a dream — spacious enough for a large island and a generous breakfast area that easily fits a full-sized table. There is a mural border that shows scenes of historic Chestertown. Pantry and plenty of storage. Upstairs, you’ll find two large bedrooms and a full hall bath, ideal for guests or loved ones. Each bedroom offers walk-in storage — no attic ladders needed! Solar operated fans keep the attic spaces cool. Additional highlights include leased solar panels which have been paid out, a large garage with ample storage, additional storage shed with electric and water. , and a fantastic location just minutes from the Chester River and the Chester River Yacht and Country Club. Two zone for heating and cooling. Come see this charming home for yourself — it’s the perfect blend of beauty, comfort, and thoughtful design!

7844 Chester Ct, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$625,000

Waterfront living on Grays Inn Creek, just five minutes from Rock Hall. Situated on a private half-acre lot with protected western-facing views, this home offers beautiful sunsets, 3–4 feet MLW, and easy boating access to the Chester River, Chestertown, Kent Narrows, and Rock Hall. The home has seen numerous updates over the past six years, including new siding, roof, HVAC, LVP flooring, carpet, an updated kitchen and main-level bathroom, appliances, and improvements to the pier. Water views take center stage from the dining area, living room, and main bedrooms, while the manageable size and low-maintenance updates make this an easy waterfront property to enjoy. The property offers plenty of privacy and parking, along with a detached garage and carport. The protected setting on Grays Inn Creek combines peaceful waterfront living with convenient access to town and some of the best boating destinations on the Upper Eastern Shore. An affordable opportunity to own waterfront near Rock Hall without taking on a large property or extensive upkeep.

Waterfront living on Grays Inn Creek, just five minutes from Rock Hall. Situated on a private half-acre lot with protected western-facing views, this home offers beautiful sunsets, 3–4 feet MLW, and easy boating access to the Chester River, Chestertown, Kent Narrows, and Rock Hall. The home has seen numerous updates over the past six years, including new siding, roof, HVAC, LVP flooring, carpet, an updated kitchen and main-level bathroom, appliances, and improvements to the pier. Water views take center stage from the dining area, living room, and main bedrooms, while the manageable size and low-maintenance updates make this an easy waterfront property to enjoy. The property offers plenty of privacy and parking, along with a detached garage and carport. The protected setting on Grays Inn Creek combines peaceful waterfront living with convenient access to town and some of the best boating destinations on the Upper Eastern Shore. An affordable opportunity to own waterfront near Rock Hall without taking on a large property or extensive upkeep.

21728 Sunnyside Ave, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Unrepresented.

$625,000

Bayfront condo with exceptional views, located in the heart of Rock Hall! Beautiful open living space for entertaining, featuring a propane fireplace and bayfront balcony with awning. The eat-in kitchen features updated countertops and a Bosch electric range. The primary bedroom has its own bayfront balcony and an updated attached bathroom. Two additional bedrooms share a full bathroom. The third-floor bedroom has a fantastic view and could be used as an office, studio, or overflow space for guests . On the ground floor, the bayfront storage room is a great space to keep fishing poles, kayak, or pool floaties to use at the condo pool! One-car garage with additional outside parking, as well as communal overflow space for guests. Tilghman’s Landing condo is a beautiful waterfront condo association! Located in the heart of everything, yet tucked away from the hustle and bustle. Enjoy the pool in the summertime and never miss a sunset on the balcony. A sandy beach is located just outside the association, and the Rock Hall beach is just down the street. Short distance to ample restaurants, shops, and marinas.

Bayfront condo with exceptional views, located in the heart of Rock Hall! Beautiful open living space for entertaining, featuring a propane fireplace and bayfront balcony with awning. The eat-in kitchen features updated countertops and a Bosch electric range. The primary bedroom has its own bayfront balcony and an updated attached bathroom. Two additional bedrooms share a full bathroom. The third-floor bedroom has a fantastic view and could be used as an office, studio, or overflow space for guests . On the ground floor, the bayfront storage room is a great space to keep fishing poles, kayak, or pool floaties to use at the condo pool! One-car garage with additional outside parking, as well as communal overflow space for guests. Tilghman’s Landing condo is a beautiful waterfront condo association! Located in the heart of everything, yet tucked away from the hustle and bustle. Enjoy the pool in the summertime and never miss a sunset on the balcony. A sandy beach is located just outside the association, and the Rock Hall beach is just down the street. Short distance to ample restaurants, shops, and marinas.

20563 Rock Hall Ave Unit 16, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

$620,000

Rare lakefront opportunity in Kent County offering exceptional privacy and a peaceful natural setting. Tucked away on 2.62 partially wooded acres along Urieville Lake, this beautifully situated property provides a secluded retreat where you can truly unwind and enjoy the outdoors. This spacious 4-bedroom, 3.5-bath home offers flexible living for families and guests alike. The layout includes the option for a first-floor bedroom, three bedrooms on the second level, and an additional bedroom in the finished walk-out basement, providing plenty of room for everyone while maintaining privacy throughout the home. The open-concept main living area is filled with natural light and showcases beautiful views of the surrounding woods and the lake beyond, creating a warm and inviting space for everyday living or entertaining. The home features two full bathrooms on the second floor, a full bath on the lower level, and a convenient half bath on the main floor, all designed with comfort and functionality in mind. The finished walk-out basement adds valuable living space with a bedroom and full bath—ideal for a guest suite, recreation room, home office, or entertainment area—with direct access to the peaceful backyard and lakefront setting. Outside, the property truly shines. The 2.62 acres offer a rare level of privacy, with mature trees and natural surroundings that create a quiet, secluded atmosphere. Whether you're relaxing by the water listening to the geese, gardening, exploring wooded paths, or enjoying lakeside sunsets, this property offers endless opportunities to connect with nature. Situated on Urieville Lake, residents can enjoy fishing, kayaking, and small boating right from their own backyard. The lake spans approximately 35 acres, shaped like the letter “Y,” and supports a healthy fishery including largemouth bass and bluegill, along with occasional catches of pumpkinseed sunfish, brown bullhead catfish, golden shiners, and common carp. If you're searching for a private waterfront escape in Kent County, where nature, space, and tranquility come together, this special property is ready to welcome you home.

Rare lakefront opportunity in Kent County offering exceptional privacy and a peaceful natural setting. Tucked away on 2.62 partially wooded acres along Urieville Lake, this beautifully situated property provides a secluded retreat where you can truly unwind and enjoy the outdoors. This spacious 4-bedroom, 3.5-bath home offers flexible living for families and guests alike. The layout includes the option for a first-floor bedroom, three bedrooms on the second level, and an additional bedroom in the finished walk-out basement, providing plenty of room for everyone while maintaining privacy throughout the home. The open-concept main living area is filled with natural light and showcases beautiful views of the surrounding woods and the lake beyond, creating a warm and inviting space for everyday living or entertaining. The home features two full bathrooms on the second floor, a full bath on the lower level, and a convenient half bath on the main floor, all designed with comfort and functionality in mind. The finished walk-out basement adds valuable living space with a bedroom and full bath—ideal for a guest suite, recreation room, home office, or entertainment area—with direct access to the peaceful backyard and lakefront setting. Outside, the property truly shines. The 2.62 acres offer a rare level of privacy, with mature trees and natural surroundings that create a quiet, secluded atmosphere. Whether you're relaxing by the water listening to the geese, gardening, exploring wooded paths, or enjoying lakeside sunsets, this property offers endless opportunities to connect with nature. Situated on Urieville Lake, residents can enjoy fishing, kayaking, and small boating right from their own backyard. The lake spans approximately 35 acres, shaped like the letter “Y,” and supports a healthy fishery including largemouth bass and bluegill, along with occasional catches of pumpkinseed sunfish, brown bullhead catfish, golden shiners, and common carp. If you're searching for a private waterfront escape in Kent County, where nature, space, and tranquility come together, this special property is ready to welcome you home.

11040 Kylie Ln, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: LPT Realty, LLC.

$617,500

Spacious in-town home with coastal charm, just 1 block from the Rock Hall beach on the Chesapeake Bay! This home offers a luxe front porch, as well as a screened-in porch, perfect for meals and entertaining. The large family room boasts a gas fireplace, built-in shelving, wood ceilings, and a sunny balcony featuring a striped awning. The eat-in kitchen has updated appliances and ample room; it opens up to the front sitting room. Just around the corner is the light-filled formal dining room. Two first-floor bedrooms share a full bathroom. Two additional bedrooms upstairs share a full bathroom. This home offers the sought after first floor living option, with ample room for guests. There is a two-car garage with interior access and plenty of room for storage, hard to find in Rock Hall. The outside space has been lovingly landscaped, including a beautiful perennial pollinator garden running the length of the driveway. This property is move-in ready for the summer! A short distance to the Rock Hall beach, many dining options, ample marinas, and shops. Don’t miss this in-town gem! This home is move in ready. The sellers will consider including some contents.

4 Beds ⋅ 2 Baths

Spacious in-town home with coastal charm, just 1 block from the Rock Hall beach on the Chesapeake Bay! This home offers a luxe front porch, as well as a screened-in porch, perfect for meals and entertaining. The large family room boasts a gas fireplace, built-in shelving, wood ceilings, and a sunny balcony featuring a striped awning. The eat-in kitchen has updated appliances and ample room; it opens up to the front sitting room. Just around the corner is the light-filled formal dining room. Two first-floor bedrooms share a full bathroom. Two additional bedrooms upstairs share a full bathroom. This home offers the sought after first floor living option, with ample room for guests. There is a two-car garage with interior access and plenty of room for storage, hard to find in Rock Hall. The outside space has been lovingly landscaped, including a beautiful perennial pollinator garden running the length of the driveway. This property is move-in ready for the summer! A short distance to the Rock Hall beach, many dining options, ample marinas, and shops. Don’t miss this in-town gem! This home is move in ready. The sellers will consider including some contents.

