Middlesboro, KY Homes

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  /18

  $90,000 Sold Jul 15, 2025

  600 S 38th St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $87/SF
  • 19 Days On Market

  Current Estimated Value $97,008

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

  600 S 38th St, Middlesboro, KY 40965
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  /16

  Est $85,923 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  306 Exeter Ave, Middlesboro, KY 40965

  306 Exeter Ave, Middlesboro, KY 40965
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  /11

  $112,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  903 Ilchester Ave, Middlesboro, KY 40965

  Great potential for a starter home or investment. Does need some work. Close to LMU, Cumberland National Park, Middlesboro Country Club, and local restaurants.

  Blake Ramey Century 21 Virginia Wilder Real Estate

  903 Ilchester Ave, Middlesboro, KY 40965
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  /27

  $290,000 Sold Nov 06, 2025

  900 Twin Fawn Trail, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,270 Sq Ft
  • Built 2010

  Last Sold Summary

  • 17% Below List Price
  • $128/SF
  • 133 Days On Market

  Current Estimated Value $279,865

  Last Listing Agent Misti McGrath Realty Group

  900 Twin Fawn Trail, Middlesboro, KY 40965
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  /16

  Est $84,533 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,870 Sq Ft

  312 S 23rd St, Middlesboro, KY 40965

  312 S 23rd St, Middlesboro, KY 40965
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  /34

  $155,000

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  123 Upper Gibson Ln, Middlesboro, KY 40965

  Schedule to see this cozy home that has 2 traditional bedrooms with closets and one room that's used as a bedroom that doesn't have a closet but an armoire is an easy solution. One nice sized bathroom as well. The home is sitting on a surveyed acre with a detached 1 car garage that has room for a workshop, storage, crafting etc. The yard is level with a gentle slope on the front edge of the

  Megan Stanaford Black Diamond Realty

  123 Upper Gibson Ln, Middlesboro, KY 40965
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  /18

  $60,000 Sold May 13, 2025

  210 Welch Ln, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,430 Sq Ft
  • Built 1982

  Last Sold Summary

  • 40% Below List Price
  • $42/SF
  • 184 Days On Market

  Current Estimated Value $84,585

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  210 Welch Ln, Middlesboro, KY 40965
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  /7

  Est $54,065 Not Listed For Sale

  403 Winchester Ave, Middlesboro, KY 40965

  403 Winchester Ave, Middlesboro, KY 40965
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  /16

  $145,000 Pending

  • 3 Beds
  • 2 Baths
  • 648 Sq Ft

  138 Robinson Ln, Middlesboro, KY 40965

  Check out this charming 3-bedroom, 2-bath home featuring a spacious covered porch, updated master bathroom, fenced backyard, and beautiful tile and hardwood flooring throughout. Conveniently located just minutes from historic downtown Middlesboro, KY.

  Beth Combs Turn Key Realty

  138 Robinson Ln, Middlesboro, KY 40965
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  /24

  $280,000 Sold Aug 29, 2025

  10 Thaxted Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,096 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $134/SF
  • 33 Days On Market

  Current Estimated Value $287,569

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  10 Thaxted Ln, Middlesboro, KY 40965
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  /6

  Est $106,793 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft

  307 W Chester Ave, Middlesboro, KY 40965

  307 W Chester Ave, Middlesboro, KY 40965
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  /28

  $139,900 Pending

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

  2523 Exeter Ave, Middlesboro, KY 40965

  Like new and move-in ready, this 2022 doublewide offers 3 bedrooms, 2 baths, modern finishes, and an easy open layout on its own .26-acre lot. A durable metal roof adds long-term peace of mind, pairing low-maintenance construction with stylish interior features. Inside, the spacious open-concept living area centers around a large kitchen island with abundant cabinetry and stainless appliances

  Jody Moore Threshold Real Estate Services

  2523 Exeter Ave, Middlesboro, KY 40965
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  /3

  $75,000 Sold Aug 13, 2025

  114 W Rochester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Built 1978

  Last Sold Summary

  • 40% Below List Price
  • $74/SF
  • 26 Days On Market

  Last Listing Agent Megan Stanaford Black Diamond Realty

  114 W Rochester Ave, Middlesboro, KY 40965
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  /51

  Est $214,478 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,925 Sq Ft

  207 S 22nd St, Middlesboro, KY 40965

  207 S 22nd St, Middlesboro, KY 40965
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  /13

  $349,900

  • Land
  • 1.69 Acres
  • $207,041 per Acre

  321 W Chester Ave, Middlesboro, KY 40965

  1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Pharmacy, Banks, Theater, Auto Repair, Hotel-Motel, Bed & Breakfast, and Multi Family Copy of Middlesboro Zoning attached. All city utilities available.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  321 W Chester Ave, Middlesboro, KY 40965
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  /30

  $265,000 Sold Aug 08, 2025

  238 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft
  • Built 2001

  Last Sold Summary

  • 5% Below List Price
  • $165/SF
  • 8 Days On Market

  Current Estimated Value $276,143

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real

  238 Windermere Dr, Middlesboro, KY 40965
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  /9

  Est $145,759 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  213 S 22nd St, Middlesboro, KY 40965

  213 S 22nd St, Middlesboro, KY 40965
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  /21

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft

  140 Wellington Dr, Middlesboro, KY 40965

  Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

  Janice Pratt Fathom Realty TN LLC

  140 Wellington Dr, Middlesboro, KY 40965
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  /38

  $282,000 Sold May 12, 2025

  904 E Cumberland Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1970

  Last Sold Summary

  • 6% Below List Price
  • $123/SF
  • 48 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  904 E Cumberland Ave, Middlesboro, KY 40965
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  /16

  Est $159,885 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,844 Sq Ft

  215 S 21st St, Middlesboro, KY 40965

  215 S 21st St, Middlesboro, KY 40965
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  /37

  $249,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,966 Sq Ft

  6 Hampton Ct, Middlesboro, KY 40965

  Beautiful split foyer home in Ambleside. The view from the front window is amazing. This well-maintained home has a primary bedroom and bath on both the floors. The kitchen is spacious with all custom built cabinets, a built-in pantry, and a breakfast bar. There are 3 bedrooms on the main floor with 2 baths. The large living room overlooks the community and a beautiful view of the mountains.

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  6 Hampton Ct, Middlesboro, KY 40965
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  /18

  $52,500 Sold Mar 19, 2025

  3777 Highway 441, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1940

  Last Sold Summary

  • 25% Below List Price
  • $50/SF
  • 21 Days On Market

  Current Estimated Value $100,157

  Last Listing Agent Patsy Barnett Coldwell Banker Bisceglia Real

  3777 Highway 441, Middlesboro, KY 40965
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  /53

  Est $498,858 Not Listed For Sale

  • 8 Beds
  • 5.5 Baths
  • 5,537 Sq Ft

  208 Arthur Heights, Middlesboro, KY 40965

  208 Arthur Heights, Middlesboro, KY 40965
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  /20

  $105,000 Pending

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

  925 Winchester Ave, Middlesboro, KY 40965

  Looking for an affordable home? This home has 3 bedrooms 2-bathrooms, a living room, kitchen and dining area and laundry room. Appliances stay with home. There is an attached carport, concrete slab for additional parking. This home has a nice deck on the back and a covered porch with a ramp on front of home. There is a storage shed that will stay also. Nice level yard, paved driveway, public

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  925 Winchester Ave, Middlesboro, KY 40965
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  /37

  $539,000 Sold Jan 05, 2026

  1308 Gloucester Ave, Middlesboro, KY 40965

  • 5 Beds
  • 3.5 Baths
  • 4,829 Sq Ft
  • Built 1965

  Last Sold Summary

  • $112/SF
  • 2 Days On Market

  Last Listing Agent Brad Cawood Turn Key Realty

  1308 Gloucester Ave, Middlesboro, KY 40965
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  /79

  Est $266,175 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,764 Sq Ft

  211 Arthur Heights, Middlesboro, KY 40965

  211 Arthur Heights, Middlesboro, KY 40965
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  /36

  $285,000

  00 Highway 217 & 1344, Middlesboro, KY 40965

  UNIQUE OPPORTUNITY PROPERTY. This property offers plenty of potential. Formerly Shillelagh garage and swimming hole, this property has above the ground fuel tanks that could provide ATV's, Side-by-side, farm equipment fuel for work or entertainment. There are Off-road trails for ATV enthusiasts to enjoy the endless trails. These 9.613 surveyed acres can be used for residential, commercial

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  00 Highway 217 & 1344, Middlesboro, KY 40965
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  /2

  $70,000 Sold Aug 18, 2025

  488 Beans Fork Rd, Middlesboro, KY 40965

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

  Last Sold Summary

  • $58/SF
  • 0 Days On Market

  Current Estimated Value $86,197

  Last Listing Agent The Dream Team Real Estate Professionals - Dreama Bolin Lake Cumberland Real Estate Professionals

  488 Beans Fork Rd, Middlesboro, KY 40965
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  /3

  Est $50,103 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  605 Exeter Ave, Middlesboro, KY 40965

  605 Exeter Ave, Middlesboro, KY 40965
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  /27

  $119,900

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  816 W Chester Ave, Middlesboro, KY 40965

  Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

  James Martin Century 21 Pinnacle

  816 W Chester Ave, Middlesboro, KY 40965
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  /30

  $400,000 Sold Jun 06, 2025

  101 Kim Ln, Middlesboro, KY 40965

  • 5 Beds
  • 4 Baths
  • 3,874 Sq Ft
  • Built 2005

  Last Sold Summary

  • 20% Below List Price
  • $103/SF
  • 352 Days On Market

  Current Estimated Value $438,534

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  101 Kim Ln, Middlesboro, KY 40965
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  /14

  Est $79,978 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,500 Sq Ft

  613 Exeter Ave, Middlesboro, KY 40965

  613 Exeter Ave, Middlesboro, KY 40965
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  /36

  $159,900

  • 3 Beds
  • 2 Baths
  • 934 Sq Ft

  45 Fourmile Run Rd, Middlesboro, KY 40965

  Newly Remodeled, move-in ready home. This home is nestled in the heart of Middlesboro on a .489 acre lot. This home has 3 bedrooms and 2 newly renovated bathrooms. The washer and dryer will stay with home. This quiet cozy home has a log cabin look with a large covered front porch. I also has a carport or breezeway to get to the garage. This home also has a fenced in chicken coop. All the

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  45 Fourmile Run Rd, Middlesboro, KY 40965
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  /19

  $166,500 Sold Mar 19, 2025

  225 N 10th St, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,014 Sq Ft
  • Built 1930

  Last Sold Summary

  • 9% Below List Price
  • $164/SF
  • 90 Days On Market

  Current Estimated Value $201,217

  Last Listing Agent Misti McGrath Realty Group

  225 N 10th St, Middlesboro, KY 40965
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  /6

  Est $79,183 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,936 Sq Ft

  707 W Chester Ave, Middlesboro, KY 40965

  707 W Chester Ave, Middlesboro, KY 40965
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  /51

  $250,000

  • 1,500 Sq Ft

  119 Wagon Hollow Rd, Middlesboro, KY 40965

  Welcome to the best of all worlds! One home and an operational store that fronts Highway 217. Several outbuildings and just over 20 acres make this the perfect property for homesteading as seller had livestock on the property at one time. The land is gently rolling to level, Pineville city water in place, spectrum internet and you're off the beaten path but just a 15 minute drive back into town.

  Megan Stanaford Black Diamond Realty

  119 Wagon Hollow Rd, Middlesboro, KY 40965
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  /25

  $134,500 Sold Jul 25, 2025

  422 Wilderness Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $158/SF
  • 38 Days On Market

  Current Estimated Value $136,793

  Last Listing Agent Megan Stanaford Black Diamond Realty

  422 Wilderness Rd, Middlesboro, KY 40965
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  /19

  Est $157,637 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 905 Sq Ft

  602 Winchester Ave, Middlesboro, KY 40965

  602 Winchester Ave, Middlesboro, KY 40965
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  /36

  $259,000

  • 4 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  206 Summit Dr, Middlesboro, KY 40965

  Beautiful move-in ready renovated Property. Home features four bedrooms 2 1/2 baths. kitchen features soft closed custom cabinets, kitchen island and stainless steel appliances. Laminated floors throughout the home. Enjoy your coffee on screened in back porch. Storage building for your tools, lawnmower etc..Property is located within minutes from Lmu main campus, Shopping, restaurants, and

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  206 Summit Dr, Middlesboro, KY 40965
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  /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 $74,314

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Real

  3575 Highway 441, Middlesboro, KY 40965

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