Tolchester Estates Homes under $500,000

Tolchester Estates Homes under $500,000

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Newest Tolchester Estates Homes under $500,000

8668 Elm Rd, Chestertown
$349,900
4 Beds ⋅ 2 Baths
Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community offer private beach and boat ramp access. Rear private deck.

8668 Elm Rd, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

21338 Virginia Ave, Chestertown
$400,000
2 Beds ⋅ 2 Baths
Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-style residence offers a harmonious blend of modern living space and coastal charm, perfectly situated approximately 800 feet from the breathtaking Chesapeake Bay. Step inside to discover an open-concept layout that seamlessly integrates the kitchen, dining, and living areas, creating an inviting space ideal for both entertaining and everyday living. The interior features luxury vinyl plank flooring that exudes sophistication while ensuring durability and ease of maintenance. The thoughtfully designed kitchen is a cook's dream, equipped with new appliances including a built-in microwave, dishwasher, stove, and refrigerator, all complemented by a sleek exhaust fan. The combination of functionality and style makes this kitchen the heart of the home. With two spacious bedrooms , and two fully appointed bathrooms, this residence offers comfort and privacy. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage provides easy access and additional storage options. Step outside onto the expansive deck, where you can bask in the serene views of the bay, perfect for morning coffee or evening gatherings under the stars. The outdoor space is an extension of the easy lifestyle this home offers, allowing you to enjoy the tranquility of nature right at your doorstep. The property is not just a home; it's a lifestyle. Living in Tolchester Estates means embracing a community that values both privacy and connection, with the Chesapeake Bay as your backdrop. Enjoy leisurely strolls along the water, or indulge in water-oriented activities that the bay has to offer. This home is designed for those who appreciate easy living, with a commitment to quality evident in every detail. From the excellent condition of the property to the thoughtful selection of materials, this residence is a jewel. Don't miss the opportunity to own a piece of paradise in this exclusive bay block location. Experience the luxury, comfort, and lifestyle that await you in this remarkable home. Your dream of coastal living starts here. Within 5 minutes of a full-service marina and "The Shanty" for fun entertainment located on a beach right in front of the Chesapeake Bay. There are also community beaches, one is about two minutes from this cottage!

21338 Virginia Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

8820 Cumberland St, Chestertown
$281,500
3 Beds ⋅ 2 Baths
Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

8732 Elm Rd, Chestertown
$289,000
3 Beds ⋅ 2 Baths
Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay, a boat ramp and a community hall for gatherings and events. Tolchester Marina, a full service operation, and The Shanty Beach Bar, "Best Kept Secret on the Bay", are just a short walk or golf cart ride away. This low maintenance home can easily be a primary resident, second home or investment property. Enjoy the easy pace and the stunning sunsets this community has to offer (some interior images were virtually staged using AI - these images do not represent the property's current furnishings or decor).

8732 Elm Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

8630 Elm Rd, Chestertown
$419,900
5 Beds ⋅ 3 Baths
Enjoy the Eastern Shore as your weekend retreat at 8630 Elm Road. Calling all boaters, fishers, hunters, beachgoers, nature and recreation lovers, investors, and residential vacation-home seekers looking for a peaceful Eastern Shore getaway—with the waterfront lifestyle without the waterfront price. Located in the waterfront community of Tolchester Estates, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. The fifth bedroom can serve as a home office, guest room or hobby space with 8 car driveway large enough for multiple families, a boat or RV. The home features stainless-steel appliances, a recently replaced washer, an approximately two-year-old water heater and an electric fireplace with custom floating shelves. Outside, enjoy the expanded deck, hot tub and fire pit. On crisp fall or winter evenings, gather around the fire for s’mores and hot chocolate. Tolchester Marina is about three blocks away, across the street from the home. The private marina welcomes visitors to its Shanty Bar, with seasonal live entertainment, and its on-site restaurant, where you can enjoy breakfast. Boating, kayaking and other water activities are nearby, and the community boat ramp is about one mile away. Local fishing charters operate from the marina; reservations and fees are separate. Transient slips may be available for overnight stays. Marina pool access is limited to eligible slip holders and overnight transient guests, subject to marina rules, fees and availability. Great Oak Landing—with its nine-hole executive golf course and Jellyfish Joel’s Beach Bar—is a 15-minute drive away. Enjoy the area’s natural setting, with opportunities to see deer and rabbits and listen to birdsong. Eastern Neck National Wildlife Refuge offers trails, wildlife viewing and seasonal deer hunts on designated days with a required refuge permit. Millington Wildlife Management Area offers about 4,000 acres of public hunting access, subject to Maryland DNR rules and season requirements. Downtown Rock Hall, with its seafood restaurants and waterfront dining, is about a 10-minute drive away. Enjoy a beach day at Ferry Park or explore Eastern Neck. Historic Chestertown is about 15 minutes away, where you can stroll the year-round Saturday farmers market, browse local vendors and bring home fresh seasonal produce. Make a day of exploring the area’s wineries, including Crow Vineyard and Broken Spoke Winery, and create your own Eastern Shore wine-tasting tour. Casa Carmen’s wine and tapas tasting room offers another inviting stop in Chestertown. Most furnishings are included, including the queen- and king-size Havertys bedroom sets, generally used mattresses approximately two to four years old, and the deck furniture. With flexible living space, outdoor gathering areas and convenient access to boating, fishing, hunting, golf, beaches, dining and nature, 8630 Elm Road is well suited to a full-time home or an Eastern Shore getaway. USDA 100% financing may be available to eligible buyers, subject to property eligibility, borrower qualification and lender approval.

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

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