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Church Hill, Chestertown
$162,000
Fantastic opportunity to own over 5 acres of buildable, level farmland with two perc approval sites. AG Zoning allows a wide range of residential, outdoor recreational and commercial uses. Property recently surveyed with a custom site plan and ready for your building plans. Property backs to 60+ acre farm in a perpetual forest conservation easement. Right of ways from 213 and neighbors driveway allow two different access points to property. Entire property is tillable. No deeded covenants or restrictions. Easy access to Route 213, Chestertown, Church Hill and Centreville. AG Tax paid by current owner. Buyer to perform own due diligence. Do not enter property without an appointment.

Church Hill, Chestertown

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

Selling Office: RE/MAX Executive.

21316 Persimmon Dr, Chestertown
$160,000
2 Beds ⋅ 1 Baths
Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a nice view from the living room/patio area. NEW CARPET in living area/hallway on the main level and upstairs! Looks great! Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all electric with a washer/dryer located on the main level. Affordable, and the opportunity to express your own vibe and decorating skills. Call for more information.

21316 Persimmon Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Samson Properties.

132 Prospect St, Chestertown
$155,000
2 Beds ⋅ 1 Baths
Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the home’s Clean, Contemporary Feel. Major Updates Include a Brand New HVAC System (2026) and New Windows (2026) for Energy Efficiency, Much More! Relax on the Inviting Covered Front Porch and Enjoy a Truly Move-In Ready Home Designed to Impress.

132 Prospect St, Chestertown

Listing courtesy of ANR Realty, LLC. Contact:

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

107 Conley Dr, Chestertown
$150,000
3 Beds ⋅ 1 Baths
Purchase of opportunity thru rehab financing for completion of a new kitchen, painting and flooring . Call for details and will assist you with your dream of owning your own home.

107 Conley Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

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.

127 Wood Duck Ln, Chestertown
$135,000
3 Beds ⋅ 2 Baths
Well priced 3 bedroom, 2 bath double wide in Duck Neck, Queen Annes County situated on a half an acre and shed , man cave and car ports included. House has a metal roof. Close to the Chester River and minutes from Deep Landing and Chestertown. The property does need work, but some sweat equity would result in a really nice place! Property can be accessed on Wood Duck Lane or Snyder Lane. The Snyder Lane entrance has a circular drive.

127 Wood Duck Ln, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

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.

21324 Persimmon Dr, Chestertown
$112,500
2 Beds ⋅ 1 Baths
2 level townhome in sought after Tolchester Village! Features a terrific open kitchen with stainless steel appliances, nice living room/dining room combination with a slider to the patio. Bedrooms are good sized and have vaulted ceilings! Tolchester Village is a quaint community that underwent a complete renovation in 2021. Public water and sewer! Common areas include a playground. Affordable, beautiful, and low maintenance!!This property is being sold as-is, property is lender-owned and US Bank is making no representations or warranties.

21324 Persimmon Dr, Chestertown

Listing courtesy of Coldwell Banker Realty - Washington. Contact:

Selling Office: Benson & Mangold, 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.

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.

5700 Johnsontown Rd, Chestertown
$80,000
3 Beds ⋅ 1 Baths
Serene 2-acre partially cleared wooded lot with existing 1900-built home, in need of major repair or possible tear-down. Value is in the land. No interior access – partial roof and floor collapse. Sellers accept no liability and are held harmless. Property includes well and septic (buyer to verify), detached building and shed. Close to water and surrounded by peace and privacy. Sold as-is; buyer to conduct own due diligence.

5700 Johnsontown Rd, Chestertown

Listing courtesy of Tesla Realty Group, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

East Street, Chestertown
$75,000
This corner lot offers a rare opportunity to build just minutes from Downtown Chestertown. Located on a quiet street and close to the Chester River, this property combines a peaceful setting with everyday convenience. The lot is perc approved and has site plans—see documents for details. With close proximity to Chestertown’s shops, galleries, and restaurants, it’s the perfect setting for those looking to enjoy small-town living with easy access to Middletown, Easton, and Annapolis.

