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105 Watermans Ct, Grasonville
$125,000
2 Beds ⋅ 2 Baths
INVESTOR ALERT! Opportunity knocks at 105 Watermans Court in Grasonville, MD! This fixer-upper is perfect for investors, flippers, or buyers looking to build sweat equity and make a home truly their own. Situated in a quiet cul-de-sac, this property offers strong potential with a spacious layout and great bones—just waiting for the right vision and updates. With some TLC and renovations, this home could truly shine. Located in the desirable community of Grasonville on Maryland’s Eastern Shore, you’ll enjoy convenient access to Route 50, local marinas, waterfront dining, and the Chesapeake Bay lifestyle. Just a short drive to Annapolis and within commuting distance to the Eastern Shore beaches or the Baltimore/Washington metro areas. Whether you’re looking for your next investment project or a chance to customize your dream home, this property is being sold as-is and priced accordingly. Bring your contractor and your imagination—this is the opportunity you’ve been waiting for!

105 Watermans Ct, Grasonville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

Barclay Cutoff Road, Barclay
$120,000
THE WAIT IS OVER - YOUR OPPORTUNITY IS HERE TO PURCHASE THIS 4+ ACRE PARCEL BUILDING LOT LOCATED WITHIN THE TOWN OF BARCLAY. Discover the perfect blend of space - this property offers a mix of cleared and wooded areas providing an ideal setting to design and build your custom home the way you envision. With No HOA, you can build with the flexibility and freedom that you desire. Having public sewer hookup available, much of the groundwork is already in place—making your building process that much easier. Enjoy peaceful rural living while still being just minutes from nearby towns, everyday amenities, and major routes. Plus, take advantage of convenient access to tax-free shopping in Delaware. Don’t miss this opportunity to own a spacious piece of land with the perfect balance of privacy and convenience—bring your vision and make it a reality! PHOTOS FORTHCOMING!

Barclay Cutoff Road, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: EXP Realty, LLC.

13706 Main St, Queen Anne
$95,000
4 Beds ⋅ 1 Baths
Located in the small town of Queen Anne, this 4-bedroom, 1-bath farmhouse is in need of extensive repairs and renovation and is being sold as-is. The home was previously used as a rental property and offers an opportunity for investors, contractors or buyers looking for a project property with potential. Features include a covered front porch, off-street parking and a small storage shed. The property shares a well with the neighboring home, which is also available for purchase (13704 Main Street). Enjoy a location less than 3/4 mile from Hillsboro Landing with access to Tuckahoe Creek for boating and fishing and under 5 miles from Tuckahoe State Park. The park is known for its 60-acre lake, presenting fishing and boating opportunities, playgrounds, and more than 20 miles of hiking, biking, and equestrian trails.

13706 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

Big Woods Rd, Church Hill
$90,000
Escape to your own private 12.26-acre retreat on Big Woods Drive in Church Hill. This wooded parcel has been thoughtfully improved for hunting and recreation, with approximately one acre strategically hinge cut to create ideal wildlife habitat and bedding areas. The result? An abundance of deer, turkey, and other native wildlife frequent the property. Whether you're looking for a private hunting tract, weekend recreational getaway, or long-term land investment, this property offers seclusion while still being conveniently located. Just about 3 miles from Route 301 North and approximately 30 minutes to the Bay Bridge, you can enjoy the quiet of the outdoors without sacrificing accessibility. If you’ve been searching for your own piece of land with privacy, mature woods, and plenty of wildlife — this is it.

Big Woods Rd, Church Hill

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: National Land Realty, LLC.

116 2nd St, Crumpton
$75,000
Rare opportunity to own a versatile parcel in the heart of Crumpton, just one block from the Chester River. This NC-20 zoned property offers a unique combination of flexibility and function, ideal for a variety of potential uses (buyer to verify). The lot is perk approved and includes an existing 3-car garage, providing immediate utility for storage, workshop space, or future plans. Located within close proximity to navigable water, this property offers the lifestyle appeal of the Eastern Shore with added convenience and accessibility. Whether you're looking to build, invest, or secure a property with multiple potential uses, this parcel delivers both present-day value and long-term opportunity. Additional property located across the street (115 2nd St) is also available for purchase separately or together.

116 2nd St, Crumpton

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

109 2nd St, Chestertown
$75,000
ONLINE AUCTION: Bidding begins 11/12/2025 @ 10:00 AM. Bidding ends 11/14/2025 @ 11:40 AM. List Price is Suggested Opening Bid. Deposit: $5,000. This +/- 1.80 acres lot of land located is in Chestertown, MD within Queen Anne’s County. A prior soil evaluation completed by the Queen Anne’s County Health Department (7/17/2009) certified suitability for a conventional mound septic system, confirming the property’s true build‐ready potential (see our documents tab). Prime Location + Proven Market Value Situated just moments from the Chester River, Wilmer Park, Chestertown Historic District, marinas, and downtown amenities, this lot appears in an area where strong sales activity is underway. Recent listings and disposals nearby include several residential lots selling in the $14,000 to $85,000 range, underscoring the compelling value of a lot with confirmed build feasibility. This parcel offers an entry point into Chestertown’s growth corridor, with the unique advantage of its verified build status fully documented. Buyer to verify all utilities, access, zoning/permits, and any development feasibility directly with Queen Anne’s County. The property also provides convenient vehicular access to MD Route 213 and MD Route 291, offering smooth connections to surrounding towns and regional highways.

109 2nd St, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact:

Selling Office: Unrepresented Buyer Office.

111 Beach Harbor Dr Unit 11F, Grasonville
$44,000
2 Beds ⋅ 1 Baths
Welcome to your perfect Eastern Shore escape in the highly sought-after Beach Harbor Camper Cooperative! This is your opportunity to own a true waterfront lifestyle without the waterfront price tag. Located just steps from Jackson Creek with access out to the Chester River, this property is ideal for boating, kayaking, paddleboarding, or simply relaxing by the water all season long. Beach Harbor is known as one of the best-kept secrets on the Shore—a gated, amenity-rich community offering a private beach, boat ramps, marina access, pool, clubhouse, playground, and more. Whether you’re looking for a weekend getaway, summer retreat, or an affordable place to enjoy 3-season living, this community delivers. Spend your days on the water, your evenings with friends and family, and your weekends escaping the stress of everyday life. With easy access on and off Kent Island and just a short drive from the bridge, this location makes getting away effortless. Properties like this don’t come around often—especially with limited availability in Beach Harbor. Don’t miss your chance to own your own slice of the Eastern Shore lifestyle.

111 Beach Harbor Dr Unit 11F, Grasonville

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

Selling Office: Century 21 Downtown.

228 Merganser Dr, Chestertown
$42,000
Situated on a quiet road, this half-acre property offers a great opportunity to enjoy the Eastern Shore lifestyle. Community water access to the Chester River is located at the end of the road and includes a boat ramp, making it easy to enjoy boating, fishing, crabbing, or paddle boarding right nearby. Located within the Queen Anne’s County school district and just minutes from downtown Chestertown. A mobile home currently exists on the property and is believed to be approximately 60 years old. Buyer to verify condition and habitability of the mobile home or remove at buyer’s discretion. Seller has no knowledge or information regarding the mobile home. Original well and septic are present on the property; buyer to verify condition and functionality of both.

228 Merganser Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

8-E Piney Narrows Rd, Chester
$35,000
Looking to own your boat slip instead of paying a hefty lease that could increase year after year? Slip 8-E at Piney Narrows Yacht Haven offers an ownership opportunity in a convenient, community-oriented marina condominium. Measuring 50' x 18' with power, the slip is set beyond a large turnaround area that makes maneuvering easier for larger vessels, including sailboats and sportfish. Located in the heart of Kent Narrows, Piney Narrows Yacht Haven offers a community pool, picnic area with BBQ grill, Yachtsman’s Club lounge, fuel dock with gas and diesel, and complimentary pump-out with fuel purchase. Water, electricity, and Wi-Fi are included. Marina amenities also include winter bubbling at all dock facilities, climate-controlled heads and showers, two laundromats, parking for slip holders and guests, and an on-site canvas shop for new work and repairs. Enjoy convenient access to Kent Narrows restaurants, nearby trails, and popular cruising destinations. Whether you’re seeking a weekend getaway or a home port for the boating season, Slip 8-E offers a comfortable place to enjoy all that Kent Island and the Chesapeake Bay have to offer.

8-E Piney Narrows Rd, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RE/MAX Leading Edge.

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