72

Kent County MD Houses for Sale

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  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $529,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home!Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 12035 Galena Rd, Massey, MD 21650
    12035 Galena Rd, Massey, MD 21650
    12035 Galena Rd, Massey, MD 21650
    /50

    $419,900

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    12035 Galena Rd, Massey, MD 21650

    OPEN HOUSE September 6th from 1:00-3:00. Welcome to this Hidden Gem on 1.11 Acre! This custom built one-level home (2x6 walls) features a partial open floor plan with 3 bedrooms and 2 full bathrooms, offering the ease and comfort of single-story living. Any outdoor enthusiast will appreciate the abundance of beautiful Scotch Pine wood from Finland on the walls, ceiling and a new Pelpro pellet

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 352-0002

    12035 Galena Rd, Massey, MD 21650
  • 390 Hurtt Ave, Millington, MD 21651
    390 Hurtt Ave, Millington, MD 21651
    390 Hurtt Ave, Millington, MD 21651
    /20

    $290,000

    • 3 Beds
    • 1.5 Baths
    • 1,982 Sq Ft

    390 Hurtt Ave, Millington, MD 21651

    Welcome to this charming Federal-style home, meticulously maintained and thoughtfully updated. As you step onto the inviting front porch and through the elegant double doors, you'll find a beautifully renovated interior. The kitchen boasts cherry cabinets, granite countertops, and stainless-steel appliances. The family room addition features a cozy wood-burning fireplace and built-in shelving.

    Agent Photo

    Demetra Rice

    Rice Premier Properties LLC

    (410) 724-1166

    390 Hurtt Ave, Millington, MD 21651
  • 396 Cypress St, Millington, MD 21651
    396 Cypress St, Millington, MD 21651
    396 Cypress St, Millington, MD 21651
    /106

    $350,000

    • 3 Beds
    • 2 Baths
    • 2,762 Sq Ft

    396 Cypress St, Millington, MD 21651

    Investment Opportunity and Motivated Seller! If you are searching for an opportunity to start or relocate your business with rental potential to offset your mortgage, your search is over. Live in one area and rent out the other two!! This income producer is located in the heart of Millington at the main intersection. With its flexible zoning, the property is well-suited for a blend of

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 705-7528

    396 Cypress St, Millington, MD 21651
  • 11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    /25

    $489,000

    • 4 Beds
    • 2 Baths
    • 2,156 Sq Ft

    11944 Augustine Herman Hwy, Kennedyville, MD 21645

    This classic home has been beautifully renovated and updated while maintaining the original charm. Enjoy cooking meals in the gourmet kitchen with stainless steel appliances, double wall oven and downdraft cooktop. The kitchen leads to the formal dining room and large open living space, perfect for entertaining. There are four bedrooms, two full bathrooms, and a third-floor bonus room, which

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 892-1081

    11944 Augustine Herman Hwy, Kennedyville, MD 21645
  • 7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    /33

    $797,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    7514 Muirfield Dr, Chestertown, MD 21620

    Beautiful home in a prime location! Prestwick offers ample privacy while only a short distance from Historic District Chestertown and just off of the Chester River Yacht and Country Club's 10th tee. Recently constructed in 2023, the house offers three bedrooms, oak floors throughout, a gourmet kitchen, and ample room for entertaining, all on one floor! The kitchen was completed with stainless

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 206-3727

    7514 Muirfield Dr, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /71

    $2,750,000 Coming Soon

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper,

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 23620 Land's End Rd, Chestertown, MD 21620
    23620 Land's End Rd, Chestertown, MD 21620
    23620 Land's End Rd, Chestertown, MD 21620
    /30

    $4,850,000

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Land's End Rd, Chestertown, MD 21620

    80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

    Stacy Kendall

    23620 Land's End Rd, Chestertown, MD 21620
  • 515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    /37

    $509,900

    • 4 Beds
    • 2 Baths
    • 2,220 Sq Ft

    515 N Kent St, Chestertown, MD 21620

    Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming

    Jody Baker Cross Street Realtors LLC

    515 N Kent St, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $795,000

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft

    200 Washington Ave, Chestertown, MD 21620

    This early 20th C gem of a traditional "Four Square" has been a Chestertown STAND-OUT RESIDENCE since originally crafted by acclaimed master builder Walter Pippin. The flawless flow of its' first floor, with discreet powder room, and the abundance of windows throughout make this corner home, with wrap-around porch, tended landscape and white picket fence an exceptional offering. Four bedrooms,

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
  • 103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    /90

