21

Kent County MD Homes for Sale with Basement

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  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    /63

    $1,799,000 Open House 5/31

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft

    21082 Wyoming Ave, Chestertown, MD 21620

    Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished basement is 1948. Additional guest house adds additional square footage, a kitchen/bath/sleeping area and living room. Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive renovation

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 883-5429

    21082 Wyoming Ave, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /24

    $299,900

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    117 N Water St Unit 3B, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /52

    $1,395,500 Open Sun 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    /106

    $845,000

    • 3 Beds
    • 2.5 Baths
    • 4,023 Sq Ft

    24576 Langford Rd, Chestertown, MD 21620

    HIGHFIELD ANNOUNCEMENT: SELLERS ARE MEETING THE MARKET WITH SUBSTANTIAL PRICE REDUCTION PLUS WILLING TO CONTRIBUTE $10,000 TO INSTALLATION of AIR CONDITIONING. HIGHFIELD, has been home to the renown architectural historian MichaelBourne and his family for almost forty-years. Mr. Bourne who authored theimportant Historic Houses of Kent County and guided the restorations of over400 historic

    Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
  • 11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    /66

    $679,000

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one unofficial bedroom in the basement,

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • 811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    /45

    $459,000

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft

    811 S Meadowview Dr, Chestertown, MD 21620

    Charming and Immaculately Maintained One-Level HomeStep onto the inviting front porch of this meticulously cared-for home, where every detail shines both inside and out. Featuring a thoughtful and spacious floor plan, this home offers a primary suite at one end and two additional bedrooms with a full bath at the opposite end for added privacy. In the heart of the home, you'll find a cozy living

    Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
  • 1 A Bayview Rd Unit 7A, Betterton, MD 21610
    1 A Bayview Rd Unit 7A, Betterton, MD 21610
    1 A Bayview Rd Unit 7A, Betterton, MD 21610
    /28

    $379,000

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    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, or

    Ashton Kelley Gunther-McClary Real Estate

    1 A Bayview Rd Unit 7A, Betterton, MD 21610
  • 12776 Still Pond Rd, Still Pond, MD 21667
    12776 Still Pond Rd, Still Pond, MD 21667
    12776 Still Pond Rd, Still Pond, MD 21667
    /67

    $379,000

    • 3 Beds
    • 1.5 Baths
    • 1,735 Sq Ft

    12776 Still Pond Rd, Still Pond, MD 21667

    Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    12776 Still Pond Rd, Still Pond, MD 21667
  • 1 Bayview Rd, Betterton, MD 21610
    1 Bayview Rd, Betterton, MD 21610
    1 Bayview Rd, Betterton, MD 21610
    /72

    $489,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    1 Bayview Rd, Betterton, MD 21610

    Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    1 Bayview Rd, Betterton, MD 21610
  • 314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    /47

    $514,500

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft

    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 your

    Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
  • 5135 Crosby Rd, Rock Hall, MD 21661
    5135 Crosby Rd, Rock Hall, MD 21661
    5135 Crosby Rd, Rock Hall, MD 21661
    /46

    $5,900,000

    • 6 Beds
    • 4.5 Baths
    • 4,214 Sq Ft

    5135 Crosby Rd, Rock Hall, MD 21661

    A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

    Courtney Chipouras TTR Sotheby's International Realty

    5135 Crosby Rd, Rock Hall, MD 21661
  • 5135 Crosby Rd, Rock Hall, MD 21661
    5135 Crosby Rd, Rock Hall, MD 21661
    5135 Crosby Rd, Rock Hall, MD 21661
    /46

    $5,900,000

    • 6 Beds
    • 4.5 Baths
    • 4,214 Sq Ft

    5135 Crosby Rd, Rock Hall, MD 21661

    A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

    Courtney Chipouras TTR Sotheby's International Realty

    5135 Crosby Rd, Rock Hall, MD 21661
  • 1 Kent Dr, Betterton, MD 21610
    1 Kent Dr, Betterton, MD 21610
    1 Kent Dr, Betterton, MD 21610
    /78

    $184,000

    • 2 Beds
    • 1 Bath
    • 658 Sq Ft

    1 Kent Dr, Betterton, MD 21610

    Charming Bungalow by the Bay!Discover the perfect coastal retreat in this delightful 2-bedroom bungalow, just one block from the beach! Nestled in a quaint town of only 283 residents, this home boasts beautiful hardwood ceilings, a screened front porch for relaxing evenings, and spacious back and side decks ideal for outdoor entertaining. The lower-level laundry and ample storage provide

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    1 Kent Dr, Betterton, MD 21610
  • 866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    /22

    $299,000

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

    866 Washington Ave, Chestertown, MD 21620

    Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

    Jeff Guthrie Cross Street Realtors LLC

    866 Washington Ave, Chestertown, MD 21620
  • 866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    866 Washington Ave, Chestertown, MD 21620
    /20

    $299,000

    • Studio
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

    Jeff Guthrie Cross Street Realtors LLC

    866 Washington Ave, Chestertown, MD 21620
  • 23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    /44

    $1,450,000

    • 3 Beds
    • 3.5 Baths
    • 4,446 Sq Ft

    23393 Cacaway Farm Ln, Chestertown, MD 21620

    **Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity**Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman-style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately150 feet of shoreline and a sandy beach, this property is a true waterfront gem.**Key Features:**- **Spacious Great Room**: Added in 2001,

    Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
  • 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
  • 26670 Maple Ave, Still Pond, MD 21667
    26670 Maple Ave, Still Pond, MD 21667
    26670 Maple Ave, Still Pond, MD 21667
    /46

    $230,000

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    26670 Maple Ave, Still Pond, MD 21667

    The listing includes 26670 Maple Avenue with a 1920 dwelling of 2024 SF on .54 acre of land as well as 26680 Maple Avenue dwelling of 1680 SF on .624 acre of land and a parcel of land 100 X 160. Both homes are in need of major repair; however, one will find potential. Final perc information for sewage system will be provided by Kent County Health Department when water table is acceptable which

    Debbie Meikle Doug Ashley Realtors, LLC

    26670 Maple Ave, Still Pond, MD 21667
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /3

    $375,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    Lovingly maintained, this charming home in Chestertown’s Historic District seamlessly blends classic character with modern comfort. Restored windows, original yellow heart pine floors, and cypress siding reflect its rich history, while newer appliances, a high-efficiency boiler, tankless on-demand hot water, 3-zone heating, and leaf filter system provide everyday ease. The third floor offers

    Casey Scattergood Cross Street Realtors LLC

    222 Mount Vernon Ave, Chestertown, MD 21620
Maryland Kent County

Homes for Sale with Basement in Kent County, MD

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