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Middlesboro, KY Homes for Sale

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  • /16

    $74,200

    $6K PRICE DROP
    • 2,256 Sq Ft

    417-A&B Avondale Ave, Middlesboro, KY 40965

    Has the up stairs new flooring some new windows roof 7 years old hot water 7 years old new gutters with gutter guards. Bring your vision and bring this fixer upper back to life. Great duplex for rental or 2 families, Walking distances to everything. Live in one and rent one out. Check it out.

    Nancy Maiden Mountain Realty

    417-A&B Avondale Ave, Middlesboro, KY 40965
  • /5

    $15,000

    $5K PRICE DROP
    • Land
    • 5,662 Sq Ft
    • $115,385 per Acre

    118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965

    Unrestricted lot in a good location in Middlesboro. Has old home on the property that does not hold any value and would need to be disposed of.

    Michael Hensley REMAX PROFESSIONAL'S

    118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965
  • /2

    $15,000

    $5K PRICE DROP
    • Land
    • 5,488 Sq Ft
    • $119,048 per Acre

    205 Exeter Ave, Middlesboro, KY 40965

    Great lot, city utilities available.

    Megan Stanaford Black Diamond Realty

    205 Exeter Ave, Middlesboro, KY 40965
  • /3

    $35,000

    • Land
    • 14,853 Sq Ft
    • $102,639 per Acre

    2107 Winchester Ave, Middlesboro, KY 40965

    PRIME LOCATION, NO FLOOD ZONE! Discover the ultimate blank canvas within the city limits. This fully cleared, level, and build ready lot offers an exceptional opportunity to build your dream home, or next investment project. Situated entirely outside the FEMA flood zone, this lot offers peace of mind and reduced insurance costs. All city utilities are ready for connection. This lot would always

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    2107 Winchester Ave, Middlesboro, KY 40965
  • /13

    $455,000

    • 5 Beds
    • 4 Baths
    • 3,146 Sq Ft

    523 N 30th St, Middlesboro, KY 40965

    Spacious All-Brick Home with Attached Guest Quarters - Prime Location! This beautifully maintained, all-brick home offers exceptional flexibility and space, featuring a main residence with 3 bedrooms, 2 bathrooms, a bonus room perfect for a home office, rec room, or additional sleeping area, and two laundry rooms for added convenience.In addition, the property includes a fully separate,

    Beth Combs Turn Key Realty

    523 N 30th St, Middlesboro, KY 40965
  • /2

    $165,000

    $24K PRICE DROP

    4607 W Cumberland Ave, Middlesboro, KY 40965

    This is a great opportunity to own investment property or live in one unit and rent the other unit to make mortgage payment, each unit has 1 bedroom, 1 full bathroom, living room, eat-in kitchen and laundry area; each unit comes with range, refrigerator, washer and dryer. Apartments sit on level lot, paved driveway, public water and public sewer, each unit has a heat pump, decks have been stained

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    4607 W Cumberland Ave, Middlesboro, KY 40965
  • /13

    $75,000

    • 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
  • /15

    $135,000

    $7K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,404 Sq Ft

    708 W Chester Ave, Middlesboro, KY 40965

    Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.

    Michael Hensley REMAX PROFESSIONAL'S

    708 W Chester Ave, Middlesboro, KY 40965
  • /31

    $160,000

    $22K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    180 Stevenson Bridge Rd, Middlesboro, KY 40965

    Charming Rustic Cabin with Modern Comforts on 2 Acres Welcome to 180 Stevenson Branch Rd in Middlesboro, KY—where country charm meets convenience. Just minutes from historic downtown Middlesboro, you'll enjoy easy access to quaint shops, local restaurants, major retailers, medical offices, banks, and hospitals—all while savoring the serenity of rural living. Nestled on a hillside and surrounded

    Beth Combs Turn Key Realty

    180 Stevenson Bridge Rd, Middlesboro, KY 40965
  • /29

    $299,000

    • 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
  • /2

    $960,000

    • 2 Beds
    • 2 Baths
    • 6,696 Sq Ft

    508 & 512 Winchester Ave, Middlesboro, KY 40965

    Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to

    Beth Combs Turn Key Realty

    508 & 512 Winchester Ave, Middlesboro, KY 40965
  • /4

    $25,000

    • Land
    • 7,492 Sq Ft
    • $145,349 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
  • /2

    $182,000

    • 2 Beds
    • 2 Baths
    • 1,608 Sq Ft

    414 S 24th St, Middlesboro, KY 40965

    Prime commercial opportunity at 414 S 24th Street in Middlesboro, KY! This versatile property offers excellent visibility and accessibility in a well-established area, just minutes from historic downtown Middlesboro and major routes. Ideal for office space, retail, professional services, or an investment property with strong potential in Bell County. Spacious layout, solid construction, and

    Beth Combs Turn Key Realty

    414 S 24th St, 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
  • /32

    $270,000

    $29K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,174 Sq Ft

    113 Hollywood Dr, Middlesboro, KY 40965

    Beautiful Traditional Brick Ranch with Basement!This home has 1698sq/ft on the main floor with an additional 1476sq/ft in the basement. Nestled in the center of Middlesboro with a curved driveway and a 2 car carport with a storage unit between them. The home has two entrances from the carport for easy entry. There are two bonus rooms with a formal living room and formal dining area. The main

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    113 Hollywood Dr, Middlesboro, KY 40965

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