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The one you’ve been waiting for! This extensively updated 3 bedroom, 2 full bath ranch boasts 1,376 square feet of open living space and a roomy 2 car garage. The property sits at the end of a quiet street and lies adjacent to farm land and a pond with a seasonal view. Enjoy serene privacy from your spacious 20 x 16 deck! The home is beautifully remodeled and updated with a new stone driveway and landscaping, HVAC, hot water heater, waterproof LVP flooring, fresh paint, and new lighting and fixtures throughout. The custom kitchen features a large walk in pantry, new stainless steel appliance package, high quality 36” soft close cabinetry, and gorgeous quartz countertops paired with a custom tile backsplash. The Primary bedroom is bright and spacious with a walk-in closet and Primary bath that impresses with a custom tiled walk-in shower. The 2nd and 3rd bedrooms are a generous size and offer easy access to a full bathroom with a tub/shower surround. This home is 10 minutes from Chestertown, 35 minutes from Middletown, DE, 12 minutes from Betterton Beach and offers quick access to numerous boat ramps and all the Chesapeake has to offer. A thoughtfully remodeled home boasting all of these features won’t last long!

11054 Austin Ln, Worton

Listing courtesy of RE/MAX Chesapeake. Contact:

Selling Office: LPT Realty, LLC.

$300,000

Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas range and microwave range hood, creating a bright and inviting space for everyday living and entertaining. The home offers four main-level bedrooms, including a comfortable owner's suite with a private ensuite bathroom. Surrounded by the beauty of Maryland's Eastern Shore, this property is ideal for those who appreciate outdoor living, with countless nearby opportunities for hunting, fishing, crabbing, boating, and exploring nature. Enjoy the charm, history, shops, dining, and waterfront attractions that make Chestertown such a sought-after destination while still embracing the peace and privacy of a rural setting. Mortgage savings may be available for buyers of this listing.

4 Beds ⋅ 2 Baths

Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas range and microwave range hood, creating a bright and inviting space for everyday living and entertaining. The home offers four main-level bedrooms, including a comfortable owner's suite with a private ensuite bathroom. Surrounded by the beauty of Maryland's Eastern Shore, this property is ideal for those who appreciate outdoor living, with countless nearby opportunities for hunting, fishing, crabbing, boating, and exploring nature. Enjoy the charm, history, shops, dining, and waterfront attractions that make Chestertown such a sought-after destination while still embracing the peace and privacy of a rural setting. Mortgage savings may be available for buyers of this listing.

304 Hadaway Dr, Chestertown

Listing courtesy of Redfin Corporation. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$299,000

This beautifully updated home in Rock Hall offers a blend of classic charm and modern improvements. The open living area features refinished original fir wood floors and flows into an updated kitchen with gas range, dishwasher, refrigerator and ample workspace that is ideal for everyday cooking or entertaining. The main level includes a bedroom and full bath, while the second-floor owner’s suite offers a spacious bedroom, full bath, and flexible office or sitting area. This home has been thoughtfully updated over the past 5 years including newer vinyl windows throughout, newer HVAC, brand-new roof, tankless water heater and gutter guards. A separate laundry room with exterior entrance is ideal for gardeners or pets. Large outbuilding with second-floor storage offers great space for hobbies or a workshop. Sitting on over 3/4 of an acre and located less than a mile from the public boat launch and landing, this home is perfect for a weekend getaway, summer retreat or year-round living.

This beautifully updated home in Rock Hall offers a blend of classic charm and modern improvements. The open living area features refinished original fir wood floors and flows into an updated kitchen with gas range, dishwasher, refrigerator and ample workspace that is ideal for everyday cooking or entertaining. The main level includes a bedroom and full bath, while the second-floor owner’s suite offers a spacious bedroom, full bath, and flexible office or sitting area. This home has been thoughtfully updated over the past 5 years including newer vinyl windows throughout, newer HVAC, brand-new roof, tankless water heater and gutter guards. A separate laundry room with exterior entrance is ideal for gardeners or pets. Large outbuilding with second-floor storage offers great space for hobbies or a workshop. Sitting on over 3/4 of an acre and located less than a mile from the public boat launch and landing, this home is perfect for a weekend getaway, summer retreat or year-round living.

5188 Skinners Neck Rd, Rock Hall

Listing courtesy of LPT Realty, LLC. Contact:

This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in excellent condition. The kitchen is equipped with a full set of newer appliances, offering both style and reliability, and the home also includes a newer washer and dryer—giving you the convenience of updated, move-in ready essentials from day one. Major systems have already been taken care of, including a new heating and cooling system (inside and out), a new hot water heater, and a newer roof and shutters. A flexible bonus room on the ground level currently houses the washer and dryer and can easily serve as a home office, TV room, or additional living space—whatever suits your needs. There is also an additional washer and dryer hookup on the upper level if preferred. Step out from the kitchen onto a private balcony, perfect for relaxing or entertaining. Truly move-in ready, this home offers a clean slate to make your own, along with the peace of mind that comes from years of thoughtful maintenance—making it feel like the perfect townhome.

