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139 Prospect St, Chestertown
$195,000
3 Beds ⋅ 1 Baths
Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.

139 Prospect St, Chestertown

Listing courtesy of Redfin Corp. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

423 Calvert St, Chestertown
$190,000
3 Beds ⋅ 2 Baths
Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely updated with all new fixtures and finishes. The main level offers ample living space, dinging room and new kitchen and laundry. Upstairs you will find three bedrooms and a full bathroom, with access from the primary bedroom as well. Outside, enjoy a newly fenced backyard, updated shed, and an extra-deep lot offering the potential for additional rear parking. A new roof installed in 2024 adds even more value and peace of mind. Boasting generous space and extensive upgrades throughout, this home presents an exceptional opportunity for a primary residence, weekend getaway, or investment property. Ideally located just moments from downtown shopping, dining, and the waterfront, you’ll love the walkable lifestyle and charm that Chestertown has to offer.

423 Calvert St, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

Lot 9 Prestwick, Chestertown
$185,000
Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.

Lot 9 Prestwick, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

31695 Olivet Cir, Galena
$182,000
3 Beds ⋅ 2 Baths
Welcome Home to 31695 Olivet Circle, this 3 bedroom 2 bath home is a great started home! Beautiful property with lots of possibilities! Off the beaten path & surrounded by nature with a detached garage.

31695 Olivet Cir, Galena

Listing courtesy of RE/MAX Chesapeake. Contact:

Selling Office: Unrepresented.

21324 Persimmon Dr, Chestertown
$175,000
2 Beds ⋅ 1 Baths
Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this beautifully updated townhome checks all the boxes. Don't miss your opportunity to own this hidden gem!

21324 Persimmon Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Douglas Realty LLC.

144 Prospect St, Chestertown
$165,000
2 Beds ⋅ 2 Baths
Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra lot, currently used for parking, but could also possibly be built on. Buyer to verify with county

144 Prospect St, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Execuhome Realty.

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.

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..

6124 Tolchester Rd, Rock Hall
$150,000
2 Beds ⋅ 1 Baths
Property is being sold "As Is". Needs a major rehab.

6124 Tolchester Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

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.

7224 Rock Hall Rd, Rock Hall
$146,000
Discover the charm of Kent County’s rural lifestyle on this fenced, 2.15-acre cleared lot. Perfectly situated along Rock Hall Road, the property features an existing two-car garage, a 6’x8’ storage shed, and mature trees framing vast pastoral views. With electric service and an existing well already in place, it’s ready for your vision—whether that’s building your dream home, creating a weekend retreat, or simply enjoying open space. Come see the peaceful setting and possibilities this property offers. Now perc approved!

7224 Rock Hall Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Cross Street Realtors 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.

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.

Black Bottom Road, Galena
$105,000
Need to get away from it all? 10 acres of privacy! Located in rural Kent County MD. but close to Rt. 301, Middletown Delaware and all that Maryland's Eastern Shore has to offer. Perfect place to build your dream home, hunting cabin, family compound. Heavily wooded and abutting vacant land owned by the state of Maryland Dept. of Natural Resources. Residential zoning. Boundary survey has been completed and corners are marked..

Black Bottom Road, Galena

Listing courtesy of BHHS Fox & Roach - Hockessin. Contact:

Selling Office: RE/MAX Associates - Newark.

21447 E Sharp St, Rock Hall
$105,000
3 Beds ⋅ 1 Baths
Major Rehab or Tear Down - bring your ideas

21447 E Sharp St, Rock Hall

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors 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.

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.

First Avenue, Betterton
$75,000
PRICE REDUCTION!! Wonderful lot in Betterton, only 2 blocks from the beach, and your chance to make wonderful memories in this community known as the "Jewel of the Chesapeake". Betterton sits right on the upper Chesapeake Bay at the mouth of the Sassafras River, an extremely popular boating area. The beach is beautiful with calm waters and amenities for a perfect day at the beach. This community is certainly a treasure and one of the areas best kept secrets! Don't miss out on your chance to build your dream home in one of the best little spots in Maryland! Water/Sewer Allocation is available through the town.

First Avenue, Betterton

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

Still Pond Creek Rd, Worton
$70,000
The last buildable lot in the Cheerful Echoes neighborhood is perc approved and ready for improvement. NO HOA! With a gentle slope and plenty of room for the backyard of your dreams, a walkout lower level can open to a patio, gardens, etc... you name it! Just a few miles from the Worton Community Center and the walking trails at Worton Park, and a convenient drive to Chestertown, Middletown, and points beyond.

Still Pond Creek Rd, Worton

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

Selling Office: EXP Realty, LLC.

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.

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.

21447 E Sharp St, Rock Hall
$50,000
3 Beds ⋅ 1 Baths
House with public water and sewer needs major renovation or tear down and replace with new home.

21447 E Sharp St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

21183 W Sharp St, Rock Hall
$45,000
Vacant lot in the town of Rock Hall.

21183 W Sharp St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

Allens Lane, Rock Hall
$39,000
Welcome to your slice of country solitude! This wooded 1-acre lot comes with a sewer allocation already in place so no septic headaches here. You’ll just need to add a well… unless, of course, you discover one hiding on the property. (The county has no records, but there’s an old house/structure tucked in the trees, so who knows what secrets it holds.) The sewer is serviced by a grinder pump, so when it’s time to connect, you’ll need to purchase the pump and pay the associated hookup fees. For the detail-oriented: This exact address is: Map 51. Grid 4A. Parcel 321. This should not be confused with Parcel 85 next door (the one with the trailers). The GIS map still needs updating, so don’t be surprised if the online version looks a little flip-flopped. The county currently charges a $95.72/quarter Vacant Lot Fee to maintain your sewer allocation until you’re ready to build but be sure to call and verify. When it's all said and done, picture this: you wrap up work, hop in the car, and within minutes you’re cracking into steamed crabs at Waterman’s Crab House, grabbing drinks at Harbour Shack, or watching the sunset from Blue Heron Oyster House & Inn. If you’re feeling adventurous, Passages Bar & Grill and a few other local spots are just around the corner. And for the water lovers? Marinas, winding creeks, and public landings are all nearby with Allen’s Landing only three minutes away. Launch the boat, drop a crab pot, or just breathe in that salty breeze. This is what “living close to the water” really means. Bring your boots, your imagination, and maybe a sense of adventure because this isn’t just land, it’s a little mystery in the making. Use 5182 Harris Road. Rockhall, MD. to take you to the house right in front of the wooded lot. The wooded lot to the right of the trailers (do not park on their property) is the property. You can park on the street before the trailers. If you’re unsure who to call at the county, your agent can find the numbers in the Agent Remarks, or you can reach out to me directly and I’ll point you in the right direction.

Allens Lane, Rock Hall

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Unrepresented.

Chesterville Forest Rd Unit PARCEL 60, Millington
$34,000
Wooded, 0.4+ acre buildable lot on Chesterville Forest Rd with sewer allocation already paid—a $11,800 value! Buyer just needs to install a grinder pump and connect. Survey and setbacks included in documents for easy due diligence. Conveniently located near Rt. 301 for quick access north to Middletown, DE, or south to the Bay Bridge.

Chesterville Forest Rd Unit PARCEL 60, Millington

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

Selling Office: Doug Ashley Realtors, LLC.

Anglewood Road, Kennedyville
$18,000
This lot is being sold with MLS listing MDKE2005748, 13983 Turners Point Road. There are deed restrictions with this lot. This lot must be maintained . No structure is allowed. Ownership of this lot provides access to the community beach and amenities and right to join the Social Organization, Kentmore Park Improvement Association (KPIA).

Anglewood Road, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Unrepresented.

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.

Third Avenue, Betterton
$12,000
One acre in Betterton with the beach and boat ramp just a few blocks away! While this lot could be buildable, one would have to build a bridge across a stream to access by vehicle and public utilities while available would need to be run out there as well. Priced as recreational land for the nature enthusiast, occasional tent camper, or hunter.

Third Avenue, Betterton

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

Selling Office: Unrepresented.

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.

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