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Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout. The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water heater. It opens to the family room with a cozy corner gas fireplace—perfect for entertaining or relaxing. The main level includes an office, primary suite with a large bath and walk-in closet, an additional bedroom and full bath, and a dedicated laundry area. A screened-in porch off the main floor provides a peaceful space to enjoy morning coffee or evening gatherings surrounded by nature. Upstairs offers an open sitting area with window seat, two additional bedrooms, and a full bath. Set on a beautifully landscaped 2.81-acre lot backing to trees, this property provides a private outdoor retreat. Additional highlights include a side-entry garage, paved driveway, and outbuilding for extra storage. Experience the best of Orchard Hill living—where quality, comfort, and natural beauty come together.

8951 Orchard Dr, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$695,000

Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside - no flood insurance needed. Enter the house through a split foyer with a few steps up to the main level and into the great room with the central kitchen, dining and living areas. The master suite is located on one end of the main level and features a large walk-in tile shower and a small private deck. The other end of the main level features a vaulted sunroom, a great spot to commune with nature or host the family crab feast. The lower walk out level offers a family room with a wood stove, two bedrooms, a full bath, a laundry room, and outdoor access. 2.5-3' MLW Buyer to verify. See Documents for Seller updates plus info on Association benefits. New roof added in 2021 and a BAT septic system was installed in 2023. Property has been well maintained but is being sold AS IS.

Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside - no flood insurance needed. Enter the house through a split foyer with a few steps up to the main level and into the great room with the central kitchen, dining and living areas. The master suite is located on one end of the main level and features a large walk-in tile shower and a small private deck. The other end of the main level features a vaulted sunroom, a great spot to commune with nature or host the family crab feast. The lower walk out level offers a family room with a wood stove, two bedrooms, a full bath, a laundry room, and outdoor access. 2.5-3' MLW Buyer to verify. See Documents for Seller updates plus info on Association benefits. New roof added in 2021 and a BAT septic system was installed in 2023. Property has been well maintained but is being sold AS IS.

10087 John Carvill Rd, Chestertown

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

Selling Office: RE/MAX Chesapeake.

$665,000

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main-floor primary suite, and practical indoor/outdoor living spaces make this the perfect home for everyday living or a weekend retreat. The well-designed first floor - featuring hardwoods, baseboards, and crown moldings throughout - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the back sunroom and exterior deck. The renovated kitchen now features solid wood cabinets, quartz countertops, stainless steel appliances, recessed lighting, and overhanging bar seating. Cozy up with a book by the living room brick fireplace with a propane insert, surrounded by classic built-in bookshelves. Passing through the back sliding doors, you will be greeted by the sunroom and oversized back deck: each perfect for crab feasts and summer bbq's. Enjoy summer evenings while overlooking the private backyard, which is fully fenced-in and has plenty of space for dogs and children. The main floor also features a primary bedroom with an ensuite bath, a large walk-in closet, and a separate office. The renovated primary bath now features ceramic tile, a standing stall shower, wainscoting, double vanity, and new recessed lights. A dining room off the kitchen with a lovely bay window flows through a pocket door into the formal living room with built-in bookcases. The main floor is finished by a renovated powder room and laundry room just off the kitchen. Upstairs, you will find two more generously sized bedrooms, a full shared bath, and a potential 4th bedroom or office space for those who work from home. An attached two-car garage includes another half bath, additional storage, and a separate workroom for those who like to tinker. Mature trees provide lots of shade and privacy around the meticulously maintained front and back yards. A generously sized storage shed is perfect for garden tools and the lawnmower. Located on a quiet, dead-end street, the neighborhood is great for dog walkers and evening strolls. Improvements made by current owner: whole kitchen remodel including cabinets, countertops, appliances, hardwood floors (2019); primary bathroom and powder room remodel including ceramic tile, standing shower stall, toilets, wainscoting, double vanity, fixtures (2017), 14 windows replaced with double-pane insulated (2017); Carrier HVAC (2017); whole-house water filter and well pressure tank (2022); crawl space improvement (2016); and professional landscaping. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. Professional photos to come!

