Welcome to 329 Union Church Road in Chestertown, located in Queen Anne’s County—a home with plenty of space, useful updates, and room to truly make it your own! Situate...

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property f...

Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added...

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...

**OPEN HOUSE Sunday September 13th 11AM-1PM** This adorable rancher will soon be at the top of your "favorites" list, with a welcoming interior and plenty to love outside...

Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch be...

Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. D...

Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a ...

Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peac...

Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary s...

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is ...

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renov...

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for...

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 ...

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...

Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bat...

MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern...

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet c...

Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0...

Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comforta...

Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in...

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood...

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effor...

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. E...

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 East...

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 ...

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square ...

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in ...

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...

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natur...

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!

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, pa...

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the he...

Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pum...

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of ...

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...

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the...

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip.  3.55 acres, partly wooded, exceptionally landscap...

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 ...

* SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath ra...

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...

103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the dive...

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living ...

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 squa...

None

Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautiful...