Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,47...

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country ...

The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintai...

Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-st...

This light-filled Chestertown rancher provides great value at a very attractive price. Located in a small quiet community, it is convenient to popular shopping areas, th...

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the fi...

***Offer deadline tomorrow Sunday, October 18 at 2pm*** Welcome home to Chesapeake Landing! Tucked back in this quiet water-access community, this 3 bed, 1 bath rancher o...

Lock the door, grab your coffee, and walk. Directly across from the Chestertown Marina in the heart of the Historic District, 204 S Water Street is the pied-à-terre the E...

Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level...

Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's ...

Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in ...

**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Ches...

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributin...

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Fully finished basement. Plenty of parking. A great place for a centrally loc...

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Histo...

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Ov...

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farm...

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunnin...

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is ...

Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining...

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Multiple offers received- Highest and best due by 9/29 at noon! Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This 4 ...

Opportunities like this don't come along every day! Welcome to 329 Union Church Road, tucked away in a highly sought-after neighborhood in Queen Anne’s County where homes...

Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportu...

This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buye...

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...

PRICE IMPROVEMENT!! 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 ...

**NEW PRICE! MOTIVATED SELLER WILLING TO CONSIDER BUYER CLOSING COST ASSISTANCE OR INTEREST RATE BUYDOWN!** Here's an opportunity worth a second look! With a fresh price ...

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesi...

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s sho...

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 ...

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homes...

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 ...

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...

Significant price correction! Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within w...

MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor and Queen Anne’s County school district. This recently updated ...

Major price reduction! Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town...

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...

Price correction! Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy acce...

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Located in the water-oriented Tolchester Estates community, this re...

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...

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a priv...

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...

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Cheste...

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 ...

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring ...