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314 Race St, Millington
$155,000
3 Beds ⋅ 1 Baths
This 3-bedroom, 1-bath home offers a wonderful opportunity for homeowners and investors alike. The front sunroom is filled with natural light and offers a versatile space for relaxing, entertaining, or enjoying the changing seasons year round. In need of updates and repairs, this home offers a great opportunity to renovate, add value, and make it your own. The backyard overlooks Cypress Branch, a peaceful tributary of the Chester River, where the gentle flow of the water creates a relaxing backdrop for everyday living. Conveniently located with easy access to US-301, this home offers the perfect balance of affordability, tranquility, and convenience. Whether you’re searching for a primary residence, weekend getaway, or investment opportunity, this home is full of potential and ready for your personal touch. This is an estate sale and being sold AS-IS. Electricity is currently disconnected. Property is located within the 100-year floodplain.

314 Race St, Millington

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Compass.

Beach Rd, Rock Hall
$150,000
Welcome to Beach Road in the quiet waterfront town of Rock Hall! Located halfway down the Eastern Shore, this property sits across the street from the wide open Chesapeake Bay. With .34 acres of cleared and flat land, this plot is perfect for development and sits perfectly in between the 2 waterfront properties to get a year round water view. Feel free to drive by the lot to see for yourself how much potential this land holds. Feel free to reach out anytime with questions regarding development. Renderings of possible homes that will fit in the zoning requirements are available upon request and a local builder is on standby to answer any additional questions about the build costs and project timeline. Do not miss this incredible opportunity to be some of the first new residents in the resurgence of Rock Hall!

Beach Rd, Rock Hall

Listing courtesy of VRA Realty. Contact:

Selling Office: Rock Hall Properties Real Estate.

207 Lincoln Dr, Chestertown
$141,000
4 Beds ⋅ 2 Baths
207 Lincoln Drive is located in Chestertown, Kent County, on Maryland's Eastern Shore. Nestled in the established Washington Park neighborhood, a 1960s community just west of Chestertown's historic downtown, the property enjoys a convenient location near the Chester River and Chesapeake Bay. Known for its charming streets, rich maritime heritage, and as the home of Washington College, Chestertown offers the perfect blend of small-town character and waterfront living. This four-bedroom, one-and-a-half-bath rancher presents an excellent opportunity for renovation and personalization. Being sold as-is, the home is ready for its next owner to restore, update, and make it their own.

207 Lincoln Dr, Chestertown

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: Monument Sotheby's International Realty.

423 Calvert St, Chestertown
$125,000
3 Beds ⋅ 2 Baths
This property is primed and ready for your finishing touches—materials included! Enjoy the convenience of being just steps from historic downtown Chestertown. LVP Flooring installed on 10/04/2025 on the main and upper levels. Carpet installed on the staircase. Materials, fixtures, applicances cabinetry, washer/dryer ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025, including new flooring, appliances, fresh paint, and a newer roof. Renovations are well underway, with all remaining materials provided, giving the next owner an incredible opportunity to add the finishing touches. The property features a fenced front entry, a deep backyard with rear parking access, and plenty of outdoor space to enjoy. Ideally located near historic downtown Chestertown, you’ll find shopping, dining, entertainment, and events just minutes away, along with the waterfront park along the scenic Chester River and the nearby Washington College campus. Offered at just $135,000, this home presents exceptional value for use as a primary residence, a second home retreat, or an investment rental. All of this in Chestertown — a charming Eastern Shore community known for its rich history, vibrant arts scene, events, riverfront beauty, and welcoming small-town atmosphere.

423 Calvert St, Chestertown

Listing courtesy of Redfin Corp. Contact:

Selling Office: Compass.

141 Prospect St, Chestertown
$120,000
4 Beds ⋅ 2 Baths
INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find! Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something special in a desirable location. Adjacent to the The Wayne Gilchrest Trail , which is a popular walking trail in Chestertown, MD, also known as the Chestertown Rail Trail. It's a paved, multi-use path that follows the route of a former railway line, connecting various parts of the town. The trail offers scenic views of the Chester River and surrounding areas, and it's a great place for walking, biking, and enjoying nature. Whether you're looking to flip, rent, or restore and make it your own, this property has endless possibilities. The layout provides room to reimagine the interior, while the surrounding lot offers privacy/seclusion for your outdoor events. Enjoy the charm of nearby Chestertown with its shops, dining, waterfront, and vibrant community. With its location, lot size, and upside potential, this diamond in the rough is a smart investment you won't want to miss. Sold AS – IS… Major Rehab Needed...

141 Prospect St, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

Lot 4 Piney Neck Rd, Rock Hall
$112,000
Build Your Waterfront Dream Retreat – Lot 4 Piney Neck Rd, Rock Hall, MD Discover a rare opportunity to own 1.39 acres of serene, partially wooded land in the heart of Rock Hall, Maryland — a beloved Chesapeake Bay waterfront town known for boating, fishing, and peaceful Eastern Shore living. This prime parcel offers deeded right-of-way access to Davis Creek and includes shared use of a private dock, previously home to a sailboat. Whether you're looking to build a weekend getaway, a full-time residence, or your custom coastal retreat, this property offers the perfect canvas. Tucked away off scenic Piney Neck Road and just minutes from the Rock Hall Marina, public beach, and Main Street restaurants, this location blends natural beauty with convenience. Enjoy calm water views, kayaking and paddleboarding, or watch herons and ospreys soar overhead while sipping coffee on your future porch. Originally purchased with the vision of building a home, the current owner is now ready to pass along this peaceful Chesapeake Bay gem to someone ready to bring that vision to life. New owner to verify all utilities, including Septic and Well. This lot offers both privacy and proximity to all that makes Rock Hall special. Don't miss this chance to own a slice of waterfront-access paradise. Take a drive out, walk the land, and imagine what you could create. Then make your offer before someone else claims this rare piece of Eastern Shore charm.

Lot 4 Piney Neck Rd, Rock Hall

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Select Land & Homes, LLC.

116 Cross St, Chestertown
$104,000
Great opportunity in the heart of Chestertown. This downtown commercial lot offers incredible potential just steps from established businesses and local amenities. Public sewer is available and accessible, making development that much more convenient. Positioned next to a professional office building, the property benefits from strong daily visibility with both foot and vehicle traffic passing by. Whether you’re envisioning a commercial storefront, office space, investment rental, or even a mixed-use concept, the flexibility here is hard to beat. Offered at an attractive price point, this is a rare chance to secure a well-located parcel in one of the Eastern Shore’s most charming and active downtown settings.

116 Cross St, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

Selling Office: Unrepresented.

1 Wilson Point Rd, Galena
$95,000
Welcome to Wilson Point Estates – Nestled in a peaceful, secluded setting, this exclusive community offers 14 generously sized lots with No Builder Tie-In but developer must approve the architectural appearance of the home. With each lot carefully placed to preserve the natural beauty and privacy of the landscape, Every residence will reflect quality craftsmanship, offering both comfort and style in a setting that feels miles away from it all yet is just minutes from Middletown , local marinas, and easy access to boating, fishing, and waterfront recreation.Surrounded by serene woodlands and scenic views, this is a place where tranquility and elegance come together, A true escape from the hustle and bustle of everyday life. Designed for those who value space, sophistication, and a strong connection to nature, This is your chance to build the home of your dreams and embrace the best of both worlds upscale living in harmony with nature.

1 Wilson Point Rd, Galena

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

Selling Office: Patterson-Schwartz Real Estate.

