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$289,900

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

2 Beds ⋅ 2 Baths

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

21146 Montana Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$325,000

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably — spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.

4 Beds ⋅ 2 Baths

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably — spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.

200 Manor Ave, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$1,450,000

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

4 Beds ⋅ 5 Baths

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$320,000

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

3 Beds ⋅ 2 Baths

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

8706 Elm Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$385,000

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

4 Beds ⋅ 3 Baths

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact: