5,043

Middlesboro, KY Homes

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    • /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

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