12,062

Kent, MD Homes

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  • /73

    $380,000 Sold Jul 30, 2025

    • 2,106 Sq Ft
    • $180/SF
    • 11 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1988

    10705 Millbrook Dr, Chestertown, MD 21620

    Nestled in the water-access community of Chesapeake Landing, this charming Cape Cod-style home offers a perfect blend of classic character and modern comfort. With over 2,100 square feet of finished living space, the home features four spacious bedrooms and three full bathrooms, ideal for flexible living arrangements. Inside, you’ll find a freshly painted bright and open layout with beautiful

    Adam Murphy RE/MAX Realty Centre, Inc.

    10705 Millbrook Dr, Chestertown, MD 21620
    • /21

      Est $246,155 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft

      4827 Piney Neck Rd, Rock Hall, MD 21661

      4827 Piney Neck Rd, Rock Hall, MD 21661
  • /31

    $485,000 Coming Soon

    • 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
  • /22

    $175,000 Sold Jul 25, 2025

    • 896 Sq Ft
    • $195/SF
    • 85 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    110 Philosophers Terrace, Chestertown, MD 21620

    Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.

    Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
    • /13

      Est $332,777 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      23399 Cloquet Rd, Chestertown, MD 21620

      23399 Cloquet Rd, 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
  • /28

    $362,500 Sold Jul 22, 2025

    • 1,600 Sq Ft
    • $227/SF
    • 41 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1989

    1 A Bayview Rd Unit 7A, Betterton, MD 21610

    Welcome to Rigbie Bluff Condominium! This is a rare opportunity for an end unit 2-bedroom condo to be available which offers breathtaking panoramic views of the Upper Chesapeake Bay and spectacular sunsets in the spring & summer. Enjoy waterfront living at its finest with your own boat slip, perfect for boating enthusiasts.Relax by the community pool, take advantage of private beach access,

    Ashton Kelley Gunther-McClary Real Estate

    1 A Bayview Rd Unit 7A, Betterton, MD 21610
    • /39

      Est $338,371 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft

      101 S College Ave, Chestertown, MD 21620

      101 S College Ave, Chestertown, MD 21620
  • /24

    $435,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,514 Sq Ft

    21055 Bayside Ave, Rock Hall, MD 21661

    Fabulous 4 Bedroom, 2 full Bath home with a detached 2 car garage has many unique features. It has a trex deck with a ramp that leads to the sliding glass door entrance of the sun room. First floor bedroom and full bath, large living room with open floor plan and separate laundry room. Second floor has plenty of space for guests. 3 bedrooms and full bath. Views of the Chesapeake Bay from

    Robin Fithian Rock Hall Properties Real Estate

    21055 Bayside Ave, Rock Hall, MD 21661
  • /9

    $190,500 Sold Jul 22, 2025

    • 882 Sq Ft
    • $216/SF
    • 50 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    619 Cannon St, Chestertown, MD 21620

    Buyer Financing fell through, so their loss is your gain! Ideally situated in Chestertown’s sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect

    Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
    • /12

      Est $317,995 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft

      203 Radcliffe Dr, Chestertown, MD 21620

      203 Radcliffe Dr, Chestertown, MD 21620
  • /2

    $360,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    5810 Clam Cove, Rock Hall, MD 21661

    Two new duplexes are currently under construction. These new homes will feature open, airy floorplans with 9 ft ceilings on the main floor and 8 ft ceilings on the second floor. There will be luxury vinyl plank flooring throughout the main living level, accompanied by warm and cozy wall-to-wall carpeting on the stairs and second floor. Energy-efficient features will include recessed LED lighting,

    Cindy Genther Rock Hall Properties Real Estate

    5810 Clam Cove, Rock Hall, MD 21661
  • /65

    $505,000 Sold Jul 21, 2025

    • 2,696 Sq Ft
    • $187/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1993

    207 Lee Ave, Galena, MD 21635

    Irresistible Cedar Retreat in Charming Galena, MD . Nestled on an acre. This is a must- see!Tucked away at the end of a quiet cul-de-sac in the picturesque town of Galena, this beautifullyupdated cedar home is the kind of property that buyers dream about, but rarely find. With itsinviting wood-burning fireplace, and sun-drenched open floor plan, every inch of this home radiates

