Middlesboro, KY Homes

/25
Est $115,476 Not Listed For Sale

512 W Chester Ave, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
- Built 1908
512 W Chester Ave, Middlesboro, KY 40965

Last Sold Summary
- 13% Above List Price
- $49/SF
- 191 Days On Market
Last Sold Price $102,500

Last Listing Agent Michael Hensley RE/MAX

/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
/18
$60,000 Sold Jul 25, 2025

3575 Highway 441, Middlesboro, KY 40965
- 2 Beds
- 1 Bath
- 1,204 Sq Ft
- Built 1930
Last Sold Summary
- 52% Below List Price
- $50/SF
- 171 Days On Market
Current Estimated Value $81,410

Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real

3575 Highway 441, Middlesboro, KY 40965

/39
Est $301,092 Not Listed For Sale

Unlisted Address
- 4 Beds
- 2.5 Baths
- 4,504 Sq Ft
- Built 1942
Unlisted Address

Last Sold Summary
- 9% Above List Price
- $61/SF
- 37 Days On Market
Last Sold Price $275,000

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

/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
/22
$272,700 Sold Jun 13, 2025

123 Twin Acres Rd, Middlesboro, KY 40965
- 4 Beds
- 2 Baths
- 3,338 Sq Ft
- Built 1987
Last Sold Summary
- 9% Below List Price
- $82/SF
- 42 Days On Market
Current Estimated Value $308,834

Last Listing Agent Ann Robinson Action Realty

123 Twin Acres Rd, Middlesboro, KY 40965

/14
Est $135,679 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
- 23% Above List Price
- $99/SF
- 202 Days On Market
Last Sold Price $110,000

Last Listing Agent Sharon Teaney Century 21 Virginia Wilder Real Estate

/16
$19,900
- Land
- 2.32 Acres
- $8,578 per Acre
LOT 9 Brush Mountain Cir, Miracle, KY 40856

Discover tranquility at Brush Mountain Farms in Bell County, KY—a 2.32-acre wooded retreat in a gated community. Enjoy peace, privacy, and wildlife, with hiking trails and a developing wildlife preserve (Boone's Ridge) visible from the property. Located just 15 minutes from Boones Ridge Wildlife Park and 20 minutes from Pineville and Middlesboro, offering easy access to town amenities. Ideal for

Tabitha House CENTURY 21 Advantage Realty

LOT 9 Brush Mountain Cir, Miracle, KY 40856
/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 $178,500

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

0 Arie Turner Ln, Middlesboro, KY 40965

/50
Est $388,337 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
- 11% Above List Price
- $95/SF
- 41 Days On Market
Last Sold Price $350,000

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

/22
$109,000
- 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
/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 $56,444

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

305 N 15th St, Middlesboro, KY 40965

/27
Est $208,886 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
- 25% Above List Price
- $111/SF
- 90 Days On Market
Last Sold Price $167,300

Last Listing Agent Michael Hensley RE/MAX

/12
$100,000
- 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
/34
$169,000 Sold May 09, 2025

127 Cawood Ln, Middlesboro, KY 40965
- 4 Beds
- 2 Baths
- 2,163 Sq Ft
- Built 1976
Last Sold Summary
- 9% Below List Price
- $78/SF
- 234 Days On Market
Current Estimated Value $189,777

Last Listing Agent Cookie Russell Realty Network, Inc

127 Cawood Ln, Middlesboro, KY 40965

/49
Est $243,464 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
- 19% Above List Price
- $122/SF
- 89 Days On Market
Last Sold Price $204,500

Last Listing Agent Janice Pratt Fathom Realty TN LLC

/4
$310,000
- 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
/33
$135,000 Sold Jun 23, 2025

2817 Ky 441, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,272 Sq Ft
- Built 2020
Last Sold Summary
- 10% Below List Price
- $106/SF
- 72 Days On Market
Last Listing Agent Sallye Broyles RE/MAX LakeTime Realty

2817 Ky 441, Middlesboro, KY 40965

/16
Est $132,377 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
- 26% Above List Price
- $77/SF
- 32 Days On Market
Last Sold Price $105,000

Last Listing Agent Michael Hensley RE/MAX

/23
$148,000 Pending
- 2 Beds
- 1 Bath
- 952 Sq Ft
359 Beans Fork Rd, Middlesboro, KY 40965

I love a good sunroom, don't you? Recently updated 2-bedroom 1 bath home is move in ready! Extra-large fenced in level yard with a garage perfect for tinkering!Electric and plumbing included in the updates. You won't find a home like this in this price range! Come see for yourself!

