Middlesboro, KY Homes

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  /55

  Est $199,631 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft

  603 W Chester Ave, Middlesboro, KY 40965

  603 W Chester Ave, Middlesboro, KY 40965
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  /19

  $44,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  406 W Rochester Ave, Middlesboro, KY 40965

  Cottage style, 3 bedroom 2 bathroom home with chain link fencing in the city limits of Middlesboro KY. PVA records show 0.18 of an acre, city water, city sewer. Home needs some work but would make a great permanent home or use as a rental. Close to LMU and all the beauty Southeastern KY offers! 5 minutes to the Cumberland Gap National Park, shopping and more! Buyer to verify all property

  Megan Stanaford Black Diamond Realty

  406 W Rochester Ave, Middlesboro, KY 40965
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  /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 $289,034

  Last Listing Agent Ann Robinson Action Realty

  123 Twin Acres Rd, Middlesboro, KY 40965
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  /12

  Est $80,896 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 948 Sq Ft

  501 W Chester Ave, Middlesboro, KY 40965

  501 W Chester Ave, Middlesboro, KY 40965
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  /21

  $79,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  72 Happy Hollow Hill Rd, Middlesboro, KY 40965

  GREAT LOCATION! This 2007 manufactured home rests on a 1 acre lot with a great view. Only a short distance to restaurants, shopping and medical facilities. This home has 3 bedrooms, 2 bathrooms. The main bathroom has a garden tub and a full walk in shower. The main bedroom has access to the laundry room that opens up into the kitchen. The layout to the home is one of great convenience. The home

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  72 Happy Hollow Hill Rd, Middlesboro, KY 40965
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  /11

  $26,000 Sold Nov 26, 2025

  0 Arie Turner Ln, Middlesboro, KY 40965

  Last Sold Summary

  • 13% Below List Price
  • 20 Days On Market

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  0 Arie Turner Ln, Middlesboro, KY 40965
• 

  

  /25

  Est $111,115 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  512 W Chester Ave, Middlesboro, KY 40965

  512 W Chester Ave, Middlesboro, KY 40965
• 

  

  /6

  $24,900 Pending

  • 3 Beds
  • 2 Baths

  13 Duncan Ln, Middlesboro, KY 40965

  Charming 3-bedroom, 2-bath manufactured home situated on an approx. 0.32-acre corner lot. The home offers a practical layout with good flow and a spacious yard

  Beth Combs Turn Key Realty

  13 Duncan Ln, Middlesboro, KY 40965
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  /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 $55,809

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

  305 N 15th St, Middlesboro, KY 40965
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  /39

  Est $325,045 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 4,504 Sq Ft

  Unlisted Address

  Unlisted Address
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  /5

  $22,500 Pending

  • Land
  • 0.36 Acre
  • $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
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  /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 $188,295

  Last Listing Agent Cookie Russell Realty Network, Inc

  127 Cawood Ln, Middlesboro, KY 40965
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  /14

  Est $119,105 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,112 Sq Ft

  713 Gloucester Ave, Middlesboro, KY 40965

  713 Gloucester Ave, Middlesboro, KY 40965
• 

  

  /40

  $525,000

  • 5 Beds
  • 2.5 Baths
  • 2,542 Sq Ft

  2004 Twin Fawn Trail, Middlesboro, KY 40965

  This gorgeous cape cod home sits on 4.4 acres with deer visiting often. This home has 5 bedrooms, 2.5 bathrooms, formal living room with fireplace, family room (could be used as formal dining room) a second fireplace in the sunroom, amazing kitchen with island, the kitchen counter tops are granite, the stainless-steel appliances stay, which include double wall ovens, gas range with gas oven

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  2004 Twin Fawn Trail, Middlesboro, KY 40965
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  /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
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  /50

  Est $401,578 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,680 Sq Ft

  202 N 24th St, Middlesboro, KY 40965

  202 N 24th St, Middlesboro, KY 40965
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  /2

  $50,000 Pending

  739 Highway 441, Middlesboro, KY 40965

  Janice Pratt Fathom Realty TN LLC

  739 Highway 441, 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 $92,455

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  716 Ilchester Ave, Middlesboro, KY 40965
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  /27

  Est $180,770 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  702 Dorchester Ave, Middlesboro, KY 40965

  702 Dorchester Ave, Middlesboro, KY 40965
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  /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
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  /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
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  /49

  Est $225,410 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  715 Worchester Ave, Middlesboro, KY 40965

  715 Worchester Ave, Middlesboro, KY 40965
• 

  

  /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
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  /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 $181,095

  Last Listing Agent Beth Combs Turn Key Realty

  919 W Rochester Ave, Middlesboro, KY 40965
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  /9

  Est $99,667 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  605 Worchester Ave, Middlesboro, KY 40965

  605 Worchester Ave, Middlesboro, KY 40965
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  /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
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  /20

  $108,000 Sold Dec 19, 2025

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977

  Last Sold Summary

  • 10% Below List Price
  • 6 Days On Market

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977
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  /16

  Est $115,003 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,368 Sq Ft

  507 Worchester Ave, Middlesboro, KY 40965

  507 Worchester Ave, Middlesboro, KY 40965
• 

  

  /23

  $150,000

  • 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
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  /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 $195,080

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  206 Nottingham Dr, Middlesboro, KY 40965
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  /48

  Est $293,119 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,300 Sq Ft

  515 Worchester Ave, Middlesboro, KY 40965

  515 Worchester Ave, Middlesboro, KY 40965
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  /2

  $17,000 Pending

  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
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  /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 $221,305

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  825 S 28th St, Middlesboro, KY 40965
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  /8

  Est $107,315 Not Listed For Sale

  • Studio
  • 2,700 Sq Ft

  305 Englewood Rd, Middlesboro, KY 40965

  305 Englewood Rd, Middlesboro, KY 40965
• 

  

  /48

  $334,900

  • 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
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  /15

  $235,000 Sold May 30, 2025

  411 S 29th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2025

  Last Sold Summary

  • $188/SF
  • 2 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  411 S 29th St, Middlesboro, KY 40965
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  /15

  Est $57,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  119 Lynnwood Rd, Middlesboro, KY 40965

  119 Lynnwood Rd, Middlesboro, KY 40965
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  /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
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  /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 $105,067

  Last Listing Agent Misti McGrath Realty Group

  234 S 46th St, Middlesboro, KY 40965
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  /15

  Est $98,598 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft

  106 Ellenwood Rd, Middlesboro, KY 40965

  106 Ellenwood Rd, Middlesboro, KY 40965

Showing Results 121 - 160, Page 4 of 18