20694 Mercer Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

$615,000

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown has to offer. This home is part of the Maryland Historic Trust. Own a piece of American history less than two hours from DC, Baltimore, and Philadelphia while enjoying the walkable lifestyle of Chestertown's Historic District. **Interior professional photos are coming soon and are going to be really special**

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown has to offer. This home is part of the Maryland Historic Trust. Own a piece of American history less than two hours from DC, Baltimore, and Philadelphia while enjoying the walkable lifestyle of Chestertown's Historic District. **Interior professional photos are coming soon and are going to be really special**

103 Maple Ave, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Cross Street Realtors LLC.

$602,500

Privacy meets modern updates on two private acres in the sought-after Kinnaird’s Point community. This thoughtfully renovated home offers a peaceful setting with convenient access to the water, located just minutes from both Chestertown and Rock Hall. The property includes two community waterfront access points, featuring a private swim beach and boat launch along Still Pond Creek and Churn Creek. Inside, the bright, open single-level layout is centered around a fully remodeled kitchen with custom cabinetry, stone countertops, and a large island, flowing seamlessly into the living and dining areas. Outdoor spaces include a screened porch, composite deck, and stamped concrete patio, all designed to enjoy the home’s peaceful setting. The primary suite features a renovated bath, while additional bedrooms, updated bathrooms, and a dedicated office provide flexible living space. Major upgrades include a new HVAC system, new windows and doors, new siding, remodeled kitchen and bathrooms, a new water heater, spray-foam attic insulation, an encapsulated crawlspace, as well as full-house replumbing and an upgraded electrical system, offering a truly move-in ready, turnkey property. An oversized attached garage with a heated and cooled workspace and a fenced backyard add functionality and privacy. Tucked within a quiet, secluded neighborhood yet close to waterfront towns, marinas, and dining, this property delivers a well-updated Eastern Shore retreat with easy access to the water.

Privacy meets modern updates on two private acres in the sought-after Kinnaird’s Point community. This thoughtfully renovated home offers a peaceful setting with convenient access to the water, located just minutes from both Chestertown and Rock Hall. The property includes two community waterfront access points, featuring a private swim beach and boat launch along Still Pond Creek and Churn Creek. Inside, the bright, open single-level layout is centered around a fully remodeled kitchen with custom cabinetry, stone countertops, and a large island, flowing seamlessly into the living and dining areas. Outdoor spaces include a screened porch, composite deck, and stamped concrete patio, all designed to enjoy the home’s peaceful setting. The primary suite features a renovated bath, while additional bedrooms, updated bathrooms, and a dedicated office provide flexible living space. Major upgrades include a new HVAC system, new windows and doors, new siding, remodeled kitchen and bathrooms, a new water heater, spray-foam attic insulation, an encapsulated crawlspace, as well as full-house replumbing and an upgraded electrical system, offering a truly move-in ready, turnkey property. An oversized attached garage with a heated and cooled workspace and a fenced backyard add functionality and privacy. Tucked within a quiet, secluded neighborhood yet close to waterfront towns, marinas, and dining, this property delivers a well-updated Eastern Shore retreat with easy access to the water.

24204 Drayton Landing Dr, Worton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Foraker Realty Co..

$590,000

Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been replaced. Electric has been updated. The list of improvements goes on. Come see this for yourself. It's gorgeous!

4 Beds ⋅ 2 Baths

Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been replaced. Electric has been updated. The list of improvements goes on. Come see this for yourself. It's gorgeous!

206 Valley, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$585,000

Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, 20 min from Rt. 301, within 2 miles of the Chester River...Look no further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. Enter in through this spacious well-lit foyer which flows directly into the rest of the house. Moving forward is the very large den/ family room that opens into this gourmet kitchen with eat in area., a formal dining room and formal living room, a separate room for an office or play room & half bath. The kitchen has brand new SS Samsung appliances, double wall ovens, new built-in induction cook top with a new exhaust hood, plenty of counter space and cabinet space, 8+' island with cabinet space underneath and your walk-in pantry. Plenty of space for all of your cooking supplies! Enjoy your back yard on the Trex deck with plenty of room for relaxing & grilling in a private back yard that is fenced in with a 6' vinyl fence. If you are looking for separate areas to entertain or space for guests, then head to the basement which has another fully loaded kitchen with SS Samsung appliances, new vinyl plank flooring, a full bathroom w/ walk in shower, a closed in room with a closet and oodles of space! The top floor has 3 Very large bedrooms with amazing closet space that has organizers in them & ceiling fans. The rooms share a full bathroom at the top of the stairs. Take the hallway/ catwalk to the double doors that enter into the amazing private primary suite. Very large space for your largest MB furniture. You will have 2 closets as you enter into the primary bath, double vanities, a step-in shower with new door, soaking tub and private lavatory, you won't want to leave this space! This home is great for the large or growing family! Exceptional items through the house are the 5-6' windows, brand new carpeting, dual stairway to the upper floor, brand new SS Appliances, completely finished basement, Open floor plan, very nice Trex deck on the back, vinyl fencing, recently replaced HVAC units with smart thermostats and all new ductwork, 2 car garage which goes right into the laundry room,( where the washer & dryer are included) and into the kitchen.

Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, 20 min from Rt. 301, within 2 miles of the Chester River...Look no further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. Enter in through this spacious well-lit foyer which flows directly into the rest of the house. Moving forward is the very large den/ family room that opens into this gourmet kitchen with eat in area., a formal dining room and formal living room, a separate room for an office or play room & half bath. The kitchen has brand new SS Samsung appliances, double wall ovens, new built-in induction cook top with a new exhaust hood, plenty of counter space and cabinet space, 8+' island with cabinet space underneath and your walk-in pantry. Plenty of space for all of your cooking supplies! Enjoy your back yard on the Trex deck with plenty of room for relaxing & grilling in a private back yard that is fenced in with a 6' vinyl fence. If you are looking for separate areas to entertain or space for guests, then head to the basement which has another fully loaded kitchen with SS Samsung appliances, new vinyl plank flooring, a full bathroom w/ walk in shower, a closed in room with a closet and oodles of space! The top floor has 3 Very large bedrooms with amazing closet space that has organizers in them & ceiling fans. The rooms share a full bathroom at the top of the stairs. Take the hallway/ catwalk to the double doors that enter into the amazing private primary suite. Very large space for your largest MB furniture. You will have 2 closets as you enter into the primary bath, double vanities, a step-in shower with new door, soaking tub and private lavatory, you won't want to leave this space! This home is great for the large or growing family! Exceptional items through the house are the 5-6' windows, brand new carpeting, dual stairway to the upper floor, brand new SS Appliances, completely finished basement, Open floor plan, very nice Trex deck on the back, vinyl fencing, recently replaced HVAC units with smart thermostats and all new ductwork, 2 car garage which goes right into the laundry room,( where the washer & dryer are included) and into the kitchen.

103 Adela Way, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Compass.

$575,000

Welcome to coastal charm at its finest. This beautifully updated 3-bedroom, 2-bath Cape Cod offers 1,680 square feet of thoughtfully designed living space in the heart of Rock Hall. Built with solid brick construction, this home seamlessly blends timeless character with modern upgrades. The main level features a stylishly updated kitchen with stainless steel appliances, warm hardwood floors, and a cozy living room centered around a wood-burning fireplace. A first-floor bedroom and full bath provide flexible living options, while the updated laundry room adds everyday convenience. Step outside to the screened-in porch—perfect for unwinding after a day on the water. Upstairs, two spacious bedrooms and a full bath are complemented by access to a private second-story deck, where you can take in serene water views of Rock Hall Harbor. Complete with your own hot tub, this outdoor space is designed for relaxation and entertaining. Ideally situated within walking distance to marinas, waterfront dining, shops, and all that Rock Hall has to offer, this home is the perfect full-time residence, weekend escape, or investment opportunity.

Welcome to coastal charm at its finest. This beautifully updated 3-bedroom, 2-bath Cape Cod offers 1,680 square feet of thoughtfully designed living space in the heart of Rock Hall. Built with solid brick construction, this home seamlessly blends timeless character with modern upgrades. The main level features a stylishly updated kitchen with stainless steel appliances, warm hardwood floors, and a cozy living room centered around a wood-burning fireplace. A first-floor bedroom and full bath provide flexible living options, while the updated laundry room adds everyday convenience. Step outside to the screened-in porch—perfect for unwinding after a day on the water. Upstairs, two spacious bedrooms and a full bath are complemented by access to a private second-story deck, where you can take in serene water views of Rock Hall Harbor. Complete with your own hot tub, this outdoor space is designed for relaxation and entertaining. Ideally situated within walking distance to marinas, waterfront dining, shops, and all that Rock Hall has to offer, this home is the perfect full-time residence, weekend escape, or investment opportunity.

20916 Bayside Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

$567,000

Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year round. This home mixes the old with the new. Character throughout this custom built home. Architectural details, crown and dentil molding. Large kitchen for casual dining and entertaining. Designer countertops and stainless appliances topped off with a Viking range and an antique coal range by AGA. Plenty of gathering space at the elongated island. Large windows bring the outside in to the kitchen. Owner suite is on the main floor. Second floor boasts a super large room and full bath for a guest/ family quarters. There is a beautiful livingroom with a fireplace and a family room with a fireplace and built in bookshelves. Excellent living spaces. The gracious dining room can host many a fine dining experience. The full size basement with indoor and outdoor access offers many possible uses from storage to crafts to games. A lovely sunny screen porch stretches across the back of the house with access to the kitchen and to the owners suite. A step from the porch takes you to the spa/ hot tub in it's own private setting. This home is being offered with an additional lot included. The lot affords this home access to the Kentmore Park Amenities. Beach, Piers, Boat ramp, and the Kentmore Park social association. This listing includes MLS listing # MDKE2005752, 0.11 acre lot on Anglewood Rd, Kentmore Park.

