Middlesboro, KY Homes

/17
$230,000

$15K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,320 Sq Ft
156 Wellington Dr, Middlesboro, KY 40965

Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is

Megan Stanaford Black Diamond Realty

156 Wellington Dr, 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 $110,000

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

0 Arie Turner Ln, Middlesboro, KY 40965

/14
Est $130,012

Not Listed For Sale

713 Gloucester Ave, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 1,112 Sq Ft
- Built 1916
713 Gloucester Ave, Middlesboro, KY 40965

Last Sold Summary
- 202 Days On Market

/12
$225,000
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
908 W Chester Ave, Middlesboro, KY 40965

This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment behind the house great for the mother-in-law. The apartment is open space with 1 bdrm and a full bath. Metal roof, vinyl siding and windows, hardwood, laminate & tile floors. Privacy and a chain link fenced in back yard, 2 storage buildings, level back yard. Great student home and rental!!

Steve Mason REMAX PROFESSIONAL'S

908 W Chester Ave, 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 $70,631

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

305 N 15th St, Middlesboro, KY 40965

/50
Est $401,592

Not Listed For Sale

202 N 24th St, Middlesboro, KY 40965
- 5 Beds
- 3.5 Baths
- 3,680 Sq Ft
- Built 1900
202 N 24th St, Middlesboro, KY 40965

Last Sold Summary
- 41 Days On Market

/5
$22,500

$8K PRICE DROP
- Land
- 15,681 Sq Ft
- $62,500 per Acre
526 Balmoral Rd, Middlesboro, KY 40965

Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

Megan Stanaford Black Diamond Realty

526 Balmoral Rd, 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 $148,192

Last Listing Agent Misti McGrath Realty Group

359 Beans Fork Rd, Middlesboro, KY 40965

/27
Est $204,575

Not Listed For Sale

702 Dorchester Ave, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,508 Sq Ft
- Built 1968
702 Dorchester Ave, Middlesboro, KY 40965

Last Sold Summary
- 90 Days On Market

/48
$575,000

Pending
- 4 Beds
- 3.5 Baths
- 3,480 Sq Ft
2794 US Hwy 25 E, Middlesboro, KY 40965

This property presents an exceptional opportunity for investment. Situated in Bell County, it is conveniently located within a short distance of Middlesboro city limits, approximately two miles away. The property boasts over 550 feet of road frontage on a highly visible traffic area, specifically on Highway 25E. This prime location offers a unique chance for investors to establish a new business

Sharon Teaney Century 21 Virginia Wilder Real Estate

2794 US Hwy 25 E, 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 $308,272

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

805 Worchester Ave, Middlesboro, KY 40965

/23
Est $86,599

Not Listed For Sale

716 Ilchester Ave, Middlesboro, KY 40965
- 4 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 1930
716 Ilchester Ave, Middlesboro, KY 40965

Last Sold Summary
- 2 Days On Market

/2
$50,000

Pending
- Land
- 2 Acres
- $25,000 per Acre
739 Highway 441, Middlesboro, KY 40965

Janice Pratt Fathom Realty TN LLC

739 Highway 441, 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 $221,462

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

810 Worchester Ave, Middlesboro, KY 40965

/49
Est $246,151

Not Listed For Sale

715 Worchester Ave, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
- Built 1985
715 Worchester Ave, Middlesboro, KY 40965

Last Sold Summary
- 89 Days On Market

/22
$99,999

$19K PRICE DROP
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
252 Chasteen Dr, Middlesboro, KY 40965

Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily

Aaron Rose Realty Network, Inc

252 Chasteen Dr, 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 $173,940

Last Listing Agent SARAH RICHARDS RE/MAX Preferred Group

140 Hickory Ln, Middlesboro, KY 40965

/16
Est $125,637

Not Listed For Sale

507 Worchester Ave, Middlesboro, KY 40965
- 3 Beds
- 1 Bath
- 1,368 Sq Ft
- Built 1918
507 Worchester Ave, Middlesboro, KY 40965

Last Sold Summary
- 32 Days On Market

/12
$85,000

$20K PRICE DROP
- 2 Beds
- 1 Bath
- 910 Sq Ft
310 Barkley Dr, Middlesboro, KY 40965

2 bed, 1 bath, manufactured home sitting on a large level lot. Conveniently located to shopping and Harrogate, TN.

Michael Hensley REMAX PROFESSIONAL'S

310 Barkley Dr, 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

/48
Est $427,580

Not Listed For Sale

515 Worchester Ave, Middlesboro, KY 40965
- 4 Beds
- 3.5 Baths
- 4,300 Sq Ft
- Built 1992
515 Worchester Ave, Middlesboro, KY 40965

Last Sold Summary
- 42 Days On Market

/16
$295,000

$15K PRICE DROP
- 5 Beds
- 3 Baths
- 2,100 Sq Ft
717 Highway 441, Middlesboro, KY 40965

Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed

Megan Stanaford Black Diamond Realty

717 Highway 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 $169,038

Last Listing Agent Beth Combs Turn Key Realty

919 W Rochester Ave, Middlesboro, KY 40965

/15
Est $96,678

Not Listed For Sale

106 Ellenwood Rd, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 810 Sq Ft
- Built 1970
106 Ellenwood Rd, Middlesboro, KY 40965

