Middlesboro, KY Homes

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  /24

  $145,000

  Sold Aug 17, 2026

  63 Old Pineville Pike, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1980

  Last Sold Summary

  • 27% Below List Price
  • $93/SF
  • 21 Days On Market

  Current Estimated Value $175,366

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  63 Old Pineville Pike, Middlesboro, KY 40965
• 

  

  

  /16

  Est $122,877

  Not Listed For Sale

  312 S 23rd St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,870 Sq Ft
  • Built 1930

  312 S 23rd St, Middlesboro, KY 40965

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Ann Robinson Mountain Realty
• 

  

  

  /3

  $17,000

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  110 Danbury Ave, Middlesboro, KY 40965

  If you've been looking for a project here it is! Handyman special, would make a super cute flip! Or at this price you can buy it for just the land!Please do not go without an agent.Buyer/Buyers agent to confirm all information

  Misti McGrath Realty Group

  110 Danbury Ave, Middlesboro, KY 40965
• 

  

  

  /27

  $290,000

  Sold Nov 06, 2025

  900 Twin Fawn Trail, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,270 Sq Ft
  • Built 2010

  Last Sold Summary

  • 17% Below List Price
  • $128/SF
  • 133 Days On Market

  Current Estimated Value $310,514

  Last Listing Agent Misti McGrath Realty Group

  900 Twin Fawn Trail, Middlesboro, KY 40965
• 

  

  

  /7

  Est $82,108

  Not Listed For Sale

  403 Winchester Ave, Middlesboro, KY 40965

  • Built 1960

  403 Winchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Brad Cawood Turn Key Realty
• 

  

  /27

  $79,900

  $40K PRICE DROP Pending

  • 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
• 

  /2

  $17,000

  Sold Jul 24, 2026

  103 Nutwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,244 Sq Ft
  • Built 1950

  Last Sold Summary

  • 43% Below List Price
  • $14/SF
  • 51 Days On Market

  Current Estimated Value $77,178

  Last Listing Agent Megan Stanaford Black Diamond Realty

  103 Nutwood Rd, Middlesboro, KY 40965
• 

  

  /6

  Est $128,634

  Not Listed For Sale

  307 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft
  • Built 1925

  307 W Chester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Cookie Russell Realty Network, Inc
• 

  

  /5

  $29,000

  • Land
  • 39,204 Sq Ft
  • $32,222 per Acre

  0 Bowling Rd Unit 1344123, Middlesboro, KY 40965

  0.9 Acres Partially cleared with wooded area in back for privacy. City limits. All utilities available. Perfect location for a home or two right next to the mountains!

  Misti McGrath Realty Group

  0 Bowling Rd Unit 1344123, Middlesboro, KY 40965
• 

  

  /37

  $250,000

  Sold Mar 04, 2026

  6 Hampton Ct, Middlesboro, KY 40965

  • 4 Beds
  • 3 Baths
  • 1,966 Sq Ft
  • Built 1985

  Last Sold Summary

  • 11% Above List Price
  • $127/SF
  • 95 Days On Market

  Current Estimated Value $215,336

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  6 Hampton Ct, Middlesboro, KY 40965
• 

  

  /53

  Est $567,008

  Not Listed For Sale

  208 Arthur Heights, Middlesboro, KY 40965

  • 8 Beds
  • 5.5 Baths
  • 5,537 Sq Ft
  • Built 1890

  208 Arthur Heights, Middlesboro, KY 40965

  Last Sold Summary

  • 411 Days On Market

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co
• 

  

  /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
• 

  

  /24

  $280,000

  Sold Aug 29, 2025

  10 Thaxted Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,096 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $134/SF
  • 33 Days On Market

  Current Estimated Value $319,973

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  10 Thaxted Ln, Middlesboro, KY 40965
• 

  

  /14

  Est $94,364

  Not Listed For Sale

  613 Exeter Ave, Middlesboro, KY 40965

  • 5 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1960

  613 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /3

  $28,000

  • Land
  • 7,405 Sq Ft
  • $164,706 per Acre

  14 Honeycutt Ln, Middlesboro, KY 40965

  COUNTY LOT, NO RESTRICTIONS!!!Flat and cleared lot in the county doesn't get much better than this!Previously home to a singlewide trailer means this location has all utilities including City water and septic.

  Misti McGrath Realty Group

  14 Honeycutt Ln, Middlesboro, KY 40965
• 

  

  /20

  $95,000

  Sold Apr 17, 2026

  925 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  Last Sold Summary

  • 10% Below List Price
  • $90/SF
  • 3 Days On Market

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  925 Winchester Ave, Middlesboro, KY 40965
• 

  

  /19

  Est $130,380

  Not Listed For Sale

  602 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 905 Sq Ft
  • Built 1950

  602 Winchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real
• 

  

  /27

  $270,000

  • 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 1476 sf 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 suite

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  113 Hollywood Dr, Middlesboro, KY 40965
• 

  

