Middlesboro, KY Homes

• 

  

  

  /20

  $240,000

  Sold Jan 30, 2026

  220 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 2003

  Last Sold Summary

  • 11% Below List Price
  • $142/SF
  • 108 Days On Market

  Current Estimated Value $251,153

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

  220 Windermere Dr, Middlesboro, KY 40965
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• 

  

  

  /18

  Est $124,592

  Not Listed For Sale

  508 Wilderness Rd, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1900

  508 Wilderness Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 19 Days On Market
• 

  

  

  /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
• 

  

  

  /27

  $164,000

  Sold Feb 21, 2026

  103 Leafwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 2 Baths
  • 1,326 Sq Ft
  • Built 1923

  Last Sold Summary

  • 1% Below List Price
  • $124/SF
  • 4 Days On Market

  Current Estimated Value $166,394

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  103 Leafwood Rd, Middlesboro, KY 40965
• 

  

  

  /49

  Est $198,381

  Not Listed For Sale

  412 Wilderness Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1931

  412 Wilderness Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 31 Days On Market
• 

  

  /46

  $325,000

  • 4 Beds
  • 2.5 Baths
  • 2,488 Sq Ft

  1015 Old Wilson Ln, Middlesboro, KY 40965

  Super nice four bedroom, two and 1/2 bath, 2488 sq ft with hardwood floors on a level lot in Middlesboro. Welcome to a home designed for the way you live. This stunning split level residence offers the perfect architectural solution for those seeking distinct spaces without sacrificing an open feel. This home offers privacy and distinct zones for living, working and relaxing.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  1015 Old Wilson Ln, Middlesboro, KY 40965
• 

  

  /15

  $145,000

  Sold Nov 25, 2025

  192 Owens Ln, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,600 Sq Ft
  • Built 1982

  Last Sold Summary

  • 12% Below List Price
  • $56/SF
  • 8 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  192 Owens Ln, Middlesboro, KY 40965
• 

  

  /21

  Est $509,384

  Not Listed For Sale

  2004 Twin Fawn Trail, Middlesboro, KY 40965

  • 5 Beds
  • 2.5 Baths
  • 2,742 Sq Ft
  • Built 2002

  2004 Twin Fawn Trail, Middlesboro, KY 40965

  Last Sold Summary

  • 205 Days On Market
• 

  /2

  $20,000

  $5K PRICE DROP Pending

  • Land
  • 13,068 Sq Ft
  • $66,667 per Acre

  2503 Exeter Ave, Middlesboro, KY 40965

  Level, city, corner Lot available for building or doublewide placement!Buyer/agent to verify all information

  Misti McGrath Realty Group

  2503 Exeter Ave, Middlesboro, KY 40965
• 

  

  /57

  $279,000

  Sold Feb 27, 2026

  440 Sams Mountain, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft
  • Built 2013

  Last Sold Summary

  • 14% Below List Price
  • $111/SF
  • 3 Days On Market

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  440 Sams Mountain, Middlesboro, KY 40965
• 

  

  /24

  Est $191,272

  Not Listed For Sale

  616 Balmoral Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 2,005 Sq Ft

  616 Balmoral Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 75 Days On Market
• 

  

  /29

  $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
• 

  

  /34

  $130,000

  Sold May 06, 2026

  123 Upper Gibson Ln, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft
  • Built 1945

  Last Sold Summary

  • 21% Below List Price
  • $119/SF
  • 20 Days On Market

  Current Estimated Value $136,741

  Last Listing Agent Megan Stanaford Black Diamond Realty

  123 Upper Gibson Ln, Middlesboro, KY 40965
• 

  

  /53

  Est $255,395

  Not Listed For Sale

  725 Balmoral Rd, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 3,450 Sq Ft
  • Built 1983

  725 Balmoral Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 46 Days On Market
• 

  

  /31

  $183,500

  $25K PRICE DROP Pending

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

  23 Castleford Way, Middlesboro, KY 40965

  Come see this move in ready home, 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 room,

