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Ranch Style Homes for Sale in Chestertown, MD

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  • 7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    /23

    $229,000

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    7415 Wilkins Ln, Chestertown, MD 21620

    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 features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    7415 Wilkins Ln, Chestertown, MD 21620
  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /25

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,096 Sq Ft

    222 Dutchess Rd, Chestertown, MD 21620

    Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    222 Dutchess Rd, Chestertown, MD 21620
  • 8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    /10

    $315,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8706 Elm Rd, Chestertown, MD 21620

    * SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * 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 water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, Chestertown, MD 21620
  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /25

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    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 property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space.The home

    Joseph A Zang III RE/MAX Chesapeake

    24775 Langford Rd, Chestertown, MD 21620
  • 7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    /37

    $455,000

    $23K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft

    7982 Radcliffe Rd, Chestertown, MD 21620

    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 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed

    Abigail Usilton Doug Ashley Realtors, LLC

    7982 Radcliffe Rd, Chestertown, MD 21620
  • 956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    956 Washington Ave, Chestertown, MD 21620
    /29

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    956 Washington Ave, Chestertown, MD 21620

    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 space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in

    Grace Crockett Doug Ashley Realtors, LLC

    956 Washington Ave, Chestertown, MD 21620
  • 10540 Tonopah Rd, Chestertown, MD 21620
    10540 Tonopah Rd, Chestertown, MD 21620
    10540 Tonopah Rd, Chestertown, MD 21620
    /21

    $269,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10540 Tonopah Rd, Chestertown, MD 21620

    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 private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

    Michele Palmer Doug Ashley Realtors, LLC

    10540 Tonopah Rd, Chestertown, MD 21620
  • 300 and 302 S Mill St, Chestertown, MD 21620
    300 and 302 S Mill St, Chestertown, MD 21620
    300 and 302 S Mill St, Chestertown, MD 21620
    /17

    $1,195,000

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    300 and 302 S Mill St, Chestertown, MD 21620

    Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 300 S

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    300 and 302 S Mill St, Chestertown, MD 21620
  • 104 Lincoln Dr, Chestertown, MD 21620
    104 Lincoln Dr, Chestertown, MD 21620
    104 Lincoln Dr, Chestertown, MD 21620
    /30

    $300,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    104 Lincoln Dr, Chestertown, MD 21620

    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, LVP flooring and a modern, neutral color palette that flows throughout. The crisp white kitchen keeps things light and timeless, while the spacious living room offers plenty of room to relax, gather and make the space your own.

    Crystal Smith RE/MAX Executive

    104 Lincoln Dr, Chestertown, MD 21620
  • 7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    /68

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,857 Sq Ft

    7828 Country Club Ln, Chestertown, MD 21620

    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 peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room

    Sarah King Cross Street Realtors LLC

    7828 Country Club Ln, Chestertown, MD 21620
  • 217 Edmore Rd, Chestertown, MD 21620
    217 Edmore Rd, Chestertown, MD 21620
    217 Edmore Rd, Chestertown, MD 21620
    /36

    $345,000

    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft

    217 Edmore Rd, Chestertown, MD 21620

    Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then.Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings.

    Michele Palmer Doug Ashley Realtors, LLC

    217 Edmore Rd, Chestertown, MD 21620
  • 216 Birch Run Rd, Chestertown, MD 21620
    216 Birch Run Rd, Chestertown, MD 21620
    216 Birch Run Rd, Chestertown, MD 21620
    /52

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    216 Birch Run Rd, Chestertown, MD 21620

    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 cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A

    Liddy Campbell TTR Sotheby's International Realty

    216 Birch Run Rd, Chestertown, MD 21620
  • 213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    213 Byford Dr, Chestertown, MD 21620
    /39

    $372,000

    $8K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,277 Sq Ft

    213 Byford Dr, Chestertown, MD 21620

    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. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other

    Grace Crockett Doug Ashley Realtors, LLC

    213 Byford Dr, Chestertown, MD 21620
  • 7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    /32

    $304,000

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

    7464 Shortall St, Chestertown, MD 21620

    Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy.The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    7464 Shortall St, Chestertown, MD 21620
  • 7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    /40

    $275,000

    • 3 Beds
    • 1 Bath
    • 975 Sq Ft

    7482 Poplar Ave, Chestertown, MD 21620

    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 privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite

    Lona Todd Taylor Properties

    7482 Poplar Ave, Chestertown, MD 21620
  • 8732 Elm Rd, Chestertown, MD 21620
    8732 Elm Rd, Chestertown, MD 21620
    8732 Elm Rd, Chestertown, MD 21620
    /22

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    8732 Elm Rd, Chestertown, MD 21620

    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 and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay,

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8732 Elm Rd, Chestertown, MD 21620
  • 896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    /34

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    896 Washington Ave, Chestertown, MD 21620

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

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    896 Washington Ave, Chestertown, MD 21620
  • 124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    /23

    $299,900

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

    124 Wilton Rd, Chestertown, MD 21620

    MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis

    Beth Green Doug Ashley Realtors, LLC

    124 Wilton Rd, Chestertown, MD 21620
  • 9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    /20

    $314,000

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,216 Sq Ft

    9126 Fairlee Rd, Chestertown, MD 21620

    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, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    9126 Fairlee Rd, Chestertown, MD 21620
Maryland Kent County

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