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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.

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.

4 Beds ⋅ 4 Baths

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

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

Country Club Estates - Live Where You Play – Just 1.5 Miles from Downtown Chestertown! Enjoy the ease of one-level living in a prime location near the Chester River Yacht & Country Club, where club members enjoy golf, poolside afternoons, and clubhouse dining are just a short walk away. The interior spanning 2,280 square feet offers a comfortable, continuous flow that makes everyday living easy, complemented by warm hardwood floors, a cozy fireplace, and generous storage throughout. Perfect for those seeking a home that combines comfort, convenience, and community.

Country Club Estates - Live Where You Play – Just 1.5 Miles from Downtown Chestertown! Enjoy the ease of one-level living in a prime location near the Chester River Yacht & Country Club, where club members enjoy golf, poolside afternoons, and clubhouse dining are just a short walk away. The interior spanning 2,280 square feet offers a comfortable, continuous flow that makes everyday living easy, complemented by warm hardwood floors, a cozy fireplace, and generous storage throughout. Perfect for those seeking a home that combines comfort, convenience, and community.

7729 Country Club Ln, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: VYBE Realty.

$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.

4 Beds ⋅ 4 Baths

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.

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!

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.

4 Beds ⋅ 4 Baths

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

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

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.

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.

9816 Fairlee Rd, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$535,000

$20,000 Price Reduction! A One-of-a-Kind Historic Treasure Reimagined for Modern Living Step into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm with contemporary luxury. Once abandoned, Mowbray Chapel has undergone a breathtaking transformation. In 2021, the entire interior was rebuilt, preserving its soaring ceilings, grand arched windows, and rich brick walls while incorporating high-end finishes and modern conveniences to create a truly one-of-a-kind living space. The fully renovated kitchen and bath provide modern amenities while maintaining historic character, and a gas wood stove and substantial woodwork enhance the warmth and charm of the space. A new well and an advanced ATU/BAT septic system rated for a 4-bedroom home offer long-term comfort and expansion potential. With new high-speed internet connectivity, you can stay connected while enjoying the serenity of this unique retreat. Set on over three acres, the property offers lush green lawns, mature trees, and a peaceful pond, providing an enchanting backdrop for year-round enjoyment. Whether you're hosting intimate gatherings or simply unwinding in the tranquil surroundings, this setting is pure magic. Mowbray Chapel presents endless opportunities, whether as a private residence, a sought-after Airbnb rental, or a charming event or wedding venue. The potential to expand or build additional structures makes this an incredible investment. Located just ten minutes from historic downtown Chestertown, you’ll enjoy easy access to boutique shopping, waterfront dining, farmers' markets, art galleries, and cultural festivals. Explore the scenic Chester River, visit Washington College, or indulge in local seafood at charming restaurants. Don’t miss this rare opportunity to own a piece of history while embracing modern luxury and investment potential. Whether you dream of a peaceful retreat, a thriving Airbnb, or a breathtaking event venue, Mowbray Chapel is ready to make your vision a reality. Seller Financing is available if needed.

1 Beds ⋅ 1 Baths

$20,000 Price Reduction! A One-of-a-Kind Historic Treasure Reimagined for Modern Living Step into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm with contemporary luxury. Once abandoned, Mowbray Chapel has undergone a breathtaking transformation. In 2021, the entire interior was rebuilt, preserving its soaring ceilings, grand arched windows, and rich brick walls while incorporating high-end finishes and modern conveniences to create a truly one-of-a-kind living space. The fully renovated kitchen and bath provide modern amenities while maintaining historic character, and a gas wood stove and substantial woodwork enhance the warmth and charm of the space. A new well and an advanced ATU/BAT septic system rated for a 4-bedroom home offer long-term comfort and expansion potential. With new high-speed internet connectivity, you can stay connected while enjoying the serenity of this unique retreat. Set on over three acres, the property offers lush green lawns, mature trees, and a peaceful pond, providing an enchanting backdrop for year-round enjoyment. Whether you're hosting intimate gatherings or simply unwinding in the tranquil surroundings, this setting is pure magic. Mowbray Chapel presents endless opportunities, whether as a private residence, a sought-after Airbnb rental, or a charming event or wedding venue. The potential to expand or build additional structures makes this an incredible investment. Located just ten minutes from historic downtown Chestertown, you’ll enjoy easy access to boutique shopping, waterfront dining, farmers' markets, art galleries, and cultural festivals. Explore the scenic Chester River, visit Washington College, or indulge in local seafood at charming restaurants. Don’t miss this rare opportunity to own a piece of history while embracing modern luxury and investment potential. Whether you dream of a peaceful retreat, a thriving Airbnb, or a breathtaking event venue, Mowbray Chapel is ready to make your vision a reality. Seller Financing is available if needed.

5179 Quaker Neck Rd, Chestertown

Listing courtesy of Hyatt & Company Real Estate, LLC. Contact:

Selling Office: Keller Williams Legacy.

Recently updated "coastal" home located in a small community of 8 homes , three miles east of historic Chestertown. The house sits on high ground, less than a mile from a small Chester River boat landing where you can easily launch a kayak, Sunfish or small power boat. This comfortable home offers same floor living for much of the house, but also has a partly finished full basement with tv room. and full bath The kitchen has custom maple cabinets, leathered granite countertops, oversize farm sink and stainless-steel appliances. The large deck overlooks the peaceful farmland edged by a wooded hedgerow and the fenced yard. Chestertown, dating to the18th Century, is the County Seat of Kent County, with courthouse, churches, hospital. shopping and restaurants and is the home of Washington College. The $300 semi-annual fee is an estimate and is for road maintenance--- see deed restrictions

Recently updated "coastal" home located in a small community of 8 homes , three miles east of historic Chestertown. The house sits on high ground, less than a mile from a small Chester River boat landing where you can easily launch a kayak, Sunfish or small power boat. This comfortable home offers same floor living for much of the house, but also has a partly finished full basement with tv room. and full bath The kitchen has custom maple cabinets, leathered granite countertops, oversize farm sink and stainless-steel appliances. The large deck overlooks the peaceful farmland edged by a wooded hedgerow and the fenced yard. Chestertown, dating to the18th Century, is the County Seat of Kent County, with courthouse, churches, hospital. shopping and restaurants and is the home of Washington College. The $300 semi-annual fee is an estimate and is for road maintenance--- see deed restrictions

Preston Lane, Chestertown

Listing courtesy of Shoreline Realty. Contact:

Selling Office: Doug Ashley Realtors, LLC.

**All offers due on 7/4 by 5 pm. Set on a picturesque 2-acre lot, this exceptional property is surrounded by lush landscaping and mature trees, creating a private and tranquil retreat from the demands of everyday life. Scenic vistas and wooded surroundings provide a peaceful ambiance, offering the perfect balance of rural charm and modern convenience. Inside, a thoughtfully designed traditional floor plan seamlessly connects the home's living spaces. The gourmet kitchen is a chef's dream, featuring premium Viking stainless steel appliances, including a gas range, built-in microwave, and refrigerator. A spacious center island with a butcher block workstation provides abundant prep space, while upgraded countertops, imported deVOL fixtures, under-cabinet lighting, and elegant glass-front cabinetry add both style and functionality. The adjoining kitchen and dining area is ideal for entertaining, allowing for effortless flow and gathering. The home offers four generously sized bedrooms, each designed with comfort and relaxation in mind. The second-floor bathroom serves as a private spa retreat, complete with a jetted soaking tub and separate stall shower. An upper-level laundry room adds everyday convenience and efficiency. Outdoor amenities are equally impressive. A detached oversized garage provides abundant storage and parking and is uniquely equipped with a bathroom and walk-in cooler, offering exceptional versatility for hobbyists, entertainers, or business use. The expansive grounds provide endless opportunities for gardening, recreation, hosting gatherings, or simply enjoying the serenity of nature in complete privacy. Located outside the charming community of Worton, this property offers the best of both worlds—a peaceful rural setting with convenient access to local marinas, dining, community center with pool and recreational opportunities. Known for its welcoming atmosphere and proximity to outdoor adventures, Worton is an ideal destination for those seeking a relaxed lifestyle without compromising accessibility. Combining luxurious features, scenic surroundings, and a highly desirable location, this remarkable property presents a rare opportunity to experience refined country living. Discover a lifestyle defined by comfort, privacy, and timeless elegance in this truly exceptional home.