3 Beds ⋅ 4 Baths

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main-floor primary suite, and practical indoor/outdoor living spaces make this the perfect home for everyday living or a weekend retreat. The well-designed first floor - featuring hardwoods, baseboards, and crown moldings throughout - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the back sunroom and exterior deck. The renovated kitchen now features solid wood cabinets, quartz countertops, stainless steel appliances, recessed lighting, and overhanging bar seating. Cozy up with a book by the living room brick fireplace with a propane insert, surrounded by classic built-in bookshelves. Passing through the back sliding doors, you will be greeted by the sunroom and oversized back deck: each perfect for crab feasts and summer bbq's. Enjoy summer evenings while overlooking the private backyard, which is fully fenced-in and has plenty of space for dogs and children. The main floor also features a primary bedroom with an ensuite bath, a large walk-in closet, and a separate office. The renovated primary bath now features ceramic tile, a standing stall shower, wainscoting, double vanity, and new recessed lights. A dining room off the kitchen with a lovely bay window flows through a pocket door into the formal living room with built-in bookcases. The main floor is finished by a renovated powder room and laundry room just off the kitchen. Upstairs, you will find two more generously sized bedrooms, a full shared bath, and a potential 4th bedroom or office space for those who work from home. An attached two-car garage includes another half bath, additional storage, and a separate workroom for those who like to tinker. Mature trees provide lots of shade and privacy around the meticulously maintained front and back yards. A generously sized storage shed is perfect for garden tools and the lawnmower. Located on a quiet, dead-end street, the neighborhood is great for dog walkers and evening strolls. Improvements made by current owner: whole kitchen remodel including cabinets, countertops, appliances, hardwood floors (2019); primary bathroom and powder room remodel including ceramic tile, standing shower stall, toilets, wainscoting, double vanity, fixtures (2017), 14 windows replaced with double-pane insulated (2017); Carrier HVAC (2017); whole-house water filter and well pressure tank (2022); crawl space improvement (2016); and professional landscaping. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. Professional photos to come!

7712 Waterview Ln, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

118 Little Harbor Way Unit 201, Chestertown

$665,000

An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called Chester River Landing. Historic downtown Chestertown and the Chester River Yacht & Country club are less than 2 minutes away, when you need a break from your enclave that includes marina, grill patio, crabbing/fishing pier, beach area for kayak launch, waterfront green space with fire pit, community garden, and pool with pool house. Unit 201 includes a nearby 1 car garage with overhead storage racks and a deeded premium boat slip (A7) A unique feature of this home is a custom HVAC and air quality system, ideal for anyone with seasonal allergies, chemical sensitivities, or just appreciative of quality air and healthy living. New GE range, LG and 03 Pure Eco Laundry System installed 2025. (Warranties convey). The lobby and all common areas have recently been beautifully redecorated and furnished. As part of CRL commitment to maintaining property excellence, the entire exterior of River House is currently receiving new siding, flashing and other pro-active improvements at no cost to the new owners.

2 Beds ⋅ 3 Baths

An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called Chester River Landing. Historic downtown Chestertown and the Chester River Yacht & Country club are less than 2 minutes away, when you need a break from your enclave that includes marina, grill patio, crabbing/fishing pier, beach area for kayak launch, waterfront green space with fire pit, community garden, and pool with pool house. Unit 201 includes a nearby 1 car garage with overhead storage racks and a deeded premium boat slip (A7) A unique feature of this home is a custom HVAC and air quality system, ideal for anyone with seasonal allergies, chemical sensitivities, or just appreciative of quality air and healthy living. New GE range, LG and 03 Pure Eco Laundry System installed 2025. (Warranties convey). The lobby and all common areas have recently been beautifully redecorated and furnished. As part of CRL commitment to maintaining property excellence, the entire exterior of River House is currently receiving new siding, flashing and other pro-active improvements at no cost to the new owners.

118 Little Harbor Way Unit 201, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

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:

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.

$650,000

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.

$629,000

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den.

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den.

201 River Rd, Chestertown

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

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.

$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.

11040 Kylie Ln, Chestertown

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

Selling Office: LPT Realty, LLC.

$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:

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!

$590,000

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:

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.

$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.

103 Adela Way, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Compass.

$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.

