Middlesboro, KY Homes

• 

  

  

  /22

  Est $110,998

  Not Listed For Sale

  407 S 22nd St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • Built 1940

  407 S 22nd St, Middlesboro, KY 40965

  Last Sold Summary

  • 47 Days On Market
• 

  

  

  /15

  $59,000

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  518 S 43rd St, Middlesboro, KY 40965

  Two bedroom, 1 bath home located in a great neighborhood. Large bedrooms, living room, and kitchen. Don't miss the opportunity to make this home your own.

  Michael Hensley REMAX PROFESSIONAL'S

  518 S 43rd St, 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 $294,926

  Last Listing Agent Misti McGrath Realty Group

  900 Twin Fawn Trail, Middlesboro, KY 40965
• 

  

  

  /19

  Est $138,136

  Not Listed For Sale

  201 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 2015

  201 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 246 Days On Market
• 

  

  

  /40

  $232,500

  $17K PRICE DROP

  • 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
• 

  

  /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 $230,948

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

  6 Hampton Ct, Middlesboro, KY 40965
• 

  

  /18

  Est $90,678

  Not Listed For Sale

  401 S 20th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 920 Sq Ft
  • Built 1996

  401 S 20th St, Middlesboro, KY 40965

  Last Sold Summary

  • 6 Days On Market
• 

  

  /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
• 

  

  /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 $300,773

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  10 Thaxted Ln, Middlesboro, KY 40965
• 

  

  /16

  Est $95,051

  Not Listed For Sale

  306 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1920

  306 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 13 Days On Market
• 

  

  /21

  $219,900

  $30K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /16

  Est $106,642

  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
• 

  /2

  $30,000

  Pending

  • 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
• 

  

  /3

  $75,000

  Sold Aug 13, 2025

  114 W Rochester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Built 1978

  Last Sold Summary

  • 40% Below List Price
  • $74/SF
  • 26 Days On Market

  Last Listing Agent Megan Stanaford Black Diamond Realty

  114 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /7

  Est $73,263

  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
• 

  

  /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
• 

  

  /30

  $265,000

  Sold Aug 08, 2025

  238 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft
  • Built 2001

  Last Sold Summary

  • 5% Below List Price
  • $165/SF
  • 8 Days On Market

  Current Estimated Value $289,230

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real

  238 Windermere Dr, Middlesboro, KY 40965
• 

  

  /6

  Est $113,176

  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
• 

  

  /36

  $285,000

  00 Highway 217 & 1344, Middlesboro, KY 40965

  UNIQUE OPPORTUNITY PROPERTY. This property offers plenty of potential. Formerly Shillelagh garage and swimming hole, this property has above the ground fuel tanks that could provide ATV's, Side-by-side, farm equipment fuel for work or entertainment. There are Off-road trails for ATV enthusiasts to enjoy the endless trails. These 9.613 surveyed acres can be used for residential, commercial

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  00 Highway 217 & 1344, 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 $115,199

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

  45 Fourmile Run Rd, Middlesboro, KY 40965
• 

  

  /53

  Est $579,617

  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
• 

  

  /27

  $94,900

  $25K 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
• 

  /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
• 

  

  /14

  Est $94,663

  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
• 

  

  /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
• 

  

  /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 $186,440

  Last Listing Agent Jennifer Ware Kentucky Land and Home

  11 Castleford Way, Middlesboro, KY 40965
• 

  

  /19

  Est $126,774

  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
• 

  

  /14

  $150,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  422 Wilderness Rd, Middlesboro, KY 40965

  Super cute starter home with 2 beds and 1 full bath. Recently remodeled with excellent updates.The backyard is an oasis with additional building with electricity. Starter home, income producing property, downsizing or whatever fits your needs, this home has it!

  Misti McGrath Realty Group

  422 Wilderness Rd, 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 $537,443

  Last Listing Agent Brad Cawood Turn Key Realty

  1308 Gloucester Ave, Middlesboro, KY 40965
• 

  

  /55

  Est $182,797

  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
• 

  

  /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
• 

  /2

  $70,000

  Sold Aug 18, 2025

  488 Beans Fork Rd, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,200 Sq Ft

  Last Sold Summary

  • $58/SF
  • 0 Days On Market

  Current Estimated Value $80,854

  Last Listing Agent The Dream Team Real Estate Professionals - Dreama Bolin Lake Cumberland Real Estate Professionals

  488 Beans Fork Rd, Middlesboro, KY 40965
• 

  

  /12

  Est $89,385

  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
• 

  

  /29

  $259,000

  $20K PRICE DROP Pending

  • 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
• 

  

  /18

  $60,000

  Sold Jul 25, 2025

  3575 Highway 441, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,204 Sq Ft
  • Built 1930

  Last Sold Summary

  • 52% Below List Price
  • $50/SF
  • 171 Days On Market

  Current Estimated Value $71,743

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real

  3575 Highway 441, Middlesboro, KY 40965
• 

  

  /25

  Est $112,248

  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
• 

  

  /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
• 

  

  /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 $223,946

  Last Listing Agent Janice Pratt Fathom Realty TN LLC

  907 Doncaster Ave, Middlesboro, KY 40965
• 

  /2

  Est $273,774

  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

Showing Results 81 - 120, Page 3 of 18