Recently Sold Middlesboro, KY Homes

/4
$130,000

Sold Aug 25, 2026

1577 Beans Fork Rd, Middlesboro, KY 40965
- Land
- 1.02 Acres
- $127,451 per Acre
Last Sold Summary
- 420% Above List Price
- 50 Days On Market
Last Listing Agent Misti McGrath Realty Group

1577 Beans Fork Rd, Middlesboro, KY 40965
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/13
$32,000

Sold Sep 18, 2026

904-A E Cumberland Ave, Middlesboro, KY 40965
- Land
- 12,196 Sq Ft
- $114,286 per Acre
Last Sold Summary
- 9% Below List Price
- 7 Days On Market
Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

904-A E Cumberland Ave, 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 $314,455

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 $218,260

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 $184,777

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
/20
$187,000

Sold Aug 20, 2026

116 N Petersborough Ave, Middlesboro, KY 40965
- 3 Beds
- 1 Bath
- 1,652 Sq Ft
- Built 1930
Last Sold Summary
- 17% Below List Price
- $113/SF
- 76 Days On Market
Current Estimated Value $211,604

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

116 N Petersborough 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 $124,000

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

TBD Rt 516 Old Cross Rd, Pineville, KY 40977
/16
$50,000

Sold Sep 11, 2026

417-A&B Avondale Ave, Middlesboro, KY 40965
- 2,256 Sq Ft
- Built 1928
Last Sold Summary
- 37% Below List Price
- $22/SF
- 74 Days On Market
Last Listing Agent Nancy Maiden Mountain Realty

417-A&B Avondale Ave, 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 $243,792

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 $94,853

Last Listing Agent Misti McGrath Realty Group

234 S 46th St, Middlesboro, KY 40965
/40
$249,900

Sold Aug 07, 2026

913 Doncaster St, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,346 Sq Ft
- Built 1998
Last Sold Summary
- $186/SF
- 61 Days On Market
Current Estimated Value $249,055

Last Listing Agent Janice Pratt Fathom Realty TN LLC

913 Doncaster 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 $334,939

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 $188,876

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 $170,466

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 $242,832

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 $296,383

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 $184,860

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 $188,340

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 $334,632

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 $302,037

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 $104,676

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 $157,646

Last Listing Agent Brad Cawood Turn Key Realty

428 Wilderness Rd, Middlesboro, KY 40965
/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 $237,442

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

1203 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 $60,846

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
/22
$135,000

Sold Sep 21, 2026

1010 W Chester Ave, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 1,275 Sq Ft
- Built 1966
Last Sold Summary
- 10% Below List Price
- $106/SF
- 31 Days On Market
Current Estimated Value $146,838

Last Listing Agent Russell Tribell Fathom Realty KY LLC

1010 W Chester Ave, 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 $121,741

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 $164,258

Last Listing Agent Dawn Risner Turn Key Realty

707 Gloucester Ave, Middlesboro, KY 40965
/72
$164,800

Sold Aug 31, 2026

713 Exeter Ave, Middlesboro, KY 40965
- 4 Beds
- 1 Bath
- 2,430 Sq Ft
- Built 1920
Last Sold Summary
- 11% Below List Price
- $68/SF
- 104 Days On Market
Current Estimated Value $163,082

Last Listing Agent Victoria Allen Century 21 Virginia Wilder Real Estate

713 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 $313,430

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 $200,624

Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

164 Walker Ln, Middlesboro, KY 40965
/30
$214,000

Sold Sep 18, 2026

127 Alpine Rd, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 2,016 Sq Ft
- Built 1960
Last Sold Summary
- 24% Below List Price
- $106/SF
- 129 Days On Market
Current Estimated Value $245,474

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

127 Alpine Rd, 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 $240,116

Last Listing Agent Dustin Daniels Mountain Realty

4921 W Cumberland Ave, Middlesboro, KY 40965

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