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

  Last Listing Agent Misti McGrath Realty Group

  102 Stone Creek Dr, Middlesboro, KY 40965
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  /15

  $170,000 Sold May 19, 2025

  1002 W Chester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 1 Bath
  • 2,073 Sq Ft
  • Built 1947

  Last Sold Summary

  • $82/SF
  • 0 Days On Market

  Current Estimated Value $179,393

  Last Listing Agent Misti McGrath Realty Group

  1002 W Chester Ave, Middlesboro, KY 40965
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  /10

  $10,000 Sold Jan 30, 2025

  175 Brush Mountain Cir, Middlesboro, KY 40965

  • Land
  • 2.86 Acres
  • $3,497 per Acre

  Last Sold Summary

  • 53% Below List Price
  • 67 Days On Market

  Last Listing Agent Jason Rains WEICHERT REALTORS - Ford Brothers

  175 Brush Mountain Cir, 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 $199,045

  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 $160,394

  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
  • 0.28 Acre
  • $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 $150,218

  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

  Last Listing Agent Misti McGrath Realty Group

  515 N 25th St, Middlesboro, KY 40965
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  /13

  $52,500 Sold Mar 19, 2025

  3765 Highway 441, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,124 Sq Ft
  • Built 1974

  Last Sold Summary

  • 25% Below List Price
  • $47/SF
  • 21 Days On Market

  Current Estimated Value $69,936

  Last Listing Agent Patsy Barnett Coldwell Banker Bisceglia Real

  3765 Highway 441, Middlesboro, KY 40965
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  /2

  $13,000 Sold Sep 25, 2025

  Lot #6 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 0.41 Acre
  • $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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  /24

  $130,000 Sold Feb 04, 2025

  205 Oakwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft
  • Built 1947

  Last Sold Summary

  • 4% Below List Price
  • $127/SF
  • 48 Days On Market

  Current Estimated Value $122,279

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  205 Oakwood 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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  /7

  $40,000 Sold May 30, 2025

  19 Venado Dr, Middlesboro, KY 40965

  • Land
  • 3.16 Acres
  • $12,658 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 238 Days On Market

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

  19 Venado Dr, Middlesboro, KY 40965
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  /18

  $58,000 Sold Jan 27, 2025

  401 S 20th St, Middlesboro, KY 40965

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

  Last Sold Summary

  • 6% Below List Price
  • $63/SF
  • 6 Days On Market

  Current Estimated Value $79,343

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  401 S 20th St, Middlesboro, KY 40965
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  /17

  $210,000 Sold May 02, 2025

  8 Abbey Ln, Middlesboro, KY 40965

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

  Last Sold Summary

  • 7% Below List Price
  • $156/SF
  • 28 Days On Market

  Current Estimated Value $219,839

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  8 Abbey Ln, Middlesboro, KY 40965
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  /50

  $525,000 Sold Mar 31, 2025

  23 Ennismore Dr, Middlesboro, KY 40965

  • 4 Beds
  • 5.5 Baths
  • 6,000 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $88/SF
  • 173 Days On Market

  Current Estimated Value $535,827

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  23 Ennismore Dr, Middlesboro, KY 40965
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  /24

  $250,000 Sold May 05, 2025

  230 Windermere Dr, Middlesboro, KY 40965

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

  Last Sold Summary

  • 14% Below List Price
  • $119/SF
  • 186 Days On Market

  Current Estimated Value $273,411

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  230 Windermere Dr, Middlesboro, KY 40965
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  /28

  $185,000 Sold Jan 23, 2025

  908 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1955

  Last Sold Summary

  • 6% Below List Price
  • $132/SF
  • 131 Days On Market

  Current Estimated Value $188,205

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  908 W Chester Ave, 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

  Last Listing Agent Brad Cawood Turn Key Realty

  115 George Ann Dr, Middlesboro, KY 40965
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  /16

  $205,000 Sold May 12, 2025

  286 Tiwani Ridge Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1992

  Last Sold Summary

  • 18% Below List Price
  • $108/SF
  • 17 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  286 Tiwani Ridge Rd, 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 $915,388

