Middlesboro, KY Homes

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  /40

  $249,000

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  301 Doe's Crossing, Middlesboro, KY 40965

  This 2-story gorgeous home sits in the mountains of Kentucky and is located in the desired subdivision of Vista Venado! This home sits on 0.944 acre. The main floor offers an open floor plan with a large living room with gas log fireplace. The living room extends to the formal dining area. The spacious kitchen has room for a breakfast table. The kitchen appliances stay with home and includes a

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  301 Doe's Crossing, Middlesboro, KY 40965
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  /7

  $40,000 Sold May 30, 2025

  19 Venado Dr, Middlesboro, KY 40965

  • Land
  • 3.16 Acres
  • $12,658 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 238 Days On Market

  Last Listing Agent Ben Madon Coldwell Banker Bisceglia Realty & Auction Co

  19 Venado Dr, Middlesboro, KY 40965
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  /6

  Est $96,108 Not Listed For Sale

  • 3 Beds

  615 Evans Dr, Middlesboro, KY 40965

  615 Evans Dr, Middlesboro, KY 40965
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  /32

  $235,200

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  11 Castleford Way, Middlesboro, KY 40965

  Renovated and truly move in ready! Proudly owned by just one owner, this home shows exceptional care from the moment you step inside. Fresh paint, new luxury vinyl and laminate flooring, and thoughtful updates throughout create a clean, modern feel. The kitchen shines with new granite countertops, an updated sink and faucet, and finishes that pair beautifully with the existing cabinetry. Down the

  Jennifer Ware Kentucky Land and Home

  11 Castleford Way, Middlesboro, KY 40965
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  /17

  $210,000 Sold May 02, 2025

  8 Abbey Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $156/SF
  • 28 Days On Market

  Current Estimated Value $253,406

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  8 Abbey Ln, Middlesboro, KY 40965
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  /53

  Est $253,671 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,813 Sq Ft

  165 Lake Hill Rd, Middlesboro, KY 40965

  165 Lake Hill Rd, Middlesboro, KY 40965
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  /21

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  908 W Chester Ave, Middlesboro, KY 40965

  This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment behind the house. The apartment is open space with 1 bdrm and a full bath. Apartment is rented. Metal roof, vinyl siding and windows, hardwood, laminate & tile floors. Privacy and a chain link fenced in back yard, 2 storage buildings, level back yard.

  Steve Mason REMAX PROFESSIONAL'S

  908 W Chester Ave, Middlesboro, KY 40965
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  /50

  $525,000 Sold Mar 31, 2025

  23 Ennismore Dr, Middlesboro, KY 40965

  • 4 Beds
  • 5.5 Baths
  • 6,000 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $88/SF
  • 173 Days On Market

  Current Estimated Value $562,535

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  23 Ennismore Dr, Middlesboro, KY 40965
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  /20

  Est $224,418 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  1013 Doncaster Ave, Middlesboro, KY 40965

  1013 Doncaster Ave, Middlesboro, KY 40965
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  /31

  $179,900

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  180 Stevenson Bridge Rd, Middlesboro, KY 40965

  Charming Rustic Cabin with Modern Comforts on 2 Acres Welcome to 180 Stevenson Branch Rd in Middlesboro, KY—where country charm meets convenience. Just minutes from historic downtown Middlesboro, you'll enjoy easy access to quaint shops, local restaurants, major retailers, medical offices, banks, and hospitals—all while savoring the serenity of rural living. Nestled on a hillside and surrounded

  Beth Combs Turn Key Realty

  180 Stevenson Bridge Rd, Middlesboro, KY 40965
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  /24

  $250,000 Sold May 05, 2025

  230 Windermere Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,099 Sq Ft
  • Built 2007

  Last Sold Summary

  • 14% Below List Price
  • $119/SF
  • 186 Days On Market

  Current Estimated Value $311,739

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  230 Windermere Dr, Middlesboro, KY 40965
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  /16

  Est $196,151 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  916 Doncaster Ave, Middlesboro, KY 40965

  916 Doncaster Ave, Middlesboro, KY 40965
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  /8

  $194,500

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  280 Parker Ln, Middlesboro, KY 40965

  Beautiful and practically brand new! This 3 bedroom 2 bath home is perfect for a sweet family! From the ground up, this home is only 3 years old. All appliances included, very well taken care of. You HAVE to see this one!!

  Misti McGrath Realty Group

  280 Parker Ln, Middlesboro, KY 40965
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  /7

  $271,500 Sold Oct 02, 2025

  115 George Ann Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Below List Price
  • $135/SF
  • 8 Days On Market

  Current Estimated Value $288,586

  Last Listing Agent Brad Cawood Turn Key Realty

  115 George Ann Dr, Middlesboro, KY 40965
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  /23

  Est $231,176 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,206 Sq Ft

  1009 W Rochester Ave, Middlesboro, KY 40965

  1009 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /23

  $225,000

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft

  615 S 22nd St, Middlesboro, KY 40965

  Come check out this beautifully renovated 2 bedroom, 2.5 bath home, metal roof, open concept, privacy fence, new concrete driveway, large back deck for entertaining, outbuilding for storage, great location, new kitchen appliances, new water heater and more! 10 minute drive Lincoln Memorial University's main campus and approx 20 minutes LMU's Vet school. Schedule today to see this pretty home.

