Kent County MD Homes For Sale

Elegant Golf Course Living on Maryland’s Eastern shore. Experience the understated elegance of Eastern Shore living in this beautifully crafted, custom-built residence o...

Prime Commercial Opportunity in Chestertown!! The Brian E. Bainbridge Health Building is a prominent, three-story commercial property offers 23,000 square feet of versati...

This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square fe...

Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this ...

INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly...

Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of pote...

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in...

Close to the Beach, Restaurants, and Marinas in Rock Hall This well-loved and nicely cared-for solid brick rancher sits on a quiet street, offering the perfect blend of ...

Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of ...

Needs work. Sold as is

Enjoy the charm of country living in this 3-bedroom, 2-bath rancher situated on just over an acre in Massey! Offering convenient one-level living, this home has a rustic,...

Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen u...

Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community o...

Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,47...

Updated Home on .63 Acres with Village Zoning! Don’t let the one bedroom fool you! This charming, well-maintained home offers more than meets the eye, with numerous upda...

A Private Waterfront Retreat off Maryland’s Sassafras!!! Welcome to your own waterfront retreat and nature sanctuary, a private one-acre property designed around the wat...

Nestled in the serene enclave of Watermans Estates, this exquisite end-of-row townhouse offers a harmonious blend of contemporary design and luxurious living. Spanning 1,...

Nestled in the serene Georgetown subdivision, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, set on a sprawling 4.76-acre lot that...

Selller has made a Major price reduction to move this propperty! Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! C...

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country ...

WELCOME TO THE EASTERN SHORE! | 5.46± ACRES | MILLINGTON, KENT COUNTY, MARYLAND Discover the beauty and peaceful charm of Maryland’s Eastern Shore with this beautiful 5....

The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintai...

Discover the Charm of Kinnairds Point in this beautiful mid-century modern home. A sloping, wooded wonderland just minutes from historic Chestertown, this inviting and en...

Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-st...

Welcome to this lovely Cape Cod-style, four-bedroom, two-full-bath home situated on .98 acre in Rock Hall, where comfortable living, peaceful surroundings, and the relaxe...

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the fi...

Just a 2 blocks from Rock Hall Harbor which accesses the Chesapeake Bay, this adorable Cape Cod is the retreat you’ve been dreaming of. Whether you’re looking for a peac...

5+/- acres of hunting or recreational land in Rock Hall! A 10' right-of-way appears to provide access from the left side of 21425 Berryman Rd. Currently walk-in access on...

Nice old home in Rock Hall located on Main Street that needs some TLC. 4 bedrooms, 2 1/2 baths, upgraded kitchen, bath, Florida room and rear deck. Maintenance free exter...

Exceptional custom live/work space located on 5 acres at the entrance of Rock Hall. Newly constructed in 2019. This home boasts a screened porch, open living space with h...

Classic home on South Main Street in the town of Rock Hall. Charming in-town farmhouse-style residence on a spacious lot, .36 acres, plus a large garage/ workshop with el...

New construction opportunity in Rock Hall with time to make it your own. The current plans feature a 1,650-square-foot ranch-style home with 3 bedrooms, 2 bathrooms, a fr...

Cleared 100 ft x 196 ft building lot with public water & sewer in the desirable Ferry Park area of Rock Hall. The lot has an existing 10' x 20' storage shed on the proper...

Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two ...

Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level...

Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's ...

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 ...

**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Ches...

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributin...

Build your Eastern Shore home on this .79-acre lot located within Rock Hall town limits, just two blocks from Rock Hall Harbor and close to Haven Harbour and Swan Creek. ...

A rare opportunity near the Chesapeake Bay! Bring your vision to life in the charming waterfront community of Betterton. This Victorian-style home offers over 2,068 sq. f...

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Fully finished basement. Plenty of parking. A great place for a centrally loc...

Welcome to 331 Devon Drive in Family friendly Coventry Farms. With 4 bedrooms and 3.5 bathrooms, this recently updated and meticulously maintained Colonial home offers e...

This former West Marine commercial property, constructed in 2001, presents a compelling investment opportunity in a rural location, characterized by its solid constructio...

10k BONUS OFFER!!! NEW CONSTRUCTION in the charming Eastern Shore town of Rock Hall! This beautiful Colonial-style home offers the perfect blend of modern construction, c...

Nearly 4 acres of privacy and natural beauty tucked away down a quiet, secluded road just outside the charming town of Galena. This wooded parcel offers favorable soils a...

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Histo...

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Ov...

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farm...

Welcome to 32050 River Road in Millington! This fully renovated brick ranch-style home offers the perfect blend of modern updates, comfortable living, and peaceful countr...

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunnin...

Ranch style home offering plenty of parking, three bedrooms and two full baths and a lot of outdoor living space on decks and the covered front porch. Located at end of ...

Home Sweet Home. How Sweet it is! Rustic Log cabin 4 Bedrooms, 2Baths. Front and rear porches, In ground Pool, 3 Car detached garage, 24X 34 detached metal building. ...

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...

