Middlesboro, KY Homes

/22
Est $319,458

Not Listed For Sale

123 Twin Acres Rd, Middlesboro, KY 40965
- 4 Beds
- 2 Baths
- 3,338 Sq Ft
- Built 1987
123 Twin Acres Rd, Middlesboro, KY 40965

Last Sold Summary
- 42 Days On Market

/13
$55,000

$20K PRICE DROP
- 2 Beds
- 1 Bath
- 792 Sq Ft
918 E Cumberland Ave, Middlesboro, KY 40965

Old home needs work with an attached older home that needs to be torn down. Great Location on Cumberland Ave behind Food City

Steve Mason REMAX PROFESSIONAL'S

918 E Cumberland Ave, 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

/19
Est $168,327

Not Listed For Sale

1408 Exeter Ave, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 1933
1408 Exeter Ave, Middlesboro, KY 40965

Last Sold Summary
- 66 Days On Market

/15
$135,000

$7K PRICE DROP
- 3 Beds
- 1 Bath
- 1,404 Sq Ft
708 W Chester Ave, Middlesboro, KY 40965

Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.

Michael Hensley REMAX PROFESSIONAL'S

708 W Chester Ave, 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 $242,543

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

4922 W Cumberland Ave, Middlesboro, KY 40965

/10
Est $110,922

Not Listed For Sale

1619 Winchester Ave, Middlesboro, KY 40965
- 2 Beds
- 1.5 Baths
- 1,364 Sq Ft
- Built 1940
1619 Winchester Ave, Middlesboro, KY 40965

Last Sold Summary
- 178 Days On Market

/31
$160,000

$22K PRICE DROP
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
180 Stevenson Bridge Rd, Middlesboro, KY 40965

Charming Rustic Cabin with Modern Comforts on 2 Acres Welcome to 180 Stevenson Branch Rd in Middlesboro, KY—where country charm meets convenience. Just minutes from historic downtown Middlesboro, you'll enjoy easy access to quaint shops, local restaurants, major retailers, medical offices, banks, and hospitals—all while savoring the serenity of rural living. Nestled on a hillside and surrounded

Kevin Carroll Backwoods Realty & Development

180 Stevenson Bridge Rd, 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

/31
Est $264,825

Not Listed For Sale

806 Cirencester Ave, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,572 Sq Ft
- Built 1969
806 Cirencester Ave, Middlesboro, KY 40965

Last Sold Summary
- 5 Days On Market

/35
$179,900

$7K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,028 Sq Ft
1200 W Chester Ave, Middlesboro, KY 40965

Charming Home for Sale in Middlesboro, KY - 1200 W Chester Ave Welcome to this inviting home located in the heart of Middlesboro! Situated on a spacious corner lot at 1200 W Chester Avenue, this property offers comfort, convenience, and small-town charm—all in one. Comfortable living spaces with plenty of natural light. Functional kitchen with ample cabinet storage Generous yard—perfect for

Megan Stanaford Black Diamond Realty

1200 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 $118,342

Last Listing Agent Megan Stanaford Black Diamond Realty

209 Dalewood Rd, Middlesboro, KY 40965

/11
Est $176,720

Not Listed For Sale

143 Dunlap Hill Loop, Middlesboro, KY 40965
- 3 Beds
- 1.5 Baths
- 1,216 Sq Ft
- Built 1999
143 Dunlap Hill Loop, Middlesboro, KY 40965

Last Sold Summary
- 70 Days On Market

/2
$960,000
- 2 Beds
- 2 Baths
- 6,696 Sq Ft
508 & 512 Winchester Ave, Middlesboro, KY 40965

Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to

Beth Combs Turn Key Realty

508 & 512 Winchester Ave, 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 $165,361

Last Listing Agent Dawn Risner Turn Key Realty

707 Gloucester Ave, Middlesboro, KY 40965

/29
Est $107,000

Not Listed For Sale

1315 N 25th St, Middlesboro, KY 40965
- 3 Beds
- 1 Bath
- 960 Sq Ft
- Built 1977
1315 N 25th St, Middlesboro, KY 40965

Last Sold Summary
- 114 Days On Market

/29
$299,000
- 5 Beds
- 2.5 Baths
- 3,068 Sq Ft
207 Arthur Heights, Middlesboro, KY 40965

CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary

Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

207 Arthur Heights, Middlesboro, KY 40965
/11
$40,000

Sold Jul 30, 2025

1809 Exeter Ave, Middlesboro, KY 40965
- 3 Beds
- 1 Bath
- 1,064 Sq Ft
- Built 1960
Last Sold Summary
- 20% Below List Price
- $38/SF
- 22 Days On Market
Current Estimated Value $44,883

Last Listing Agent Misti McGrath Realty Group

1809 Exeter Ave, Middlesboro, KY 40965

/25
Est $87,584

Not Listed For Sale

1323 N 25th St, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
- Built 1900
1323 N 25th St, Middlesboro, KY 40965

Last Sold Summary
- 27 Days On Market

/72
$165,000

$20K PRICE DROP
- 4 Beds
- 1 Bath
- 2,430 Sq Ft
713 Exeter Ave, Middlesboro, KY 40965