**All offers due on 7/4 by 5 pm. Set on a picturesque 2-acre lot, this exceptional property is surrounded by lush landscaping and mature trees, creating a private and tranquil retreat from the demands of everyday life. Scenic vistas and wooded surroundings provide a peaceful ambiance, offering the perfect balance of rural charm and modern convenience. Inside, a thoughtfully designed traditional floor plan seamlessly connects the home's living spaces. The gourmet kitchen is a chef's dream, featuring premium Viking stainless steel appliances, including a gas range, built-in microwave, and refrigerator. A spacious center island with a butcher block workstation provides abundant prep space, while upgraded countertops, imported deVOL fixtures, under-cabinet lighting, and elegant glass-front cabinetry add both style and functionality. The adjoining kitchen and dining area is ideal for entertaining, allowing for effortless flow and gathering. The home offers four generously sized bedrooms, each designed with comfort and relaxation in mind. The second-floor bathroom serves as a private spa retreat, complete with a jetted soaking tub and separate stall shower. An upper-level laundry room adds everyday convenience and efficiency. Outdoor amenities are equally impressive. A detached oversized garage provides abundant storage and parking and is uniquely equipped with a bathroom and walk-in cooler, offering exceptional versatility for hobbyists, entertainers, or business use. The expansive grounds provide endless opportunities for gardening, recreation, hosting gatherings, or simply enjoying the serenity of nature in complete privacy. Located outside the charming community of Worton, this property offers the best of both worlds—a peaceful rural setting with convenient access to local marinas, dining, community center with pool and recreational opportunities. Known for its welcoming atmosphere and proximity to outdoor adventures, Worton is an ideal destination for those seeking a relaxed lifestyle without compromising accessibility. Combining luxurious features, scenic surroundings, and a highly desirable location, this remarkable property presents a rare opportunity to experience refined country living. Discover a lifestyle defined by comfort, privacy, and timeless elegance in this truly exceptional home.

11929 Colly Cove Ln, Worton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Real Broker, LLC - Chester.

Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality craftsmanship, comfort, and modern convenience. Built in 2017, this 3 bedroom, 2 bathroom home features an inviting open layout with luxury plank hardwood flooring throughout the main living areas, granite countertops, abundant cabinet storage, and a cozy propane fireplace. The spacious primary suite includes a large walk-in closet and a luxurious en-suite bath complete with a soaking tub and separate shower. Enjoy relaxing mornings on the screened porch or unwind evenings around the fire pit on the paver patio just off the living room. Additional highlights include a 2-car attached garage, sprinkler system, hot water on demand, new propane furnace installed in 2026, and new dryer in 2025. Conveniently located close to all of Chestertown amenities, with a voluntary HOA of just $100/year. Showings begin 5/22 — this is one you won’t want to miss!

Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality craftsmanship, comfort, and modern convenience. Built in 2017, this 3 bedroom, 2 bathroom home features an inviting open layout with luxury plank hardwood flooring throughout the main living areas, granite countertops, abundant cabinet storage, and a cozy propane fireplace. The spacious primary suite includes a large walk-in closet and a luxurious en-suite bath complete with a soaking tub and separate shower. Enjoy relaxing mornings on the screened porch or unwind evenings around the fire pit on the paver patio just off the living room. Additional highlights include a 2-car attached garage, sprinkler system, hot water on demand, new propane furnace installed in 2026, and new dryer in 2025. Conveniently located close to all of Chestertown amenities, with a voluntary HOA of just $100/year. Showings begin 5/22 — this is one you won’t want to miss!

1014 Twin Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.