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 $151,207

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 $157,031

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 $223,320

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

140 Chasteen Dr, 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 $113,326

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

921 Winchester Ave, Middlesboro, KY 40965
/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 $176,930

Last Listing Agent Beth Combs Turn Key Realty

414 SE North 24th St, 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 $191,812

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 $102,587

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 $122,523

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 $273,207

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 $168,891

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 $77,231

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 $128,000

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 $164,700

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

1425 Highway 441, 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 $132,099

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 $181,539

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 $281,908

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 $135,830

Last Listing Agent Lisa Stacy-Gibbs Backwoods Realty & Development

413 S 26th St, Middlesboro, KY 40965
/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 $567,667

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

423 N 10th 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 $159,025

Last Listing Agent Jody Moore Threshold Real Estate Services

2523 Exeter Ave, Middlesboro, KY 40965
/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 $422,307

Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

2824 W Cumberland 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 $310,514

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 $215,336

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

6 Hampton Ct, Middlesboro, KY 40965
/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 $319,973

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
/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 $304,108

Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real

238 Windermere Dr, 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 $121,243

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
/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 $567,667

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

423 N 10th St, 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 $244,337

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 $183,374

Last Listing Agent Jennifer Ware Kentucky Land and Home

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 $556,546

Last Listing Agent Brad Cawood Turn Key Realty

1308 Gloucester Ave, Middlesboro, KY 40965
/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 $121,610

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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