  /36

  $97,000

  Sold Mar 18, 2026

  45 Fourmile Run Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 934 Sq Ft
  • Built 2000

  Last Sold Summary

  • 44% Below List Price
  • $104/SF
  • 103 Days On Market

  Current Estimated Value $121,243

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  45 Fourmile Run Rd, Middlesboro, KY 40965
• 

  

  /55

  Est $196,761

  Not Listed For Sale

  603 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • Built 1946

  603 W Chester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 92 Days On Market

  Last Listing Agent Beth Combs Turn Key Realty
• 

  

  /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
• 

  /2

  $2,750,000

  Sold Jun 01, 2026

  200 Colonial Heights, Middlesboro, KY 40965

  • 99 Beds
  • 58 Baths
  • 50,352 Sq Ft
  • Built 1982

  Last Sold Summary

  • $55/SF

  Last Listing Agent Chris McHargue Huddleston Real Estate

  200 Colonial Heights, Middlesboro, KY 40965
• 

  

  /12

  Est $95,814

  Not Listed For Sale

  501 W Chester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 948 Sq Ft
  • Built 1940

  501 W Chester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co
• 

  

  /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
• 

  

  /29

  $240,000

  Sold Jun 23, 2026

  206 Summit Dr, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 1,832 Sq Ft
  • Built 1962

  Last Sold Summary

  • 14% Below List Price
  • $131/SF
  • 129 Days On Market

  Current Estimated Value $244,337

  Last Listing Agent Sharon Teaney Century 21 Virginia Wilder Real Estate

  206 Summit Dr, Middlesboro, KY 40965
• 

  

  /25

  Est $130,156

  Not Listed For Sale

  512 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 1908

  512 W Chester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 191 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /48

  $575,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,480 Sq Ft

  2794 US Hwy 25 E, Middlesboro, KY 40965

  This property presents an exceptional opportunity for investment. Situated in Bell County, it is conveniently located within a short distance of Middlesboro city limits, approximately two miles away. The property boasts over 550 feet of road frontage on a highly visible traffic area, specifically on Highway 25E. This prime location offers a unique chance for investors to establish a new business

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  2794 US Hwy 25 E, Middlesboro, KY 40965
• 

  

  /32

  $189,500

  Sold May 20, 2026

  11 Castleford Way, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1987

  Last Sold Summary

  • 21% Below List Price
  • $172/SF
  • 26 Days On Market

  Current Estimated Value $185,022

  Last Listing Agent Jennifer Ware Rock N' Realty LLC

  11 Castleford Way, Middlesboro, KY 40965
• 

  /2

  Est $297,293

  Not Listed For Sale

  2504 Cumberland Ave, Middlesboro, KY 40965

  • 4 Beds
  • 3 Baths
  • 3,054 Sq Ft
  • Built 1942

  2504 Cumberland Ave, Middlesboro, KY 40965
• 

  /2

  $50,000

  Pending

  • Land
  • 2 Acres
  • $25,000 per Acre

  739 Highway 441, Middlesboro, KY 40965

  Janice Pratt AAA Realty, Inc.

  739 Highway 441, Middlesboro, KY 40965
• 

  

  /37

  $539,000

  Sold Jan 05, 2026

  1308 Gloucester Ave, Middlesboro, KY 40965

  • 5 Beds
  • 3.5 Baths
  • 4,829 Sq Ft
  • Built 1965

  Last Sold Summary

  • $112/SF
  • 2 Days On Market

  Current Estimated Value $556,546

  Last Listing Agent Brad Cawood Turn Key Realty

  1308 Gloucester Ave, Middlesboro, KY 40965
• 

  

  /14

  Est $140,728

  Not Listed For Sale

  713 Gloucester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,112 Sq Ft
  • Built 1916

  713 Gloucester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 202 Days On Market

  Last Listing Agent Sharon Teaney Century 21 Virginia Wilder Real Estate
• 

  

  /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
• 

  

  /32

  $240,000

  Sold May 29, 2026

  907 Doncaster Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $172/SF
  • 17 Days On Market

  Current Estimated Value $235,658

  Last Listing Agent Janice Pratt Fathom Realty TN LLC

  907 Doncaster Ave, Middlesboro, KY 40965
• 

  

  /50

  Est $386,681

  Not Listed For Sale

  202 N 24th St, Middlesboro, KY 40965

  • 5 Beds
  • 3.5 Baths
  • 3,680 Sq Ft
  • Built 1900

  202 N 24th St, Middlesboro, KY 40965

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate
• 

  

  /12

  $85,000

  $20K PRICE DROP Pending

  • 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
• 

  

  /11

  $26,000

  Sold Nov 26, 2025

  0 Arie Turner Ln, Middlesboro, KY 40965

  • Land
  • 2 Acres
  • $13,000 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 20 Days On Market

  Current Estimated Value $176,000

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  0 Arie Turner Ln, Middlesboro, KY 40965
• 

  

  /27

  Est $210,057

  Not Listed For Sale

  702 Dorchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 1968

  702 Dorchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /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
• 

  

  /6

  $50,000

  Sold Nov 03, 2025

  305 N 15th St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $57/SF
  • 16 Days On Market

  Current Estimated Value $73,361

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  305 N 15th St, Middlesboro, KY 40965

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