$552,000

The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be disappointed. This is the last avaiable lot in this community so don't wait! Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a separate office making this a great option for those who work from home. A first floor bedroom is idea for a guest room, play room, in-law quarters and more. The home is adorned with luxury vinyl plank flooring and plush carpeting, creating a warm and welcoming atmosphere throughout. Set on a generous 1-acre lot that adjoins open space, this property offers a serene outdoor setting, perfect for enjoying nature or future landscaping projects. The side-entry attached garage provides easy access and additional storage. With its excellent condition and thoughtful design, this home is ready to embrace new memories. Experience the perfect blend of comfort and modern living in this exceptional property. Buy with ease when purchasing this new construction home. No HOA

The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be disappointed. This is the last avaiable lot in this community so don't wait! Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a separate office making this a great option for those who work from home. A first floor bedroom is idea for a guest room, play room, in-law quarters and more. The home is adorned with luxury vinyl plank flooring and plush carpeting, creating a warm and welcoming atmosphere throughout. Set on a generous 1-acre lot that adjoins open space, this property offers a serene outdoor setting, perfect for enjoying nature or future landscaping projects. The side-entry attached garage provides easy access and additional storage. With its excellent condition and thoughtful design, this home is ready to embrace new memories. Experience the perfect blend of comfort and modern living in this exceptional property. Buy with ease when purchasing this new construction home. No HOA

216 Blakefield Dr, Chestertown

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

Selling Office: Anne Arundel Properties, Inc..

$550,000

Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard and evenings just minutes from historic Chestertown's shops, dining, and Washington College. Seamless indoor-outdoor flow make this the ultimate retreat—perfect for entertaining with indoor and outdoor spaces. This home has a complete in-law-suite perfect for hosting guests, accommodating extended family, or creating a private home office with serene water views. This deceivingly large 5-bedroom, 4-bath home features; extensive landscaping, lovely gazebo and brand-new roof.

5 Beds ⋅ 4 Baths

Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard and evenings just minutes from historic Chestertown's shops, dining, and Washington College. Seamless indoor-outdoor flow make this the ultimate retreat—perfect for entertaining with indoor and outdoor spaces. This home has a complete in-law-suite perfect for hosting guests, accommodating extended family, or creating a private home office with serene water views. This deceivingly large 5-bedroom, 4-bath home features; extensive landscaping, lovely gazebo and brand-new roof.

302 Rosin Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

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.

$545,000

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:

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.

$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.

110 S Queen St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

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.

$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.

9816 Fairlee Rd, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

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:

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:

Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanticoke Home offers a flexible floor plan, updated kitchen, spacious backyard, and brand new Florida/Sun room, designed for both relaxation and entertaining. The heart of the home feautures a gourmet kitchen with granite counter tops, SS appliances, custom built ins, and connects to the family room with an amazing built in wood stove, warming the entire home. Sitting on a generous 2 acre lot (not reflected on tax record), and surrounded by lush farmland, this property offers you so much potential. Keep the extra lot as a natural buffer, or build a garage/workshop/granny annex, or just sell it on. You can't go wrong! Great Oak Estates offer direct access for its residents ($100 annually) to all the Marina amenities including: Outdoor pool, restaurant, 9 hole golf course, picnic and playground area by the water. And a beautiful sandy beach on the calm waters of Fairlee Creek.

5 Beds ⋅ 4 Baths

Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanticoke Home offers a flexible floor plan, updated kitchen, spacious backyard, and brand new Florida/Sun room, designed for both relaxation and entertaining. The heart of the home feautures a gourmet kitchen with granite counter tops, SS appliances, custom built ins, and connects to the family room with an amazing built in wood stove, warming the entire home. Sitting on a generous 2 acre lot (not reflected on tax record), and surrounded by lush farmland, this property offers you so much potential. Keep the extra lot as a natural buffer, or build a garage/workshop/granny annex, or just sell it on. You can't go wrong! Great Oak Estates offer direct access for its residents ($100 annually) to all the Marina amenities including: Outdoor pool, restaurant, 9 hole golf course, picnic and playground area by the water. And a beautiful sandy beach on the calm waters of Fairlee Creek.

