Middlesboro, KY Homes

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  /50

  $232,500

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  4921 W Cumberland Ave, Middlesboro, KY 40965

  Charming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beautifully maintained 3-bedroom, 2-bathroom home located close to shopping, restaurants, schools, and parks — everything you need is just minutes away! Inside, you'll find a warm and inviting layout featuring hardwood and vinyl flooring, offering both style and durability. The spacious living areas are perfect

  

  Dustin Daniels

  Mountain Realty

  (606) 713-0736

  4921 W Cumberland Ave, Middlesboro, KY 40965
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  /12

  $1,600 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  814 W Chester Ave, Middlesboro, KY 40965

  Property Id: 2369055Welcome to your new home at 814 West Chester Ave! This charming 3-bedroom, 2-bathroom single family home in Middlesboro, KY is perfect for you and your furry friends. Enjoy amenities like a dishwasher, washer/dryer in unit, and a spacious lawn. Don't miss out on this cozy oasis near parks and local attractions. Available for rent starting 2026-02-01 for $1600/month.

  814 W Chester Ave, Middlesboro, KY 40965
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  /11

  $152,500 Sold Oct 10, 2025

  102 Stone Creek Dr, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $160/SF
  • 9 Days On Market

  Current Estimated Value $146,876

  Last Listing Agent Misti McGrath Realty Group

  102 Stone Creek Dr, Middlesboro, KY 40965
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  /8

  Est $65,407 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  108 S 8th St, Middlesboro, KY 40965

  108 S 8th St, Middlesboro, KY 40965
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  /18

  $170,000

  • 4 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  409 Meadow Ln, Middlesboro, KY 40965

  This 4 bedroom home is located just minutes away from Downtown Middlesboro KY. This home features open kitchen/ dinning area , plenty of space and a great back yard area. Don't miss your chance to own this wonderful home.

  

  Brad Cawood

  Turn Key Realty

  (606) 755-9266

  409 Meadow Ln, Middlesboro, KY 40965
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  /15

  $170,000 Sold May 19, 2025

  1002 W Chester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 1 Bath
  • 2,073 Sq Ft
  • Built 1947

  Last Sold Summary

  • $82/SF
  • 0 Days On Market

  Current Estimated Value $207,171

  Last Listing Agent Misti McGrath Realty Group

  1002 W Chester Ave, Middlesboro, KY 40965
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  /13

  Est $101,284 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,627 Sq Ft

  514 Avondale Ave, Middlesboro, KY 40965

  514 Avondale Ave, Middlesboro, KY 40965
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  /2

  $165,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  4605 W Cumberland Ave, Middlesboro, KY 40965

  One level ranch style home with 3 bedrooms, 2 bathrooms, living room, eat in kitchen, laundry room, central heat and air, nice level yard, paved driveway covered front porch, high speed internet available, double pane windows, public water and public sewer, hardwood floors, storage shed, range, refrigerator, washer and dryers stay with home, This home is less than half a mile from hospital.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  4605 W Cumberland Ave, Middlesboro, KY 40965
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  /30

  $202,000 Sold Feb 17, 2026

  140 Chasteen Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Below List Price
  • $112/SF
  • 4 Days On Market

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

  140 Chasteen Dr, Middlesboro, KY 40965
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  /20

  Est $131,072 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,456 Sq Ft

  316 Avondale Ave, Middlesboro, KY 40965

  316 Avondale Ave, Middlesboro, KY 40965
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  /32

  $164,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,209 Sq Ft

  140 Hickory Ln, Middlesboro, KY 40965

  3-bedroom, 2-bath home situated on a spacious 0.66-acre lot, offering the perfect blend of privacy and convenience. Located just minutes from all the amenities Middlesboro has to offer, this property provides easy access to shopping, dining, schools, and highways. Enjoy the generous outdoor space with plenty of room for gardening, entertaining, or future improvements. A great opportunity for

  SARAH RICHARDS RE/MAX Preferred Group

  140 Hickory Ln, Middlesboro, KY 40965
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  /2

  $167,000 Sold Sep 15, 2025

  414 SE North 24th St, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 10% Below List Price
  • $104/SF
  • 2 Days On Market

  Current Estimated Value $172,852

  Last Listing Agent Beth Combs Turn Key Realty

  414 SE North 24th St, Middlesboro, KY 40965
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  /28

  Est $87,923 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 770 Sq Ft

  333 Avondale Ave, Middlesboro, KY 40965

  333 Avondale Ave, Middlesboro, KY 40965
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  /57

  $285,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft

  440 Sams Mountain, Middlesboro, KY 40965

  This is a very nice private home. Comes with lot 10-11. Open concept with a lot of windows to let the sun light in, master on the main level, 2 car garage, wood deck, large kitchen with a long island with a flat gas range, with bar stools. This is a must see!! Close to town but in a quiet area. Don't wait call today for your showing!BUYER TO VERIFY SQUARE FOOTAGE!!

