18

Middlesboro, KY Homes for Sale under $100,000

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  • /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
  • /28

    $59,900

    • Land
    • 4.24 Acres
    • $14,127 per Acre

    1197 Beans Fork Rd, Middlesboro, KY 40965

    Opportunity awaits on this 4.24-acre tract offering a peaceful setting with endless potential. The property was previously improved with a home that has recently been lost to fire, presenting a unique chance to start fresh and bring your vision to life. With utilities previously in place (buyer to verify), this parcel may offer a head start for rebuilding, whether you're considering a custom

    SARAH RICHARDS RE/MAX Preferred Group

    1197 Beans Fork Rd, Middlesboro, KY 40965
  • /5

    $30,000

    • Land
    • 1.26 Acres
    • $23,810 per Acre

    0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965

    LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

    Sharon Teaney Century 21 Virginia Wilder Real Estate

    0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965
  • /2

    $50,000

    • Land
    • 16,639 Sq Ft
    • $130,890 per Acre

    0000 Edgewood Rd, Middlesboro, KY 40965

    Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

    Megan Stanaford Black Diamond Realty

    0000 Edgewood Rd, Middlesboro, KY 40965
  • /2

    $79,000

    $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    923 Winchester Ave, Middlesboro, KY 40965

    This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    923 Winchester Ave, Middlesboro, KY 40965
  • /2

    $20,000

    $5K PRICE DROP
    • Land
    • 13,068 Sq Ft
    • $66,667 per Acre

    2503 Exeter Ave, Middlesboro, KY 40965

    Level, city, corner Lot available for building or doublewide placement!Buyer/agent to verify all information

    Misti McGrath Realty Group

    2503 Exeter Ave, Middlesboro, KY 40965
  • /11

    $49,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 924 Sq Ft

    6, Middlesboro, KY 40965

    Don't miss out on your chance to own this slightly used 2025 3 bedroom 2 bath home in the heart of Middlesboro. Located in a family friendly community that values affordability with space rent at $175. Available for showings now!

    Neely Gray VMF Homes

    6, Middlesboro, KY 40965
  • /19

    $44,000

    $10K 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
  • /5

    $22,500

    $8K PRICE DROP
    • Land
    • 15,681 Sq Ft
    • $62,500 per Acre

    526 Balmoral Rd, Middlesboro, KY 40965

    Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

    Megan Stanaford Black Diamond Realty

    526 Balmoral Rd, Middlesboro, KY 40965
  • /16

    $19,900

    $10K PRICE DROP
    • Land
    • 2.32 Acres
    • $8,578 per Acre

    LOT 9 Brush Mountain Cir, Miracle, KY 40856

    Discover tranquility at Brush Mountain Farms in Bell County, KY—a 2.32-acre wooded retreat in a gated community. Enjoy peace, privacy, and wildlife, with hiking trails and a developing wildlife preserve (Boone's Ridge) visible from the property. Located just 15 minutes from Boones Ridge Wildlife Park and 20 minutes from Pineville and Middlesboro, offering easy access to town amenities. Ideal for

    Tabitha House CENTURY 21 Advantage Realty

    LOT 9 Brush Mountain Cir, Miracle, KY 40856
  • /22

    $99,999

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    252 Chasteen Dr, Middlesboro, KY 40965

    Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily

    Aaron Rose Realty Network, Inc

    252 Chasteen Dr, Middlesboro, KY 40965
  • /12

    $85,000

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

    310 Barkley Dr, Middlesboro, KY 40965

    2 bed, 1 bath, manufactured home sitting on a large level lot. Conveniently located to shopping and Harrogate, TN.

    Michael Hensley REMAX PROFESSIONAL'S

    310 Barkley Dr, Middlesboro, KY 40965
  • /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

    $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
  • /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
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