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$839,500
3 Beds ⋅ 3 Baths
**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 and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

102 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$8,000
Build Your Dream Home on Two Expansive Lots in Chesapeake Landing! 15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks! Enjoy the charm of Chestertown living, just minutes from Historic Downtown Chestertown, the scenic Chesapeake Bay, and Washington College. Conveniently close to local parks, restaurants, and waterfront amenities, this location combines tranquility with accessibility. Don’t miss this incredible chance to secure your lot and bring your dream home to life. Opportunities like this don’t come often—act now and make your vision a reality!

Clarissa Rd, Chestertown

Listing courtesy of EXP Realty, LLC. Contact: (866) 825-7169
$55,000
Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

Georgetown Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$150,000

Caulks Field Road, Chestertown

Listing courtesy of RE/MAX Allegiance. Contact:

$150,000
Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty. Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and the beautiful Chester River, which flows right through Chestertown. Whether you're looking for a peaceful retreat or a place to create your forever home, this is an opportunity you don’t want to miss!

Georgetown Rd Se, Chestertown

Listing courtesy of RE/MAX Allegiance. Contact: