Middlesboro, KY Homes

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  /16

  $147,000

  Sold Oct 27, 2025

  428 Wilderness Rd, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1960

  Last Sold Summary

  • 8% Below List Price
  • $111/SF
  • 64 Days On Market

  Current Estimated Value $154,492

  Last Listing Agent Brad Cawood Turn Key Realty

  428 Wilderness Rd, Middlesboro, KY 40965
• 

  

  

  /31

  Est $274,704

  Not Listed For Sale

  806 Cirencester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1969

  806 Cirencester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 5 Days On Market

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

  

  

  /22

  $149,999

  Pending

  • 2 Beds
  • 1 Bath
  • 1,275 Sq Ft

  1010 W Chester Ave, Middlesboro, KY 40965

  Charming Renovated Ranch in the Heart of Middlesboro! Welcome home to 1010 W Chester Avenue, a cozy and beautifully updated 2-bedroom, 1-bath brick ranch right in the heart of Middlesboro, KY. If you've been looking for that perfect blend of classic hometown charm and worry-free modern living, this is the one you've been waiting for. Step inside this solid traditional brick home and you'll

  Russell Tribell Fathom Realty KY LLC

  1010 W Chester Ave, Middlesboro, KY 40965
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  /32

  $225,000

  Sold Aug 17, 2026

  1203 Winchester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft
  • Built 1966

  Last Sold Summary

  • 6% Below List Price
  • $92/SF
  • 7 Days On Market

  Current Estimated Value $237,404

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  1203 Winchester Ave, Middlesboro, KY 40965
• 

  

  

  /11

  Est $168,451

  Not Listed For Sale

  143 Dunlap Hill Loop, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,216 Sq Ft
  • Built 1999

  143 Dunlap Hill Loop, Middlesboro, KY 40965

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Linda Pope Renaissance Realty Group
• 

  /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
• 

  

  /6

  $60,000

  Sold Sep 03, 2025

  515 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1940

  Last Sold Summary

  • $55/SF
  • 17 Days On Market

  Current Estimated Value $68,034

  Last Listing Agent Misti McGrath Realty Group

  515 Winchester Ave, Middlesboro, KY 40965
• 

  

  /25

  Est $107,492

  Not Listed For Sale

  1323 N 25th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1900

  1323 N 25th St, Middlesboro, KY 40965

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Janice Pratt AAA Realty, Inc.
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  /29

  $279,000

  $20K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,068 Sq Ft

  207 Arthur Heights, Middlesboro, KY 40965

  CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  207 Arthur Heights, Middlesboro, KY 40965
• 

  

  /20

  $60,000

  Sold Apr 03, 2026

  72 Happy Hollow Hill Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 2007

  Last Sold Summary

  • 25% Below List Price
  • $32/SF
  • 18 Days On Market

  Current Estimated Value $60,180

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  72 Happy Hollow Hill Rd, Middlesboro, KY 40965
• 

  

  /21

  Est $95,260

  Not Listed For Sale

  116 Willow St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft
  • Built 1924

  116 Willow St, Middlesboro, KY 40965

  Last Sold Summary

  • 150 Days On Market

  Last Listing Agent David Gambrell Coldwell Banker Bisceglia Realty & Auction Co
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  /72

  $165,000

  $20K PRICE DROP Pending

  • 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
• 

  /2

  $22,500

  Sold Oct 17, 2025

  Lot #2 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 12,196 Sq Ft
  • $80,357 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 3 Days On Market

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

  Lot #2 Bellwood Rd, Middlesboro, KY 40965
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  /6

  Est $87,184

  Not Listed For Sale

  114 Willow St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft
  • Built 1800

  114 Willow St, Middlesboro, KY 40965

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent David Gambrell Coldwell Banker Bisceglia Realty & Auction Co
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  /4

  $22,000

  $3K PRICE DROP

  • Land
  • 7,492 Sq Ft
  • $127,907 per Acre

  109 Bloomsbury Ave, Middlesboro, KY 40965

  50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

  Megan Stanaford Black Diamond Realty

  109 Bloomsbury Ave, Middlesboro, KY 40965
• 

  

  /24

  $220,000

  Sold Aug 29, 2025

  4922 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,989 Sq Ft
  • Built 1967

  Last Sold Summary

  • 24% Below List Price
  • $111/SF
  • 117 Days On Market

  Current Estimated Value $251,820

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  4922 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /4

  Est $96,995

  Not Listed For Sale

  111 Cherry St, Middlesboro, KY 40965

  • Built 1920

  111 Cherry St, Middlesboro, KY 40965

  Last Sold Summary

  • 146 Days On Market

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

  /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
• 

  