Misti McGrath Realty Group

359 Beans Fork Rd, Middlesboro, KY 40965
/23
$77,000 Sold May 16, 2025

716 Ilchester Ave, Middlesboro, KY 40965
- 4 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 1930
Last Sold Summary
- 3% Below List Price
- $45/SF
- 2 Days On Market
Current Estimated Value $85,262

Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

716 Ilchester Ave, Middlesboro, KY 40965

/48
Est $402,368 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
- 10% Below List Price
- $104/SF
- 42 Days On Market
Last Sold Price $447,750

Last Listing Agent Michael Hensley RE/MAX

/2
$17,000 Pending
- Land
- 1.14 Acres
- $14,912 per Acre
0 Home Run Rd, Middlesboro, KY 40965

Take a look at this beautiful land with 1.14 acres located in city limits of Middlesboro, KY. Doublewide homes welcome, it is unrestricted and has city water, city sewer and electric available! Sits fronting a paved street and is close to downtown Middlesboro.

Virginia Wilder Century 21 Virginia Wilder Real Estate

0 Home Run Rd, 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 $164,020

Last Listing Agent SARAH RICHARDS RE/MAX Preferred Group

140 Hickory Ln, Middlesboro, KY 40965

/8
Est $154,730 Not Listed For Sale

305 Englewood Rd, Middlesboro, KY 40965
- Studio
- 2,700 Sq Ft
- Built 1950
305 Englewood Rd, Middlesboro, KY 40965

Last Sold Summary
- 89% Above List Price
- $30/SF
- 0 Days On Market
Last Sold Price $82,000

Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

/48
$324,900 Pending
- 5 Beds
- 3 Baths
- 2,250 Sq Ft
805 Worchester Ave, Middlesboro, KY 40965

This home has been brought back beyond its Glory!! Completely remodeled from the sub flooring to the roof. This 5 bds, 3 full baths,new kitchen w/Quartz counter tops, marble back splash, stainless appliances, new LVP flooring, Breath taking bathrooms, master on the main, 3 bdrms upstairs with a full bath 2 HVAC units. 2 car garage w new garage doors. Also, a fenced in back yard!! NOT IN THE

Steve Mason REMAX PROFESSIONAL'S

805 Worchester Ave, Middlesboro, KY 40965
/2
$8,000 Sold Nov 18, 2025

4163 441, Middlesboro, KY 40965
- Land
- 0.4 Acre
- $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

/15
Not Listed For Sale

119 Lynnwood Rd, Middlesboro, KY 40965
- 3 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 2000
119 Lynnwood Rd, Middlesboro, KY 40965

Last Sold Summary
- 4% Above List Price
- $55/SF
- 189 Days On Market
Last Sold Price $55,000

Last Listing Agent David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

/3
$175,000
- 4 Beds
- 2 Baths
- 1,664 Sq Ft
102 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

102 Redwood Rd Unit A & B, 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 $173,098

Last Listing Agent Beth Combs Turn Key Realty

919 W Rochester Ave, Middlesboro, KY 40965

/15
Est $108,840 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
- 13% Above List Price
- $119/SF
- 30 Days On Market
Last Sold Price $96,500

Last Listing Agent Dawn Risner Turn Key Realty

/52
$2,500,000
- 3 Beds
- 1.5 Baths
- 1,976 Sq Ft
259 Watson Ln, Middlesboro, KY 40965

Offering for the first time on the market, this beautiful 92 acre property with 82 acres within city limits and 10 acres in the county. There is a beautiful hayfield and from that hayfield downtown Middlesboro can be seen as well as a view of the Pinnacle. This property comes with 2 homes. The main house has 3 bedrooms, 1 full bathroom and a half bathroom, foyer with staircase leading upstairs,

Virginia Wilder Century 21 Virginia Wilder Real Estate

259 Watson Ln, 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 $109,000

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

TBD Rt 516 Old Cross Rd, Pineville, KY 40977

/24
Est $136,847 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
- 5% Above List Price
- $127/SF
- 48 Days On Market
Last Sold Price $130,000

Last Listing Agent Michael Hensley RE/MAX

/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
/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 $202,867

Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

206 Nottingham Dr, Middlesboro, KY 40965

/27
Est $292,106 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
- 19% Above List Price
- $82/SF
- 127 Days On Market
Last Sold Price $245,000

Last Listing Agent Ann Robinson Action Realty

/2
$490,000 Pending
- 7 Beds
- 5 Baths
- 6,276 Sq Ft
142 Edgewood Rd, Middlesboro, KY 40965

A One-of-a-Kind Dream Home with Spectacular Views!This stunning home offers breathtaking views from every window and boasts 7 spacious bedrooms, 3 full bathrooms, and 2 half bathrooms—plenty of room for the entire family!Step inside and be captivated by the grand staircase and an incredible private library, perfect for quiet moments or working from home. The walkout basement is

Lisa Stacy-Gibbs Turn Key Realty

142 Edgewood Rd, 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 $229,812

Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

825 S 28th St, Middlesboro, KY 40965

/38
Est $162,821 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
- 63% Above List Price
- $46/SF
- 179 Days On Market
Last Sold Price $100,000

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

Showing Results 121 - 160, Page 4 of 18

Kentucky Bell County Middlesboro

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