$296,500

2 Beds ⋅ 3 Baths

This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in excellent condition. The kitchen is equipped with a full set of newer appliances, offering both style and reliability, and the home also includes a newer washer and dryer—giving you the convenience of updated, move-in ready essentials from day one. Major systems have already been taken care of, including a new heating and cooling system (inside and out), a new hot water heater, and a newer roof and shutters. A flexible bonus room on the ground level currently houses the washer and dryer and can easily serve as a home office, TV room, or additional living space—whatever suits your needs. There is also an additional washer and dryer hookup on the upper level if preferred. Step out from the kitchen onto a private balcony, perfect for relaxing or entertaining. Truly move-in ready, this home offers a clean slate to make your own, along with the peace of mind that comes from years of thoughtful maintenance—making it feel like the perfect townhome.

108 Oak Leaf Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$295,000

Desirable end-unit, 3-story townhome located in the heart of Chestertown, just moments from downtown and adjacent to the new YMCA. This well-maintained home features newer carpet and paint, a one-year-old stove (purchased new for $4,000), and a hot water heater just two years old. A newer full-size stackable washer and dryer adds convenience. Enjoy both sunrise and sunset views with an east-facing front that fills the home with beautiful morning light and a west-facing rear offering stunning evening sunsets. The balcony has been recently stained, and the first-floor patio has been thoughtfully converted into a deck with built-in wood flower boxes—perfect for outdoor enjoyment. The versatile first level offers flexible space ideal for a bedroom, office, or exercise room, complete with a gas fireplace and sliding door access to the deck. The garage includes a built-in loft, workbench, and shelving for added storage and functionality. Upstairs, the primary suite features a vaulted ceiling and a spacious en-suite bath with soaking tub and walk-in shower. A mature maple tree enhances the backyard setting, providing charm and seasonal beauty. Move-in ready and ideally located—this home offers comfort, updates, and convenience all in one.

Desirable end-unit, 3-story townhome located in the heart of Chestertown, just moments from downtown and adjacent to the new YMCA. This well-maintained home features newer carpet and paint, a one-year-old stove (purchased new for $4,000), and a hot water heater just two years old. A newer full-size stackable washer and dryer adds convenience. Enjoy both sunrise and sunset views with an east-facing front that fills the home with beautiful morning light and a west-facing rear offering stunning evening sunsets. The balcony has been recently stained, and the first-floor patio has been thoughtfully converted into a deck with built-in wood flower boxes—perfect for outdoor enjoyment. The versatile first level offers flexible space ideal for a bedroom, office, or exercise room, complete with a gas fireplace and sliding door access to the deck. The garage includes a built-in loft, workbench, and shelving for added storage and functionality. Upstairs, the primary suite features a vaulted ceiling and a spacious en-suite bath with soaking tub and walk-in shower. A mature maple tree enhances the backyard setting, providing charm and seasonal beauty. Move-in ready and ideally located—this home offers comfort, updates, and convenience all in one.

107 Oak Leaf Dr, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$294,000

Welcome to this beautifully updated 3 bedroom, 1 bathroom home with an oversized two car detached garage that combines modern upgrades with country charm. Step inside to find brand new LVP flooring throughout, fresh paint and abundant natural light. The new kitchen is the heart of the home, featuring quartz countertops, new stainless steel appliances and crisp white shaker cabinetry. The bathroom has been completely remodeled with stylish tilework, modern fixtures and a sleek vanity. Other upgrades include a new roof, new siding, hot water heater and updated lighting - giving you peace of mind for years to come. As well as nice big craftsman style trim for doorways, around windows and as well as baseboard trim. The home also includes a clean, unfinished basement with high ceilings, freshly painted walls, ceiling and floors. Ready for finishing to add even more living space. Enjoy the outdoors with a new deck off the side of the house, perfect for entertaining and take advantage of the oversized 2 car garage, ideal for storage, a workshop or hobbies. Set on a peaceful lot, the property offers beautiful views of wide open farmland right from your front yard, creating a private and relaxing retreat. This home is move in ready and waiting for its next owner to enjoy all the thoughtful upgrades and tranquil setting.

Welcome to this beautifully updated 3 bedroom, 1 bathroom home with an oversized two car detached garage that combines modern upgrades with country charm. Step inside to find brand new LVP flooring throughout, fresh paint and abundant natural light. The new kitchen is the heart of the home, featuring quartz countertops, new stainless steel appliances and crisp white shaker cabinetry. The bathroom has been completely remodeled with stylish tilework, modern fixtures and a sleek vanity. Other upgrades include a new roof, new siding, hot water heater and updated lighting - giving you peace of mind for years to come. As well as nice big craftsman style trim for doorways, around windows and as well as baseboard trim. The home also includes a clean, unfinished basement with high ceilings, freshly painted walls, ceiling and floors. Ready for finishing to add even more living space. Enjoy the outdoors with a new deck off the side of the house, perfect for entertaining and take advantage of the oversized 2 car garage, ideal for storage, a workshop or hobbies. Set on a peaceful lot, the property offers beautiful views of wide open farmland right from your front yard, creating a private and relaxing retreat. This home is move in ready and waiting for its next owner to enjoy all the thoughtful upgrades and tranquil setting.

25135 Smithville Rd, Worton

Listing courtesy of RE/MAX Advantage Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$293,000

Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining. The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is inviting. This home offers three comfortable bedrooms and two full bathrooms, along with modern upgrades including ENERGY STAR windows and an updated washer and dryer. Situated on a generous 0.41-acre lot, the property provides plenty of outdoor space for relaxing, gardening, or entertaining. The surrounding community is known for its welcoming atmosphere, with nearby parks and recreational areas that support an active lifestyle. Conveniently located just a short drive from Downtown Chestertown, you’ll enjoy easy access to local shops, dining, and waterfront charm. Move-in ready and beautifully updated, this home combines comfort, functionality, and location — an excellent opportunity to enjoy Eastern Shore living at its best.

Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining. The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is inviting. This home offers three comfortable bedrooms and two full bathrooms, along with modern upgrades including ENERGY STAR windows and an updated washer and dryer. Situated on a generous 0.41-acre lot, the property provides plenty of outdoor space for relaxing, gardening, or entertaining. The surrounding community is known for its welcoming atmosphere, with nearby parks and recreational areas that support an active lifestyle. Conveniently located just a short drive from Downtown Chestertown, you’ll enjoy easy access to local shops, dining, and waterfront charm. Move-in ready and beautifully updated, this home combines comfort, functionality, and location — an excellent opportunity to enjoy Eastern Shore living at its best.

301 Lincoln Dr, Chestertown

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

Selling Office: Foraker Realty Co..

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.

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:

Selling Office: Cross Street Realtors LLC.

✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡✨

2 Beds ⋅ 3 Baths

✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡✨

522 High St, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: CR Realty.

Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-unit townhome offering space, comfort, and convenience. This three-level home is ideally located near shopping, the YMCA, and local schools, making everyday living easy and accessible. The ground level features a front-entry one-car garage with interior access, leading to a versatile finished space that can be used as a home office, gym, recreation room, or additional living area. This level also offers walk-out access to the rear, adding even more functionality. Upstairs on the main level, you’ll find a spacious living room with beautiful wood flooring, perfect for relaxing or entertaining. A convenient half bath is located nearby for guests. The kitchen offers both functionality and style, featuring upgraded granite countertops, tile flooring, a pantry closet, and an island with an electric stove and downdraft ventilation system. The adjoining dining area provides a comfortable space for meals and gatherings. Just off the kitchen, step out onto a nice rear deck with a pergola that backs to trees—an ideal spot to unwind or enjoy outdoor dining. The third level features two generously sized bedrooms, including a primary suite with an attached bathroom complete with a walk-in shower. A full hall bath serves the additional bedroom, and a hall closet houses a front-load stackable washer and dryer for added convenience. Additional closets provide ample storage space. As an end unit, this home enjoys extra privacy and natural light. Located in an HOA community with very little maintenance required, this home offers easy living in a peaceful and convenient setting.

2 Beds ⋅ 3 Baths

Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-unit townhome offering space, comfort, and convenience. This three-level home is ideally located near shopping, the YMCA, and local schools, making everyday living easy and accessible. The ground level features a front-entry one-car garage with interior access, leading to a versatile finished space that can be used as a home office, gym, recreation room, or additional living area. This level also offers walk-out access to the rear, adding even more functionality. Upstairs on the main level, you’ll find a spacious living room with beautiful wood flooring, perfect for relaxing or entertaining. A convenient half bath is located nearby for guests. The kitchen offers both functionality and style, featuring upgraded granite countertops, tile flooring, a pantry closet, and an island with an electric stove and downdraft ventilation system. The adjoining dining area provides a comfortable space for meals and gatherings. Just off the kitchen, step out onto a nice rear deck with a pergola that backs to trees—an ideal spot to unwind or enjoy outdoor dining. The third level features two generously sized bedrooms, including a primary suite with an attached bathroom complete with a walk-in shower. A full hall bath serves the additional bedroom, and a hall closet houses a front-load stackable washer and dryer for added convenience. Additional closets provide ample storage space. As an end unit, this home enjoys extra privacy and natural light. Located in an HOA community with very little maintenance required, this home offers easy living in a peaceful and convenient setting.