22360 Great Oak Landing Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Compass Realty, Inc..

Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The kitchen is open to the breakfast area and living room, creating a cohesive main living area. The living room includes a built-in fireplace, while a formal dining room sits just off the kitchen. The kitchen features granite countertops and tile flooring, which continues through the pantry and mudroom. All other countertops throughout the home are upgraded. A spacious laundry room and pantry are conveniently located off the kitchen. The first floor also includes a powder room and a first-floor extra room ideal for a home office or study. A spacious entryway from the attached two-car garage or additional side entrance provides a practical everyday entry. The first-floor primary suite offers comfortable main-level living and includes cathedral ceilings, a private door leading to a roomy composite back deck, and an attached bathroom with marble heated flooring and a walk-in shower, along with a spacious walk-in closet. Upstairs, the home offers two bedrooms with a loft area in between , providing flexible additional living space. Custom inlay flooring is featured in the formal dining room, living room, foyer, primary suite and first-floor extra room, tastefully alternating wood types and adding subtle character. Overall, this home offers quality construction, thoughtful design, and a layout that works well for everyday living. Still more details and touches to be seen when you come to visit. This home truly is move in ready.

Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The kitchen is open to the breakfast area and living room, creating a cohesive main living area. The living room includes a built-in fireplace, while a formal dining room sits just off the kitchen. The kitchen features granite countertops and tile flooring, which continues through the pantry and mudroom. All other countertops throughout the home are upgraded. A spacious laundry room and pantry are conveniently located off the kitchen. The first floor also includes a powder room and a first-floor extra room ideal for a home office or study. A spacious entryway from the attached two-car garage or additional side entrance provides a practical everyday entry. The first-floor primary suite offers comfortable main-level living and includes cathedral ceilings, a private door leading to a roomy composite back deck, and an attached bathroom with marble heated flooring and a walk-in shower, along with a spacious walk-in closet. Upstairs, the home offers two bedrooms with a loft area in between , providing flexible additional living space. Custom inlay flooring is featured in the formal dining room, living room, foyer, primary suite and first-floor extra room, tastefully alternating wood types and adding subtle character. Overall, this home offers quality construction, thoughtful design, and a layout that works well for everyday living. Still more details and touches to be seen when you come to visit. This home truly is move in ready.

204 Double Creek Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

There’s no place like home! Welcome to the Flyway neighborhood in Chestertown, where this 4 bedroom, 3.5 bath home offers a flexible layout with both formal and casual living spaces. The front entry opens to a formal dining room and a separate bonus room that can serve as a living room, playroom, or home office. The family room with propane fireplace flows into the eat-in kitchen that features a breakfast bar, pantry, and space for a table. Just off the kitchen is a half bathroom and interior access to the 2 car garage. Sliding glass doors lead to a composite deck with steps down to the spacious fenced backyard, all situated on a 1 acre lot offering space to enjoy outdoor living. Upstairs is the primary suite with two walk-in closets and a private bath with dual vanity and walk-in shower. A secondary suite includes its own private bath and walk-in closet, while two additional bedrooms share a hall bath. Laundry is conveniently located on the upper level. Recent updates include a new roof on the home and shed (2025) and recently replaced water heaters (downstairs in 2025, upstairs in 2019). Conveniently located just minutes from downtown Chestertown’s shops, restaurants, waterfront, and Washington College. Schedule your showing today!

$512,500

There’s no place like home! Welcome to the Flyway neighborhood in Chestertown, where this 4 bedroom, 3.5 bath home offers a flexible layout with both formal and casual living spaces. The front entry opens to a formal dining room and a separate bonus room that can serve as a living room, playroom, or home office. The family room with propane fireplace flows into the eat-in kitchen that features a breakfast bar, pantry, and space for a table. Just off the kitchen is a half bathroom and interior access to the 2 car garage. Sliding glass doors lead to a composite deck with steps down to the spacious fenced backyard, all situated on a 1 acre lot offering space to enjoy outdoor living. Upstairs is the primary suite with two walk-in closets and a private bath with dual vanity and walk-in shower. A secondary suite includes its own private bath and walk-in closet, while two additional bedrooms share a hall bath. Laundry is conveniently located on the upper level. Recent updates include a new roof on the home and shed (2025) and recently replaced water heaters (downstairs in 2025, upstairs in 2019). Conveniently located just minutes from downtown Chestertown’s shops, restaurants, waterfront, and Washington College. Schedule your showing today!

