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Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after location. Just a short stroll to Downtown Chestertown, Washington College, and the Chester River, this home offers both convenience and long-term potential.

217 Philosophers Ter, Chestertown

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

Selling Office: Cross Street Realtors LLC.

Well situated 70s Ranch. Original kitchen and baths. Hardwood floors. 3 beds, 2 baths.

Well situated 70s Ranch. Original kitchen and baths. Hardwood floors. 3 beds, 2 baths.

521 N Kent St, Chestertown

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

Selling Office: TTR Sotheby's International Realty.

Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash, stainless appliances, and an ample pantry for storage. Six-over-six oversized windows throughout the home, extra tall doors, a transom window over the front door, and a ten-foot door to the screen porch allows light to pour inside. A full and separate laundry room remove that chore from the living space and offer a dedicated work room with storage. The Primary Suite includes a generous walk-in closet and en suite bath. Since 2021, upgrades and improvements include: screened porch, Leafguard on all gutters, shed to coordinate with the home’s aesthetics, asphalt driveway, thoughtful landscaping, water treatment system, and is wired for IQ Fiber (formerly ThinkBig) for internet. This home is absolutely, without question, turnkey and ready for its new stewards!

Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash, stainless appliances, and an ample pantry for storage. Six-over-six oversized windows throughout the home, extra tall doors, a transom window over the front door, and a ten-foot door to the screen porch allows light to pour inside. A full and separate laundry room remove that chore from the living space and offer a dedicated work room with storage. The Primary Suite includes a generous walk-in closet and en suite bath. Since 2021, upgrades and improvements include: screened porch, Leafguard on all gutters, shed to coordinate with the home’s aesthetics, asphalt driveway, thoughtful landscaping, water treatment system, and is wired for IQ Fiber (formerly ThinkBig) for internet. This home is absolutely, without question, turnkey and ready for its new stewards!

23264 Clarissa Rd, Chestertown

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

Selling Office: Rosendale Realty.

Meticulously maintained and full of charm, this delightful three-bedroom, two-bath rambler is perfectly situated on an oversized double lot, offering both comfort and exceptional outdoor space. From the moment you arrive, you’ll appreciate the care and attention this home has received, making it truly move-in ready. Step inside to a bright and inviting open floor plan designed for easy living and entertaining. The spacious living room features a soaring cathedral ceiling and a ceiling fan, creating an airy and welcoming atmosphere. This space flows seamlessly into the kitchen and dining area, allowing for effortless gatherings with family and friends. The dining area is enhanced by a beautiful custom chair rail molding detail that adds character and elegance, while sliding glass doors provide abundant natural light and direct access to the backyard, perfect for indoor-outdoor living. The kitchen is both functional and stylish, offering warm wood cabinetry, recessed lighting, and a vaulted ceiling that adds to the home’s open and spacious feel. The bedroom area includes a comfortable primary suite complete with a private ensuite bath, along with two additional bedrooms, each featuring ceiling fans for year-round comfort. A well-appointed hall bath conveniently serves the two additional bedrooms, providing both functionality and privacy for family members or guests. Step outside and discover an incredible backyard retreat that truly sets this property apart. Fully enclosed with a privacy fence, the expansive yard offers plenty of room to relax, play, or entertain. Enjoy evenings on the patio, stroll along the walking paths, or unwind under the beautiful gazebo. A cozy fire pit creates the perfect gathering spot for cooler nights. One of the standout features of this property is the impressive three-bay workshop with electric, ideal for hobbyists, craftsmen, or anyone in need of substantial workspace and storage. With its thoughtful updates, inviting layout, and exceptional outdoor amenities, this home offers a rare opportunity to enjoy both comfort and versatility in a peaceful setting.