Last Sold Summary
- 30 Days On Market

/4
$22,000

$3K PRICE DROP
- Land
- 1.02 Acres
- $21,569 per Acre
1577 Beans Fork Rd, Middlesboro, KY 40965

OVER 1 ACRE AND NO RESTRICTIONS!!! Live peaceful, level and free on your own land.Bring your own home or build your own home, in the quiet top of Beans Fork.Utilities available All reasonable offers entertained Home on land holds zero value, please do not enter without agent

Misti McGrath Realty Group

1577 Beans Fork Rd, 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 $114,000

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

TBD Rt 516 Old Cross Rd, Pineville, KY 40977

/34
Est $203,457

Not Listed For Sale

127 Cawood Ln, Middlesboro, KY 40965
- 4 Beds
- 2 Baths
- 2,163 Sq Ft
- Built 1976
127 Cawood Ln, Middlesboro, KY 40965

Last Sold Summary
- 234 Days On Market

/3
$125,000

$50K PRICE DROP
- 4 Beds
- 2 Baths
- 1,664 Sq Ft
120 Redwood Rd Unit A & B, Middlesboro, KY 40965

Great investment opportunity with this one. Built in 2000 per appraisal, this property offers a total of 1,664 square feet and is currently occupied by reliable, long-term tenants. Each unit features 2 bedrooms and 1 bathroom, providing comfortable living space for residents. The address, listed as 102 A&B Redwood Road, originates from a previous appraisal. The property is confirmed per the

Megan Stanaford Black Diamond Realty

120 Redwood Rd Unit A & B, Middlesboro, KY 40965
/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 $202,499

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

206 Nottingham Dr, Middlesboro, KY 40965

/16
Est $93,710

Not Listed For Sale

309 Oakwood Rd, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1938
309 Oakwood Rd, Middlesboro, KY 40965

Last Sold Summary
- 93 Days On Market

/20
$229,500
- 6 Beds
- 6 Baths
- 2,700 Sq Ft
623 N 20th St, Middlesboro, KY 40965

Excellent investment opportunity with a strong ~9% cap rate at asking price! This unique 4-unit property offers incredible versatility-perfect as a pure cash-flowing asset or an ideal opportunity to live in one unit while renting out the other three. The property consists of four fully occupied units: a main multi-family building featuring one 2-bedroom unit and two 1-bedroom units, plus a

Derek Eisenberg Continental Real Estate Group

623 N 20th St, 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 $229,960

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

825 S 28th St, Middlesboro, KY 40965

/24
Est $122,850

Not Listed For Sale

205 Oakwood Rd, Middlesboro, KY 40965
- 2 Beds
- 1.5 Baths
- 1,020 Sq Ft
- Built 1947
205 Oakwood Rd, Middlesboro, KY 40965

Last Sold Summary
- 48 Days On Market

/9
$139,000
- Land
- 5.33 Acres
- $26,079 per Acre
312 Blakely Ln, Middlesboro, KY 40965

Rare find! 5.33 undeveloped acres in Middlesboro on Blakely Lane, off Cumberland Ave. Zoned R-1. Land is mostly level with a drop to the creek behind. Portion near the creek is in the floor plain. Several building sites on the land above the flood plain. Easy access to Cumberland Ave yet away from the noise and traffic.

Ann Robinson Action Realty

312 Blakely Ln, 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

/27
Est $293,806

Not Listed For Sale

103 Sherwood Rd, Middlesboro, KY 40965
- 4 Beds
- 3 Baths
- 3,000 Sq Ft
- Built 1965
103 Sherwood Rd, Middlesboro, KY 40965

Last Sold Summary
- 127 Days On Market

/20
$215,000

$10K PRICE DROP
- 3 Beds
- 1 Bath
- 1,652 Sq Ft
116 N Petersborough Ave, Middlesboro, KY 40965

Exceptional 3 bedrooms, 1 bath home in the heart of Middlesboro. Located just off Cumberland Ave on 30th St, this home's location is what you have been looking for--within walking distance of downtown, schools, and the hospital. Just down the street from the T-ball field and the city pool. With hardwood floors throughout and beautiful wood trim, this house is waiting for a family to make it a

Kevin Bisceglia Coldwell Banker Bisceglia Real

116 N Petersborough Ave, 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 $91,276

Last Listing Agent Misti McGrath Realty Group

234 S 46th St, Middlesboro, KY 40965

/38
Est $168,942

Not Listed For Sale

504 Manchester Ave, Middlesboro, KY 40965
- 4 Beds
- 3 Baths
- 2,182 Sq Ft
- Built 1940
504 Manchester Ave, Middlesboro, KY 40965

Last Sold Summary
- 179 Days On Market

/18
$135,000
- 2 Beds
- 1 Bath
- 1,120 Sq Ft
2002 Winchester Ave, Middlesboro, KY 40965

CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car

Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

2002 Winchester Ave, Middlesboro, KY 40965

Showing Results 121 - 160, Page 4 of 18

Kentucky Bell County Middlesboro

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