Recently Sold Middlesboro, KY Homes

• 

  

  

  /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
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• 

  

  

  /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
• 

  

  

  /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 $110,000

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  0 Arie Turner Ln, 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 $70,631

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

  305 N 15th St, Middlesboro, KY 40965
• 

  

  

  /23

  $150,000

  Sold Jun 04, 2026

  359 Beans Fork Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 1920

  Last Sold Summary

  • $158/SF
  • 61 Days On Market

  Current Estimated Value $148,192

  Last Listing Agent Misti McGrath Realty Group

  359 Beans Fork Rd, Middlesboro, KY 40965
• 

  

  /48

  $324,900

  Sold Apr 17, 2026

  805 Worchester Ave, Middlesboro, KY 40965

  • 5 Beds
  • 3 Baths
  • 2,250 Sq Ft
  • Built 1942

  Last Sold Summary

  • 7% Below List Price
  • $144/SF
  • 169 Days On Market

  Current Estimated Value $308,272

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  805 Worchester Ave, Middlesboro, KY 40965
• 

  

  /17

  $222,500

  Sold May 22, 2026

  810 Worchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1950

  Last Sold Summary

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

  Current Estimated Value $221,462

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  810 Worchester Ave, Middlesboro, KY 40965
• 

  

  /32

  $173,675

  Sold Mar 27, 2026

  140 Hickory Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • Built 2009

  Last Sold Summary

  • 5% Above List Price
  • 15 Days On Market

  Current Estimated Value $176,527

  Last Listing Agent SARAH RICHARDS RE/MAX Preferred Group

  140 Hickory Ln, Middlesboro, KY 40965
• 

  /2

  $8,000

  Sold Nov 18, 2025

  4163 441, Middlesboro, KY 40965

  • Land
  • 17,424 Sq Ft
  • $20,000 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 82 Days On Market

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

  4163 441, Middlesboro, KY 40965
• 

  /2

  $167,000

  Sold Sep 15, 2025

  919 W Rochester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,024 Sq Ft
  • Built 2010

  Last Sold Summary

  • 10% Below List Price
  • $83/SF
  • 4 Days On Market

  Current Estimated Value $169,038

  Last Listing Agent Beth Combs Turn Key Realty

  919 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /20

  $108,000

  Sold Dec 19, 2025

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977

  • Land
  • 11 Acres
  • $9,818 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 6 Days On Market

  Current Estimated Value $114,000

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977
• 

  

  /26

  $190,000

  Sold Aug 21, 2025

  206 Nottingham Dr, Middlesboro, KY 40965

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

  Last Sold Summary

  • 5% Below List Price
  • $179/SF
  • 2 Days On Market

  Current Estimated Value $202,499

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  206 Nottingham Dr, Middlesboro, KY 40965
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  /32

  $231,000

  Sold Oct 22, 2025

  825 S 28th St, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 2004

  Last Sold Summary

  • 14% Below List Price
  • $114/SF
  • 151 Days On Market

  Current Estimated Value $229,960

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  825 S 28th St, Middlesboro, KY 40965
• 

  /2

  $32,500

  Sold Mar 19, 2026

  0 Windermere, Middlesboro, KY 40965

  • Land
  • 29,185 Sq Ft
  • $48,507 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 41 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  0 Windermere, Middlesboro, KY 40965
• 

  

  /10

  $90,000

  Sold Nov 19, 2025

  234 S 46th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 2013

  Last Sold Summary

  • 17% Below List Price
  • $97/SF
  • 47 Days On Market

  Current Estimated Value $91,276

  Last Listing Agent Misti McGrath Realty Group

  234 S 46th St, Middlesboro, KY 40965
• 

  

  /10

  $293,000

  Sold Feb 06, 2026

  314 Picadilly Ct, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 2,576 Sq Ft
  • Built 1999

  Last Sold Summary

  • $114/SF
  • 9 Days On Market

  Current Estimated Value $312,774

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

  314 Picadilly Ct, Middlesboro, KY 40965
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  /15

  $175,000

  Sold Jan 13, 2026

  708 Ilchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Built 1980

  Last Sold Summary

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

  Current Estimated Value $180,515

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  708 Ilchester Ave, Middlesboro, KY 40965
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  /18

  $168,000

  Sold Apr 22, 2026

  409 Meadow Ln, Middlesboro, KY 40965

  • 4 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $150/SF
  • 29 Days On Market

  Current Estimated Value $167,944

  Last Listing Agent Brad Cawood Turn Key Realty

  409 Meadow Ln, Middlesboro, KY 40965
• 

  

  /17

  $239,500

  Sold Nov 19, 2025

  5 Abbey Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $196/SF
  • 86 Days On Market

  Current Estimated Value $207,495

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  5 Abbey Ln, Middlesboro, KY 40965
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  /48

  $275,000

  Sold Nov 03, 2025

  109 Hollywood Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 3,544 Sq Ft

  Last Sold Summary

  • 11% Below List Price
  • $78/SF
  • 159 Days On Market

  Current Estimated Value $280,458

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

  109 Hollywood Dr, Middlesboro, KY 40965
• 

  

  /30

  $168,700

  Sold Jan 21, 2026

  3008 State Highway 441, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Built 1900

  Last Sold Summary

  • 16% Below List Price
  • $94/SF
  • 104 Days On Market

  Current Estimated Value $175,712

  Last Listing Agent Brad Cawood Turn Key Realty

  3008 State Highway 441, Middlesboro, KY 40965
• 

  

  /16

  $180,000

  Sold Oct 21, 2025

  106 S 38th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1971

  Last Sold Summary

  • 20% Below List Price
  • $128/SF

  Current Estimated Value $179,005

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

  106 S 38th St, Middlesboro, KY 40965
• 

  /2

  $6,000

  Sold Dec 31, 2025

  lot 34 Brush Mountain Cir, Miracle, KY 40856

  • Land
  • 2.58 Acres
  • $2,326 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 141 Days On Market

  Last Listing Agent Megan Stanaford Black Diamond Realty

  lot 34 Brush Mountain Cir, Miracle, KY 40856
• 

  

  /33

  $340,000

  Sold May 18, 2026

  3306 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,126 Sq Ft
  • Built 1976

  Last Sold Summary

  • 3% Below List Price
  • $160/SF
  • 1 Day On Market

  Current Estimated Value $335,582

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  3306 W Cumberland Ave, Middlesboro, KY 40965
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  /66

  $305,000

  Sold May 14, 2026

  832 N 25th St, Middlesboro, KY 40965

  • 6 Beds
  • 3.5 Baths
  • 4,033 Sq Ft

  Last Sold Summary

  • 10% Below List Price
  • $76/SF
  • 278 Days On Market

  Current Estimated Value $312,609

  Last Listing Agent Blake Ramey Century 21 Virginia Wilder Real Estate

  832 N 25th St, Middlesboro, KY 40965
• 

  

  /19

  $87,000

  Sold Jan 20, 2026

  101 Earle Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1970

  Last Sold Summary

  • 17% Below List Price
  • $79/SF
  • 111 Days On Market

  Current Estimated Value $98,843

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  101 Earle Ln, Middlesboro, KY 40965
• 

  

  /18

  $175,000

  Sold Dec 31, 2025

  114 W Rochester Ave, Middlesboro, KY 40965

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

  Last Sold Summary

  • $174/SF
  • 15 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  114 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /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 $146,367

  Last Listing Agent Brad Cawood Turn Key Realty

  428 Wilderness Rd, 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 $69,047

  Last Listing Agent Misti McGrath Realty Group

  515 Winchester Ave, 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 $60,000

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  72 Happy Hollow Hill Rd, 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
• 

  

  /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 $242,543

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  4922 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /36

  $275,000

  Sold Aug 12, 2025

  709 Balmoral Rd, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • Built 1982

  Last Sold Summary

  • $141/SF
  • 5 Days On Market

  Last Listing Agent D.J Wilder Century 21 Virginia Wilder Real Estate

  709 Balmoral Rd, 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 $118,342

  Last Listing Agent Megan Stanaford Black Diamond Realty

  209 Dalewood 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 $165,361

  Last Listing Agent Dawn Risner Turn Key Realty

  707 Gloucester Ave, Middlesboro, KY 40965
• 

  

  /11

  $40,000

  Sold Jul 30, 2025

  1809 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft
  • Built 1960

  Last Sold Summary

  • 20% Below List Price
  • $38/SF
  • 22 Days On Market

  Current Estimated Value $44,883

  Last Listing Agent Misti McGrath Realty Group

  1809 Exeter Ave, 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 $322,289

  Last Listing Agent Jennifer Skidmore Highland Heritage Realty

  1087 Brush Mountain Cir, Miracle, KY 40856
• 

  

  /15

  $160,000

  Sold Jul 14, 2025

  810 S 28th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 2008

  Last Sold Summary

  • 2% Below List Price
  • $154/SF
  • 19 Days On Market

  Current Estimated Value $183,031

  Last Listing Agent Ben Madon Coldwell Banker Bisceglia Realty & Auction Co

  810 S 28th St, Middlesboro, KY 40965
• 

  

  /30

  $107,500

  Sold Jul 31, 2025

  3202 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft
  • Built 1977

  Last Sold Summary

  • 13% Below List Price
  • $53/SF
  • 7 Days On Market

  Current Estimated Value $124,062

  Last Listing Agent Elizabeth Mills Huddleston Real Estate

  3202 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /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

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