Tolchester Estates Real Estate

Welcome to Tolchester Estates, a hidden gem nestled in the charming town of Chestertown, Maryland. This picturesque subdivision offers a unique blend of serene living and vibrant community life, making it the perfect place to call home.

Tolchester Estates is situated in Kent County, where the beauty of nature meets the rich history of the Eastern Shore. Residents enjoy the tranquility of waterfront living, with many homes offering stunning views of the Chesapeake Bay and easy access to local marinas. The lush landscapes and beautifully manicured lawns create an inviting atmosphere, perfect for families, retirees, and anyone seeking a peaceful retreat.

This delightful community is not just about stunning homes; it boasts a strong sense of camaraderie among neighbors. Regular community events, such as summer barbecues and holiday celebrations, foster connections and friendships that last a lifetime. Families will appreciate the nearby parks and recreational facilities, providing ample opportunities for outdoor activities, from hiking and biking to fishing and boating.

Tolchester Estates is conveniently located just a short drive from downtown Chestertown, where you can explore charming boutiques, delightful restaurants, and cultural attractions. The town’s rich history is showcased in its architecture and museums, while vibrant art scenes and farmers' markets add to the community’s charm.

Whether you’re looking to settle down or invest in a vacation home, Tolchester Estates offers a unique lifestyle that combines the best of waterfront living with the warmth of a close-knit community. Discover your dream home in this idyllic subdivision today!

Newest Listings in Tolchester Estates

$424,900

5 Beds ⋅ 3 Baths

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 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore. The home offers five generously sized bedrooms, providing comfortable space for family, guests, or work-from-home needs. The versatile fifth bedroom can function as a home office, guest room, flex space, or secondary suite, depending on your needs. The upgraded kitchen features bright white cabinetry, updated countertops and backsplash, stainless-steel Whirlpool appliances, and a KitchenAid dishwasher. The French-door refrigeratorincludes a front water and ice dispenser for added convenience. Attractive ceiling fans throughout the home add both comfort and style. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. With five bedrooms, the layout offers excellent flexibility, and the fifth bedroom can also serve as a home office, guest room, or additional flex space. The partially finished one-car garage offers added versatility beyond traditional vehicle parking and storage. It can also serve as a game room, entertainment area, recreation space, hobby room, home gym, or additional flex space, giving buyers even more options for how they use the home. Step outside to an expanded rear deck, hot tub, and fire-pit/seating area, ideal for relaxing or entertaining. Boating enthusiasts will appreciate the nearby seasonal marina with restaurants and a dive bar 3 blocks away and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. Additional updates include an approximately two-year-old water heater and a private well with an upgraded water-treatment/softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Whether used as a primary residence, vacation home, weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package.

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

$315,000

3 Beds ⋅ 2 Baths

* 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 rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

8706 Elm Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

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