Kent County MD Homes For Sale

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...

Welcome to peaceful country living in this cozy 2-bedroom, 1-bath manufactured home. Nestled in a serene setting, this home offers several recent improvements. Major upda...

Second story, waterfront condo in historic Chestertown. Private boat slip. Many more details and pictures to come. Stay tuned! You won't want to miss this!

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is ...

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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Waterfront living on Grays Inn Creek, just five minutes from Rock Hall. Situated on a private half-acre lot with protected western-facing views, this home offers beautifu...

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...

Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally wel...

Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This downtown Chestertown diamond in the rough offers strong ARV potent...

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...

Discover a remarkable investment opportunity in Kent County with this charming 3-bedroom, 2-bathroom manufactured ranch-style home, built in 2006. Spanning 1,680 sq. ft. ...

SELLER WELCOMES ALLREASONABLE OFFERS! Discover easy one-level living at this three-bedroom, two-bath ranch home located in Galena’s Sassafras subdivision. Set on a cleare...

Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car ...

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

Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

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...

This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on .31 acres, ...

Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added...

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...

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 Chestertown. The pro...

This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light,...

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026, 10:00 AM. Bidding ends 99/28/2026, 1:00 PM. The ...

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...

Nestled in the charming WORTON subdivision, this delightful ranch-style home, built in 2020, offers a perfect blend of modern comfort and inviting warmth. With 1,144 squa...

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

Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch be...

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 ...

Waterfront condo in Rigbie Bluff with elevated, unobstructed waterfront views! This second-floor unit offers two levels of comfortable living with beautiful Chesapeake Ba...

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...

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is ...

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renov...

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...

Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with...

Seller is super motivated and may have found their next home so this must go! All offers welcomed! Home recently appraised for $501,000. Welcome to 16 Howell Point Road...

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...

Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bat...

Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Che...

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...

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 location offers excelle...

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 ...

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 access to the Chester ...

Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0...

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 your dream home in Worton, MD! This stunning center hall Colonial-style property boasts 4 bedrooms, 2.5 bathrooms, and sits on over 6 acres of picturesque land...

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...

Welcome to 20714 Wilkins Avenue, a rare opportunity in the heart of charming Rock Hall. Perfectly positioned less than two blocks from the beach, this home is within walk...

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...

Charming historic home offers 6 bedrooms and plenty of space to make your own. Located in the quaint village of Still Pond, it combines timeless character with modern upd...

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 ...

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. E...

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...

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square ...

*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 ...

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in ...

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington Col...

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 10/6/2026, 10:00 AM. Bidding ends 10/8/2026, 12:45 PM. The ...

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/6/2026, 10:00 AM. Bidding ends 10/8/2026, 12:50 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...

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/2/2026, 10:00 AM. Bidding ends 10/6/2026, 12:40 PM. The ...

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...

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/1/2026, 10:00 AM. Bidding ends 10/5/2026, 12:00 PM. The ...

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...

Imagine building your dream luxury waterfront home on one of the most spectacular homesites the Chesapeake Bay has to offer. This exceptional waterfront lot boasts breath...

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...

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, f...

Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades inclu...

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!

Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Ba...

Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven ...

Warm and Welcoming 3-Bedroom Colonial with a Private Backyard and spacious primary suite. Come home to the comfort and charm of this inviting 3-bedroom, 2.5-bath Colonial...

Build your dream home in Little Neck Farm! Lot #30 is a spacious residential property on Hagy Road with a deeded deep-water boat slip. The future home site offers beautif...

****NEW PATH TO WATER FOR YOUR GATOR OR UTV**** This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself,...

Brand-new construction in the Crosby Woods Subdivision! This beautifully designed 3-bedroom, 2-bathroom home offers comfortable one-level living on a private 0.835-acre l...

Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, rece...

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportuni...

FEELING LUCKY? HERE IS YOUR CHANCE! 106 Acre Recreational Farm surrounded by woods offers a unique lifestyle for Hunting, Fishing, Horses. 26 ac grain farm plus acres o...

Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywa...

FEELING LUCKY? WELL STEP UP, THIS IS YOUR CHANCE! BIG BUCK FARM * GEESE * DUCKS & GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy awaits Surrounded by w...

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, lo...

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportu...

Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed ...

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the he...

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly posi...

Unique opportunity to expand or start your business just minutes from the Eastern Shore thoroughfares of Routes 301 and 213 and also just outside of downtown Chestertown....

Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The ...

Welcome to Wymont Park, a sought-after waterfront community on picturesque Still Pond Creek, where every day feels like a vacation on Maryland's Eastern Shore. From sippi...

Discover the possibilities on this beautiful 4+ acre parcel. Recently surveyed, with water and sewer allocations paid, a value exceeding $16,000! This property offers a ...