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Middlesboro, KY 1-Story Homes for Sale

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  • /20

    $399,000

    • 3 Beds
    • 3 Baths
    • 3,397 Sq Ft

    103 Kingsbury Woods Rd, Middlesboro, KY 40965

    Rare opportunity to own a premier golf course property on Hole #2 at the Middlesboro Golf Course—one of only four homes situated directly on the course. Perfectly positioned on a generous 0.67-acre lot, this spacious residence offers a grand total living space, including a finished basement, providing plenty of room to live, entertain, and relax. With three bedrooms and three full baths, the home

    Anthony Gigilo ListWithFreedom.com

    103 Kingsbury Woods Rd, Middlesboro, KY 40965
  • /3

    $50,000

    • 3 Beds
    • 1 Bath
    • 728 Sq Ft

    105 Nutwood Rd, Middlesboro, KY 40965

    3 bed, 1 bath fixer-upper in Middlesboro, KY! Great investment opportunity—flip, rent, or make it your own. City water/sewer (per public record). Priced for potential—bring your ideas!

    Megan Stanaford Black Diamond Realty

    105 Nutwood Rd, Middlesboro, KY 40965
  • /17

    $139,900

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    405 S 37th St, Middlesboro, KY 40965

    Looking for a home to raise your family? Don't let this one go by! Spacious 4 bedrooms, 2 bath home with a fenced in yard, this one is just the right size for a growing family. Just minutes from the hospital and schools, yet tucked away on a side street with little traffic. Let us show you your new home today! Schedule a showing before it's gone.

    Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

    405 S 37th St, Middlesboro, KY 40965
  • /27

    $104,900

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,240 Sq Ft

    816 W Chester Ave, Middlesboro, KY 40965

    Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

    James Martin Century 21 Pinnacle

    816 W Chester Ave, Middlesboro, KY 40965
  • /19

    $40,000

    $14K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,230 Sq Ft

    406 W Rochester Ave, Middlesboro, KY 40965

    Cottage style, 3 bedroom 2 bathroom home with chain link fencing in the city limits of Middlesboro KY. PVA records show 0.18 of an acre, city water, city sewer. Home needs some work but would make a great permanent home or use as a rental. Close to LMU and all the beauty Southeastern KY offers! 5 minutes to the Cumberland Gap National Park, shopping and more! Buyer to verify all property

    Megan Stanaford Black Diamond Realty

    406 W Rochester Ave, Middlesboro, KY 40965
  • /16

    $295,000

    $15K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,100 Sq Ft

    717 Highway 441, Middlesboro, KY 40965

    Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed

    Megan Stanaford Black Diamond Realty

    717 Highway 441, Middlesboro, KY 40965
  • /3

    $125,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,664 Sq Ft

    120 Redwood Rd Unit A & B, Middlesboro, KY 40965

    Great investment opportunity with this one. Built in 2000 per appraisal, this property offers a total of 1,664 square feet and is currently occupied by reliable, long-term tenants. Each unit features 2 bedrooms and 1 bathroom, providing comfortable living space for residents. The address, listed as 102 A&B Redwood Road, originates from a previous appraisal. The property is confirmed per the

    Megan Stanaford Black Diamond Realty

    120 Redwood Rd Unit A & B, Middlesboro, KY 40965
  • /18

    $135,000

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    2002 Winchester Ave, Middlesboro, KY 40965

    CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    2002 Winchester Ave, Middlesboro, KY 40965
  • /35

    $179,900

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,028 Sq Ft

    1200 W Chester Ave, Middlesboro, KY 40965

    Charming Home for Sale in Middlesboro, KY - 1200 W Chester Ave Welcome to this inviting home located in the heart of Middlesboro! Situated on a spacious corner lot at 1200 W Chester Avenue, this property offers comfort, convenience, and small-town charm—all in one. Comfortable living spaces with plenty of natural light. Functional kitchen with ample cabinet storage Generous yard—perfect for

    Megan Stanaford Black Diamond Realty

    1200 W Chester Ave, Middlesboro, KY 40965
  • /67

    $180,000

    $5K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 2,430 Sq Ft

    713 Exeter Ave, Middlesboro, KY 40965

    Welcome to the stunning 713 Exeter Ave located in the lovely town of Middlesboro KY, less than 5 minutes to downtown Middlesboro, 15 minutes from LMU, & super close to Norris Lake. This home makes a perfect residence for anyone looking in the area and would make a great rental property as well! This home offers ample space with 4 bedrooms on the main level and tons of potential for a loft or 2

    Victoria Allen Century 21 Virginia Wilder Real Estate

    713 Exeter Ave, Middlesboro, KY 40965
  • /30

    $279,900

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    127 Alpine Rd, Middlesboro, KY 40965

    This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    127 Alpine Rd, Middlesboro, KY 40965
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