115 Acorn Dr, Chestertown

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

Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms have recently all been refinished. Through the front door is the well-lit family room with a large bay window allowing the beautiful outdoor views. Flow into the large kitchen with plenty of room for your kitchen table and you could even add a small island. Lots of counter space and cabinet space with all appliances included. There is plenty of room inside of the laundry room with the washer & dryer included as well! If you have a pet, there is a small to medium sized pet door that leads into the fenced in back yard. This home is located in between both of Chestertown's grocery stores, just off of Rt. 213, less than 2 miles to Downtown , 20 minutes to Rt. 301. Schedule your appointment to see your New Home!

Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms have recently all been refinished. Through the front door is the well-lit family room with a large bay window allowing the beautiful outdoor views. Flow into the large kitchen with plenty of room for your kitchen table and you could even add a small island. Lots of counter space and cabinet space with all appliances included. There is plenty of room inside of the laundry room with the washer & dryer included as well! If you have a pet, there is a small to medium sized pet door that leads into the fenced in back yard. This home is located in between both of Chestertown's grocery stores, just off of Rt. 213, less than 2 miles to Downtown , 20 minutes to Rt. 301. Schedule your appointment to see your New Home!

107 Malone Ave, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$287,500

**SELLERS HAVE FOUND PROPERTY OF CHOICE; BRING YOUR BEST OFFER!**Welcome to this inviting, move-in-ready rancher tucked away in a tranquil Chestertown setting. Offering three bedrooms and two full baths, the home showcases fresh paint, new flooring, sleek stainless steel appliances, and stunning Beechwood butcher block countertops. Natural light pours in through the Anderson windows, filling the home with warmth. Step outside to a spacious backyard designed for both relaxation and lifestyle—complete with a deck, storage shed, and a chicken coop for those who dream of fresh eggs and a touch of homestead living. All just minutes from the Chester River Yacht Club, marina, and golf course, this property blends modern comfort with timeless country charm.

**SELLERS HAVE FOUND PROPERTY OF CHOICE; BRING YOUR BEST OFFER!**Welcome to this inviting, move-in-ready rancher tucked away in a tranquil Chestertown setting. Offering three bedrooms and two full baths, the home showcases fresh paint, new flooring, sleek stainless steel appliances, and stunning Beechwood butcher block countertops. Natural light pours in through the Anderson windows, filling the home with warmth. Step outside to a spacious backyard designed for both relaxation and lifestyle—complete with a deck, storage shed, and a chicken coop for those who dream of fresh eggs and a touch of homestead living. All just minutes from the Chester River Yacht Club, marina, and golf course, this property blends modern comfort with timeless country charm.

7483 Shortall St, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: ExecuHome Realty.

$285,000

Charming Fully Renovated 3 Bed, 2 Bath Rancher in Rock Hall, Move-In Ready! Welcome to your dream home in Skinners Neck, nestled on the peaceful outskirts of Rock Hall, Maryland; a coastal gem known for its small town charm and waterfront lifestyle. This fully renovated 3-bedroom, 2-bath rancher offers modern comfort, spacious living, and a prime location just minutes from local stores, restaurants, schools/child care, and public boat ramps. Step inside to discover a bright, open floor plan with luxury vinyl plank waterproof flooring throughout. The large living and dining areas flow seamlessly into a stunning remodeled kitchen, complete with quartz countertops, brand-new appliances, ample cabinet storage, and a central island with bar seating; ideal for entertaining or casual meals. The split bedroom layout ensures privacy, with the spacious master suite tucked away on one side of the home. Enjoy the luxury of his and hers closets, a fully renovated en-suite bathroom with a soaking tub, separate walk-in shower, and large vanity. Two additional bedrooms share an updated full bath, perfect for guests or family. Whether you're looking for a forever home, a vacation escape, or a low-maintenance state retreat, this home has everything you need! Property Highlights: - 3 Bedrooms, 2 Full Baths - Fully Renovated Interior - LVP Waterproof Flooring Throughout - Open-Concept Living & Dining Areas - Modern Kitchen with Beautiful Quartz Countertops, Brand New Stainless Steel Appliances & Cabinets - Large Kitchen Island with Bar Seating - Gas Fireplace - Brand New Hot Water Heater - Private Master Suite with Soaking Tub & Walk-in Shower - Brand New Washer and Dryer - Large Front Porch - Spacious Secluded Backyard **Owner is licensed real estate agent**

Charming Fully Renovated 3 Bed, 2 Bath Rancher in Rock Hall, Move-In Ready! Welcome to your dream home in Skinners Neck, nestled on the peaceful outskirts of Rock Hall, Maryland; a coastal gem known for its small town charm and waterfront lifestyle. This fully renovated 3-bedroom, 2-bath rancher offers modern comfort, spacious living, and a prime location just minutes from local stores, restaurants, schools/child care, and public boat ramps. Step inside to discover a bright, open floor plan with luxury vinyl plank waterproof flooring throughout. The large living and dining areas flow seamlessly into a stunning remodeled kitchen, complete with quartz countertops, brand-new appliances, ample cabinet storage, and a central island with bar seating; ideal for entertaining or casual meals. The split bedroom layout ensures privacy, with the spacious master suite tucked away on one side of the home. Enjoy the luxury of his and hers closets, a fully renovated en-suite bathroom with a soaking tub, separate walk-in shower, and large vanity. Two additional bedrooms share an updated full bath, perfect for guests or family. Whether you're looking for a forever home, a vacation escape, or a low-maintenance state retreat, this home has everything you need! Property Highlights: - 3 Bedrooms, 2 Full Baths - Fully Renovated Interior - LVP Waterproof Flooring Throughout - Open-Concept Living & Dining Areas - Modern Kitchen with Beautiful Quartz Countertops, Brand New Stainless Steel Appliances & Cabinets - Large Kitchen Island with Bar Seating - Gas Fireplace - Brand New Hot Water Heater - Private Master Suite with Soaking Tub & Walk-in Shower - Brand New Washer and Dryer - Large Front Porch - Spacious Secluded Backyard **Owner is licensed real estate agent**

5086 Skinners Neck Rd, Rock Hall

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$277,000

This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living area, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new LVP flooring, with the half bath offering enough space to easily add a full-size shower or tub if desired. The kitchen has been updated with stainless steel appliances, making it both stylish and functional. Enjoy relaxing on the inviting front porch, where you'll have a front-row seat to the town's Fourth of July parade. Upstairs, you'll find two cozy bedrooms and a full bathroom with a new vanity and brand-new luxury vinyl plank flooring. The current owners combined two bedrooms to create a spacious primary bedroom, but the layout could easily be converted back to three bedrooms if needed. Underneath the carpet reveals the same wide plank flooring as downstairs. The outdoor space is just as impressive, featuring a large, fully fenced backyard with a 6-foot privacy/security fence and an oversized garage/barn complete with a brand-new barn door—perfect for storage, hobbies, or a workshop.To top it all off, both the home and the garage are in the process of getting brand new roofs! Hurry, this one won't last!

This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living area, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new LVP flooring, with the half bath offering enough space to easily add a full-size shower or tub if desired. The kitchen has been updated with stainless steel appliances, making it both stylish and functional. Enjoy relaxing on the inviting front porch, where you'll have a front-row seat to the town's Fourth of July parade. Upstairs, you'll find two cozy bedrooms and a full bathroom with a new vanity and brand-new luxury vinyl plank flooring. The current owners combined two bedrooms to create a spacious primary bedroom, but the layout could easily be converted back to three bedrooms if needed. Underneath the carpet reveals the same wide plank flooring as downstairs. The outdoor space is just as impressive, featuring a large, fully fenced backyard with a 6-foot privacy/security fence and an oversized garage/barn complete with a brand-new barn door—perfect for storage, hobbies, or a workshop.To top it all off, both the home and the garage are in the process of getting brand new roofs! Hurry, this one won't last!

6022 N Main St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: LPT Realty, LLC.

$275,000

Sellers are offering $5,000 in closing cost help for an acceptable offer! Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite bath, while the main living level features a seamless flow from kitchen to dining and family room—ideal for everyday living and entertaining. Upstairs, the primary bedroom boasts vaulted ceilings and a private balcony, alongside an additional bedroom and full bath. The garage provides ideal storage for water toys, fishing gear, or a golf cart. Whether you’re looking for a full-time residence or an easy weekend escape, this home delivers the best of Rock Hall living.

Sellers are offering $5,000 in closing cost help for an acceptable offer! Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite bath, while the main living level features a seamless flow from kitchen to dining and family room—ideal for everyday living and entertaining. Upstairs, the primary bedroom boasts vaulted ceilings and a private balcony, alongside an additional bedroom and full bath. The garage provides ideal storage for water toys, fishing gear, or a golf cart. Whether you’re looking for a full-time residence or an easy weekend escape, this home delivers the best of Rock Hall living.

21103 Striper Run, Rock Hall

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

Selling Office: Benson & Mangold, LLC.

$275,000

Original Primary School No. 3 | c.1840 | Near Kennedyville Featured in Historic Homes of Kent County Step back in time with this one-of-a-kind historic treasure — the original Primary School No. 3, circa 1840, lovingly preserved and waiting for its next chapter. Listed in Historic Homes of Kent County, this unique property sits on just under two acres, offering timeless charm, unmatched character, and rare opportunity. Set back from the road and tucked along tree-lined boundaries, the home offers exceptional privacy while evoking a deep sense of history. As you walk through the home, original details greet you at every turn — from the beloved deep window sills and antique newel post staircase to the charming fireplaces that anchor the living spaces. These historic elements are truly priceless, offering a chance to bring the past to life with your own personal vision. The property also features multiple outbuildings full of potential. One offers ample workshop space — ideal for restoring and reviving this special home. Another two-level structure could serve as an artisan’s studio, a creative retreat, or simply provide additional storage for tools and equipment. There’s even a shed with a lean-to that could comfortably house a few small animals, creating a homestead feel. Whether you're seeking a historic restoration project, a quiet country retreat, or a unique piece of Maryland's heritage, this property is a rare find — rich in character, wrapped in history, and full of promise.

Original Primary School No. 3 | c.1840 | Near Kennedyville Featured in Historic Homes of Kent County Step back in time with this one-of-a-kind historic treasure — the original Primary School No. 3, circa 1840, lovingly preserved and waiting for its next chapter. Listed in Historic Homes of Kent County, this unique property sits on just under two acres, offering timeless charm, unmatched character, and rare opportunity. Set back from the road and tucked along tree-lined boundaries, the home offers exceptional privacy while evoking a deep sense of history. As you walk through the home, original details greet you at every turn — from the beloved deep window sills and antique newel post staircase to the charming fireplaces that anchor the living spaces. These historic elements are truly priceless, offering a chance to bring the past to life with your own personal vision. The property also features multiple outbuildings full of potential. One offers ample workshop space — ideal for restoring and reviving this special home. Another two-level structure could serve as an artisan’s studio, a creative retreat, or simply provide additional storage for tools and equipment. There’s even a shed with a lean-to that could comfortably house a few small animals, creating a homestead feel. Whether you're seeking a historic restoration project, a quiet country retreat, or a unique piece of Maryland's heritage, this property is a rare find — rich in character, wrapped in history, and full of promise.

27741 Lambs Meadow Rd, Kennedyville

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Looking for a 3 bed farmhouse in Millington with classic charm and modern updates? This warm and friendly 1920 single family home offers 1508 square feet on a 0.17 acre lot with a 2021 roof, vinyl siding, three second floor bedrooms, one full bath, and a half bath off the kitchen. A wrapped front and side porch sets the tone, while a rear wooden deck opens to the yard for easy outdoor living. The heated rear garage includes driveway parking and a setup that allows welder hookup, ideal for hobby work or small trades. Inside, the layout provides a cozy front living space, practical kitchen flow, and natural light throughout. Located in Millington with quick access to Route 301.

$274,000

Looking for a 3 bed farmhouse in Millington with classic charm and modern updates? This warm and friendly 1920 single family home offers 1508 square feet on a 0.17 acre lot with a 2021 roof, vinyl siding, three second floor bedrooms, one full bath, and a half bath off the kitchen. A wrapped front and side porch sets the tone, while a rear wooden deck opens to the yard for easy outdoor living. The heated rear garage includes driveway parking and a setup that allows welder hookup, ideal for hobby work or small trades. Inside, the layout provides a cozy front living space, practical kitchen flow, and natural light throughout. Located in Millington with quick access to Route 301.

356 Cypress St, Millington

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

Selling Office: RE/MAX Chesapeake.

$270,000

Turn-key, one-level living in the heart of charming downtown Millington! Welcome to 423 Cypress Street, a beautifully maintained and thoughtfully updated home that is truly move-in ready!! Take advantage of the seller’s option to convey the home fully furnished as they relocate out of state. This stress-free property has been lovingly cared for, and it shows in every detail. Major updates include new windows (2020), a brand-new fenced yard, a new deck perfect for outdoor enjoyment, and bathroom updates featuring a Bath Fitter system with a lifetime warranty. Additional improvements include new gutters with LeafFilter protection and a new washer and dryer, offering peace of mind and low-maintenance living for years to come. Enjoy the ease of single-level living in a revitalized small-town community while still being conveniently located near Route 301 for quick commuting access. Millington’s local shops, dining, parks, and nearby waterways make this an ideal home base for those seeking both charm and convenience. Pride of ownership shines throughout, making this home an excellent opportunity for first-time buyers, downsizers, or anyone looking for a well-cared-for property in a welcoming Eastern Shore community.

Turn-key, one-level living in the heart of charming downtown Millington! Welcome to 423 Cypress Street, a beautifully maintained and thoughtfully updated home that is truly move-in ready!! Take advantage of the seller’s option to convey the home fully furnished as they relocate out of state. This stress-free property has been lovingly cared for, and it shows in every detail. Major updates include new windows (2020), a brand-new fenced yard, a new deck perfect for outdoor enjoyment, and bathroom updates featuring a Bath Fitter system with a lifetime warranty. Additional improvements include new gutters with LeafFilter protection and a new washer and dryer, offering peace of mind and low-maintenance living for years to come. Enjoy the ease of single-level living in a revitalized small-town community while still being conveniently located near Route 301 for quick commuting access. Millington’s local shops, dining, parks, and nearby waterways make this an ideal home base for those seeking both charm and convenience. Pride of ownership shines throughout, making this home an excellent opportunity for first-time buyers, downsizers, or anyone looking for a well-cared-for property in a welcoming Eastern Shore community.

