Recently Sold Middlesboro, KY Homes

/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 $155,688

Last Listing Agent Misti McGrath Realty Group

102 Stone Creek Dr, Middlesboro, KY 40965
/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 $158,061

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

4605 W Cumberland Ave, Middlesboro, KY 40965
/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 $225,304

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

140 Chasteen Dr, Middlesboro, KY 40965
/30
$65,000

Sold Jul 31, 2026

316 Exeter Ave, Middlesboro, KY 40965
- 4 Beds
- 2 Baths
- 2,592 Sq Ft
- Built 1920
Last Sold Summary
- 48% Below List Price
- $25/SF
- 12 Days On Market
Current Estimated Value $121,398

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

316 Exeter Ave, Middlesboro, KY 40965
/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 $110,333

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

921 Winchester Ave, Middlesboro, KY 40965
/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
/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 $193,958

Last Listing Agent Misti McGrath Realty Group

515 N 25th St, Middlesboro, KY 40965
/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
/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 $97,896

Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

1009 E Cumberland Ave, Middlesboro, KY 40965
/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 $116,266

Last Listing Agent Misti McGrath Realty Group

1720 Exeter Ave, Middlesboro, KY 40965
/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 $273,308

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

220 Windermere Dr, Middlesboro, KY 40965
/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 $172,095

Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

103 Leafwood Rd, Middlesboro, KY 40965
/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
/2
$70,000

Sold Jul 08, 2026

923 Winchester Ave, Middlesboro, KY 40965
- 1 Bed
- 1 Bath
- 800 Sq Ft
- Built 1940
Last Sold Summary
- 29% Below List Price
- $88/SF
- 159 Days On Market
Current Estimated Value $84,247

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

923 Winchester Ave, Middlesboro, KY 40965
/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
/2
$12,000

Sold Jul 09, 2026

2503 Exeter Ave, Middlesboro, KY 40965
- Land
- 13,068 Sq Ft
- $40,000 per Acre
Last Sold Summary
- 52% Below List Price
- 110 Days On Market
Current Estimated Value $78,667

Last Listing Agent Misti McGrath Realty Group

2503 Exeter Ave, Middlesboro, KY 40965
/29
$155,000

Sold Jul 27, 2026

1425 Highway 441, Middlesboro, KY 40965
- 3 Beds
- 1.5 Baths
- 1,242 Sq Ft
- Built 1985
Last Sold Summary
- 6% Below List Price
- $125/SF
- 30 Days On Market
Current Estimated Value $158,975

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

1425 Highway 441, Middlesboro, KY 40965
/10
$245,000

Sold Aug 07, 2026

2802 W Cumberland Ave, Middlesboro, KY 40965
- 3 Beds
- 1.5 Baths
- 1,304 Sq Ft
- Built 1924
Last Sold Summary
- 6% Below List Price
- $188/SF
- 13 Days On Market
Current Estimated Value $252,973

Last Listing Agent Misti McGrath Realty Group

2802 W Cumberland Ave, Middlesboro, KY 40965
/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 $133,209

Last Listing Agent Megan Stanaford Black Diamond Realty

123 Upper Gibson Ln, Middlesboro, KY 40965
/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
/31
$183,500

Sold Jul 17, 2026

23 Castleford Way, Middlesboro, KY 40965
- 3 Beds
- 1.5 Baths
- 1,080 Sq Ft
- Built 1986
Last Sold Summary
- 12% Below List Price
- $170/SF
- 25 Days On Market
Current Estimated Value $183,000

Last Listing Agent Beth Combs Backwoods Realty & Development

23 Castleford Way, Middlesboro, KY 40965
/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 $285,203

Last Listing Agent Brad Cawood Turn Key Realty

115 George Ann Dr, Middlesboro, KY 40965
/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 $134,102

Last Listing Agent Lisa Stacy-Gibbs Backwoods Realty & Development

413 S 26th St, 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
/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 $154,315

Last Listing Agent Jody Moore Threshold Real Estate Services

2523 Exeter Ave, Middlesboro, KY 40965
/24
$145,000

Sold Aug 17, 2026

63 Old Pineville Pike, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
- Built 1980
Last Sold Summary
- 27% Below List Price
- $93/SF
- 21 Days On Market
Current Estimated Value $181,530

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

63 Old Pineville Pike, Middlesboro, KY 40965
/46
$85,000

Sold Sep 10, 2026

1720 Exeter Ave, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 1,456 Sq Ft
- Built 1922
Last Sold Summary
- 32% Below List Price
- $58/SF
- 64 Days On Market
Current Estimated Value $116,266

Last Listing Agent Victoria Allen Century 21 Virginia Wilder Real Estate

1720 Exeter Ave, 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 $314,499

Last Listing Agent Misti McGrath Realty Group

900 Twin Fawn Trail, Middlesboro, KY 40965
/2
$17,000

Sold Jul 24, 2026

103 Nutwood Rd, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 1,244 Sq Ft
- Built 1950
Last Sold Summary
- 43% Below List Price
- $14/SF
- 51 Days On Market
Current Estimated Value $77,178

Last Listing Agent Megan Stanaford Black Diamond Realty

103 Nutwood Rd, Middlesboro, KY 40965
/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 $218,267

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

6 Hampton Ct, 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
/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 $129,002

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
/29
$240,000

Sold Jun 23, 2026

206 Summit Dr, Middlesboro, KY 40965
- 4 Beds
- 2.5 Baths
- 1,832 Sq Ft
- Built 1962
Last Sold Summary
- 14% Below List Price
- $131/SF
- 129 Days On Market
Current Estimated Value $233,068

Last Listing Agent Sharon Teaney Century 21 Virginia Wilder Real Estate

206 Summit Dr, Middlesboro, KY 40965
/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 $185,022

Last Listing Agent Jennifer Ware Rock N' Realty LLC

11 Castleford Way, Middlesboro, KY 40965
/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 $554,359

Last Listing Agent Brad Cawood Turn Key Realty

1308 Gloucester Ave, Middlesboro, KY 40965
/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 $236,418

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 $114,000

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 $72,384

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 $155,476

Last Listing Agent Misti McGrath Realty Group

359 Beans Fork Rd, Middlesboro, KY 40965

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