  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 $290,712

  Last Listing Agent Brad Cawood Turn Key Realty

  9 Ennismore Dr, Middlesboro, KY 40965
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  /49

  $186,000 Sold May 05, 2025

  412 Wilderness Rd, Middlesboro, KY 40965

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

  Last Sold Summary

  • 2% Below List Price
  • $81/SF
  • 31 Days On Market

  Current Estimated Value $198,956

  Last Listing Agent Dustin Daniels Mountain Realty

  412 Wilderness Rd, Middlesboro, KY 40965
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  /15

  $87,000 Sold Mar 11, 2025

  1200 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,028 Sq Ft
  • Built 1958

  Last Sold Summary

  • 27% Below List Price
  • $85/SF
  • 64 Days On Market

  Current Estimated Value $98,026

  Last Listing Agent Blake Ramey Century 21 Virginia Wilder Real Estate

  1200 W Chester Ave, 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 $71,433

  Last Listing Agent Misti McGrath Realty Group

  1813 Winchester Ave, Middlesboro, KY 40965
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  /18

  $235,000 Sold Jan 31, 2025

  2103 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,100 Sq Ft
  • Built 1920

  Last Sold Summary

  • 68% Above List Price
  • $112/SF
  • 692 Days On Market

  Current Estimated Value $222,444

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

  2103 Winchester Ave, Middlesboro, KY 40965
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  /20

  $106,000 Sold Jan 30, 2025

  409 Shillilah Village, Middlesboro, KY 40965

  • 1 Bed
  • 1 Bath
  • 676 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $157/SF
  • 71 Days On Market

  Last Listing Agent Dawn Risner Turn Key Realty

  409 Shillilah Village, Middlesboro, KY 40965
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  /9

  $24,501 Sold Jan 02, 2025

  311 S 22nd St, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,548 Sq Ft
  • Built 1909

  Last Sold Summary

  • 8% Below List Price
  • $16/SF
  • 10 Days On Market

  Current Estimated Value $96,063

  Last Listing Agent Aaron Brailer RealHome Services and Solutions, Inc.

  311 S 22nd St, 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 $394,308

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  2824 W Cumberland Ave, Middlesboro, KY 40965
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  /16

  $46,000 Sold Mar 28, 2025

  309 Oakwood Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1938

  Last Sold Summary

  • 8% Below List Price
  • $38/SF
  • 93 Days On Market

  Current Estimated Value $89,318

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  309 Oakwood Rd, Middlesboro, KY 40965
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  /25

  $102,500 Sold Feb 19, 2025

  512 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 1908

  Last Sold Summary

  • 24% Below List Price
  • $49/SF
  • 191 Days On Market

  Current Estimated Value $107,517

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  512 W Chester 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 $96,273

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

  600 S 38th St, Middlesboro, KY 40965
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  /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

  Last Listing Agent Misti McGrath Realty Group

  900 Twin Fawn Trail, Middlesboro, KY 40965
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  /18

  $60,000 Sold May 13, 2025

  210 Welch Ln, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,430 Sq Ft
  • Built 1982

  Last Sold Summary

  • 40% Below List Price
  • $42/SF
  • 184 Days On Market

  Current Estimated Value $70,138

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  210 Welch Ln, 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 $284,169

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  10 Thaxted Ln, Middlesboro, KY 40965
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  /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 $269,294

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real

  238 Windermere Dr, Middlesboro, KY 40965
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  /38

  $282,000 Sold May 12, 2025

  904 E Cumberland Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1970

  Last Sold Summary

  • 6% Below List Price
  • $123/SF
  • 48 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  904 E Cumberland Ave, 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 $915,388

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  423 N 10th St, Middlesboro, KY 40965
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  /18

  $52,500 Sold Mar 19, 2025

  3777 Highway 441, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1940

  Last Sold Summary

  • 25% Below List Price
  • $50/SF
  • 21 Days On Market

  Current Estimated Value $94,440

  Last Listing Agent Patsy Barnett Coldwell Banker Bisceglia Real

  3777 Highway 441, Middlesboro, KY 40965

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