108 Pine St, Chestertown
$85,000
3 Beds ⋅ 1 Baths
Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown’s most “walkable” corridors. With estimated renovation investment of $60K-$80K+, comparable renovated properties in this location are selling for $275K-$300K, creating potential equity of $80K-$125K for buyers with vision and capability. Close proximity to Washington College creates built-in rental demand from students, faculty, and staff. Plus easy access to Downtown Chestertown shops, restaurants, and waterfront parks are minutes away on foot. Starbucks and grocery stores are easily accessible. This is a prime location renovation opportunity where comparable updated homes command premium pricing. The renovation reality. This property requires full renovation and is priced accordingly. Systems, finishes, and layout will need comprehensive updating. Estimated investment ranges from $60,000 to $80,000+ depending on finish level and scope decisions. This is a project for experienced investors, renovation contractors, or buyers with construction capability who understand forced appreciation through strategic improvements. The opportunity math works. Purchase at $115,000. Invest $60K-$80K in renovations. All-in cost: $175K-$195K. Recent comparable sales for fully renovated 3-bedroom homes in walkable Chestertown locations are selling in the $275K-$300K range. Your potential equity position: $80,000 to $125,000 upon completion. Multiple exit strategies. Flip after renovation for immediate profit. Hold as rental property serving Washington College market with strong rental history in the area. Owner-occupy and build instant equity while creating your ideal home. The location flexibility supports whatever investment strategy fits your goals. Property sold AS-IS. Serious buyers should conduct thorough inspections and due diligence. This is a renovation project, not a cosmetic update - price reflects condition and opportunity. Act quickly on clear value plays. Properties offering this equity spread in prime walkable locations move fast when priced correctly.

108 Pine St, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

Selling Office: Rosendale Realty.

2 Sassafras Cove Rd, Galena
$85,000
Welcome to Wilson Point Estates – Nestled in a peaceful, secluded setting, this exclusive community offers 14 generously sized lots with No Builder Tie-In but developer must approve the architectural appearance of the home. With each lot carefully placed to preserve the natural beauty and privacy of the landscape, Every residence will reflect quality craftsmanship, offering both comfort and style in a setting that feels miles away from it all yet is just minutes from Middletown , local marinas, and easy access to boating, fishing, and waterfront recreation.Surrounded by serene woodlands and scenic views, this is a place where tranquility and elegance come together, A true escape from the hustle and bustle of everyday life. Designed for those who value space, sophistication, and a strong connection to nature, This is your chance to build the home of your dreams and embrace the best of both worlds upscale living in harmony with nature.

2 Sassafras Cove Rd, Galena

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

Selling Office: Patterson-Schwartz Real Estate.

11200 Boyer Ln, Worton
$75,000
Tucked away on a quiet, winding lane, this scenic 2-acre property offers the perfect blend of privacy and possibility. Enjoy peaceful farm views out front and a wooded backdrop behind—about half an acre is already cleared and maintained lawn with the remaining 1.5 acre woods. The existing home can be removed to make way for your vision. While the current well and septic will need to be replaced, the groundwork has been laid for your future build. The perc test has already been completed and approved for a 3-bedroom home, saving you significant time and expense. Sellers had planned an addition (see survey), but a change in plans creates a great opportunity for the next owner. Ideally located just 10 minutes from Chestertown, 15 minutes to Betterton Beach, and 30 minutes to Middletown—enjoy the best of small-town charm with easy access to everyday conveniences. Buyers are encouraged to perform due diligence with the county to confirm building plans. If you’ve been searching for the right mix of location, privacy, and value in Kent County—with perc approval already in hand—this is it!

11200 Boyer Ln, Worton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Unrepresented.

32072 Shorewood Rd, Galena
$60,000
***PRICE REDUCED***Due to job transfer, owners must sell. Their loss your Gain! Build Your Dream Home in Shorewood Estates! Choose your own builder or pick up where seller's left off. This .69-acre elevated lot backs to woods and has passed perc test Looking for peace, quiet, and a true Eastern Shore lifestyle? Welcome to Shorewood Estates, a private water-oriented community on Swantown Creek off the Sassafras River. —perfect for your dream build. Their loss is your gain. Generations have grown up here thanks to the unbeatable lifestyle: 2 community beach areas, fishing pond, and a neighborhood dock with boat slips (lottery basis). Whether you love boating, Kayaking, fishing, or simply soaking in the natural surroundings, you’ll find it here. Enjoy the tranquility of a tucked-away community while staying within easy reach of shopping, dining, and healthcare. With a voluntary Civic Association of just $100/year, Shorewood offers incredible value and an authentic Eastern Shore experience. Don’t miss your chance to Live Where You Play—Bring your builder and start building memories today.

32072 Shorewood Rd, Galena

Listing courtesy of Integrity Real Estate. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

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