Welcome to the stunning 713 Exeter Ave located in the lovely town of Middlesboro KY, less than 5 minutes to downtown Middlesboro, 15 minutes from LMU, & super close to Norris Lake. This home makes a perfect residence for anyone looking in the area and would make a great rental property as well! This home offers ample space with 4 bedrooms on the main level and tons of potential for a loft or 2

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 $322,289

Last Listing Agent Jennifer Skidmore Highland Heritage Realty

1087 Brush Mountain Cir, Miracle, KY 40856

/21
Est $103,660

Not Listed For Sale

116 Willow St, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 904 Sq Ft
- Built 1924
116 Willow St, Middlesboro, KY 40965

Last Sold Summary
- 150 Days On Market

/4
$24,000

$1K PRICE DROP
- Land
- 7,492 Sq Ft
- $139,535 per Acre
109 Bloomsbury Ave, Middlesboro, KY 40965

50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

Megan Stanaford Black Diamond Realty

109 Bloomsbury Ave, Middlesboro, KY 40965
/15
$160,000

Sold Jul 14, 2025

810 S 28th St, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,040 Sq Ft
- Built 2008
Last Sold Summary
- 2% Below List Price
- $154/SF
- 19 Days On Market
Current Estimated Value $183,031

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

810 S 28th St, Middlesboro, KY 40965

/6
Est $90,431

Not Listed For Sale

114 Willow St, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 904 Sq Ft
- Built 1800
114 Willow St, Middlesboro, KY 40965

Last Sold Summary
- 61 Days On Market

/2
$182,000
- 2 Beds
- 2 Baths
- 1,608 Sq Ft
414 S 24th St, Middlesboro, KY 40965

Prime commercial opportunity at 414 S 24th Street in Middlesboro, KY! This versatile property offers excellent visibility and accessibility in a well-established area, just minutes from historic downtown Middlesboro and major routes. Ideal for office space, retail, professional services, or an investment property with strong potential in Bell County. Spacious layout, solid construction, and

Beth Combs Turn Key Realty

414 S 24th St, Middlesboro, KY 40965
/30
$107,500

Sold Jul 31, 2025

3202 W Cumberland Ave, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 2,044 Sq Ft
- Built 1977
Last Sold Summary
- 13% Below List Price
- $53/SF
- 7 Days On Market
Current Estimated Value $124,062

Last Listing Agent Elizabeth Mills Huddleston Real Estate

3202 W Cumberland Ave, Middlesboro, KY 40965

/4
Est $122,251

Not Listed For Sale

111 Cherry St, Middlesboro, KY 40965
- Built 1920
111 Cherry St, Middlesboro, KY 40965

Last Sold Summary
- 146 Days On Market

/30
$279,900
- 3 Beds
- 2 Baths
- 2,016 Sq Ft
127 Alpine Rd, Middlesboro, KY 40965

This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is

Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

127 Alpine Rd, Middlesboro, KY 40965
/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

/3
Est $124,077

Not Listed For Sale

216 Barkley Dr, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,728 Sq Ft
216 Barkley Dr, Middlesboro, KY 40965

Last Sold Summary
- 152 Days On Market

/32
$270,000

$29K PRICE DROP
- 3 Beds
- 2.5 Baths
- 3,174 Sq Ft
113 Hollywood Dr, Middlesboro, KY 40965

Beautiful Traditional Brick Ranch with Basement!This home has 1698sq/ft on the main floor with an additional 1476sq/ft in the basement. Nestled in the center of Middlesboro with a curved driveway and a 2 car carport with a storage unit between them. The home has two entrances from the carport for easy entry. There are two bonus rooms with a formal living room and formal dining area. The main

Kevin Bisceglia Coldwell Banker Bisceglia Real

113 Hollywood Dr, 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 $185,059

Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

164 Walker Ln, Middlesboro, KY 40965

/43
Est $377,776

Not Listed For Sale

72 Everett Money Rd, Middlesboro, KY 40965
- 3 Beds
- 5 Baths
- 3,000 Sq Ft
- Built 1997
72 Everett Money Rd, Middlesboro, KY 40965

Last Sold Summary
- 79 Days On Market

/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 $241,426

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

218 Windermere Dr, Middlesboro, KY 40965

/25
Est $137,496

Not Listed For Sale

194 Lick Fork Rd, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 1,564 Sq Ft
194 Lick Fork Rd, Middlesboro, KY 40965

Last Sold Summary
- 131 Days On Market

/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 $228,956

Last Listing Agent Dustin Daniels Mountain Realty

4921 W Cumberland Ave, Middlesboro, KY 40965

/24
Est $205,731

Not Listed For Sale

150 Wellington Dr, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,140 Sq Ft
- Built 1993
150 Wellington Dr, Middlesboro, KY 40965

Last Sold Summary
- 4 Days On Market

/24
Est $282,528

Not Listed For Sale

230 Windermere Dr, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 2,099 Sq Ft
- Built 2007
230 Windermere Dr, Middlesboro, KY 40965

Last Sold Summary
- 186 Days On Market

/26
Est $228,661

Not Listed For Sale

212 Windermere Dr, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,476 Sq Ft
- Built 2001
212 Windermere Dr, Middlesboro, KY 40965

Last Sold Summary
- 7 Days On Market

Showing Results 201 - 240, Page 6 of 18

Kentucky Bell County Middlesboro

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