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 ...

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be s...

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 ...

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington Col...

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathroom...

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home se...

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, f...

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

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. Eas...

✨ 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 ho...

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an...

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...

NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square f...

Price Reduction! VERY motivated seller—open to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect ...

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot wa...

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 commun...

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...

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...

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What used to be known as the 'Pomona Store' is back on the market with fresh updates throughout! 4 bedroom house with in-law suite (additional 2 rooms on main level) and ...

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek....

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock H...