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Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor an...
- 3 Beds
- 5 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The pro...
- 3 Beds
- 1 Baths
Listing courtesy of RE/MAX Chesapeake. Contact:
Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that ...
- 4 Beds
- 2 Baths
Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The ...
- 3 Beds
- 2 Baths
Listing courtesy of Samson Properties. Contact: 7033788810
Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but hig...
- 5 Beds
- 5 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its...
- 2 Beds
- 2 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Welcome to country living ! Nestled on over an acre, this solid brick rancher offers nearly 2,000 square feet of living space with many possibilities. Enjoy the peace and...
- 3 Beds
- 1 Baths
Listing courtesy of Keller Williams Flagship. Contact:
Selling Office: .
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 ...
- 3 Beds
- 2 Baths
Listing courtesy of Pearson Smith Realty, LLC. Contact: 5713861075
Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra ...
- 2 Beds
- 2 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Well maintained Beautiful Brick Rancher nestled on 2.16 Acres in Chestertown and a short distance to Historic Downtown. 3 Spacious Bedrooms all with Hardwood Flooring an...
- 3 Beds
- 2 Baths
Listing courtesy of Keller Williams Realty. Contact:
Selling Office: .
Exceptional renovation that offers everything you could want in a waterfront home.
- 3 Beds
- 2 Baths
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!
- 3 Beds
- 1 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
2 level townhome in sought after Tolchester Village! Features a terrific open kitchen with stainless steel appliances, nice living room/dining room combination with a sli...
- 2 Beds
- 1 Baths
Listing courtesy of Coldwell Banker Realty - Washington. Contact:
Selling Office: .
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 c...
- 2 Beds
- 1 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd...
- 3 Beds
- 1 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Classic Country Cape Cod on an acre in the country with a large Detached Garage. What more could you ask for ? This home is in a quiet country setting in the trees overlo...
- 4 Beds
- 2 Baths
Listing courtesy of Rosendale Realty. Contact:
Selling Office: .
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 (Dec...
- 3 Beds
- 2 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: .
Rare lakefront opportunity in Kent County offering exceptional privacy and a peaceful natural setting. Tucked away on 2.62 partially wooded acres along Urieville Lake, th...
- 4 Beds
- 4 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
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...
- 3 Beds
- 2 Baths
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: .
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 reno...
- 3 Beds
- 1 Baths
Listing courtesy of Real Broker LLC. Contact:
Selling Office: .
As - Is
- 3 Beds
- 2 Baths
Listing courtesy of LPT Realty, LLC. Contact:
Selling Office: .
117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...
- 1 Beds
- 1 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...
- 2 Beds
- 1 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...
- 1 Beds
- 1 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...
- 3 Beds
- 3 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
**Listing price is for FOUR units for sale as an investment package! 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a ...
- 7 Beds
- 5 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, ...
- 4 Beds
- 2 Baths
Listing courtesy of Taylor Properties. Contact:
Selling Office: .
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 sew...
- 4 Beds
- 2 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Situated on an open .59 acre lot in Queen Anne’s County, this charming 3 bedroom, 2.5 bath built home in 2014 offers buyers the perfect blend of modern comfort with spaci...
- 3 Beds
- 3 Baths
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
Serene 2-acre partially cleared wooded lot with existing 1900-built home, in need of major repair or possible tear-down. Value is in the land. No interior access – part...
- 3 Beds
- 1 Baths
Listing courtesy of Tesla Realty Group, LLC. Contact:
Selling Office: .
None
- 1 Beds
- 1 Baths
Listing courtesy of Select Land & Homes, LLC. Contact:
Selling Office: .
This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher bloc...
- 2 Beds
- 2 Baths
Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
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 sel...
- 3 Beds
- 1 Baths
Listing courtesy of Select Land & Homes, LLC. Contact:
Selling Office: .
Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.
- 4 Beds
- 3 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
$20,000 Price Reduction! A One-of-a-Kind Historic Treasure Reimagined for Modern Living Step into history with this extraordinary Greek Revival chapel, originally built i...
- 1 Beds
- 1 Baths
Listing courtesy of Hyatt & Company Real Estate, LLC. Contact:
Selling Office: .
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 countr...
- 2 Beds
- 1 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: .
This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof ...
- 2 Beds
- 2 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Enjoy the serenity of waterfront living in this delightful 2-bedroom, 1-bath ranch home nestled on a double lot along the scenic Chester River. This cozy retreat offers s...
- 2 Beds
- 1 Baths
Listing courtesy of Iron Valley Real Estate of Central PA. Contact:
Selling Office: .
Looking for a home that has an oversized two car garage with electric, heated floors, water, toilet hookup bonus room above and a heated Florida room? Or are you looking ...
- 3 Beds
- 2 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This...
- 3 Beds
- 2 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
WELCOME TO 209 RIVERSHORE RD., CHESTERTOWN MD.,, Your natural waterfront retreat on the Chester River. Enjoy your time outside or inside of this tranquil property. As you...
- 2 Beds
- 2 Baths
Listing courtesy of Douglas Realty LLC. Contact:
Selling Office: .
None
- 3 Beds
- 1 Baths
Listing courtesy of Taylor Properties. Contact:
Selling Office: .
Farmhouse located on two acre cleared lot that overlooks farmland. Improvements have been made to the property, including a metal farm/garage/workshop building with ele...
- 2 Beds
- 1 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Welcome to this expansive, move-in-ready colonial in the sought-after Coventry Farms II community. Built in 2011 with all available square footage upgrades, this home off...
- 4 Beds
- 3 Baths
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:
Selling Office: .
Opportunity knocks! This 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in Queen Anne’s County. Enjoy the convenience of high-speed internet while taking in th...
- 3 Beds
- 2 Baths
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
Discover the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Whether...
- 3 Beds
- 2 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: .
This is it! This is the one you and your horse have been dreaming about! Absolutely darling 4+ acre farmette! Charm charm charm plus function function function. Turnkey a...
- 3 Beds
- 3 Baths
Listing courtesy of EXP Realty, LLC. Contact:
Selling Office: .
This property is in great condition, with a nice kitchen, a living/dining room combo on the main level, a utility room and plenty of storage space. The living room has a...
- 3 Beds
- 1 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Welcome to 105 Justin Buch Drive, a delightful single-family home nestled in a quiet community on the Queen Anne's side of Chestertown, MD. This charming residence offers...
- 3 Beds
- 2 Baths
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: .
Lovely all one floor living in quiet neighborhood with updated features throughout! Brand new gorgeous kitchen with white shaker cabinetry featuring dovetail construction...
- 3 Beds
- 2 Baths
Listing courtesy of FSBO Broker. Contact:
Selling Office: .None Available Real Estate & Homes
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