Tolchester Estates Homes for Sale

Tolchester Estates Homes for Sale

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Tolchester Estates and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

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Newest Tolchester Estates Homes for Sale

8820 Cumberland St, Chestertown
$312,500
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
$424,900
5 Beds ⋅ 3 Baths
Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Set in a waterfront community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Qualified buyers may be eligible for 0% down financing. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a 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. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

8706 Elm Rd, Chestertown
$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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