  Steve Mason REMAX PROFESSIONAL'S

  440 Sams Mountain, Middlesboro, KY 40965
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  /17

  $160,000 Sold Jul 03, 2025

  524 E Lothbury Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $200/SF
  • 5 Days On Market

  Current Estimated Value $147,794

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  524 E Lothbury Ave, Middlesboro, KY 40965
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  /17

  Est $75,973 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  205 S 9th St, Middlesboro, KY 40965

  205 S 9th St, Middlesboro, KY 40965
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  /34

  $369,900 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,684 Sq Ft

  409 Fairview Rd, Middlesboro, KY 40965

  This 4 bedroom, 3 1/2 bath ranch is sitting on 2.17 acres just minutes from downtown Middlesboro, but is considered outside the city limits. With a view of the mountains, this brick ranch has an in-ground pool, a sunroom that has a view of the mountains, a long paved driveway and plenty of garage space. The detached garage could be used for a workshop or for more storage. The property has been

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  409 Fairview Rd, Middlesboro, KY 40965
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  /2

  $10,000 Sold Oct 17, 2025

  Lot #1 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 0.28 Acre
  • $35,714 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 42 Days On Market

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

  Lot #1 Bellwood Rd, Middlesboro, KY 40965
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  /8

  Est $113,868 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  215 Armadale Ave, Middlesboro, KY 40965

  215 Armadale Ave, Middlesboro, KY 40965
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  /53

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  129 Lower Gibson Ln, Middlesboro, KY 40965

  🏡 The Château on the Creek - Home for Sale in Middlesboro, KY (Bell County) Welcome to The Château on the Creek, a beautifully updated 3-bedroom, 2.5-bathroom home in Middlesboro, KY (Bell County). Offering 1,856 sq. ft. of living space, a detached garage, and a backyard oasis, this move-in ready property combines timeless charm with modern updates. The exterior has been completely redone

  Michael Hensley REMAX PROFESSIONAL'S

  129 Lower Gibson Ln, Middlesboro, KY 40965
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  /20

  $148,400 Sold Jul 16, 2025

  112 Parker Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • Built 2011

  Last Sold Summary

  • 2% Above List Price
  • $103/SF
  • 174 Days On Market

  Current Estimated Value $156,927

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

  112 Parker Ln, Middlesboro, KY 40965
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  /45

  Est $302,163 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,349 Sq Ft

  915 E Lothbury Ave, Middlesboro, KY 40965

  915 E Lothbury Ave, Middlesboro, KY 40965
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  /20

  $197,000

  • 3 Beds
  • 1.5 Baths
  • 1,238 Sq Ft

  1200 W Chester Ave, Middlesboro, KY 40965

  Have you been looking for a cozy home on a quiet, family-friendly street to raise your family? You need to put this one on your ''must see'' list. Newly remodeled with new floors, new lights, new windows, new doors, and new fencing! With 3 bedrooms and 1 and 1/2 baths, this home is the perfect starter home. The fenced in yard is flat with lots of room for kids--don't miss out on this one.

  Patsy Barnett Coldwell Banker Bisceglia Real

  1200 W Chester Ave, Middlesboro, KY 40965
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  /24

  $196,000 Sold Nov 26, 2025

  515 N 25th St, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,000 Sq Ft
  • Built 1918

  Last Sold Summary

  • 2% Below List Price
  • $98/SF
  • 117 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  515 N 25th St, Middlesboro, KY 40965
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  /34

  Est $190,472 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  215 S 15th St, Middlesboro, KY 40965

  215 S 15th St, Middlesboro, KY 40965
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  /20

  $189,000 Pending

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1208 Hwy 217 Hwy Unit 217, Middlesboro, KY 40965

  Here is your opportunity to own a home in a desirable community. Approximately 11 acres in the Hutch or Clear Fork area of Bell County. Property has lots of good fencing. The home on the property is in fair condition and may need to be upgraded or remodeled. This is a rare opportunity to have a home in the country that so many dream of. Call me today and come check out this Beautiful Property!!!!