    $595,000

    • 4 Beds
    • 3.5 Baths
    • 5,576 Sq Ft

    103 Adela Way, Chestertown, MD 21620

    Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, then look no further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. As you enter into the foyer with space up to the top floor, brightly lit with a chandelier and oak wood flooring you can access the formal dining room and the formal living room on each side. Moving

    Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
  • 7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    /18

    $635,000

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft

    7729 Country Club Ln, Chestertown, MD 21620

    Country Club Estates - Live Where You Play – Just 1.5 Miles from Downtown Chestertown!Enjoy the ease of one-level living in a prime location near the Chester River Yacht & Country Club, where club members enjoy golf, poolside afternoons, and clubhouse dining are just a short walk away. The interior spanning 2,280 square feet offers a comfortable, continuous flow that makes everyday living

    Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $440,000

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft

    907 N Meadowview Dr, Chestertown, MD 21620

    Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The eat-in kitchen provides plenty

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
  • 10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    /20

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    10165 John Carvill Rd, Chestertown, MD 21620

    Beautiful Brick Rancher in Great Oak Estates – Chestertown, MDNestled on 1.33 acres in the desirable Great Oak Estates community, just a short walk or golf cart drive to Safe Harbor Great Oak Landing marina, restaurant and golf course. This spacious 2,700 sq. ft. brick rancher blends timeless craftsmanship with classic Eastern Shore charm. Built with solid construction, the home features

    Daniel Hercher Chesapeake Real Estate Associates, LLC

    10165 John Carvill Rd, Chestertown, MD 21620
  • 251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    251 Devon Dr, Chestertown, MD 21620
    /54

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,935 Sq Ft

    251 Devon Dr, Chestertown, MD 21620

    Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula

    Debbie Meikle Doug Ashley Realtors, LLC

    251 Devon Dr, Chestertown, MD 21620
  • 26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    /15

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    26933 Mallard Rd, Chestertown, MD 21620

    Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
  • 201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    /23

    $470,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    201 Birch Run Rd, Chestertown, MD 21620

    This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /22

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a New Encapsulated Crawl Space, New Roof with 50-year shingles and a transferable warranty, new water and sewer lines

    Stacy Kendall Cross Street Realtors LLC

    101 Birch Run Rd, Chestertown, MD 21620
  • 21424 Catholic Ave, Rock Hall, MD 21661
    21424 Catholic Ave, Rock Hall, MD 21661
    21424 Catholic Ave, Rock Hall, MD 21661
    /21

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,247 Sq Ft

    21424 Catholic Ave, Rock Hall, MD 21661

    Welcoming to the newly renovated 21424 Catholic Ave! Situated on a large in-town parcel, the largest residential lot on Catholic Ave. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT and engineered hardwood flooring. The welcoming living space contains original wood accents, adding much charm to this newly updated home. There are three bedrooms,

    Lynn Hilfiker Gunther-McClary Real Estate

    21424 Catholic Ave, Rock Hall, MD 21661
  • 11960 Flour Mill St, Kennedyville, MD 21645
    11960 Flour Mill St, Kennedyville, MD 21645
    11960 Flour Mill St, Kennedyville, MD 21645
    /53

    $539,000

    • 7 Beds
    • 5 Baths
    • 3,136 Sq Ft

    11960 Flour Mill St, Kennedyville, MD 21645

    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 bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    11960 Flour Mill St, Kennedyville, MD 21645
  • 31569 Jim Davis Rd, Galena, MD 21635
    31569 Jim Davis Rd, Galena, MD 21635
    31569 Jim Davis Rd, Galena, MD 21635
    /3

    $529,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 2,660 Sq Ft

    31569 Jim Davis Rd, Galena, MD 21635

    COMING SOON!!!!Spacious 5-Bedroom Raised Ranch on 2 acres with Inground Pool, Pole Barn & Transferable Leased Tesla Solar Panels.Welcome to your country retreat just minutes from Route 301 and Delaware Shopping... This 5-Bedroom, 2.5 Bath raised ranch offers the perfect blend of comfort, convenience, efficiency and outdoor living.Inside, bedrooms located on the main level for easy

    Lori Cichocki-Leonardi Remax Vision

    31569 Jim Davis Rd, Galena, MD 21635
  • 5829 N Main St, Rock Hall, MD 21661
    5829 N Main St, Rock Hall, MD 21661
    5829 N Main St, Rock Hall, MD 21661
    /12

