Tolchester Estates Real Estate

Welcome to Tolchester Estates, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers a unique blend of serene living and vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle.

Tolchester Estates is strategically located near the scenic banks of the Chester River, providing residents with breathtaking views and easy access to a variety of outdoor activities. Whether you enjoy kayaking, fishing, or simply strolling along the waterfront, this delightful community has it all. The lush landscapes and well-maintained parks invite you to explore nature and unwind in the fresh air.

The homes in Tolchester Estates exude warmth and character, with a range of architectural styles that cater to diverse tastes. Each property is thoughtfully designed, featuring spacious layouts, modern amenities, and beautiful outdoor spaces perfect for entertaining or relaxing. With a strong sense of community, neighbors often come together for seasonal events and gatherings, fostering lasting friendships and creating a welcoming atmosphere.

Conveniently located just a short drive from the historic downtown Chestertown, residents can enjoy an array of local shops, restaurants, and cultural attractions. The town is known for its rich history and vibrant arts scene, offering plenty of opportunities for exploration and engagement.

If you’re looking for a peaceful retreat with a strong sense of community, Tolchester Estates is the perfect place to call home. Discover the charm of this lovely subdivision and experience the best of Maryland living!

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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