  Beth Combs Backwoods Realty & Development

  23 Castleford Way, Middlesboro, KY 40965
• 

  

  /34

  $310,000

  Sold Mar 24, 2026

  409 Fairview Rd, Middlesboro, KY 40965

  • 4 Beds
  • 3.5 Baths
  • 2,684 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $115/SF
  • 29 Days On Market

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  409 Fairview Rd, Middlesboro, KY 40965
• 

  

  /6

  Est $99,170

  Not Listed For Sale

  615 Evans Dr, Middlesboro, KY 40965

  • 3 Beds
  • Built 1975

  615 Evans Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 156 Days On Market
• 

  

  /27

  $24,900

  Pending

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  13 Duncan Ln, Middlesboro, KY 40965

  This property is now under auctionterms. All Bids must be submitted during the auction via the property service listing page at This sale is subject to a 5% or $2,500 minimum buyer s premium pursuant to the auction Terms & Conditions. All bids will be subject toseller approval (minimums may apply). This property is now under auction terms. All Bids must be submitted during the auction

  Beth Combs Turn Key Realty

  13 Duncan Ln, Middlesboro, KY 40965
• 

  

  /7

  $271,500

  Sold Oct 02, 2025

  115 George Ann Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Below List Price
  • $135/SF
  • 8 Days On Market

  Current Estimated Value $267,096

  Last Listing Agent Brad Cawood Turn Key Realty

  115 George Ann Dr, Middlesboro, KY 40965
• 

  

  /31

  Est $148,622

  Not Listed For Sale

  135 Highpoint Rd, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1950

  135 Highpoint Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 161 Days On Market
• 

  

  /38

  $239,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,455 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. There is a gas fireplace that could be a dining room or an extension of the living room. The dining area is right off the galley kitchen with a door leading onto the carpeted porch easy for entertaining or cooking outside. There is easy access from the carport right into the

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  1203 Winchester Ave, Middlesboro, KY 40965
• 

  

  /16

  $1,250,000

  Sold Sep 05, 2025

  423 N 10th St, Middlesboro, KY 40965

  Last Sold Summary

  • 530 Days On Market

  Current Estimated Value $587,667

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

  423 N 10th St, Middlesboro, KY 40965
• 

  

  /20

  Est $223,108

  Not Listed For Sale

  1013 Doncaster Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1996

  1013 Doncaster Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 67 Days On Market
• 

  

  /37

  $350,000

  • 5 Beds
  • 4 Baths
  • 3,195 Sq Ft

  717 S 27th St, Middlesboro, KY 40965

  This open floor plan home is waiting for your large family. This home features 5 bedrooms and 4 full baths, cathedral ceilings, a rock fireplace in the living room, and a full, unfinished basement just waiting for you to make more living space. Located in downtown with an out-of-town feel, get in to see this home now. *Buyer to verify acreage and septic.

  Barry Turner RE/MAX LakeTime Realty London

  717 S 27th St, Middlesboro, KY 40965
• 

  

  /31

  $270,800

  Sold Jun 30, 2025

  9 Ennismore Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 1,974 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Below List Price
  • $137/SF
  • 85 Days On Market

  Current Estimated Value $323,821

  Last Listing Agent Brad Cawood Turn Key Realty

  9 Ennismore Dr, Middlesboro, KY 40965
• 

  

  /16

  Est $203,649

  Not Listed For Sale

  916 Doncaster Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1996

  916 Doncaster Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 115 Days On Market
• 

  

  /11

  $214,999

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 3,948 Sq Ft

  2621 W Cumberland Ave, Middlesboro, KY 40965

  Opportunities are built on the right properties and this could be the one! The potential of this home is limitless. a home with instant equity to put your finishing touches on!