206 Flyway Ln, Chestertown

Listing courtesy of Integrity Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$500,500

Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line “Meyers” well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitting room. The MBR features wainscotting on all walls; crown molding; custom wide molding around all 3 doors and the closet with remote controlled ceiling fan with dimmable light. Large living room with stunning fireplace. Wide, extra-long mantle, matching storage cabinets on both sides of fireplace, large picture window and crown molding. Two full bathrooms with showers are upstairs, each with new, in 2024, quiet, yet powerful Panasonic exhaust fan and LED light. One Powder Room is downstairs. Bright and airy, extra-long dining room. Tray ceiling. dimmable LED ceiling lights on separate, inner and outer ring circuits for versatility. Ceiling centerline is pre-wired (includes 3-way switches) for one or more chandelier lights; Pass-through window to kitchen with fancy tempered glass shelf. Family room with dropped ceiling bar area. Bar sink, granite counters, gorgeous glass door cabinets, wood-burning stove, versatile lighting, and a slider door to a the main level sunroom. Modern, ample-sized kitchen with movable island. Nearly new, upscale glass cooktop/oven, dishwasher and microwave. Build-in refrigerator surrounded by cabinets. Double sink, disposal and PC workstation with shelving matching cabinet. Extraordinary lighting includes under and over cabinet lights plus a ceiling fan with fancy light globes and attractive light globes over sink. MAJOR ADDITION & REHAB done in 2013: Extended DR by 13 feet and added 2nd story sunroom/sitting room on top of DR extension Total rehab of 1st floor sunroom. Top quality, long lasting architectural roof shingle for entire house; new flashing and roof vent seals. Both sunrooms have attractive, casement-style windows for exceptional ventilation. Seven Ceiling fans with attractive lighting: MBR, BR2, BR3, 2nd story sunroom/sitting room, kitchen and 2 on the porch. All four Slider Doors (servicing the porch and the 2 sunrooms) have built-in blinds for privacy and versatile light and view control. Spacious screened porch with porch swing. Massive stone and paver patio area includes three 10x10 ft flat, paved areas for table & chairs. Large Campfire ring within the patio. Two lovely, Amish garden sheds in excellent condition and loaded with options: 12x16 ft. shed installed in 2010, and a 10x14 ft. shed installed in 2021. Huge 16x18 ft. Raised Deck using long-life Trex engineered planks; custom Pergola over one corner. Deep Shaded, 10 x 12 ft Outer Patio Area with Pergola. Mature Trees for great privacy and shade, especially around property perimeter. Three-level, split rail fence on rear and side yard property lines. (Left-side fence only is owned and maintained by the neighbor.) Extra-Wide Driveway. Paved Parking for 10 vehicles! Also suitable for camping trailer or boat.

Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line “Meyers” well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitting room. The MBR features wainscotting on all walls; crown molding; custom wide molding around all 3 doors and the closet with remote controlled ceiling fan with dimmable light. Large living room with stunning fireplace. Wide, extra-long mantle, matching storage cabinets on both sides of fireplace, large picture window and crown molding. Two full bathrooms with showers are upstairs, each with new, in 2024, quiet, yet powerful Panasonic exhaust fan and LED light. One Powder Room is downstairs. Bright and airy, extra-long dining room. Tray ceiling. dimmable LED ceiling lights on separate, inner and outer ring circuits for versatility. Ceiling centerline is pre-wired (includes 3-way switches) for one or more chandelier lights; Pass-through window to kitchen with fancy tempered glass shelf. Family room with dropped ceiling bar area. Bar sink, granite counters, gorgeous glass door cabinets, wood-burning stove, versatile lighting, and a slider door to a the main level sunroom. Modern, ample-sized kitchen with movable island. Nearly new, upscale glass cooktop/oven, dishwasher and microwave. Build-in refrigerator surrounded by cabinets. Double sink, disposal and PC workstation with shelving matching cabinet. Extraordinary lighting includes under and over cabinet lights plus a ceiling fan with fancy light globes and attractive light globes over sink. MAJOR ADDITION & REHAB done in 2013: Extended DR by 13 feet and added 2nd story sunroom/sitting room on top of DR extension Total rehab of 1st floor sunroom. Top quality, long lasting architectural roof shingle for entire house; new flashing and roof vent seals. Both sunrooms have attractive, casement-style windows for exceptional ventilation. Seven Ceiling fans with attractive lighting: MBR, BR2, BR3, 2nd story sunroom/sitting room, kitchen and 2 on the porch. All four Slider Doors (servicing the porch and the 2 sunrooms) have built-in blinds for privacy and versatile light and view control. Spacious screened porch with porch swing. Massive stone and paver patio area includes three 10x10 ft flat, paved areas for table & chairs. Large Campfire ring within the patio. Two lovely, Amish garden sheds in excellent condition and loaded with options: 12x16 ft. shed installed in 2010, and a 10x14 ft. shed installed in 2021. Huge 16x18 ft. Raised Deck using long-life Trex engineered planks; custom Pergola over one corner. Deep Shaded, 10 x 12 ft Outer Patio Area with Pergola. Mature Trees for great privacy and shade, especially around property perimeter. Three-level, split rail fence on rear and side yard property lines. (Left-side fence only is owned and maintained by the neighbor.) Extra-Wide Driveway. Paved Parking for 10 vehicles! Also suitable for camping trailer or boat.