Meticulously maintained and full of charm, this delightful three-bedroom, two-bath rambler is perfectly situated on an oversized double lot, offering both comfort and exceptional outdoor space. From the moment you arrive, you’ll appreciate the care and attention this home has received, making it truly move-in ready. Step inside to a bright and inviting open floor plan designed for easy living and entertaining. The spacious living room features a soaring cathedral ceiling and a ceiling fan, creating an airy and welcoming atmosphere. This space flows seamlessly into the kitchen and dining area, allowing for effortless gatherings with family and friends. The dining area is enhanced by a beautiful custom chair rail molding detail that adds character and elegance, while sliding glass doors provide abundant natural light and direct access to the backyard, perfect for indoor-outdoor living. The kitchen is both functional and stylish, offering warm wood cabinetry, recessed lighting, and a vaulted ceiling that adds to the home’s open and spacious feel. The bedroom area includes a comfortable primary suite complete with a private ensuite bath, along with two additional bedrooms, each featuring ceiling fans for year-round comfort. A well-appointed hall bath conveniently serves the two additional bedrooms, providing both functionality and privacy for family members or guests. Step outside and discover an incredible backyard retreat that truly sets this property apart. Fully enclosed with a privacy fence, the expansive yard offers plenty of room to relax, play, or entertain. Enjoy evenings on the patio, stroll along the walking paths, or unwind under the beautiful gazebo. A cozy fire pit creates the perfect gathering spot for cooler nights. One of the standout features of this property is the impressive three-bay workshop with electric, ideal for hobbyists, craftsmen, or anyone in need of substantial workspace and storage. With its thoughtful updates, inviting layout, and exceptional outdoor amenities, this home offers a rare opportunity to enjoy both comfort and versatility in a peaceful setting.

2032 Pondtown Rd, Chestertown

Listing courtesy of Northrop Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

Price Improvement! This pristine rancher is barely three and a half years old and still looks brand new! Exceptionally well maintained and move-in ready! The home sits on nearly one-half acre (.457) and is one of the largest lots in the neighborhood. The lot is shaped in such a manner this it's like getting two for the price of one! There is plenty of space for play and entertaining immediately behind the house, while another equally large section of land branches off and runs behind the neighboring homes. The second section of the property can also be accessed from Cee-Jay Rd. The owner has spoken with the county and understands that a 30x40 detached garage can be built on the property. The widened driveway will easily accomodate your cars, boats, campers, and trailers. Moving inside, the kitchen features granite counter tops and stainless steel appliances. Gorgeous luxury vinyl plank flooring runs throughout the kitchen, laundry room, family room, hallway, and the two full bathrooms. All four bedrooms are carpeted. The home features an efficient heat pump system, a conditioned crawl space, and a tankless hot water heater for those long showers. The roof is protected with long-life Architectural Shingles. A new 12x16 storage shed (2025) with loft storage is included.

4 Beds ⋅ 2 Baths

Price Improvement! This pristine rancher is barely three and a half years old and still looks brand new! Exceptionally well maintained and move-in ready! The home sits on nearly one-half acre (.457) and is one of the largest lots in the neighborhood. The lot is shaped in such a manner this it's like getting two for the price of one! There is plenty of space for play and entertaining immediately behind the house, while another equally large section of land branches off and runs behind the neighboring homes. The second section of the property can also be accessed from Cee-Jay Rd. The owner has spoken with the county and understands that a 30x40 detached garage can be built on the property. The widened driveway will easily accomodate your cars, boats, campers, and trailers. Moving inside, the kitchen features granite counter tops and stainless steel appliances. Gorgeous luxury vinyl plank flooring runs throughout the kitchen, laundry room, family room, hallway, and the two full bathrooms. All four bedrooms are carpeted. The home features an efficient heat pump system, a conditioned crawl space, and a tankless hot water heater for those long showers. The roof is protected with long-life Architectural Shingles. A new 12x16 storage shed (2025) with loft storage is included.

148 Step Rd, Chestertown

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023 - this Smart Home is tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.

$364,900

4 Beds ⋅ 3 Baths

New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023 - this Smart Home is tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.

108 Flying Cloud Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Coldwell Banker Realty.

$364,000

Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm, walkability, and timeless appeal. This traditional 3-bedroom, 2-full-bath home features an open and inviting living room filled with natural light. All windows have been updated and replaced, the crawl space has been professionally repaired, encapsulated, and equipped with a dehumidifier for added efficiency and comfort. The roof and heating/cooling system are both on the newer side, offering added peace of mind for years to come. The home has earned a Certificate of Completion from the Delmarva Power Home Performance with Energy Star Program, ensuring enhanced energy efficiency throughout. Enjoy relaxing in the bright sunroom or spending quiet moments in the fenced backyard—perfect for outdoor living and entertaining. A backyard shed provides convenient storage for tools, bikes, and more. Truly move-in ready, this home is waiting for you to make it your own!

Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm, walkability, and timeless appeal. This traditional 3-bedroom, 2-full-bath home features an open and inviting living room filled with natural light. All windows have been updated and replaced, the crawl space has been professionally repaired, encapsulated, and equipped with a dehumidifier for added efficiency and comfort. The roof and heating/cooling system are both on the newer side, offering added peace of mind for years to come. The home has earned a Certificate of Completion from the Delmarva Power Home Performance with Energy Star Program, ensuring enhanced energy efficiency throughout. Enjoy relaxing in the bright sunroom or spending quiet moments in the fenced backyard—perfect for outdoor living and entertaining. A backyard shed provides convenient storage for tools, bikes, and more. Truly move-in ready, this home is waiting for you to make it your own!

303 E Campus Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$361,500

Highly sought after downtown Historic Chestertown. This 3 unit property is ready to rent. Recently updated and renovated throughout the years, pride of ownership is apparent. The main level has a Studio with new kitchen, full bath and large living area. There is a door to the new deck and quiet back yard. Heating is a gas unit and cooling would be a window unit- super efficient space. The main level also has a 1 bedroom unit. It too has a door to the deck and back yard. The upper level has a 2 bedroom unit. The wood floors have been refinished and other flooring has been updated. Each unit has a seperate leased propane tank. The front porch was re-decked 3 years ago. Live in one and rent the others- great way to get to live in this spectacular historic town!! Too many updates to list. Book a tour today

517 High St, Chestertown

Listing courtesy of L. C. Parker Real Estate. Contact:

Selling Office: Select Land & Homes, LLC.

$360,000

Practically brand new and just 2 years young with access to the Chester River, this beautifully maintained home is perfectly situated in a desirable water-oriented community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting. Enjoy easy access to the Chester River—you can drive your boat to the community ramp at the end of the street, or even take a nice short walk down to the water, to spend your days crabbing, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, this 3-bedroom, 2 full bath home features durable and stylish LVP flooring throughout and a thoughtfully designed split floor plan. The spacious primary suite is privately situated on one side of the home and offers a walk-in shower, dual vanity, and a beautifully appointed bath. On the opposite side, you’ll find two additional bedrooms and a full bath with a tub/shower combo—ideal for guests or flexible living. The kitchen and living room are centrally located, creating an inviting and functional space for everyday living and entertaining. A standout bonus—an unfinished upstairs area of 544 additional SF, already in place and ready for your vision! Use it for storage now or finish it off for additional bedrooms, a home office, or recreation space. Step outside and enjoy both a charming front porch—perfect for morning coffee—and a massive back deck ideal for entertaining, grilling, or simply relaxing while taking in the peaceful surroundings. The generously sized yard with mature trees offers both privacy and room to enjoy the outdoors. Even more exciting—the county has indicated plans to pave the road in the near future. Added perk: fiber optic Talkie Internet is already available at the property, making working from home or streaming a breeze. Move-in ready, full of potential, and located in a charming waterfront community—this one checks all the boxes!

Practically brand new and just 2 years young with access to the Chester River, this beautifully maintained home is perfectly situated in a desirable water-oriented community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting. Enjoy easy access to the Chester River—you can drive your boat to the community ramp at the end of the street, or even take a nice short walk down to the water, to spend your days crabbing, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, this 3-bedroom, 2 full bath home features durable and stylish LVP flooring throughout and a thoughtfully designed split floor plan. The spacious primary suite is privately situated on one side of the home and offers a walk-in shower, dual vanity, and a beautifully appointed bath. On the opposite side, you’ll find two additional bedrooms and a full bath with a tub/shower combo—ideal for guests or flexible living. The kitchen and living room are centrally located, creating an inviting and functional space for everyday living and entertaining. A standout bonus—an unfinished upstairs area of 544 additional SF, already in place and ready for your vision! Use it for storage now or finish it off for additional bedrooms, a home office, or recreation space. Step outside and enjoy both a charming front porch—perfect for morning coffee—and a massive back deck ideal for entertaining, grilling, or simply relaxing while taking in the peaceful surroundings. The generously sized yard with mature trees offers both privacy and room to enjoy the outdoors. Even more exciting—the county has indicated plans to pave the road in the near future. Added perk: fiber optic Talkie Internet is already available at the property, making working from home or streaming a breeze. Move-in ready, full of potential, and located in a charming waterfront community—this one checks all the boxes!

