**To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms an...

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This spectacular waterfront retreat offers over 3,500 square feet of living space on 0.76 acres, ideally located within the town limits of Rock Hall. With an elevator, fi...

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner ...

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head ...

****NEW PATH TO WATER FOR YOUR GATOR OR UTV**** This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself,...

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...

Unique opportunity offering two adjoining parcels with exceptional potential in Rock Hall. Parcel 1 consists of approximately 1.4 acres located on Geen Lane and is zoned ...

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms a...

This former West Marine commercial property, constructed in 2001, presents a compelling investment opportunity in a rural location, characterized by its solid constructio...

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms an...

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 ...

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 ...

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square fe...

Commercial Development Site on busy MD Rte 213, Prime location across from new Starbucks and Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, re...

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The ...

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

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 an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of differen...

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

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered together. Located in the heart of Chestertown, this ch...

Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. ...

Imagine building your dream luxury waterfront home on one of the most spectacular homesites the Chesapeake Bay has to offer. This exceptional waterfront lot boasts breath...

Enjoy a long, secluded driveway to a 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Grey’s Inn Creek. The home features ...

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

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...