  Danny Wilson Coldwell Banker Bisceglia Realty & Auction Co

  1208 Hwy 217 Hwy Unit 217, Middlesboro, KY 40965
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  /13

  $52,500 Sold Mar 19, 2025

  3765 Highway 441, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,124 Sq Ft
  • Built 1974

  Last Sold Summary

  • 25% Below List Price
  • $47/SF
  • 21 Days On Market

  Current Estimated Value $68,971

  Last Listing Agent Patsy Barnett Coldwell Banker Bisceglia Real

  3765 Highway 441, Middlesboro, KY 40965
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  /11

  Est $162,394 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,360 Sq Ft

  403 E Lothbury Ave, Middlesboro, KY 40965

  403 E Lothbury Ave, Middlesboro, KY 40965
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  /28

  $229,900

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  1203 Winchester Ave, Middlesboro, KY 40965

  Beautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal living room with hardwood floors and a gas fireplace. The dining area is right off the galley kitchen, which has a door leading onto the carpeted porch-perfect for entertaining or cooking outside. There is easy access from the carport right into the large open den/family room. Also on the main level there is

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  1203 Winchester Ave, Middlesboro, KY 40965
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  /2

  $13,000 Sold Sep 25, 2025

  Lot #6 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 0.41 Acre
  • $31,707 per Acre

  Last Sold Summary

  • 35% Below List Price
  • 14 Days On Market

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

  Lot #6 Bellwood Rd, Middlesboro, KY 40965
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  /89

  Est $280,108 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,297 Sq Ft

  115 Dead Horse Hollow, Middlesboro, KY 40965

  115 Dead Horse Hollow, Middlesboro, KY 40965
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  /24

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  63 Old Pineville Pike, Middlesboro, KY 40965

  Remodeled and gorgeous! This home has completely remodeled throughout with gorgeous kitchen and new bathrooms! This home was stripped down to the studs! Laminate floors are waterproof. The master bathroom has a double bowl sink, nice walk-in shower. There are 3 bedrooms and 2 full bathroom, large living room, kitchen with new farmhouse sink. The kitchen extends to dining room, range,

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  63 Old Pineville Pike, Middlesboro, KY 40965
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  /20

  $240,000 Sold Jan 30, 2026

  220 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 2003

  Last Sold Summary

  • 11% Below List Price
  • $142/SF
  • 108 Days On Market

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

  220 Windermere Dr, Middlesboro, KY 40965
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  /18

  Est $102,993 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  508 Wilderness Rd, Middlesboro, KY 40965

  508 Wilderness Rd, Middlesboro, KY 40965
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  /7

  $189,000 Pending

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1208 Kentucky 217, Middlesboro, KY 40965

  Here is your opportunity to own a home in a desirable community. Approximately 11 acres in the Hutch or Clear Fork area of Bell County. Property has lots of good fencing This is a rare opportunity to have a home in the country that so many dream of. Call me today and come check out this Beautiful Property!!!!

  Danny Wilson Coldwell Banker Bisceglia Realty & Auction Co

  1208 Kentucky 217, Middlesboro, KY 40965
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  /27

  $164,000 Sold Feb 21, 2026

  103 Leafwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 2 Baths
  • 1,326 Sq Ft
  • Built 1923

  Last Sold Summary

  • 1% Below List Price
  • $124/SF
  • 4 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  103 Leafwood Rd, Middlesboro, KY 40965
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  /24

  Est $164,156 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,005 Sq Ft

  616 Balmoral Rd, Middlesboro, KY 40965

  616 Balmoral Rd, Middlesboro, KY 40965
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  /35

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  807 Exeter Ave, Middlesboro, KY 40965

  New custom built home in the heart of Middlesboro. This home features three (3) bedrooms and two (2) bathrooms. Walking up to the home you are immediately greeted with a covered front porch constructed using composite decking and adorned with large columns. As you enter this home you are met with a spacious living room/kitchen/dinning room designed in an open concept style. Kitchen is complete

  Janice Pratt Fathom Realty TN LLC

  807 Exeter Ave, Middlesboro, KY 40965
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  /15

  $145,000 Sold Nov 25, 2025

  192 Owens Ln, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,600 Sq Ft
  • Built 1982

  Last Sold Summary

  • 12% Below List Price
  • $56/SF
  • 8 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  192 Owens Ln, Middlesboro, KY 40965
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  /53

  Est $274,430 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,450 Sq Ft

  725 Balmoral Rd, Middlesboro, KY 40965

  725 Balmoral Rd, Middlesboro, KY 40965

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