240 Merganser Dr, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$360,000

Welcome to Pine Cove. A small peaceful enclave of homes that sits oh so close to the Chester River and the Deep Landing Boat Launch. Surrounded by working farms and pastoral views this beautifully maintained home is just 9 years young. Boasting an open concept layout with soaring cathedral ceilings in the main living areas, a gourmet kitchen with granite counters, stainless-steel appliances, and hardwood floors throughout, you will fall in love with this idyllic rural retreat. One level living is the key to comfort and ease. Two bedrooms and a full bath on one side of the house and a gorgeous Owners suite on the other side with a generous walk-in closet and Spa like bath with stand-up shower and a soaking tub. A double vanity ensures room for all your needs. Laundry and mechanicals are just off the hallway by the owner's suite and garage access is just off the main foyer. Storage shelving in the double size garage will stay with the home and there is an additional storage shed in the back yard. The back yard is fully fenced with a pretty vinyl fence just the right size for small pets. You will also find garden beds and bird feeder poles. The rear of the house boasts a custom deck for your entertaining pleasure. Many perennials and lovely landscaping bring the front and back yards to life and attracts birds and pollinators alike. It's a short walk down to the local Boat ramp and the river for your summer activities. Come and see how this beautiful turnkey home can be yours!

Welcome to Pine Cove. A small peaceful enclave of homes that sits oh so close to the Chester River and the Deep Landing Boat Launch. Surrounded by working farms and pastoral views this beautifully maintained home is just 9 years young. Boasting an open concept layout with soaring cathedral ceilings in the main living areas, a gourmet kitchen with granite counters, stainless-steel appliances, and hardwood floors throughout, you will fall in love with this idyllic rural retreat. One level living is the key to comfort and ease. Two bedrooms and a full bath on one side of the house and a gorgeous Owners suite on the other side with a generous walk-in closet and Spa like bath with stand-up shower and a soaking tub. A double vanity ensures room for all your needs. Laundry and mechanicals are just off the hallway by the owner's suite and garage access is just off the main foyer. Storage shelving in the double size garage will stay with the home and there is an additional storage shed in the back yard. The back yard is fully fenced with a pretty vinyl fence just the right size for small pets. You will also find garden beds and bird feeder poles. The rear of the house boasts a custom deck for your entertaining pleasure. Many perennials and lovely landscaping bring the front and back yards to life and attracts birds and pollinators alike. It's a short walk down to the local Boat ramp and the river for your summer activities. Come and see how this beautiful turnkey home can be yours!

720 Deep Landing Rd, Chestertown

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Charming American Foursquare on a half-acre corner lot, just one block from the Chester River on the Queen Anne's County side of Historic Chestertown. The home features a welcoming front porch, 3 bedrooms, 2 full baths, an office on the main level, hardwood floors, and many original details. Recent updates include a new upstairs bathroom, new electric panel, and a 2-year-old roof. The walk-up attic and large shed/garage provide ample storage. Walk over the bridge to downtown and the Farmer's Market. Would make a great primary or second home.

$359,900

Charming American Foursquare on a half-acre corner lot, just one block from the Chester River on the Queen Anne's County side of Historic Chestertown. The home features a welcoming front porch, 3 bedrooms, 2 full baths, an office on the main level, hardwood floors, and many original details. Recent updates include a new upstairs bathroom, new electric panel, and a 2-year-old roof. The walk-up attic and large shed/garage provide ample storage. Walk over the bridge to downtown and the Farmer's Market. Would make a great primary or second home.

221 Old Bridge Rd, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$359,000

Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR $314,000 with .39 acres after recordation this acreage will be subdivided MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS

4 Beds ⋅ 2 Baths

Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR $314,000 with .39 acres after recordation this acreage will be subdivided MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS

8833 Georgetown Rd, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$355,000

A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. **See updated zoning info and description from town office in Documents. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here.

349 & 351 High St, Chestertown

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

Selling Office: Taylor Properties.

$354,900

This property features a 3-bedroom, 1-full-bathroom home with a detached 3-car garage and sits on 2.08 acres. The primary bedroom opens out to a new covered deck. The seller has completed several updates including a new roof, encapsulated crawlspace, updated back deck, regraded and add new stone to the driveway, and installed a new HVAC system. The property also features a 50-amp camper hookup. This property is zoned village center zoned. Conveniently located, it is in close proximity to Chestertown and Route 301, with easy access to Middletown and Annapolis.

3 Beds ⋅ 1 Baths

This property features a 3-bedroom, 1-full-bathroom home with a detached 3-car garage and sits on 2.08 acres. The primary bedroom opens out to a new covered deck. The seller has completed several updates including a new roof, encapsulated crawlspace, updated back deck, regraded and add new stone to the driveway, and installed a new HVAC system. The property also features a 50-amp camper hookup. This property is zoned village center zoned. Conveniently located, it is in close proximity to Chestertown and Route 301, with easy access to Middletown and Annapolis.

2010 Mcginnes Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

Selling Office: RE/MAX Components.

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

4 Beds ⋅ 2 Baths

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

213 Byford Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Cross Street Realtors LLC.

Selling Office: Unrepresented Buyer Office.

1 Beds ⋅ 1 Baths

25195 Lovers Ln, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage or expansion. Additional features include an attached garage and a screened porch perfect for enjoying the outdoors. Tolchester Estates offers the relaxed Eastern Shore lifestyle buyers love—quiet streets and access to the Bay.

Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage or expansion. Additional features include an attached garage and a screened porch perfect for enjoying the outdoors. Tolchester Estates offers the relaxed Eastern Shore lifestyle buyers love—quiet streets and access to the Bay.

21111 Texas Ave, Chestertown

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

Selling Office: Douglas Realty LLC.

Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment.

Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment.

10751 Millbrook Dr, Chestertown

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

This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car garage/workshop, you’ll have plenty of room for vehicles, projects, or storage. Step inside to a spacious living room that flows seamlessly into the kitchen, complete with gorgeous granite countertops and newer stainless-steel appliances. The cozy primary bedroom is complete with a wood-burning fireplace ideal for relaxing evenings. Enjoy your morning coffee on the welcoming front porch just across the street from views of the Chester River, or host gatherings in the fenced-in backyard with space for play and gardening. You also have peace of mind with a newer HVAC system (2023) and solar panels for a more energy efficient home! Located towards the end of this peaceful street, you’re close to Chestertown’s historic charm, Washington College, a nearby boat ramp, and tax-free shopping just across the Delaware line and still located in Queen Anne's County!

$349,500

This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car garage/workshop, you’ll have plenty of room for vehicles, projects, or storage. Step inside to a spacious living room that flows seamlessly into the kitchen, complete with gorgeous granite countertops and newer stainless-steel appliances. The cozy primary bedroom is complete with a wood-burning fireplace ideal for relaxing evenings. Enjoy your morning coffee on the welcoming front porch just across the street from views of the Chester River, or host gatherings in the fenced-in backyard with space for play and gardening. You also have peace of mind with a newer HVAC system (2023) and solar panels for a more energy efficient home! Located towards the end of this peaceful street, you’re close to Chestertown’s historic charm, Washington College, a nearby boat ramp, and tax-free shopping just across the Delaware line and still located in Queen Anne's County!

126 Char Nor Manor Blvd, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: RE/MAX Executive.

$349,000

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

$340,000

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

204 Rolling Rd, Chestertown

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

Selling Office: Select Land & Homes, LLC.

$339,900

3 Beds ⋅ 3 Baths

103 Flying Cloud Dr, Chestertown

Listing courtesy of American Premier Realty, LLC. Contact:

Selling Office: American Premier Realty, LLC.

$339,900

Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases lovely water views, making it the perfect place to unwind or entertain. Step outside to enjoy the fresh bay breeze from the deck, and take advantage of the storage shed for extra space. The property also includes an enclosed fenced area, ideal for storing tools, trash cans, or outdoor equipment while keeping everything neatly tucked away. Whether you’re looking for a tranquil retreat or a charming year-round residence, The Cottage offers a welcoming atmosphere and scenic surroundings you’ll love coming home to.

2 Beds ⋅ 1 Baths

Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases lovely water views, making it the perfect place to unwind or entertain. Step outside to enjoy the fresh bay breeze from the deck, and take advantage of the storage shed for extra space. The property also includes an enclosed fenced area, ideal for storing tools, trash cans, or outdoor equipment while keeping everything neatly tucked away. Whether you’re looking for a tranquil retreat or a charming year-round residence, The Cottage offers a welcoming atmosphere and scenic surroundings you’ll love coming home to.

