25

Middlesboro, KY Houses for Sale

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  • /67

    $185,000

    • 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
  • /19

    $210,000

    • 3 Beds
    • 1 Bath
    • 728 Sq Ft

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

    2 homes (103 and 105 Nutwood) and a duplex (120 Redwood) currently used as rental properties, priced to sell. Call to schedule a showing.

    Megan Stanaford Black Diamond Realty

    120 Nutwood Rd Unit A & B, Middlesboro, KY 40965
  • /32

    $195,000

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft

    11 Castleford Way, Middlesboro, KY 40965

    This one checks the boxes and close to Major Regional Colleges! Renovated, truly move in ready, county taxed (not city!), and not in a flood zone, this home is an ideal match for first time buyers, downsizers, or anyone wanting low maintenance living. It also sits in a prime location just minutes from major regional colleges like Southeast Kentucky Community & Technical College (5-10 minutes) and

    Jennifer Ware Kentucky Land and Home

    11 Castleford Way, 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

    $245,000

    • 3 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    156 Wellington Dr, Middlesboro, KY 40965

    Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is

    Megan Stanaford Black Diamond Realty

    156 Wellington Dr, Middlesboro, KY 40965
  • /24

    $175,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    63 Old Pineville Pike, Middlesboro, KY 40965

    Remodeled and gorgeous! This home has completely remodeled throughout with gorgeous kitchen and new bathrooms! This home was stripped down to the studs! Laminate floors are waterproof. The master bathroom has a double bowl sink, nice walk-in shower. There are 3 bedrooms and 2 full bathroom, large living room, kitchen with new farmhouse sink. The kitchen extends to dining room, range, refrigerator

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    63 Old Pineville Pike, Middlesboro, KY 40965
  • /32

    $239,900

    • 4 Beds
    • 2.5 Baths
    • 2,456 Sq Ft

    1203 Winchester Ave, Middlesboro, KY 40965

    Beautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal living room with hardwood floors and a gas fireplace. The dining area is right off the galley kitchen, which has a door leading onto the carpeted porch-perfect for entertaining or cooking outside. There is easy access from the carport right into the large open den/family room. Also on the main level there is

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    1203 Winchester Ave, Middlesboro, KY 40965
  • /27

    $202,500

    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    23 Castleford Way, Middlesboro, KY 40965

    Located in the desirable Ambleside subdivision, this beautifully decorated and well-maintained two-story home features soft, relaxing paint colors throughout and gorgeous luxury vinyl flooring that creates a warm and inviting atmosphere.This charming home offers 3 spacious bedrooms and 1.5 bathrooms. The main level includes a comfortable living room, formal dining room, kitchen, and a large

    Beth Combs Turn Key Realty

    23 Castleford Way, Middlesboro, KY 40965
  • /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
  • /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
  • /15

    $142,000

    • 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
  • /40

    $249,000

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

    301 Doe's Crossing, Middlesboro, KY 40965

    This 2-story gorgeous home sits in the mountains of Kentucky and is located in the desired subdivision of Vista Venado! This home sits on 0.944 acre. The main floor offers an open floor plan with a large living room with gas log fireplace. The living room extends to the formal dining area. The spacious kitchen has room for a breakfast table. The kitchen appliances stay with home and includes a

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    301 Doe's Crossing, Middlesboro, KY 40965
  • /29

    $259,000

    • 4 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    206 Summit Dr, Middlesboro, KY 40965

    Beautiful move-in ready renovated Property. Home features four bedrooms 2 1/2 baths. kitchen features soft closed custom cabinets, kitchen island and stainless steel appliances. Laminated floors throughout the home. Enjoy your coffee on screened in back porch. Storage building for your tools, lawnmower etc..Property is located within minutes from Lmu main campus, Shopping, restaurants, and

    Sharon Teaney Century 21 Virginia Wilder Real Estate

    206 Summit Dr, Middlesboro, KY 40965
  • /17

    $159,900

    • 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
  • /2

    $99,000

    • 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
  • /21

    $219,900

    • 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
  • /33

    $499,000

    • 5 Beds
    • 2.5 Baths
    • 2,542 Sq Ft

    2004 Twin Fawn Trail, Middlesboro, KY 40965

    This gorgeous cape cod home sits on 4.4 acres with deer visiting often. This home has 5 bedrooms, 2.5 bathrooms, formal living room with fireplace, family room (could be used as formal dining room) a second fireplace in the sunroom, amazing kitchen with island, the kitchen counter tops are granite, the stainless-steel appliances stay, which include double wall ovens, gas range with gas oven

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    2004 Twin Fawn Trail, Middlesboro, KY 40965
  • /16

    $130,000

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    918 E Cumberland Ave, Middlesboro, KY 40965

    This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and one bath with a large kitchen and large living room. This home needs some attention but has a lot of potential. The downstairs could be used as apartment or extra living space. There is another home on the property and might be possible to repair.

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    918 E Cumberland Ave, Middlesboro, KY 40965
  • /22

    $109,000

    • 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

    $100,000

    • 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
  • /52

    $2,500,000

    • 3 Beds
    • 1.5 Baths
    • 1,976 Sq Ft

    259 Watson Ln, Middlesboro, KY 40965

    Offering for the first time on the market, this beautiful 92 acre property with 82 acres within city limits and 10 acres in the county. There is a beautiful hayfield and from that hayfield downtown Middlesboro can be seen as well as a view of the Pinnacle. This property comes with 2 homes. The main house has 3 bedrooms, 1 full bathroom and a half bathroom, foyer with staircase leading upstairs,

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    259 Watson Ln, Middlesboro, KY 40965
  • /31

    $170,000

    • 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
  • /32

    $299,000

    • 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

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    113 Hollywood Dr, Middlesboro, KY 40965
  • /2

    $30,000

    • 2 Beds
    • 1 Bath
    • 1,244 Sq Ft

    103 Nutwood Rd, Middlesboro, KY 40965

    Great investment opportunity. 2 bedroom 1 bathroom home, city utilities. Call for showings.

    Megan Stanaford Black Diamond Realty

    103 Nutwood Rd, Middlesboro, KY 40965
  • /27

    $109,900

    • 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

Why Live in Middlesboro

Middlesboro, Kentucky, is a small city located in a meteor crater just west of the historic Cumberland Gap. This unique location provides residents with access to a variety of recreational and historic sites, including the Cumberland Gap National Historical Park. The park offers miles of trails leading to caves, creeks, scenic viewpoints, and Civil War landmarks, making it a prime spot for those seeking things to do outdoors. Middlesboro also features several city parks and the historic Middlesboro Country Club, the oldest continuously operating golf course in America. The city is home to a mix of Craftsman-style and midcentury ranch homes, with some properties dating back to the 1910s. While new construction has been limited since the 1990s, there are communities for manufactured homes available. Community events like the Cumberland Mountain Fall Festival and activities at Binghamtown Baptist Church and the Middlesboro-Bell County Public Library foster a strong sense of community. The main street area along Cumberland Avenue hosts local coffee shops, pizza parlors, and other eateries, while 12th Street offers chain restaurants and big box retailers. However, residents should be aware of potential flooding due to the city's topography and heavy traffic around the Cumberland Gap Tunnel during peak hours. Middlesboro Independent Schools have average ratings, and the city is also home to the Middlesboro Campus for Southeast Kentucky Community & Technical College.

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