  /14

  $118,000

  Sold Feb 27, 2026

  209 Dalewood Rd, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2020

  Last Sold Summary

  • $75/SF
  • 78 Days On Market

  Current Estimated Value $120,047

  Last Listing Agent Megan Stanaford Black Diamond Realty

  209 Dalewood Rd, Middlesboro, KY 40965
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  /3

  Est $124,605

  Not Listed For Sale

  216 Barkley Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  216 Barkley Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 152 Days On Market

  Last Listing Agent David Gambrell Coldwell Banker Bisceglia Realty & Auction Co
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  /30

  $249,000

  $31K PRICE DROP Pending

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

  127 Alpine Rd, Middlesboro, KY 40965

  This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  127 Alpine Rd, Middlesboro, KY 40965
• 

  

  /21

  $169,900

  Sold May 22, 2026

  707 Gloucester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1954

  Last Sold Summary

  • $143/SF
  • 3 Days On Market

  Current Estimated Value $164,258

  Last Listing Agent Dawn Risner Turn Key Realty

  707 Gloucester Ave, Middlesboro, KY 40965
• 

  

  /43

  Est $424,358

  Not Listed For Sale

  72 Everett Money Rd, Middlesboro, KY 40965

  • 3 Beds
  • 5 Baths
  • 3,000 Sq Ft
  • Built 1997

  72 Everett Money Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Cookie Russell Realty Network, Inc
• 

  

  /32

  $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
• 

  

  /50

  $312,000

  Sold Nov 03, 2025

  1087 Brush Mountain Cir, Miracle, KY 40856

  • 2 Beds
  • 3 Baths
  • 2,024 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $154/SF
  • 0 Days On Market

  Current Estimated Value $314,790

  Last Listing Agent Jennifer Skidmore Highland Heritage Realty

  1087 Brush Mountain Cir, Miracle, KY 40856
• 

  

  /25

  Est $90,495

  Not Listed For Sale

  194 Lick Fork Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,564 Sq Ft

  194 Lick Fork Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 131 Days On Market

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

  

  /52

  $555,000

  Sold Jan 20, 2026

  850 Big Buck Ln, Middlesboro, KY 40965

  • 5 Beds
  • 4 Baths
  • 4,331 Sq Ft
  • Built 2022

  Last Sold Summary

  • 7% Below List Price
  • $128/SF
  • 116 Days On Market

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  850 Big Buck Ln, Middlesboro, KY 40965
• 

  

  /26

  Est $212,855

  Not Listed For Sale

  206 Nottingham Dr, Middlesboro, KY 40965

  • 2 Beds
  • 2 Baths
  • 1,059 Sq Ft
  • Built 1994

  206 Nottingham Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S
• 

  

  /25

  $176,500

  Sold Feb 11, 2026

  164 Walker Ln, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft
  • Built 2012

  Last Sold Summary

  • 1% Above List Price
  • $170/SF
  • 12 Days On Market

  Current Estimated Value $200,391

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  164 Walker Ln, Middlesboro, KY 40965
• 

  

  /24

  Est $200,208

  Not Listed For Sale

  150 Wellington Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1993

  150 Wellington Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 4 Days On Market

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

  

  /50

  $223,000

  Sold Mar 30, 2026

  4921 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Below List Price
  • $117/SF
  • 137 Days On Market

  Current Estimated Value $247,354

  Last Listing Agent Dustin Daniels Mountain Realty

  4921 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /30

  Est $304,108

  Not Listed For Sale

  238 Windermere Dr, Middlesboro, KY 40965

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

  238 Windermere Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real
• 

  

  /24

  Est $282,880

  Not Listed For Sale

  230 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,099 Sq Ft
  • Built 2007

  230 Windermere Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 186 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /26

  Est $250,391

  Not Listed For Sale

  218 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2002

  218 Windermere Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 18 Days On Market

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

  

  /26

  Est $229,695

  Not Listed For Sale

  212 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft
  • Built 2001

  212 Windermere Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Dustin Daniels Mountain Realty
• 

  

  /23

  Est $230,236

  Not Listed For Sale

  118 Wellington Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1988

  118 Wellington Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 92 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /23

  Est $231,647

  Not Listed For Sale

  9 Castleford Way, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1985

  9 Castleford Way, Middlesboro, KY 40965

  Last Sold Summary

  • 118 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /23

  Est $187,476

  Not Listed For Sale

  6 Castleford Way, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1985

  6 Castleford Way, Middlesboro, KY 40965

  Last Sold Summary

  • 2 Days On Market

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

  

  /23

  Est $197,601

  Not Listed For Sale

  12 Abbey Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,021 Sq Ft
  • Built 1985

  12 Abbey Ln, Middlesboro, KY 40965

  Last Sold Summary

  • 2 Days On Market

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

  

  /17

  Est $228,856

  Not Listed For Sale

  8 Abbey Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft
  • Built 1986

  8 Abbey Ln, Middlesboro, KY 40965

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

Showing Results 201 - 240, Page 6 of 18