21125 Iowa Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Douglas Realty LLC.

$335,320

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown . Surrounded by mature trees and bordered by a serene cornfield, this property provides a peaceful retreat from the hustle and bustle of everyday life. The home has been thoughtfully designed to accommodate comfortable everyday living as well as entertaining guests. The spacious rear deck is an ideal spot for hosting gatherings, enjoying morning coffee, or simply relaxing while taking in the natural beauty of the surroundings. Step inside to discover a modernized kitchen equipped with updated appliances and ample counter space, making meal preparation a pleasure. The bathrooms have been tastefully updated to combine style and functionality, while new windows throughout the home allow for plenty of natural light and energy efficiency. Freshly painted interiors and new doors add to the home’s inviting atmosphere, and the newer washer and dryer provide added convenience. Significant system upgrades enhance the home’s comfort and reliability, including a newer HVAC system that ensures efficient heating and cooling year-round. The upgraded BATS septic system offers peace of mind, and the whole-house Puronics water filtration system guarantees clean, fresh water for you and your family. Additionally, a 200 amp service with solar panels, inverter, and 24-7 monitoring have been installed to help reduce electric bills, providing long-term savings and contributing to a more sustainable lifestyle. The oversized 2-car garage features new doors and openers, offering ample space for vehicles and storage. An amazing qnd spacious 23'X24' familyroom with decorative concrete floors off of the garage comes ready for your inspired finishing touches. The possibilities are endless! Pool-table, ping-pong championship, darts. It's got you covered. A Kegerator is there for you and family and friends before you cozy up and watch your favorite movie on the big screen or have a game night. Enter the mud room for a large double-door pantry closet, a seperate washer-dryer area with cabinetry above. Outside, ammenities include a custom Amish Built shed that provides even more storage options for tools, equipment, or outdoor gear. Even the home, garage, and shed have been painted with custom colors that make the newer architectural roof really pop! Located just half a mile from Fairlee Creek, this home offers easy access to boating, fishing, swimming, and other water activities, making it an ideal spot for those who love the outdoors. Experience the best of Eastern Shore living in this exceptional home that combines privacy, modern amenities, and a beautiful natural setting. Whether you’re looking for a peaceful retreat or a place to entertain family and friends, this Fairlee property is ready to welcome you home. Offers may be entered ONLINE through Thursday, July 9, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown . Surrounded by mature trees and bordered by a serene cornfield, this property provides a peaceful retreat from the hustle and bustle of everyday life. The home has been thoughtfully designed to accommodate comfortable everyday living as well as entertaining guests. The spacious rear deck is an ideal spot for hosting gatherings, enjoying morning coffee, or simply relaxing while taking in the natural beauty of the surroundings. Step inside to discover a modernized kitchen equipped with updated appliances and ample counter space, making meal preparation a pleasure. The bathrooms have been tastefully updated to combine style and functionality, while new windows throughout the home allow for plenty of natural light and energy efficiency. Freshly painted interiors and new doors add to the home’s inviting atmosphere, and the newer washer and dryer provide added convenience. Significant system upgrades enhance the home’s comfort and reliability, including a newer HVAC system that ensures efficient heating and cooling year-round. The upgraded BATS septic system offers peace of mind, and the whole-house Puronics water filtration system guarantees clean, fresh water for you and your family. Additionally, a 200 amp service with solar panels, inverter, and 24-7 monitoring have been installed to help reduce electric bills, providing long-term savings and contributing to a more sustainable lifestyle. The oversized 2-car garage features new doors and openers, offering ample space for vehicles and storage. An amazing qnd spacious 23'X24' familyroom with decorative concrete floors off of the garage comes ready for your inspired finishing touches. The possibilities are endless! Pool-table, ping-pong championship, darts. It's got you covered. A Kegerator is there for you and family and friends before you cozy up and watch your favorite movie on the big screen or have a game night. Enter the mud room for a large double-door pantry closet, a seperate washer-dryer area with cabinetry above. Outside, ammenities include a custom Amish Built shed that provides even more storage options for tools, equipment, or outdoor gear. Even the home, garage, and shed have been painted with custom colors that make the newer architectural roof really pop! Located just half a mile from Fairlee Creek, this home offers easy access to boating, fishing, swimming, and other water activities, making it an ideal spot for those who love the outdoors. Experience the best of Eastern Shore living in this exceptional home that combines privacy, modern amenities, and a beautiful natural setting. Whether you’re looking for a peaceful retreat or a place to entertain family and friends, this Fairlee property is ready to welcome you home. Offers may be entered ONLINE through Thursday, July 9, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

22481 Goose Hollow Dr, Chestertown

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: Samson Properties.

