Recently Sold Middlesboro, KY Homes

/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 $235,658

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 $176,000

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 $73,361

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 $160,015

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 $323,836

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 $219,738

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 $192,025

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 $187,308

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 $120,000

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 $211,418

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

206 Nottingham Dr, Middlesboro, KY 40965
/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 $238,971

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

825 S 28th St, Middlesboro, KY 40965
/24
$152,500

Sold Jul 21, 2026

1807 Winchester Ave, Middlesboro, KY 40965
- 3 Beds
- 1 Bath
- 1,104 Sq Ft
- Built 1958
Last Sold Summary
- 2% Below List Price
- $138/SF
- 15 Days On Market
Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

1807 Winchester Ave, 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 $93,533

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 $335,750

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

314 Picadilly Ct, Middlesboro, KY 40965
/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 $193,728

Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

708 Ilchester Ave, Middlesboro, KY 40965
/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 $172,220

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 $232,108

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

5 Abbey Ln, Middlesboro, KY 40965
/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 $290,736

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 $185,002

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 $187,509

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 $333,240

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

3306 W Cumberland Ave, Middlesboro, KY 40965
/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 $305,285

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 $110,128

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 $154,492

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 $68,034

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 $60,180

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 $251,820

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 $120,047

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 $162,948

Last Listing Agent Dawn Risner Turn Key Realty

707 Gloucester 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 $314,790

Last Listing Agent Jennifer Skidmore Highland Heritage Realty

1087 Brush Mountain Cir, Miracle, KY 40856
/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
/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
/26
$225,000

Sold Aug 08, 2025

218 Windermere Dr, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
- Built 2002
Last Sold Summary
- 10% Below List Price
- $174/SF
- 18 Days On Market
Current Estimated Value $250,391

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

218 Windermere Dr, Middlesboro, KY 40965
/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

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