Tolchester Estates Homes with Gravel Driveway Parking desc

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 spirit, making it the perfect place to call home. Located in Kent County, Tolchester Estates is just a stone's throw away from the beautiful Chesapeake Bay, providing residents with stunning waterfront views and plenty of recreational opportunities.

The homes in Tolchester Estates are designed with both comfort and style in mind. Each property features a charming gravel driveway, which not only enhances the aesthetic appeal but also provides ample parking space for you and your guests. The rustic charm of gravel driveways complements the natural beauty of the surrounding landscapes, creating an inviting atmosphere that welcomes you home.

As you explore Tolchester Estates, you'll find a range of architectural styles, from cozy cottages to spacious family homes, each thoughtfully situated on generous lots that offer both privacy and outdoor space. The community is known for its friendly neighbors and strong sense of camaraderie, making it easy to forge lasting friendships.

With easy access to local amenities, including shops, restaurants, and schools, Tolchester Estates is perfectly positioned for both convenience and tranquility. Whether you’re looking for a weekend getaway or a permanent residence, this subdivision promises a lifestyle that combines the best of both worlds. Discover the charm of Tolchester Estates—where your dream home awaits amidst the beauty of Kent County!

Newest Tolchester Estates Homes with Gravel Driveway Parking desc

$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:

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