    Kim Simpson Thyme Real Estate Co LLC

    207 Lee Ave, Galena, MD 21635
    • /36

      Est $927,996 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,352 Sq Ft

      9831 Breezecroft Ln, Chestertown, MD 21620

      9831 Breezecroft Ln, Chestertown, MD 21620
  • /3

    $360,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    5812 Clam Cove, Rock Hall, MD 21661

    Two new duplexes are currently under construction. These new homes will feature open, airy floorplans with 9 ft ceilings on the main floor and 8 ft ceilings on the second floor. There will be luxury vinyl plank flooring throughout the main living level, accompanied by warm and cozy wall-to-wall carpeting on the stairs and second floor. Energy-efficient features will include recessed LED lighting,

    Cindy Genther Rock Hall Properties Real Estate

    5812 Clam Cove, Rock Hall, MD 21661
  • /10

    $85,000 Sold Jul 18, 2025

    • Land
    • 0.80 Acre
    • $106,250 per Acre
    • 2 Days On Market

    0 Griffith Dr Unit MDKE2005256, Galena, MD 21635

    Build your dream home on 0.8 acres in the desirable Hunter's Run subdivision! This gorgeous parcel is located just a short distance from 213 and Route 301 making for a quick drive to the Sassafras River, local restaurants and marinas, Middletown, DE and Chestertown, MD! See documents for perc letter on file from 2020. Highlighted property lines that appear in the listing photos are approximate.

    Jason Zang RE/MAX Chesapeake

    0 Griffith Dr Unit MDKE2005256, Galena, MD 21635
    • /93

      Est $843,231 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 5,118 Sq Ft

      30741 Duck Puddle Rd, Kennedyville, MD 21645

      30741 Duck Puddle Rd, Kennedyville, MD 21645
  • /33

    $440,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    11779 Augustine Herman Hwy, Kennedyville, MD 21645

    This is the one you’ve been waiting for! With over 2,100 square feet of living space, this 4-bedroom, 2-bath home sits on a spacious half-acre lot and has all the room you need—inside and out. The layout is so functional, with three bedrooms and a full bath on the main level, plus an XL living room with a cozy gas fireplace and loads of natural light.The real showstopper? The entire

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    11779 Augustine Herman Hwy, Kennedyville, MD 21645
  • /18

    $205,000 Sold Jul 18, 2025

    • 1,216 Sq Ft
    • $169/SF
    • 24 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    310 Hilltop Ln, Chestertown, MD 21620

    Super clean, well-maintained and move-in ready! This charming 3-bedroom, 2.5-bath townhouse offers affordable, low-maintenance living. The main level features a bright kitchen, convenient half bath, in-unit laundry, a spacious living room, and an open dining area with sliding doors leading to a private patio and beautifully maintained common grounds. High Speed internet available. HOA covers lawn

    Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
    • /29

      Est $376,479 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,256 Sq Ft

      21053 Striper Run, Rock Hall, MD 21661

      21053 Striper Run, Rock Hall, MD 21661
  • /56

    $544,500 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    11307 Urieville Ln, Worton, MD 21678

    Your private retreat awaits! Nestled on nearly 4 acres in Worton, Maryland, this beautifully renovated Cape Cod offers the perfect blend of space, comfort, and functionality. Featuring four spacious bedrooms and two full bathrooms, this home is ideal for multi-generational living or a growing family with two main-level bedrooms and a full bath.Step inside to find new LVP flooring, brand

    Crystal Smith RE/MAX Executive

    11307 Urieville Ln, Worton, MD 21678
  • /39

    $350,000 Sold Jul 18, 2025

    • 1,080 Sq Ft
    • $324/SF
    • 29 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1900

    420 Cannon St, Chestertown, MD 21620

    Fabulous location in the Chestertown Historic District with lots of room for expansion among brand new luxury homes! 420 Cannon sits on a 5,000 square foot lot that fronts on historic Cannon Street and is surrounded by the new Cannon Square development. Enjoy it in comfort now with plenty of room for new equity over time: Maybe double the house? Add a first floor bedroom suite? A garage? (As

    Beth Ostrander Doug Ashley Realtors, LLC

    420 Cannon St, Chestertown, MD 21620
    • /27

      Est $275,074 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      316 Roosevelt Dr, Chestertown, MD 21620

      316 Roosevelt Dr, Chestertown, MD 21620
  • /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
  • /32

    $266,500 Sold Jul 18, 2025

    • 1,456 Sq Ft
    • $183/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    9 Belmont Place, Betterton, MD 21610

    Welcome to Honeysuckle Lodge at Betterton Beach. Tucked away on a private 1.4 acre partially wooded lot, this charming home is an easy stroll down the street to beautiful Betterton Beach - the best and biggest sandy, nettle-free Bayfront beach in Kent County. Other close-by amenities include a community park with tennis courts, basketball courts and a childrens playground, a community dock,

    Paula Ruckelshaus Long & Foster Real Estate, Inc.

    9 Belmont Place, Betterton, MD 21610
    • /30

      Est $477,639 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,304 Sq Ft

      105 S Kent St, Chestertown, MD 21620

      105 S Kent St, 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
  • /45

    $485,000 Sold Jul 18, 2025

    • 3,420 Sq Ft
    • $142/SF
    • 79 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2010

    314 Devon Dr, Chestertown, MD 21620

    Welcome to 314 Devon Drive in Chestertown—a beautifully designed 4-bedroom, 3.5-bath home where comfort meets style in every room. From the moment you step into the grand foyer, you’ll feel the openness and care that’s gone into every detail.The heart of the home is the spacious kitchen, featuring a large island that’s perfect for prepping meals, gathering with friends, or simply enjoying

    Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
    • /36

      Est $229,478 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,304 Sq Ft

      21010 Rock Hall Ave, Rock Hall, MD 21661

      21010 Rock Hall Ave, Rock Hall, MD 21661
  • /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
  • /17

    $365,000 Sold Jul 18, 2025

    • 1,626 Sq Ft
    • $224/SF
    • 202 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    5816 Clam Cove, Rock Hall, MD 21661

    Two new duplexes now complete and ready for new owners! These new homes feature open, airy floorplans with 9 ft ceilings on the main floor and 8 ft ceilings on second floor. There's luxury vinyl plank flooring throughout the main living level with warm and cozy wall-to-wall carpeting on the stairs and second floor. Energy efficient features incude recessed LED lighting, R-49 ceiling and R-22 wall

    Cindy Genther Rock Hall Properties Real Estate

    5816 Clam Cove, Rock Hall, MD 21661
    • /33

      Est $373,549 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft

      13037 Augustine Herman Hwy, Kennedyville, MD 21645

      13037 Augustine Herman Hwy, Kennedyville, MD 21645
  • /27

    $395,000

    • 3 Beds
    • 2 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
  • /48

    $335,500 Sold Jul 15, 2025

    • 1,680 Sq Ft
    • $200/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    5824 Clam Cove, Rock Hall, MD 21661

    Prepare for cuteness overload in the heart of Rock Hall! This charming property is nestled in an equally delightful town, just a short stroll from shops, restaurants, and the waterfront. You’ll fall in love with the timeless charm and inviting atmosphere of this cottage.Inside, the home features an open-concept living space, three generously sized bedrooms, and two and a half bathrooms,

    Johnice Comer Compass

    5824 Clam Cove, Rock Hall, MD 21661
    • /44

      Est $645,463 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,536 Sq Ft

      225 Washington Ave, Chestertown, MD 21620

      225 Washington Ave, 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
  • /40

    $1,100,000 Sold Jul 14, 2025

    • 4,148 Sq Ft
    • $265/SF
    • 2 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2005

    24196 Still Pond Neck Rd, Worton, MD 21678

    Think the beach without the crowds! Nestled in a secluded location along the Chesapeake Bay, this rare beach-style home offers the perfect coastal escape with a private sandy beach just steps from your door. Designed with a spacious and inviting floor plan, the home features soaring ceilings with exposed beams, wood floors, and a third-floor observation room that offers magical panoramic views of

    William Norris Select Land & Homes, LLC

    24196 Still Pond Neck Rd, Worton, MD 21678
    • /32

      Est $505,454 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,700 Sq Ft

      311 Mayfair Dr, Chestertown, MD 21620

      311 Mayfair Dr, 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
  • /20

    $310,000 Sold Jul 14, 2025

    • 1,056 Sq Ft
    • $294/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1977

    10490 Worton Rd, Worton, MD 21678

    Welcome to 10490 Worton Rd a beautifully renovated rancher nestled in the heart of Kent County. This 3-bedroom, 1-bath home was transformed in 2023 with thoughtful upgrades throughout. Enjoy peace of mind with a new roof, HVAC system, siding, windows, hot water heater, and more.Step inside to discover a stylish, living space featuring updated flooring, a modern kitchen with new

    Laura Anthony Benson & Mangold, LLC

    10490 Worton Rd, Worton, MD 21678

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