Kent County MD Homes For Sale

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 wes...

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...

This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updat...

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...

Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights. A diamond in the rough and ready for n...

Enjoy your own private waterfront access with a dock perfect for launching a canoe, kayak, or paddleboard. While the water at the dock is not deep enough for larger boats...

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...

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and East...

List Price is opening bid. Online Auction Only! Bidding begins Saturday, August 15 and ends Thursday, August 20, 2026 at 1:00 PM. Exceptional Multi-Family Investment Oppo...

Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attac...

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked ...

Welcome to your Eastern Shore oasis, an impressive nearly 3,700-square-foot home offering river access on almost 2 acres, a boat slip, stunning water views, and beautifu...

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...

Coming Soon in Rock Hall! Freshly renovated and ready to welcome you home. This property offers a bright new feel from the moment you step inside. Thoughtful updates and ...

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 ...

This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-pla...

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitch...

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable locatio...

Charming 3-bedroom, 2-bath rancher situated on a 0.4-acre lot in Ferry Park, just one block from Rock Hall Beach. This 1,458 sq. ft. home features an open-concept kitchen...

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...

Nestled in the charming Rock Hall community, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained resid...

Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure, recording is in process....

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/4/2026, 10:00 AM. Bidding ends 8/6/2026, 12:50 PM. The li...

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/4/2026, 10:00 AM. Bidding ends 8/6/2026, 1:00 PM. The lis...

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

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...

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, thi...

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/3/2026, 10:00 AM. Bidding ends 8/5/2026, 12:20 PM. The li...

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...

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathroom...

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...

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 8/11/2026, 10:00 AM. Bidding ends 8/13/2026, 11:40 AM. The ...

Welcome to 21128 Striper Run, a charming 3-bedroom, 2.5-bath home nestled in the heart of Rock Hall. Offering an exceptional opportunity to own in one of Maryland's most ...

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants...

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...

136 N Main St is Coming Soon in Galena! Your next home may be closer than you think. This inviting Colonial combines classic character with thoughtful updates across near...

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 ...

Wonderful location on the edge of Rock Hall. Property backs up to farmland. Watch the Fireworks from your backyard. Walk to downtown. Close to Landings,Marinas, and Resta...

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

Bring Your Best Offer! 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 celebra...

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...

This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to...

Welcome to Rigbie Bluff, where coastal charm meets modern comfort. This rare furnished 2-bedroom, 2-bath end-unit top floor condominium offers panoramic views of the uppe...

COMING SOON - NEW ROOF!!! Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjo...

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...

Charming home nestled on a spacious lot in the Rock Hall area. This property offers comfortable single-level living with a functional layout, generous outdoor space, and ...

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...

DOG DAYS OF SUMMER * DEER DAYS OF FALL ** 106 Acre Property, surrounded by woods offers a unique lifestyle for Hunting, Fishing, Horses. This peaceful setting offers yo...

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...

ONCE IN A LIFETIME BIG BUCK FARM PLUS GEESE, WOOD DUCKS AND GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy is found Surrounded by woods with a unique...

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...

Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, a...

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...

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 ...

This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a commercially zoned 2.6+/- parcel...

This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a 4 bedroom, 2.5 baths extremely we...

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 b...

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 ...

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of ...

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Eas...

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the...

Good as New. Renovated from top to bottom. Pictures say it all. On the outside we have a new roof, windows, and siding . Inside you will not have to do a thing exce...

Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all ...

✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic ho...

Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gentl...

This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the begi...

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the...

Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, t...

Versatile commercial property, featuring just over 23,000 sq ft of workshop and/or warehouse space on 6.71 acres. Conveniently located on 298, just over 30 minutes to Mid...

Versatile commercial property, featuring just over 23,000 sq ft of workshop and/or warehouse space on 6.71 acres. Conveniently located on 298, just over 30 minutes to Mid...

This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currentl...

Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter sp...

Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, t...

Rent Now. Buy Later. Qualified buyers have the opportunity to Rent with the Option to Buy, making homeownership possible while allowing additional time to prepare for clo...

Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully...

AMAZING PRICE REDUCTION! Open house on this very special home on July 11th. Sassafras Riverfront Retreat | Log cabin custom built home with Deep Water Pier, (seller had t...

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip.  3.55 acres, partly wooded, exceptionally landscap...

Spacious in-town home with coastal charm, just 1 block from the Rock Hall beach on the Chesapeake Bay!  This home offers a luxe front porch, as well as a screened-in porc...

Located on the upper Chester River in Millington, River Bend Lane offers the perfect blend of convenience and waterfront lifestyle just seconds from Route 301 for easy co...

Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing...

Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing...

Escape to the peace and quiet of the countryside with this beautiful private wooded 2-acre lot, tucked away down a secluded gravel lane. Offering a perfect blend of matur...

Unique opportunity offering two adjoining parcels with exceptional potential in Rock Hall. Parcel 1 consists of approximately 1.4 acres located on Geen Lane and is zoned ...

Tucked away on a peaceful 0.47-acre lot surrounded by trees, this custom-built contemporary home offers the kind of privacy and natural beauty that’s hard to find. From t...

WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, ...

Build your Eastern Shore getaway on this desirable in‑town lot in the heart of Rock Hall, just moments from marinas, waterfront dining, and all the charms of this beloved...

This nice wooded lot on Crosby Rd is 0.2 mile to Long Cove Marina and Long Cove County Landing. Rock Hall Yacht Club is just up the road on McKinleyville Rd. With 142 ft...

Situated at the end of a quiet dead-end street with only a handful of neighboring homes, this private 1/2 acre lot with a 1250 SF Rancher , 3 bedroom, 2 bath offers a se...

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...

Welcome to 5120 Eastern Neck Road—an exceptional opportunity to own a .50-acre homesite just outside the charming waterfront town of Rock Hall. Perfectly positioned for b...

Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtf...

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot wa...

This 10,000 SF commercial building presents a prime investment opportunity with significant investment potential. Located on an irregularly shaped parcel, the property of...

Amazing waterfront community on the Sassafras river. This Kentmore Park cottage was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement...

Two parcels combine for a total of 5.22 acres, offering a rare blend of space, versatility, and opportunity. The separate 3.21-acre parcel is perc-approved and buildable,...

Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC s...

Buyer's remorse means this house is again available at an amazing price! Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a l...