East Street, Chestertown

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

Selling Office: Doug Ashley Realtors, 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.

110 Prospect St, Chestertown
$55,000
3 Beds ⋅ 2 Baths
Investor Alert - Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The Spacious Kitchen, Living Areas and Bedrooms Provide Room to Breathe and Personalize. Head Out Back to Enjoy the Enclosed Rear Porch, Yard and a Convenient Storage Shed that offers Ample Space for Tools, Equipment, and More. This Home is Ready for Your Personal Touches. A Little Cosmetic Love will go a Long Way in Unlocking Serious Equity and Making this Property Truly Shine. Whether you're an Investor, Flipper, or Savvy First-Time Buyer Looking to Build Sweat Equity, This is the Opportunity You've Been Waiting For. Sold As-Is.

110 Prospect St, Chestertown

Listing courtesy of ANR Realty, LLC. Contact:

Selling Office: Samson Properties.

144 Char Nor Manor Blvd, Chestertown
$50,000
Invest in improving your quality of life with one of the last remaining homesites in Char Nor Manor, a water oriented community on the Chester River. At over a half acre, this allows space for many possibilities. Just across the street from the wetlands and river, this property embodies the Eastern Shore lifestyle. A soil evaluation has already been performed with favorable results. A buyer would need to get a property survey recorded to take the last steps for the perc approval. This community is located just minutes from the shops and restaurants of Chestertown and less than 2 hours from Philadelphia, Baltimore, and Washington DC.

144 Char Nor Manor Blvd, Chestertown

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

Selling Office: Berkshire Hathaway Homeservice Homesale Realty.

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.

Elm Road, Chestertown
$35,000
Water oriented community of Tolchester Estates. Public record says Montgomery but the correct address is Elm Road. Approved for sewer allocation. Please see recent survey in documents.

Elm Road, Chestertown

Listing courtesy of The Hogans Agency. Contact:

Selling Office: Kevin Dey Realty.

23628 Canvasback Rd, Chestertown
$25,000
Waterfront lot in the community of Chesapeake Landing, just outside of Chestertown. This lot has failed previous perc tests and is most likely not buildable.

23628 Canvasback Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

23698 L Rd, Chestertown
$15,000
Property record consists of two lots for a total of 2.6 Acres zoned Village. Please notify listing agent if you intend to walk the property.

23698 L Rd, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Unrepresented.

Elm Road, Chestertown
$13,000
One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by. County states water/sewer allocation is available. Buyer to confirm with due diligence.

Elm Road, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

Caulks Field Road, Chestertown
$11,000

Caulks Field Road, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Select Land & Homes, LLC.

206 Burchard Sawmill Rd, Chestertown
$9,000
Rare opportunity to own 1.05-Acre Vacant Land in Chestertown, MD! Located at 206 Burchard Sawmill Rd. Surrounded by natural beauty and close to local amenities, this lot provides both privacy and convenience. Don’t miss out on this rare chance to own land in historic Chestertown! The property sell AS IS. Buyer will need to verify zoning and utilities.

206 Burchard Sawmill Rd, Chestertown

Listing courtesy of XRealty.NET LLC. Contact:

Selling Office: Patterson-Schwartz Real Estate.

Lots 253-254 Carimon Road, Chestertown
$7,200
Kent County Health Dept has no record of perc

Lots 253-254 Carimon Road, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

Lot 24 & 25 Buck Neck, Chestertown
$5,000
Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek. Lot failed percolation Test in March of 1989.

Lot 24 & 25 Buck Neck, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

Sandpiper Road, Chestertown
$3,000
Recreational lot- access community amenities, bird watch, garden, make a trail, firewood, etc. Not buildable unless the county adds public sewer in the future. RVs are not permitted. Chespeake Landing has walking trails, community boat ramp, and a new restaurant at the marina to enjoy!

Sandpiper Road, Chestertown

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

Selling Office: Realty ONE Group Capital.

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