8620 Park Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

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

$500,000

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore.

2 Beds ⋅ 3 Baths

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore.

101 S Mill St, Chestertown

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

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

$495,000

Nestled in the charming Byford Development, this beautifully renovated home exudes warmth and comfort, making it the perfect retreat. With a thoughtful renovation completed in 2020, this residence boasts a blend of traditional and farmhouse styles, featuring a stunning brick and vinyl exterior that invites you in. Step inside to discover a spacious 2,220 sq. ft. layout, where modern amenities meet classic charm. The heart of the home is the gourmet kitchen, complete with upgraded countertops, stainless steel appliances, and a convenient island that encourages gatherings. This home offers four generous bedrooms and 2.5 bathrooms. Enjoy the comfort of hardwood floors throughout the main level, complemented by ceiling fans and window treatments that enhance the cozy atmosphere. The main floor laundry adds convenience to your daily routine, while the unfinished basement provides ample storage or potential for future expansion. Outside, the circular driveway and attached garage offer easy access and plenty of parking. Set on a spacious 0.34-acre lot, this home is a perfect blend of comfort and functionality, ready to welcome you home. Don't miss the opportunity to make this inviting space your own!

Nestled in the charming Byford Development, this beautifully renovated home exudes warmth and comfort, making it the perfect retreat. With a thoughtful renovation completed in 2020, this residence boasts a blend of traditional and farmhouse styles, featuring a stunning brick and vinyl exterior that invites you in. Step inside to discover a spacious 2,220 sq. ft. layout, where modern amenities meet classic charm. The heart of the home is the gourmet kitchen, complete with upgraded countertops, stainless steel appliances, and a convenient island that encourages gatherings. This home offers four generous bedrooms and 2.5 bathrooms. Enjoy the comfort of hardwood floors throughout the main level, complemented by ceiling fans and window treatments that enhance the cozy atmosphere. The main floor laundry adds convenience to your daily routine, while the unfinished basement provides ample storage or potential for future expansion. Outside, the circular driveway and attached garage offer easy access and plenty of parking. Set on a spacious 0.34-acre lot, this home is a perfect blend of comfort and functionality, ready to welcome you home. Don't miss the opportunity to make this inviting space your own!

515 N Kent St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$495,000

An amazing home located just a few blocks from Washington College! This mostly brick Cape Cod has 4 bedrooms, 3 full baths, formal dining room, living room with fireplace, first floor primary bedroom with cathedral ceiling, Florida room, full basement with fireplace and a 2 car attached garage. The primary bath and Florida room both have radiant floor heating. The 3 bedrooms on the second level are spacious and offer built-ins. There is even a family room with built-ins! The kitchen has all of the major appliances and granite counters. This home has wood floors throughout most of the house. Oil heat, heat pump and central A/C provide for indoor comfort year round. A rear deck provides for outdoor enjoyment. There is a shed for additional storage. This home is situated on a corner and just a short distance to shopping, hospital and downtown Historic Chestertown.

An amazing home located just a few blocks from Washington College! This mostly brick Cape Cod has 4 bedrooms, 3 full baths, formal dining room, living room with fireplace, first floor primary bedroom with cathedral ceiling, Florida room, full basement with fireplace and a 2 car attached garage. The primary bath and Florida room both have radiant floor heating. The 3 bedrooms on the second level are spacious and offer built-ins. There is even a family room with built-ins! The kitchen has all of the major appliances and granite counters. This home has wood floors throughout most of the house. Oil heat, heat pump and central A/C provide for indoor comfort year round. A rear deck provides for outdoor enjoyment. There is a shed for additional storage. This home is situated on a corner and just a short distance to shopping, hospital and downtown Historic Chestertown.

201 Greenwood Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact: