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Price Reduced Homes for Sale in Middlesboro, KY

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  • /26

    $199,900

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,612 Sq Ft

    140 Wellington Dr, Middlesboro, KY 40965

    Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

    Janice Pratt Fathom Realty TN LLC

    140 Wellington Dr, Middlesboro, KY 40965
  • /45

    $279,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,032 Sq Ft

    400 Gloucester Ave, Middlesboro, KY 40965

    Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also

    Sheila Durham Coldwell Banker Bisceglia Real

    400 Gloucester Ave, Middlesboro, KY 40965
  • /47

    $175,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,168 Sq Ft

    8 Castleford Way, Middlesboro, KY 40965

    Welcome to 8 Castleford Way located in the beautiful subdivision Ambleside. This home is also conveniently located near National & state parks. This home includes a screened back porch and fenced backyard. Master Bed / Bath on main level of the home including the living room, kitchen, and laundry! Call or text today to schedule your showing!

    Victoria Allen Century 21 Virginia Wilder Real Estate

    8 Castleford Way, Middlesboro, KY 40965
  • /22

    $219,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,544 Sq Ft

    812 Worchester Ave, Middlesboro, KY 40965

    Isn't she lovely?! Located right in the middle of Middlesboro Ky. 4 bedroom 2 bath home with a beautiful kitchen! Yard space for all the things on a quiet street. Excellent home to check out today!

    Misti McGrath Realty Group

    812 Worchester Ave, Middlesboro, KY 40965
  • /34

    $149,000

    $26K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft

    64 Dunlap Hollow Rd, Middlesboro, KY 40965

    This home is turnkey and ready to move right in; it has been well maintained over the years. This home has 4 Bedrooms, 2 Full Baths, Dining Room and a Kitchen that comes with Range, Refrigerator, Dishwasher and Microwave plus the laundry room has a washer and dryer set that will stay with home. Step out the back door and just a few steps up the hill is a wonderful workshop and a storage shed.

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    64 Dunlap Hollow Rd, Middlesboro, KY 40965
  • /45

    $299,900

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,664 Sq Ft

    926 Doncaster Ave, Middlesboro, KY 40965

    Looking for a HOME and not just another house? This is it! With 5 bedrooms, 2 baths, a bonus room to use as a den or rec room, and even special features like a light equipped with a built-in blue tooth speaker in the master bathroom. This home was built with 'family living' in mind. The kitchen is equipped with a new island/breakfast bar that seats six and blends seamlessly with the dining area.

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    926 Doncaster Ave, Middlesboro, KY 40965
  • /15

    $155,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 792 Sq Ft

    815 Dorchester Ave, Middlesboro, KY 40965

    Welcome to Historic Middlesboro KY - Beautifully Renovated Home with Stunning Mountain Views! Situated on an easy-to-maintain 0.29-acre lot, this charming home in the heart of Middlesboro KY JUST MINUTES FROM ONE OF THE OLDEST GOLF COURSES--This House blends historic charm with modern updates. Enjoy breathtaking views of the Cumberland Mountains, Cumberland Gap National Park, and the iconic

    Lisa Stacy-Gibbs Backwoods Realty & Development

    815 Dorchester Ave, Middlesboro, KY 40965
  • /13

    $35,000

    $40K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 792 Sq Ft

    918 E Cumberland Ave, Middlesboro, KY 40965

    Old home needs work with an attached older home that needs to be torn down. Great Location on Cumberland Ave behind Food City

    Steve Mason REMAX PROFESSIONAL'S

    918 E Cumberland Ave, Middlesboro, KY 40965
  • /35

    $264,900

    $34K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,068 Sq Ft

    207 Arthur Heights, Middlesboro, KY 40965

    CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    207 Arthur Heights, Middlesboro, KY 40965
  • /4

    $21,000

    $4K PRICE DROP
    • Land
    • 7,492 Sq Ft
    • $122,093 per Acre

    109 Bloomsbury Ave, Middlesboro, KY 40965

    50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

    Megan Stanaford Black Diamond Realty

    109 Bloomsbury Ave, Middlesboro, KY 40965
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