Newest Homes for Sale in Middlesboro, KY

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  /3

  $29,000

  $6K PRICE DROP

  • Land
  • 14,853 Sq Ft
  • $85,044 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
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  /5

  $855,000

  • 2 Beds
  • 2 Baths
  • 15,119 Sq Ft

  725 19th St, Middlesboro, KY 40965

  Prime Multifamily Investment Opportunity Presenting a well-established commercial apartment building in the heart of Middlesboro, Kentucky. Built in 1990, this single-story property offers approximately 15,225 square feet of space ideally suited for residential rental units, providing stable cash flow in a convenient location. Strategically positioned on N 19th Street, the building benefits from

  Beth Combs Backwoods Realty & Development

  725 19th St, Middlesboro, KY 40965
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  /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 Backwoods Realty & Development

  508 & 512 Winchester Ave, Middlesboro, KY 40965
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  /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 Backwoods Realty & Development

  414 S 24th St, Middlesboro, KY 40965
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  /16

  $295,000

  $15K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,100 Sq Ft

  717 Highway 441, Middlesboro, KY 40965

  Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed

  Megan Stanaford Black Diamond Realty

  717 Highway 441, Middlesboro, KY 40965
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  /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
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  /28

  $39,900

  $20K PRICE DROP

  • Land
  • 4.24 Acres
  • $9,410 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
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  /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
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  /17

  $230,000

  $15K PRICE DROP

  • 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
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  /20

  $369,000

  $30K PRICE DROP

  • 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
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  /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
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  /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
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  /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
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  /51

  $250,000

  • 1,500 Sq Ft

  119 Wagon Hollow Rd, Middlesboro, KY 40965

  Welcome to the best of all worlds! One home and an operational store that fronts Highway 217. Several outbuildings and just over 20 acres make this the perfect property for homesteading as seller had livestock on the property at one time. The land is gently rolling to level, Pineville city water in place, spectrum internet and you're off the beaten path but just a 15 minute drive back into town.

  Megan Stanaford Black Diamond Realty

  119 Wagon Hollow Rd, Middlesboro, KY 40965
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  /17

  $129,900

  $30K 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
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  /22

  $97,000

  $22K 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
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  /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
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  /13

  $275,000

  $75K PRICE DROP

  • Land
  • 1.69 Acres
  • $162,722 per Acre

  321 W Chester Ave, Middlesboro, KY 40965

  1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Pharmacy, Banks, Theater, Auto Repair, Hotel-Motel, Bed & Breakfast, and Multi Family Copy of Middlesboro Zoning attached. All city utilities available.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  321 W Chester Ave, Middlesboro, KY 40965
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  $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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