Recently Sold Middlesboro, KY Homes

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  /11

  $152,500

  Sold Oct 10, 2025

  102 Stone Creek Dr, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $160/SF
  • 9 Days On Market

  Current Estimated Value $146,269

  Last Listing Agent Misti McGrath Realty Group

  102 Stone Creek Dr, Middlesboro, KY 40965
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  /2

  $170,000

  Sold Jun 04, 2026

  4605 W Cumberland Ave, Middlesboro, KY 40965

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

  Last Sold Summary

  • 3% Above List Price
  • $161/SF
  • 37 Days On Market

  Current Estimated Value $147,953

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  4605 W Cumberland Ave, Middlesboro, KY 40965
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  /30

  $202,000

  Sold Feb 17, 2026

  140 Chasteen Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Below List Price
  • $112/SF
  • 4 Days On Market

  Current Estimated Value $210,422

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

  140 Chasteen Dr, Middlesboro, KY 40965
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  /15

  $105,000

  Sold Apr 17, 2026

  921 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $78/SF
  • 98 Days On Market

  Current Estimated Value $108,450

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  921 Winchester Ave, Middlesboro, KY 40965
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  /2

  $167,000

  Sold Sep 15, 2025

  414 SE North 24th St, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 10% Below List Price
  • $104/SF
  • 2 Days On Market

  Current Estimated Value $157,318

  Last Listing Agent Beth Combs Turn Key Realty

  414 SE North 24th St, Middlesboro, KY 40965
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  /17

  $160,000

  Sold Jul 03, 2025

  524 E Lothbury Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $200/SF
  • 5 Days On Market

  Current Estimated Value $150,674

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  524 E Lothbury Ave, Middlesboro, KY 40965
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  /2

  $10,000

  Sold Oct 17, 2025

  Lot #1 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 12,196 Sq Ft
  • $35,714 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 42 Days On Market

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

  Lot #1 Bellwood Rd, Middlesboro, KY 40965
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  /20

  $148,400

  Sold Jul 16, 2025

  112 Parker Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • Built 2011

  Last Sold Summary

  • 2% Above List Price
  • $103/SF
  • 174 Days On Market

  Current Estimated Value $170,959

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

  112 Parker Ln, Middlesboro, KY 40965
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  /24

  $196,000

  Sold Nov 26, 2025

  515 N 25th St, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,000 Sq Ft
  • Built 1918

  Last Sold Summary

  • 2% Below List Price
  • $98/SF
  • 117 Days On Market

  Current Estimated Value $183,752

  Last Listing Agent Misti McGrath Realty Group

  515 N 25th St, Middlesboro, KY 40965
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  /2

  $13,000

  Sold Sep 25, 2025

  Lot #6 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 17,859 Sq Ft
  • $31,707 per Acre

  Last Sold Summary

  • 35% Below List Price
  • 14 Days On Market

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

  Lot #6 Bellwood Rd, Middlesboro, KY 40965
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  /18

  $95,000

  Sold May 22, 2026

  1009 E Cumberland Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1935

  Last Sold Summary

  • 17% Below List Price
  • $112/SF
  • 12 Days On Market

  Current Estimated Value $108,938

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  1009 E Cumberland Ave, Middlesboro, KY 40965
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  /15

  $84,000

  Sold Apr 30, 2026

  1720 Exeter Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,456 Sq Ft
  • Built 1922

  Last Sold Summary

  • 12% Above List Price
  • $58/SF
  • 152 Days On Market

  Current Estimated Value $71,215

  Last Listing Agent Misti McGrath Realty Group

  1720 Exeter Ave, Middlesboro, KY 40965
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  /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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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /3

  $100,000

  Sold Feb 04, 2026

  413 S 26th St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1939

  Last Sold Summary

  • 43% Below List Price
  • $99/SF
  • 104 Days On Market

  Current Estimated Value $103,869

  Last Listing Agent Lisa Stacy-Gibbs Turn Key Realty

  413 S 26th St, Middlesboro, KY 40965
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  /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
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  /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

  $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
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  /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
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  /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 $150,771

  Last Listing Agent Jody Moore Threshold Real Estate Services

  2523 Exeter Ave, Middlesboro, KY 40965
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  /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
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  /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
• 

  

  /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
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  /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
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  /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
• 

  

  /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
• 

  

  /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
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  /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
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  /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
• 

  /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
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  /16

  $1,250,000

  Sold Sep 05, 2025

  423 N 10th St, Middlesboro, KY 40965

  • Land
  • 64.84 Acres
  • $19,278 per Acre

  Last Sold Summary

  • 530 Days On Market

  Current Estimated Value $587,667

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  423 N 10th St, Middlesboro, KY 40965
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  /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
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  /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
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  /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
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  /25

  $134,500

  Sold Jul 25, 2025

  422 Wilderness Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $158/SF
  • 38 Days On Market

  Current Estimated Value $148,691

  Last Listing Agent Megan Stanaford Black Diamond Realty

  422 Wilderness Rd, Middlesboro, KY 40965

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