    $465,000 Coming Soon

    • 3 Beds
    • 4 Baths
    • 1,264 Sq Ft

    5829 N Main St, Rock Hall, MD 21661

    More information and photos coming soon! Fully renovated, spacious home with commercial or residential zoning use. Extensive upgrades, all new appliances, bathrooms, engineered hardwood floors, hardiplank exterior, and much more! This home has been tastefully finished with high-end new and selective antiques, echoing a coastal antique style. 3 bedrooms, each with an en-suite full

    Lynn Hilfiker Gunther-McClary Real Estate

    5829 N Main St, Rock Hall, MD 21661
  • 25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    /31

    $485,000 Open Sat 10:30AM - 12:30PM

    • 3 Beds
    • 2 Baths
    • 2,162 Sq Ft

    25800 Collins Ave, Chestertown, MD 21620

    Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
  • 100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    /2

    $515,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft

    100 Adela Way, Chestertown, MD 21620

    Preparing for Market- Don't miss this. Stunning and well maintained home on a corner lot with fenced yard, finished basement, sauna room, private office and 2 car garage. Recently replaced: HVAC, Roof and Water Heater. More details to come- On Market by Sept 15, 2025.

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
  • 228 Phelps Ave, Galena, MD 21635
    228 Phelps Ave, Galena, MD 21635
    228 Phelps Ave, Galena, MD 21635
    /49

    $329,000

    • 4 Beds
    • 1.5 Baths
    • 1,720 Sq Ft

    228 Phelps Ave, Galena, MD 21635

    Nestled on a spacious corner lot in the heart of Galena, this historic American Four Square blends timeless character with modern updates. Known for its barn-style outbuildings—perfect for storage, workshop space, or future restoration—this property offers both charm and functionality.Outdoor living is at its best with a beautifully restored in-ground swimming pool, ideal for entertaining

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    228 Phelps Ave, Galena, MD 21635
  • 13699 Still Pond Rd, Still Pond, MD 21667
    13699 Still Pond Rd, Still Pond, MD 21667
    13699 Still Pond Rd, Still Pond, MD 21667
    /55

    $1,100,000

    • 4 Beds
    • 2.5 Baths
    • 4,504 Sq Ft

    13699 Still Pond Rd, Still Pond, MD 21667

    Endless Possibilities on 20 Rolling Acres at Dawnwood Farm — Discover the magic of Maryland’s Eastern Shore at this captivating 20-acre farmstead, where heritage charm meets modern comfort. Whether you're a dreamer, a doer, or a little of both, this property offers something extraordinary for every kind of buyer—from adventure-seeking families and aspiring homesteaders to seasoned growers and

    Liddy Campbell TTR Sotheby's International Realty

    13699 Still Pond Rd, Still Pond, MD 21667
  • 5648 S Main St, Rock Hall, MD 21661
    5648 S Main St, Rock Hall, MD 21661
    5648 S Main St, Rock Hall, MD 21661
    /36

    $395,000

    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft

    5648 S Main St, Rock Hall, MD 21661

    Welcome to 5648 S. Main Street, a charming, original Rock Hall home. The owners took great care to throughly update the home over the years, and preserve the original style. The moulding was hand routed to match the original style of older homes in Rock Hall. Throughout the home the wood floors flow nicely with the wooden ceilings and custom built-ins. Downstairs, there is a full bathroom,

    Julia Hilfiker Gunther-McClary Real Estate

    5648 S Main St, Rock Hall, MD 21661
  • 10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    /50

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft

    10751 Millbrook Dr, Chestertown, MD 21620

    Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another

    Linda Austin Long & Foster Real Estate, Inc.

    10751 Millbrook Dr, Chestertown, MD 21620
  • 122 S Main St, Galena, MD 21635
    122 S Main St, Galena, MD 21635
    122 S Main St, Galena, MD 21635
    /25

    $255,000

    • 3 Beds
    • 1.5 Baths
    • 1,684 Sq Ft

    122 S Main St, Galena, MD 21635

    Come with vision and sweaty equity to make this sturdy home shine once again! Large deep lot with mature shade trees, paved driveway, and over-sized detached pull through 2 car garage. Home sold AS-IS, inspections for informational purposes only.

