18

Middlesboro, KY Homes for Sale under $200,000

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  • /13

    $140,000

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

    413 S 26th St, Middlesboro, KY 40965

    This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from downtown Middlesboro and the Cumberland Gap National Park. This home has had some great improvements such as a new roof and new windows installed. don't miss your opportunity to call this your own.

    Agent Photo

    Brad Cawood

    Turn Key Realty

    (606) 402-3803

    413 S 26th St, Middlesboro, KY 40965
  • /18

    $118,500

    $7K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,426 Sq Ft

    123 Cawood Ln, Middlesboro, KY 40965

    Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back mudroom/workshop provides

    Agent Photo

    Dustin Daniels

    Mountain Realty

    (606) 717-1149

    123 Cawood Ln, Middlesboro, KY 40965
  • /23

    $165,000

    • 3 Beds
    • 1.5 Baths
    • 1,242 Sq Ft

    1425 Highway 441, Middlesboro, KY 40965

    This brick ranch style home has 3 bedrooms, 1.5 bathrooms, living room, eat-in kitchen that extends to dining area, range, refrigerator, new dishwasher, washer and dryer stay with home; double pane windows; 1 car attached garage with pull down ladder to access attic partially floored for storage; yard is partially fenced with chain link fence for pets, nice yard; the septic system was replaced

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    1425 Highway 441, Middlesboro, KY 40965
  • /31

    $185,000

    $23K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    23 Castleford Way, Middlesboro, KY 40965

    Back on the market at no fault of the seller! Located in the desirable Ambleside subdivision, this beautifully maintained and tastefully decorated two-story home features soft, calming paint colors, gorgeous luxury vinyl flooring, and a warm, welcoming feel throughout. This charming home offers 3 spacious bedrooms and 1.5 bathrooms. The main level includes a comfortable living room, formal dining

    Beth Combs Turn Key Realty

    23 Castleford Way, Middlesboro, KY 40965
  • /24

    $155,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    1807 Winchester Ave, Middlesboro, KY 40965

    Three-bedroom traditional brick ranch home. Located on a level lot convenient to the local hospital and downtown Middlesboro.

    Michael Hensley REMAX PROFESSIONAL'S

    1807 Winchester 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
  • /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
  • /4

    $164,000

    • 700 Sq Ft

    1801 Exeter Ave, Middlesboro, KY 40965

    2 HOMES with one FULLY remodeled home in back 2 bedroom 1 bath Cute as a button! Home on corner lot needs work but would be a very smart investment. With access to ATV friendly roads, close to stores and hospital.1801 Exeter and 1801 1/2 Exeter

    Misti McGrath Realty Group

    1801 Exeter Ave, 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 Real

    405 S 37th St, Middlesboro, KY 40965
  • /41

    $134,000

    $1K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,844 Sq Ft

    215 S 21st St, Middlesboro, KY 40965

    Megan Stanaford Black Diamond Realty

    215 S 21st 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
  • /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
  • /9

    $139,000

    • Land
    • 5.33 Acres
    • $26,079 per Acre

    312 Blakely Ln, Middlesboro, KY 40965

    Rare find! 5.33 undeveloped acres in Middlesboro on Blakely Lane, off Cumberland Ave. Zoned R-1. Land is mostly level with a drop to the creek behind. Portion near the creek is in the floor plain. Several building sites on the land above the flood plain. Easy access to Cumberland Ave yet away from the noise and traffic.

    Ann Robinson Action Realty

    312 Blakely Ln, 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
  • /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
  • /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
  • /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
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