  Kelsey Kelley Keller Williams Legacy Group

  2621 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /16

  $147,979

  Sold Feb 26, 2026

  138 Robinson Ln, Middlesboro, KY 40965

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

  Last Sold Summary

  • 10% Below List Price
  • $228/SF
  • 19 Days On Market

  Last Listing Agent Beth Combs Turn Key Realty

  138 Robinson Ln, Middlesboro, KY 40965
• 

  

  /23

  Est $239,002

  Not Listed For Sale

  1009 W Rochester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,206 Sq Ft
  • Built 1992

  1009 W Rochester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 5 Days On Market
• 

  

  /20

  $189,000

  Pending

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1208 Hwy 217 Hwy Unit 217, Middlesboro, KY 40965

  Here is your opportunity to own a home in a desirable community. Approximately 11 acres in the Hutch or Clear Fork area of Bell County. Property has lots of good fencing. The home on the property is in fair condition and may need to be upgraded or remodeled. This is a rare opportunity to have a home in the country that so many dream of. Call me today and come check out this Beautiful Property!!!!

  Danny Wilson Coldwell Banker Bisceglia Realty & Auction Co

  1208 Hwy 217 Hwy Unit 217, Middlesboro, KY 40965
• 

  

  /17

  $65,000

  Sold Jul 29, 2025

  1813 Winchester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1924

  Last Sold Summary

  • 38% Below List Price
  • $64/SF
  • 154 Days On Market

  Current Estimated Value $80,109

  Last Listing Agent Misti McGrath Realty Group

  1813 Winchester Ave, Middlesboro, KY 40965
• 

  

  /12

  Est $75,977

  Not Listed For Sale

  712 Balmoral Rd, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1965

  712 Balmoral Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 26 Days On Market
• 

  

  /24

  $159,000

  $41K PRICE DROP

  • 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
• 

  

  /28

  $150,000

  Sold Mar 25, 2026

  2523 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 2022

  Last Sold Summary

  • 7% Above List Price
  • $89/SF
  • 3 Days On Market

  Current Estimated Value $147,499

  Last Listing Agent Jody Moore Threshold Real Estate Services

  2523 Exeter Ave, Middlesboro, KY 40965
• 

  

  /6

  Est $244,141

  Not Listed For Sale

  205 Fairview Rd, Middlesboro, KY 40965

  • Studio
  • 1,616 Sq Ft
  • Built 1976

  205 Fairview Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 10 Days On Market
• 

  

  /7

  $189,000

  Pending

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1208 Kentucky 217, Middlesboro, KY 40965

  Here is your opportunity to own a home in a desirable community. Approximately 11 acres in the Hutch or Clear Fork area of Bell County. Property has lots of good fencing This is a rare opportunity to have a home in the country that so many dream of. Call me today and come check out this Beautiful Property!!!!

  Danny Wilson Coldwell Banker Bisceglia Realty & Auction Co

  1208 Kentucky 217, Middlesboro, KY 40965
• 

  

  /40

  $390,000

  Sold Aug 27, 2025

  2824 W Cumberland Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1928

  Last Sold Summary

  • 2% Below List Price
  • $156/SF
  • 21 Days On Market

  Current Estimated Value $395,504

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  2824 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /11

  Est $121,020

  Not Listed For Sale

  302 W Rochester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1975

  302 W Rochester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 75 Days On Market
• 

  

  /46

  $125,000

  • 2 Beds
  • 1 Bath
  • 1,456 Sq Ft

  1720 Exeter Ave, Middlesboro, KY 40965

  Welcome to 1720 Exeter Avenue, this adorable fixer has tons of potential with 2 living areas, a detached garage, brand new metal roof, and a fully fenced yard! Less than 5 minutes to schools and hospital, and only 15 minutes from LMU Harrogate main campus. Offered at a great price! Call or text today to schedule a showing!

  Victoria Allen Century 21 Virginia Wilder Real Estate

  1720 Exeter Ave, Middlesboro, KY 40965
• 

  

  /18

  $90,000

  Sold Jul 15, 2025

  600 S 38th St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $87/SF
  • 19 Days On Market

  Current Estimated Value $101,689

  Last Listing Agent David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  600 S 38th St, Middlesboro, KY 40965

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