    John Carroll Village Real Estate Company LLC

    122 S Main St, Galena, MD 21635
  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $395,000

    • 4 Beds
    • 3 Baths
    • 2,630 Sq Ft

    23043 Bay Shore Spur, Chestertown, MD 21620

    Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, Chestertown, MD 21620
  • 7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    /26

    $305,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    7483 Shortall St, Chestertown, MD 21620

    Welcome to this inviting, move-in-ready rancher tucked away in a tranquil Chestertown setting. Offering three bedrooms and two full baths, the home showcases fresh paint, new flooring, sleek stainless steel appliances, and stunning Beechwood butcher block countertops. Natural light pours in through the Anderson windows, filling the home with warmth. Step outside to a spacious backyard designed

    Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
  • 24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, Chestertown, MD 21620
    24415 Chestertown Rd, Chestertown, MD 21620
    /29

    $279,900

    • 2 Beds
    • 1 Bath
    • 1,110 Sq Ft

    24415 Chestertown Rd, Chestertown, MD 21620

    Minutes from the heart of Chestertown and a short drive to Rock Hall, this 2-bedroom, 1-bath home offers the perfect balance of small-town convenience and peaceful countryside living. Inside, you’ll find warm hardwood floors and an unfinished basement—ideal for storage, a home gym, or even your future office space. Outside, the large, level yard provides plenty of room to garden, play, or simply

    Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
  • 24906 Lambs Meadow Rd, Worton, MD 21678
    24906 Lambs Meadow Rd, Worton, MD 21678
    24906 Lambs Meadow Rd, Worton, MD 21678
    /47

    $324,900

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    24906 Lambs Meadow Rd, Worton, MD 21678

    MOTIVATED SELLER!!! BRING ALL OFFERS. NEWLY RENOVATED (Summer-2025)! One of the largest lots in Kent County- NEARLY AN ACRE OF LAND. No HOA!!! This is your oasis home by THE WATER. MOTIVATED SELLER. GREAT OPPORTUNITY to own an UPDATED ALL BRICK rancher home with a fully finished basement ON .78 ACRES. You will enjoy this sun-lit, bright, airy 3-bedroom 2 bath detached home, WITH A FINISHED

    Pamela Dotson Norstar Realty LLC

    24906 Lambs Meadow Rd, Worton, MD 21678
  • 5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    /7

    $125,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    5700 Johnsontown Rd, Chestertown, MD 21620

    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

    Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
  • 108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    108 S Kent St, Chestertown, MD 21620
    /19

    $315,000

    • 1 Bed
    • 1.5 Baths
    • 936 Sq Ft

    108 S Kent St, Chestertown, MD 21620

    Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedroom, 1.5 bath home is in the center of town, within walking distance to the farmers market and all the shops and restaurants. Just 4 blocks from Chestertown's waterfront promenade. There is potential for a second bedroom upstairs. Adorable backyard. Perfect for one or two people as a full-time residence

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    108 S Kent St, Chestertown, MD 21620
  • 21384 E Sharp St, Rock Hall, MD 21661
    21384 E Sharp St, Rock Hall, MD 21661
    21384 E Sharp St, Rock Hall, MD 21661
    /22

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft

    21384 E Sharp St, Rock Hall, MD 21661

    Built in 1900 and thoughtfully renovated in recent years, this 3-bedroom, 2-bathroom colonial blends timeless character with modern updates. Situated on a 1/3 acre lot, it’s just a short walk to Rock Hall’s Main Street—perfect for enjoying local favorites like Fallfest, Pirates & Wenches Weekend, shops, and dining.Start your mornings on the screened-in front porch, sipping coffee and

    Robin Fithian Rock Hall Properties Real Estate

    21384 E Sharp St, Rock Hall, MD 21661
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $167,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    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

    Jeff Guthrie Cross Street Realtors LLC

    141 Prospect St, Chestertown, MD 21620
  • 866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    /34

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    This duplex is a prime investment located on Washington Avenue in historic Chestertown, Maryland, offering many amenities. It is within walking distance of shopping, entertainment, schools, and medical facilities. Unit A is freshly updated with a spacious living room and dining room. The kitchen offers lots of storage and a stackable washer/dryer. It is a 2-bedroom apartment with a full bath. The

    Kathleen Brenton Brenton Realty Group

    866 Washington Ave, Chestertown, MD 21620
  • 29341 Glencoe Rd, Kennedyville, MD 21645
    29341 Glencoe Rd, Kennedyville, MD 21645
    29341 Glencoe Rd, Kennedyville, MD 21645
    /10

    $995,000

    • 2 Beds
    • 1.5 Baths
    • 1,566 Sq Ft

    29341 Glencoe Rd, Kennedyville, MD 21645

    Nestled along the tranquil banks of the Sassafras River, this charming brick fixer-upper presents a rare opportunity to own a waterfront paradise. Imagine waking up to sweeping river views and sipping coffee from the expansive enclosed porch as the sun rises.Though the home requires renovating, its potential is undeniable. Offering over 1,500 sq ft of functional space, this 2-bedroom

    Christine Catalano Coldwell Banker Realty

    29341 Glencoe Rd, Kennedyville, MD 21645

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