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

$289,900

2 Beds ⋅ 2 Baths

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 Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

21146 Montana Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$320,000

3 Beds ⋅ 2 Baths

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:

Start Your Search