2 Beds ⋅ 3 Baths

Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year round. This home mixes the old with the new. Character throughout this custom built home. Architectural details, crown and dentil molding. Large kitchen for casual dining and entertaining. Designer countertops and stainless appliances topped off with a Viking range and an antique coal range by AGA. Plenty of gathering space at the elongated island. Large windows bring the outside in to the kitchen. Owner suite is on the main floor. Second floor boasts a super large room and full bath for a guest/ family quarters. There is a beautiful livingroom with a fireplace and a family room with a fireplace and built in bookshelves. Excellent living spaces. The gracious dining room can host many a fine dining experience. The full size basement with indoor and outdoor access offers many possible uses from storage to crafts to games. A lovely sunny screen porch stretches across the back of the house with access to the kitchen and to the owners suite. A step from the porch takes you to the spa/ hot tub in it's own private setting. This home is being offered with an additional lot included. The lot affords this home access to the Kentmore Park Amenities. Beach, Piers, Boat ramp, and the Kentmore Park social association. This listing includes MLS listing # MDKE2005752, 0.11 acre lot on Anglewood Rd, Kentmore Park.

13983 Turners Point Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Unrepresented.

$562,000

Custom-built waterfront gem nestled on the picturesque Chester River in Kent County. This stunning 3-bedroom, 2.5-bathroom home, constructed in 2006, spans a total of 4821 square feet and offers an open floor plan ideal for everyday living and entertaining indoors and out! Upgrades abound! Step inside to discover a home rich in upgrades and architectural detail. Soaring 9-foot and cathedral ceilings, dramatic two-story spaces, and gleaming hardwood floors create an airy, inviting atmosphere. The kitchen is enhanced with upgraded countertops and lighting, while a cozy wood-burning fireplace anchors the main living area. The main-level primary suite provides convenience and comfort, and a full unfinished basement with rough-in plumbing offers endless potential for future expansion. Additional features include a central vacuum system, and numerous thoughtful enhancements throughout. Set on a private 0.5-acre lot, the property truly shines with 75 feet of prime waterfront along the Chester River. With approximately 6 feet of mean low water depth, this is a boater’s dream—perfect for boating, kayaking, swimming, and fishing right from your own backyard. Ideally located, the home offers close proximity to historic Chestertown’s charm, dining, and waterfront amenities, while also being just a short drive to Middletown, Delaware—home to the vibrant Westown area and tax-free shopping.

Custom-built waterfront gem nestled on the picturesque Chester River in Kent County. This stunning 3-bedroom, 2.5-bathroom home, constructed in 2006, spans a total of 4821 square feet and offers an open floor plan ideal for everyday living and entertaining indoors and out! Upgrades abound! Step inside to discover a home rich in upgrades and architectural detail. Soaring 9-foot and cathedral ceilings, dramatic two-story spaces, and gleaming hardwood floors create an airy, inviting atmosphere. The kitchen is enhanced with upgraded countertops and lighting, while a cozy wood-burning fireplace anchors the main living area. The main-level primary suite provides convenience and comfort, and a full unfinished basement with rough-in plumbing offers endless potential for future expansion. Additional features include a central vacuum system, and numerous thoughtful enhancements throughout. Set on a private 0.5-acre lot, the property truly shines with 75 feet of prime waterfront along the Chester River. With approximately 6 feet of mean low water depth, this is a boater’s dream—perfect for boating, kayaking, swimming, and fishing right from your own backyard. Ideally located, the home offers close proximity to historic Chestertown’s charm, dining, and waterfront amenities, while also being just a short drive to Middletown, Delaware—home to the vibrant Westown area and tax-free shopping.

31667 W Edge Rd, Millington

Listing courtesy of Century 21 Gold Key Realty. Contact:

Selling Office: Gunther-McClary Real Estate.

$560,000

Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car detached garage all on 6 acres in Galena, MD! Upon entry, you'll notice the incredible amount of parking and the convenient circular driveway, making it easy for residents and guests to come and go seamlessly. The main living area features a wood-burning fireplace, great for staying cozy in the cooler months. The eat-in kitchen, complete with large island, has been updated with granite counters and features tile flooring, plenty of cabinet space, and tons of room for a table. Just off the kitchen, the screened porch is a wonderful place to hang, eat crabs in the summer months, and enjoy morning coffee. Down the hall, a formal dining room can fit a massive table to accommodate friends and family, or it can be converted into an office or recreation room. A first floor bedroom and full bathroom are conveniently located on the far side of the home for privacy. Rounding out the main level is the laundry room and half bathroom. Upstairs, the enormous primary bedroom features a walk-in closet, massive bonus room with mini split heating and cooling, and access to the primary bathroom. Down the hall, an additional bedroom rounds out the living space. The detached 3 car garage is more than just a garage - it could serve as an excellent workshop and also features an additional covered area on the back of the garage, great for lawncare storage. Use your 6 acres creatively! If you're a gardener or a hunter, this could be your paradise! Bring your goats and horses! This home is great for the car enthusiast, too - the 5 total garage spaces alone make for an incredibly rare property! There are so many awesome possibilities at 13981 Mill Creek Lane!

Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car detached garage all on 6 acres in Galena, MD! Upon entry, you'll notice the incredible amount of parking and the convenient circular driveway, making it easy for residents and guests to come and go seamlessly. The main living area features a wood-burning fireplace, great for staying cozy in the cooler months. The eat-in kitchen, complete with large island, has been updated with granite counters and features tile flooring, plenty of cabinet space, and tons of room for a table. Just off the kitchen, the screened porch is a wonderful place to hang, eat crabs in the summer months, and enjoy morning coffee. Down the hall, a formal dining room can fit a massive table to accommodate friends and family, or it can be converted into an office or recreation room. A first floor bedroom and full bathroom are conveniently located on the far side of the home for privacy. Rounding out the main level is the laundry room and half bathroom. Upstairs, the enormous primary bedroom features a walk-in closet, massive bonus room with mini split heating and cooling, and access to the primary bathroom. Down the hall, an additional bedroom rounds out the living space. The detached 3 car garage is more than just a garage - it could serve as an excellent workshop and also features an additional covered area on the back of the garage, great for lawncare storage. Use your 6 acres creatively! If you're a gardener or a hunter, this could be your paradise! Bring your goats and horses! This home is great for the car enthusiast, too - the 5 total garage spaces alone make for an incredibly rare property! There are so many awesome possibilities at 13981 Mill Creek Lane!

13981 Mill Creek Ln, Galena

Listing courtesy of RE/MAX Chesapeake. Contact:

Selling Office: RE/MAX Chesapeake.

$560,000

Almost new (built 12/2024) adorable arts and craft style home located on one of Rock Hall's most desirable streets! This charming home features an open living/entertainment area with 9 ft ceilings. Oversized windows with deep sills flood the rooms with natural light. Three large bedrooms and two baths offer plenty of space for family and friends. There's a full width covered front porch where you can enjoy chatting with the friendly folks in this charming town. Steps away from Rock Hall Harbor, marinas and shops, you'll enjoy in-town living in this nearly new, but classic style home.

Almost new (built 12/2024) adorable arts and craft style home located on one of Rock Hall's most desirable streets! This charming home features an open living/entertainment area with 9 ft ceilings. Oversized windows with deep sills flood the rooms with natural light. Three large bedrooms and two baths offer plenty of space for family and friends. There's a full width covered front porch where you can enjoy chatting with the friendly folks in this charming town. Steps away from Rock Hall Harbor, marinas and shops, you'll enjoy in-town living in this nearly new, but classic style home.

5791 S Hawthorne Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: TTR Sotheby's International Realty.

$555,000

Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

26933 Mallard Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$550,000

Nestled on a beautiful 4.26 acre lot in the peaceful countryside of Galena, MD, this charming ranch style home offers the perfect blend of comfort, space and outdoor living. Featuring 3 bedrooms and 2.5 baths with over 1500 square feet of living space, this property is ideal for those looking to enjoy a relaxed lifestyle with room to spread out. Inside, you’ll find a thoughtfully updated home with recent improvements throughout, including a remodeled kitchen (2022), remodeled primary bath (2024), and updated paint and flooring in the living room and primary bedroom (2025). The spacious living room flows into the kitchen and dining area, creating a warm and inviting space for everyday living and entertaining. Step outside and take in everything this property has to offer. Standing seam metal roof installed in 2021. A beautiful covered back porch/deck, added in 2021, overlooks the property and provides the perfect setting for morning coffee or evening gatherings. The large man-made pond adds a peaceful focal point to the land and attracts local wildlife, creating a true country retreat feel. The outdoor amenities continue with a fenced 16x33 fiberglass in-ground saltwater pool installed in 2022, complete with a surrounding concrete patio, perfect for summer entertaining. For those needing storage, workshop space, or hobby space, the property also features a large 20x40 pole barn shop with electric and concrete flooring, in addition to the attached 23x27 garage. Additional highlights include: 2 bedrooms + bonus room/3rd bedroom with mini-split HVAC 2.5 bathrooms Spacious laundry room Walk-in closet in the primary suite Covered and uncovered deck spaces totaling over 500 sq ft Crawl space encapsulation Septic recently serviced Surrounded by Kent County farmland and open skies, this property offers the kind of privacy, functionality, and lifestyle opportunities that are hard to find. Whether you’re looking for a peaceful homestead, hobby farm potential, or simply more room to enjoy life outdoors, this property delivers. Additional professional photos coming.

Nestled on a beautiful 4.26 acre lot in the peaceful countryside of Galena, MD, this charming ranch style home offers the perfect blend of comfort, space and outdoor living. Featuring 3 bedrooms and 2.5 baths with over 1500 square feet of living space, this property is ideal for those looking to enjoy a relaxed lifestyle with room to spread out. Inside, you’ll find a thoughtfully updated home with recent improvements throughout, including a remodeled kitchen (2022), remodeled primary bath (2024), and updated paint and flooring in the living room and primary bedroom (2025). The spacious living room flows into the kitchen and dining area, creating a warm and inviting space for everyday living and entertaining. Step outside and take in everything this property has to offer. Standing seam metal roof installed in 2021. A beautiful covered back porch/deck, added in 2021, overlooks the property and provides the perfect setting for morning coffee or evening gatherings. The large man-made pond adds a peaceful focal point to the land and attracts local wildlife, creating a true country retreat feel. The outdoor amenities continue with a fenced 16x33 fiberglass in-ground saltwater pool installed in 2022, complete with a surrounding concrete patio, perfect for summer entertaining. For those needing storage, workshop space, or hobby space, the property also features a large 20x40 pole barn shop with electric and concrete flooring, in addition to the attached 23x27 garage. Additional highlights include: 2 bedrooms + bonus room/3rd bedroom with mini-split HVAC 2.5 bathrooms Spacious laundry room Walk-in closet in the primary suite Covered and uncovered deck spaces totaling over 500 sq ft Crawl space encapsulation Septic recently serviced Surrounded by Kent County farmland and open skies, this property offers the kind of privacy, functionality, and lifestyle opportunities that are hard to find. Whether you’re looking for a peaceful homestead, hobby farm potential, or simply more room to enjoy life outdoors, this property delivers. Additional professional photos coming.

31531 Jim Davis Rd, Galena

Listing courtesy of Patterson-Schwartz Real Estate. Contact:

Selling Office: Foraker Realty Co..

$550,000

43.6 acre Kent County hobby & hunting farm- Deer, turkey & ducks. 17 acres tillable, 25 acres of woodland 1 acre impoundment pond. Matapeake/mattapex soils Free & clear of all farm & hunting leases House & buildings have no contributory value Do NOT enter the farm without the permission of the listing agent. Do NOT enter the old house or the barns. They are unsafe.

1 Beds ⋅ 1 Baths

43.6 acre Kent County hobby & hunting farm- Deer, turkey & ducks. 17 acres tillable, 25 acres of woodland 1 acre impoundment pond. Matapeake/mattapex soils Free & clear of all farm & hunting leases House & buildings have no contributory value Do NOT enter the farm without the permission of the listing agent. Do NOT enter the old house or the barns. They are unsafe.

25051 Smithville Rd, Worton

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Davis Real Estate, Inc..

$546,500

Originally built in 1930. Completely updated and tastefully renovated. Perfect year round or seasonal cottage. In the very special private community of Kenmtore Park. Year round activities for all. Nightly get together at the Big Pier to capture the most beautiful sunsets on the Sassafras River. Morning coffee is served on the deck off of the kitchen. Invite friends over for a day at the beach then a casual dinner served on the secluded patio off the entertainment room. Great place also for a fire pit in the cooler months. All bedrooms are on the opposite side of the home from the entertainment room and the patio for convenient privacy. Walk to the beach or ride down on a golf car, there is always something to watch and usually someone to talk with. Kentmore is close to Galena on the North side. Visit the enchanting Cross Street Market and the Sassy market. Get take out from Twinnys or Galena Pizza. Upscale dining at the Kitty Knight or the Fish Whistle. Head South from Kentmore and come across Washington College and all the amenities of Historic Chestertown. Jump on your boat or hitch a ride on a neighbor's boat for a great day on the river. Boating, wakeboarding, skiing or tubing. Jet ski anyone? At night view the endless unobstructed sky and a million stars, planets, and the moon.

Originally built in 1930. Completely updated and tastefully renovated. Perfect year round or seasonal cottage. In the very special private community of Kenmtore Park. Year round activities for all. Nightly get together at the Big Pier to capture the most beautiful sunsets on the Sassafras River. Morning coffee is served on the deck off of the kitchen. Invite friends over for a day at the beach then a casual dinner served on the secluded patio off the entertainment room. Great place also for a fire pit in the cooler months. All bedrooms are on the opposite side of the home from the entertainment room and the patio for convenient privacy. Walk to the beach or ride down on a golf car, there is always something to watch and usually someone to talk with. Kentmore is close to Galena on the North side. Visit the enchanting Cross Street Market and the Sassy market. Get take out from Twinnys or Galena Pizza. Upscale dining at the Kitty Knight or the Fish Whistle. Head South from Kentmore and come across Washington College and all the amenities of Historic Chestertown. Jump on your boat or hitch a ride on a neighbor's boat for a great day on the river. Boating, wakeboarding, skiing or tubing. Jet ski anyone? At night view the endless unobstructed sky and a million stars, planets, and the moon.

28781 Valley Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$545,000

Lock the door, grab your coffee, and walk. Directly across from the Chestertown Marina in the heart of the Historic District, 204 S Water Street is the pied-à-terre the Eastern Shore was made for. Thoughtfully restored, the home pairs period character with an open, easy-living floor plan and a full bath on the main level. Out back, the rear porch and low-maintenance yard are made for slow mornings and long summer evenings. Step out the front door to the Chester River, Wilmer Park, and the marina. Stroll a few blocks of brick sidewalks to galleries, cafés, the oyster bar, live theatre, and the Saturday Farmers Market. Tall ships at Downrigging, jazz in the park, sunsets on the river: it's all right here. About 90 minutes from DC and Philadelphia, it's close enough for every weekend and charming enough to stay for good.

2 Beds ⋅ 2 Baths

Lock the door, grab your coffee, and walk. Directly across from the Chestertown Marina in the heart of the Historic District, 204 S Water Street is the pied-à-terre the Eastern Shore was made for. Thoughtfully restored, the home pairs period character with an open, easy-living floor plan and a full bath on the main level. Out back, the rear porch and low-maintenance yard are made for slow mornings and long summer evenings. Step out the front door to the Chester River, Wilmer Park, and the marina. Stroll a few blocks of brick sidewalks to galleries, cafés, the oyster bar, live theatre, and the Saturday Farmers Market. Tall ships at Downrigging, jazz in the park, sunsets on the river: it's all right here. About 90 minutes from DC and Philadelphia, it's close enough for every weekend and charming enough to stay for good.

204 S Water St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Sharon Real Estate P.C..

$545,000

Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district! A rare Water Street opportunity—see your boat from the front porch and enjoy walkable waterfront living in Chestertown. This thoughtfully rebuilt historic home offers 4 bedrooms, 3.5 baths, flexible guest spaces, and a water-view deck built to support a hot tub. Perfect as a primary residence or low-maintenance Chesapeake pied-à-terre for DC, Baltimore, and Philadelphia weekenders. Quality finishes include Andersen composite windows with plantation shutters, Heartland appliances, handcrafted cabinetry, and excellent storage. Walk to parks, dining, shops, arts, and the harbor. Vacant lot next door is separately owned.

Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district! A rare Water Street opportunity—see your boat from the front porch and enjoy walkable waterfront living in Chestertown. This thoughtfully rebuilt historic home offers 4 bedrooms, 3.5 baths, flexible guest spaces, and a water-view deck built to support a hot tub. Perfect as a primary residence or low-maintenance Chesapeake pied-à-terre for DC, Baltimore, and Philadelphia weekenders. Quality finishes include Andersen composite windows with plantation shutters, Heartland appliances, handcrafted cabinetry, and excellent storage. Walk to parks, dining, shops, arts, and the harbor. Vacant lot next door is separately owned.

206 S Water St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$541,500

Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical office and workspace on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate business growth.

110 S Queen St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$541,500

Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth.

Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth.

110 S Queen St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$540,000

Welcome to 14504 John Peel Road, located in a desirable waterfront-oriented community in Galena offering private community dock access and the opportunity to enjoy the Eastern Shore lifestyle. Conveniently located just minutes from Route 301, this spacious 4-bedroom, 2.5-bath Colonial offers over 2,300 square feet of comfortable living space with plenty of room for everyone. The main level features a beautiful kitchen with cherry cabinetry and lvp flooring, a dining area or family room with an electric fireplace, and a convenient half bath. Enjoy additional living space in the screened-in porch, perfect for relaxing and taking in the peaceful surroundings. The front of the home offers two formal living rooms, providing flexible space for entertaining, a home office, or additional gathering areas. Upstairs you’ll find all four bedrooms and two full bathrooms, including a spacious primary suite with a Juliet balcony. The basement offers even more possibilities with a wood stove and additional space for storage, hobbies, or recreation. An attached two-car garage adds everyday convenience.

Welcome to 14504 John Peel Road, located in a desirable waterfront-oriented community in Galena offering private community dock access and the opportunity to enjoy the Eastern Shore lifestyle. Conveniently located just minutes from Route 301, this spacious 4-bedroom, 2.5-bath Colonial offers over 2,300 square feet of comfortable living space with plenty of room for everyone. The main level features a beautiful kitchen with cherry cabinetry and lvp flooring, a dining area or family room with an electric fireplace, and a convenient half bath. Enjoy additional living space in the screened-in porch, perfect for relaxing and taking in the peaceful surroundings. The front of the home offers two formal living rooms, providing flexible space for entertaining, a home office, or additional gathering areas. Upstairs you’ll find all four bedrooms and two full bathrooms, including a spacious primary suite with a Juliet balcony. The basement offers even more possibilities with a wood stove and additional space for storage, hobbies, or recreation. An attached two-car garage adds everyday convenience.

14504 John Peel Rd, Galena

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: RE/MAX Associates - Newark.

$535,000

Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of property. This rancher gives you plenty of space both inside and out. Recently, there was an addition of a mudroom and a second owners suite. Both owners suites have their own bathroom and walk-in shower and one even has a jetted Jacuzzi tub to help you unwind after a long day. There is upgraded flooring through-out, whether it be hardwood or tile, every room feels polished and upscale. The living room includes a woodstove that was installed in 2025 along with a new chimney pipe. There is a creek directly behind your property, which means, water is just a short stroll away. Enjoy tons of natural light in the spacious kitchen where quartz countertops are partnered with a Stainless Steel Refrigerator, built-in microwave and stove. Soft-close cabinets and drawers add to the upscale feel. This home has three spacious bedrooms and three full baths. The un-finished lower level provides you with even more space for storage or it can be your very own blank canvas to finish and increase your living space. The laundry area is in the basement and the washer and dryer will stay with the home. The sliding glass door in the kitchen allows access to your deck and backyard. Enjoy the peace and quiet. Don't be surprised if you see ducks, turkey or deer, they have been known to enjoy the 6+ acres too! The water treatment system has been thoroughly maintained and will convey with the home. High Speed Talkie internet is available. New windows installed throughout most of the home in 2020. This is an Amazing Home! It is turn-key and ready to Welcome its New Owners.