423 Cypress St, Millington

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$270,000

One level rancher with new HVAC, new 200 amp electric panel. The water conditioner is owned, and the water heater is about 2 years old. There is a wall mounted propane heater, but with the new HVAC this can be removed if desired. The current owner says the wall unit heated the entire home for him. The home has beautiful farmland views, mature trees, and has a lovely cottage feel. Last sold in 2001, this property has been updated with an enclosed porch, a trex deck, and a patio area. Just enough room for efficient and tidy living. Very well maintained! Easy to show - location is about 8 to10 minutes outside of Chestertown. The one car garage has a workshop area, and for the summer months there is a ceiling mounted exhaust fan which makes for comfortable workspace.

One level rancher with new HVAC, new 200 amp electric panel. The water conditioner is owned, and the water heater is about 2 years old. There is a wall mounted propane heater, but with the new HVAC this can be removed if desired. The current owner says the wall unit heated the entire home for him. The home has beautiful farmland views, mature trees, and has a lovely cottage feel. Last sold in 2001, this property has been updated with an enclosed porch, a trex deck, and a patio area. Just enough room for efficient and tidy living. Very well maintained! Easy to show - location is about 8 to10 minutes outside of Chestertown. The one car garage has a workshop area, and for the summer months there is a ceiling mounted exhaust fan which makes for comfortable workspace.

24339 Chestertown Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$269,000

Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. *SELLER ASSISTANCE AVAILABLE TOWARDS CLOSING COSTS* This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements throughout. Inside, you’ll find beautiful LVP flooring, a bright open-concept layout, and a stunning kitchen featuring granite countertops, a tile backsplash, stainless steel appliances, and plenty of space to gather after a day on the water, experiencing Chestertown and all the other towns nearby! Owner had a pre home inspection for your convenance! The home is good to go! For peace of mind, all major systems are new, including a brand-new roof, and a home inspection has already been completed with items addressed, making this home truly move-in ready. The layout offers comfort and privacy with the primary suite tucked away on one side of the home, while the three additional bedrooms are located on the opposite side, perfect for maybe or a home office setup. The home is connected to public water and sewer, and also offers fiber internet, giving you modern convenience in a laid-back coastal setting. Step outside and enjoy the freedom that comes with no restrictions—bring your boat, RV, or water toys, and if you’ve been dreaming of building a pole barn or workshop, you can do that here too. Located just minutes from creeks, rivers, and the Chesapeake Bay, this home places you right in the heart of one of the Eastern Shore’s most beloved boating towns. Rock Hall may only have one traffic light, but it’s full of life—with marinas, waterfront restaurants, coffee shops, boutiques, ice cream stops, and a quaint downtown. The town hosts events throughout the year, creating that true small-town vibe where everyone knows your name—or soon will. If you’ve been searching for a fun, beachy lifestyle with small-town charm, modern updates, and room for your boats and hobbies, this home delivers. Rock Hall — where nice people live. *some photos have been enhanced with virtual staging*

4 Beds ⋅ 2 Baths

Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. *SELLER ASSISTANCE AVAILABLE TOWARDS CLOSING COSTS* This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements throughout. Inside, you’ll find beautiful LVP flooring, a bright open-concept layout, and a stunning kitchen featuring granite countertops, a tile backsplash, stainless steel appliances, and plenty of space to gather after a day on the water, experiencing Chestertown and all the other towns nearby! Owner had a pre home inspection for your convenance! The home is good to go! For peace of mind, all major systems are new, including a brand-new roof, and a home inspection has already been completed with items addressed, making this home truly move-in ready. The layout offers comfort and privacy with the primary suite tucked away on one side of the home, while the three additional bedrooms are located on the opposite side, perfect for maybe or a home office setup. The home is connected to public water and sewer, and also offers fiber internet, giving you modern convenience in a laid-back coastal setting. Step outside and enjoy the freedom that comes with no restrictions—bring your boat, RV, or water toys, and if you’ve been dreaming of building a pole barn or workshop, you can do that here too. Located just minutes from creeks, rivers, and the Chesapeake Bay, this home places you right in the heart of one of the Eastern Shore’s most beloved boating towns. Rock Hall may only have one traffic light, but it’s full of life—with marinas, waterfront restaurants, coffee shops, boutiques, ice cream stops, and a quaint downtown. The town hosts events throughout the year, creating that true small-town vibe where everyone knows your name—or soon will. If you’ve been searching for a fun, beachy lifestyle with small-town charm, modern updates, and room for your boats and hobbies, this home delivers. Rock Hall — where nice people live. *some photos have been enhanced with virtual staging*

6374 Rock Hall Rd, Rock Hall

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

Selling Office: Crown Homes Real Estate.

$264,900

Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless-steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Ask about Special Financing Offers and how to get $6,300 or more in closing help from the builders' preferred lender!

Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless-steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Ask about Special Financing Offers and how to get $6,300 or more in closing help from the builders' preferred lender!

109 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Real Broker, LLC.

$264,900

Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

101 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$264,900

Minutes from the heart of Chestertown and a short drive to Rock Hall, this 2-bedroom, 1-bath home offers the perfect balance of small-town convenience and peaceful countryside living. Inside, you’ll find warm hardwood floors and an unfinished basement—ideal for storage, a home gym, or even your future office space. Outside, the large, level yard provides plenty of room to garden, play, or simply relax while enjoying the rural backdrop. With two driveways for easy access and ample parking, this property combines functionality with potential. Ready for your finishing touches, it’s a great opportunity to create your own Eastern Shore retreat.

2 Beds ⋅ 1 Baths

Minutes from the heart of Chestertown and a short drive to Rock Hall, this 2-bedroom, 1-bath home offers the perfect balance of small-town convenience and peaceful countryside living. Inside, you’ll find warm hardwood floors and an unfinished basement—ideal for storage, a home gym, or even your future office space. Outside, the large, level yard provides plenty of room to garden, play, or simply relax while enjoying the rural backdrop. With two driveways for easy access and ample parking, this property combines functionality with potential. Ready for your finishing touches, it’s a great opportunity to create your own Eastern Shore retreat.

24415 Chestertown Rd, Chestertown

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

Selling Office: Remax Vision.

$262,000

Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 1 additional bedroom adds options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front foot fee of $5,000 that can be paid off with installments, annually over 5-10 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 1 additional bedroom adds options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front foot fee of $5,000 that can be paid off with installments, annually over 5-10 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

10971 Bottom Rd, Worton

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: RE/MAX Chesapeake.

$260,000

Professional Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that is - below market value! Only 3 years young and in excellent condition, this home offers the benefits of newer construction. Conveniently located with an easy commute to Route 301 and just around the corner from the newer YMCA. Enjoy all that Chestertown has to offer, from its charming small-town atmosphere and wonderful restaurants to artistic venues, community events, and Washington College. A must-see for buyers looking for a newer home, excellent condition, and exceptional value in a great location!

Professional Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that is - below market value! Only 3 years young and in excellent condition, this home offers the benefits of newer construction. Conveniently located with an easy commute to Route 301 and just around the corner from the newer YMCA. Enjoy all that Chestertown has to offer, from its charming small-town atmosphere and wonderful restaurants to artistic venues, community events, and Washington College. A must-see for buyers looking for a newer home, excellent condition, and exceptional value in a great location!

249 Island Lark Way, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$259,900

Welcome to 25003 Heather Ln! This well maintained 3 bedroom, 2 full bath home offers the ease of first floor living in a quiet neighborhood. Inside, you'll find an open concept layout with high ceilings that create a bright, spacious feel, along with modern finishes throughout. Outside, the huge yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Move in ready and conveniently located, this home is one you won't want to miss. Schedule your showing today!

Welcome to 25003 Heather Ln! This well maintained 3 bedroom, 2 full bath home offers the ease of first floor living in a quiet neighborhood. Inside, you'll find an open concept layout with high ceilings that create a bright, spacious feel, along with modern finishes throughout. Outside, the huge yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Move in ready and conveniently located, this home is one you won't want to miss. Schedule your showing today!

25003 Heather Ln, Worton

Listing courtesy of Crown Homes Real Estate. Contact:

Selling Office: The Land Group.

$259,900

Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Up to $7,500 in closing help available on select models when using builders partner lender and title company.

Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Up to $7,500 in closing help available on select models when using builders partner lender and title company.

107 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$258,000

Lovely 4 Bedroom home with 1 and 1/2 baths located just outside of town. This home has 2 separate entrances at the front of the house. One can be entered and separated from the whole house living space. Great for an office with 1/2 bath or used as another bedroom if you need 4. Kitchen leads to separate laundry and mud room and exits to the back yard with a view of acres of open space fields.

4 Beds ⋅ 2 Baths

Lovely 4 Bedroom home with 1 and 1/2 baths located just outside of town. This home has 2 separate entrances at the front of the house. One can be entered and separated from the whole house living space. Great for an office with 1/2 bath or used as another bedroom if you need 4. Kitchen leads to separate laundry and mud room and exits to the back yard with a view of acres of open space fields.

6445 Edesville Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

$255,000

Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

318 Lincoln, Chestertown

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

Selling Office: Samson Properties of DE, LLC.

$250,000

This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking the side and backyard, complete with a new shed—perfect for relaxing or entertaining. The second floor is carpeted and includes a generously sized primary bedroom. and two additional bedrooms. A full bathroom on the second floor offers convenient access from the primary bedroom. Ideally located near Washington College, this home places you moments from Historic Chestertown and the Chester River. Indulge in exceptional dining, charming cafés, shopping, art galleries, the Memorial Weekend Tea Party and more.