$334,000

Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! The right wing of the house has two bedrooms and a full bathroom. The left wing has the master bedroom that includes a spacious full bathroom, and walk-in closet. With the recent price change, this property now offers an exceptional opportunity—whether you’re looking for a primary residence, a weekend retreat, or a vacation home on Maryland’s Eastern Shore. The flexible layout and generous acreage make this home ideal for a relaxing getaway, with plenty of room for outdoor entertaining, hobbies, or storing boats, bikes, or recreational gear. Inside, enjoy an open-concept design with easy one-level living—perfect for hosting guests. Outside, a wide blacktop driveway provides ample parking for multiple vehicles, an RV, or a boat. The expansive yard offers space to garden, gather with family and friends, or unwind under the stars after a day on the water or exploring the area. Located just minutes from historic downtown Chestertown, nearby marinas, dining, shopping, and waterfront activities—with convenient access to major routes into Delaware and Pennsylvania—this property offers the ideal balance of peaceful rural living and easy travel. A rare combination of acreage, versatility, and affordability—now at an even better price. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape. FHA, VA, USDA, and conventional financing welcome!

Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! The right wing of the house has two bedrooms and a full bathroom. The left wing has the master bedroom that includes a spacious full bathroom, and walk-in closet. With the recent price change, this property now offers an exceptional opportunity—whether you’re looking for a primary residence, a weekend retreat, or a vacation home on Maryland’s Eastern Shore. The flexible layout and generous acreage make this home ideal for a relaxing getaway, with plenty of room for outdoor entertaining, hobbies, or storing boats, bikes, or recreational gear. Inside, enjoy an open-concept design with easy one-level living—perfect for hosting guests. Outside, a wide blacktop driveway provides ample parking for multiple vehicles, an RV, or a boat. The expansive yard offers space to garden, gather with family and friends, or unwind under the stars after a day on the water or exploring the area. Located just minutes from historic downtown Chestertown, nearby marinas, dining, shopping, and waterfront activities—with convenient access to major routes into Delaware and Pennsylvania—this property offers the ideal balance of peaceful rural living and easy travel. A rare combination of acreage, versatility, and affordability—now at an even better price. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape. FHA, VA, USDA, and conventional financing welcome!

8750 Georgetown Rd, Chestertown

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

Selling Office: EXIT Preferred Realty.

$332,000

OPEN HOUSE SATURDAY 3/7/26 FROM 11am-1pm HOPE TO SEE YOU THERE !!! Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a ½-acre lot backing to peaceful farmland. Offering privacy and scenic views, this property blends comfort, space, and thoughtful upgrades throughout. Recent improvements include vinyl siding, a newer roof, and luxury vinyl plank flooring, with original hardwoods underneath for added value and charm. The spacious 12×27 eat-in kitchen is ideal for gatherings and features granite countertops and stainless steel appliances. Both bathrooms are generously sized, with the primary bath showcasing a classic cast iron tub with shower head. A newly added laundry/mudroom enhances everyday convenience and leads directly to a new 14×16 concrete patio and fenced rear yard, perfect for pets, play, or outdoor entertaining. Stay cozy during the colder months with a family room woodstove and warm forced-air heat. The detached two-car garage is topped with a durable 5-year-old metal roof, offering both storage and peace of mind. Town water and sewer add to the home’s practicality. Ideally located between the historic charm of Chestertown and the waterfront town of Rock Hall, this home offers access to quaint shops, fine waterfront dining, boating, hiking and biking trails, the YMCA, and the arts and cultural events of Washington College. A wonderful opportunity to enjoy a simpler lifestyle with a little something for everyone. Approximately 1.5 hour drive to Washington, DC and the Delaware beaches. If this lifestyle is for you, call me to schedule your personal showing.