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Charming "TINY" house within quiet community of Worton off the main thoroughfare. Woods, public water and sewer, mature trees, deck with view of woods. One bedroom and ba...

Escape to Little Neck Farm, an exceptional 350-acre waterfront community on Maryland’s Eastern Shore, where natural beauty, privacy, and access to the Chesapeake Bay come...

Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportu...

This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buye...

Small detached dwelling on secluded .50 Acre lot. Property recently acquired through tax foreclosure. Seller has no knowledge of the property including condition of septi...

ONE-LEVEL LIVING IN GALENA—SELLER WELCOMES ALL REASONABLE OFFERS! This three-bedroom, two-bath ranch offers a practical layout, manageable homesite, and the opportunity t...

Impressive Masterpiece on Swantown Creek with 2 Boat Lifts! Exquisitely Crafted, the high quality upgrades have created an oasis for serenity, relaxation and entertainin...

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head ...

Nestled in charming Watermans Estates, this traditional duplex home offers a perfect blend of comfort and style. With 1,720 sq ft, the inviting interior features warm woo...

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property f...

Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and m...

Wooded building lot on Judefind Ave in Rock Hall town limits. No flood plain, no critical area, no wetlands. Water & sewer hook ups will be required. Lot is 75 ft wide by...

PRICE IMPROVEMENT!! Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown ...

**NEW PRICE! MOTIVATED SELLER WILLING TO CONSIDER BUYER CLOSING COST ASSISTANCE OR INTEREST RATE BUYDOWN!** Here's an opportunity worth a second look! With a fresh price ...

Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an op...

Recently Renovated Rancher with Inviting Outdoor Living! Welcome to 25213 Porters Grove Road in Worton, Maryland! This beautifully refreshed 3-bedroom, 2-full-bath ranch...

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesi...

Come make your home in Betterton - the Jewel of the Chesapeake - where the Sassafras meets the Bay! Small town charm makes this an especially beautiful place to live - ...

Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that ...

Nestled in a serene enclave, this exceptional 0.55-acre lot offers a rare opportunity to create your dream retreat, perfectly positioned just a block away from the tranqu...

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homes...

Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set on 3.5 acres in a private, peaceful setting and thoughtfully designed for bot...

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 ...

There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over...

Welcome to 21191 West Sharp Street - conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergon...

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for...

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this invitin...

SELLER-PAID 2-1 INTEREST RATE BUYDOWN AVAILABLE! Make homeownership more affordable with lower mortgage payments for the first two years! For example, based on an assumed...

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The ...

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its...

Significant price correction! Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within w...

Welcome to 25133 Smithville Rd.! This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features...

Major price reduction! Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town...

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet c...

Rare opportunity to acquire both the real estate and established business of Blue Heron Oyster House & Inn, a highly popular neighborhood restaurant in the heart of Rock ...

Price correction! Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy acce...

Enjoy the Eastern Shore as your weekend retreat at 8630 Elm Road. Calling all boaters, fishers, hunters, beachgoers, nature and recreation lovers, investors, and resident...

Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered fr...

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathroom...

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effor...

Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. ...

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a priv...

Adorable arts & craft style home with many upgrades and amenities. The original wood floors are warm and welcoming, wile the custom cabinetry and concrete countertops an...

Enjoy a long, secluded driveway to a 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Grey’s Inn Creek. The home features ...

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be s...

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Cheste...

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring ...

Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will apprec...

Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Cro...

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 11/9/2026, 10:00 AM. Bidding ends 11/11/2026, 12:30 PM. The...

*Open Every Tuesday and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring througho...

A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and s...

Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard of...

Beautifully updated while preserving its character, this charming home is ideally located just a short distance from the Rock Hall Harbor and Chesapeake Bay, offering eas...

Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with glea...

Unique opportunity to restore and customize the historic former "Rock Hall Shirt Factory!" This 5,558± sq. ft. building is situated on a 0.31± acre in-town lot and offers...

Rare opportunity to purchase five contiguous parcels totaling 3.765± acres in a prime location near Rock Hall Harbor. Parcel 505 features an older manufactured home situa...

321 West Street in Millington, Maryland is now available for you. This lovely 5-year-old home features vinyl siding, three bedrooms and 2 full bathrooms; Inside, you'l...

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natur...

Bring your vision to this rare 15-acre property offering privacy, natural beauty, and endless possibilities. Mostly wooded with a picturesque pond, this property is an id...

15.5 + Acres- Build, Hunt, or Escape! Enjoy approximately 15.5 acres of beautiful open land in a peaceful setting. Previously perced by the prior owner, this property of...

UPDATED HOME, 1.66 ACRES, public water and sewer, and NO HOA - ALL FOR $299,500! Discover the value of this beautifully updated 3-bedroom, 1.5-bath home. Featuring a BRAN...

Sweet corner property in downtown Rock Hall, right on the 4th of July parade route! Just two blocks from the Rock Hall Harbor/ Chesapeake Bay. A welcoming home with a spa...

Investment Opportunity Commercial and Mult- Family rentals - The current commercial space is being used for an antique store. Great location on corner lot. The parcels ...

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!