OPEN HOUSE SATURDAY 3/7/26 FROM 11am-1pm HOPE TO SEE YOU THERE !!! Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a ½-acre lot backing to peaceful farmland. Offering privacy and scenic views, this property blends comfort, space, and thoughtful upgrades throughout. Recent improvements include vinyl siding, a newer roof, and luxury vinyl plank flooring, with original hardwoods underneath for added value and charm. The spacious 12×27 eat-in kitchen is ideal for gatherings and features granite countertops and stainless steel appliances. Both bathrooms are generously sized, with the primary bath showcasing a classic cast iron tub with shower head. A newly added laundry/mudroom enhances everyday convenience and leads directly to a new 14×16 concrete patio and fenced rear yard, perfect for pets, play, or outdoor entertaining. Stay cozy during the colder months with a family room woodstove and warm forced-air heat. The detached two-car garage is topped with a durable 5-year-old metal roof, offering both storage and peace of mind. Town water and sewer add to the home’s practicality. Ideally located between the historic charm of Chestertown and the waterfront town of Rock Hall, this home offers access to quaint shops, fine waterfront dining, boating, hiking and biking trails, the YMCA, and the arts and cultural events of Washington College. A wonderful opportunity to enjoy a simpler lifestyle with a little something for everyone. Approximately 1.5 hour drive to Washington, DC and the Delaware beaches. If this lifestyle is for you, call me to schedule your personal showing.

23055 Old Fairlee Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$330,000

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

8312 Broad Neck Rd, Chestertown

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: LPT Realty, LLC.

$330,000

Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13

Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13

129 Parma Rd, Chestertown

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

Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace of mind knowing the entire house has been meticulously updated with major systems and aesthetic finishes, including: Exterior: New Roof, New Siding, New Windows, and a crisp, modern look. Mechanicals: Brand New Heater, New Central A/C, New Plumbing, New Electrical Service, and a New Hot Water Heater. Interior Finishes: New Flooring and fresh, tasteful New Paint throughout. The heart of the home is the all-new, open-concept kitchen, perfect for entertaining and daily life: New Cabinets, Granite Countertops, Tile Backsplash, Stainless Steel Appliance Package. The fully renovated bathroom shines with a new tub/shower featuring elegant tiled walls and floor, new fixtures, and a stylish new vanity. A separate, dedicated laundry room within the house provides excellent convenience and extra storage space, a powder room or second full bath could be easily added to this room as well. The versatile layout includes a second living area that can easily be utilized as a Fourth Bedroom or a dedicated Home Office, adapting to your needs. Out back, you'll find: A beautiful Paver Patio for outdoor dining and relaxation. Plenty of room for parking. A Large, Detached Two-Car Garage is a massive bonus! The garage has its own new roof, siding, windows, electric, and new electric doors, making it perfect for a workshop, home business, hobbyist, or simply superior storage. Don't lift a finger—simply turn the key and start living! This is an unparalleled opportunity for a like-new home in a great Fairlee location. Note: Seller is a licensed Maryland Realtor. Schedule your showing today!

$330,000

3 Beds ⋅ 1 Baths

Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace of mind knowing the entire house has been meticulously updated with major systems and aesthetic finishes, including: Exterior: New Roof, New Siding, New Windows, and a crisp, modern look. Mechanicals: Brand New Heater, New Central A/C, New Plumbing, New Electrical Service, and a New Hot Water Heater. Interior Finishes: New Flooring and fresh, tasteful New Paint throughout. The heart of the home is the all-new, open-concept kitchen, perfect for entertaining and daily life: New Cabinets, Granite Countertops, Tile Backsplash, Stainless Steel Appliance Package. The fully renovated bathroom shines with a new tub/shower featuring elegant tiled walls and floor, new fixtures, and a stylish new vanity. A separate, dedicated laundry room within the house provides excellent convenience and extra storage space, a powder room or second full bath could be easily added to this room as well. The versatile layout includes a second living area that can easily be utilized as a Fourth Bedroom or a dedicated Home Office, adapting to your needs. Out back, you'll find: A beautiful Paver Patio for outdoor dining and relaxation. Plenty of room for parking. A Large, Detached Two-Car Garage is a massive bonus! The garage has its own new roof, siding, windows, electric, and new electric doors, making it perfect for a workshop, home business, hobbyist, or simply superior storage. Don't lift a finger—simply turn the key and start living! This is an unparalleled opportunity for a like-new home in a great Fairlee location. Note: Seller is a licensed Maryland Realtor. Schedule your showing today!

23110 Old Fairlee Rd, Chestertown

Listing courtesy of Real Broker LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$329,000

Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!