  Megan Stanaford Black Diamond Realty

  615 S 22nd St, Middlesboro, KY 40965
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  /3

  $100,000 Sold Feb 04, 2026

  413 S 26th St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1939

  Last Sold Summary

  • 43% Below List Price
  • $99/SF
  • 104 Days On Market

  Last Listing Agent Lisa Stacy-Gibbs Turn Key Realty

  413 S 26th St, Middlesboro, KY 40965
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  /12

  Est $71,960 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  712 Balmoral Rd, Middlesboro, KY 40965

  712 Balmoral Rd, Middlesboro, KY 40965
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  /4

  $49,900

  • Land
  • 0.34 Acre
  • $146,765 per Acre

  1107 Winchester Ave, Middlesboro, KY 40965

  Large building lot in Middlesboro. Zoned R-2 Residential, the lot has plenty of room to build a home. It's rare to find a lot in Middlesboro that is level and ready for building.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  1107 Winchester Ave, Middlesboro, KY 40965
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  /16

  $205,000 Sold May 12, 2025

  286 Tiwani Ridge Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1992

  Last Sold Summary

  • 18% Below List Price
  • $108/SF
  • 17 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  286 Tiwani Ridge Rd, Middlesboro, KY 40965
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  /6

  Est $249,707 Not Listed For Sale

  • Studio
  • 1,616 Sq Ft

  205 Fairview Rd, Middlesboro, KY 40965

  205 Fairview Rd, Middlesboro, KY 40965
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  /15

  $115,000

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

  921 Winchester Ave, Middlesboro, KY 40965

  This country style home has 2 bedrooms with optional 3rd bedroom, 2 bathrooms, living room, dining room, kitchen, and large laundry room, central heat and air is about 6 years old, insulated windows are about 10 years old, seller is installing new cook stove and refrigerator, home has city water and city sewer, high speed internet available, concrete driveway, storage shed stays with home. Level

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  921 Winchester Ave, Middlesboro, KY 40965
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  /16

  $1,250,000 Sold Sep 05, 2025

  423 N 10th St, Middlesboro, KY 40965

  Last Sold Summary

  • 530 Days On Market

  Current Estimated Value $884,050

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

  423 N 10th St, Middlesboro, KY 40965
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  /11

  Est $120,137 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  302 W Rochester Ave, Middlesboro, KY 40965

  302 W Rochester Ave, Middlesboro, KY 40965
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  /2

  $140,000 Pending

  • 4 Beds
  • 2 Baths
  • 995 Sq Ft

  172 Beans Fork Rd, Middlesboro, KY 40965

  Blake Ramey Century 21 Virginia Wilder Real Estate

  172 Beans Fork Rd, Middlesboro, KY 40965
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  /31

  $270,800 Sold Jun 30, 2025

  9 Ennismore Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 1,974 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Below List Price
  • $137/SF
  • 85 Days On Market

  Current Estimated Value $323,517

  Last Listing Agent Brad Cawood Turn Key Realty

  9 Ennismore Dr, Middlesboro, KY 40965
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  /22

  Est $99,909 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft

  407 S 22nd St, Middlesboro, KY 40965

  407 S 22nd St, Middlesboro, KY 40965
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  /5

  $30,000

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965

  LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965
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  /49

  $186,000 Sold May 05, 2025

  412 Wilderness Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1931

  Last Sold Summary

  • 2% Below List Price
  • $81/SF
  • 31 Days On Market

  Current Estimated Value $222,984

  Last Listing Agent Dustin Daniels Mountain Realty

  412 Wilderness Rd, Middlesboro, KY 40965
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  /10

  Est $110,329 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,188 Sq Ft

  216 W Rochester Ave, Middlesboro, KY 40965

  216 W Rochester Ave, Middlesboro, KY 40965
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  /16

  $130,000

  • 3 Beds
  • 1 Bath
  • 792 Sq Ft

  918 E Cumberland Ave, Middlesboro, KY 40965

  This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and one bath with a large kitchen and large living room. This home needs some attention but has a lot of potential. The downstairs could be used as apartment or extra living space. There is another home on the property and might be possible to repair.

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  918 E Cumberland Ave, Middlesboro, KY 40965
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  /17

  $65,000 Sold Jul 29, 2025

  1813 Winchester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1924

  Last Sold Summary

  • 38% Below List Price
  • $64/SF
  • 154 Days On Market

  Current Estimated Value $81,616

  Last Listing Agent Misti McGrath Realty Group

  1813 Winchester Ave, Middlesboro, KY 40965
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  /19

  Est $130,562 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  201 Exeter Ave, Middlesboro, KY 40965

  201 Exeter Ave, Middlesboro, KY 40965
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  /15

  $68,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,456 Sq Ft

  1720 Exeter Ave, Middlesboro, KY 40965

  Super cute house with a great lay out! Fenced in corner lot, excellent outdoor space with oversized garage, a little tlc and this home will shine!

  Misti McGrath Realty Group

  1720 Exeter Ave, Middlesboro, KY 40965
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  /40

  $390,000 Sold Aug 27, 2025

  2824 W Cumberland Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1928

  Last Sold Summary

  • 2% Below List Price
  • $156/SF
  • 21 Days On Market

  Current Estimated Value $395,702

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  2824 W Cumberland Ave, Middlesboro, KY 40965
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  /9

  Est $72,967 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,616 Sq Ft

  205 Exeter Ave, Middlesboro, KY 40965

  205 Exeter Ave, Middlesboro, KY 40965
• 

  /2

  $99,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  923 Winchester Ave, Middlesboro, KY 40965

  This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  923 Winchester Ave, Middlesboro, KY 40965
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  /16

  $46,000 Sold Mar 28, 2025

  309 Oakwood Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1938

  Last Sold Summary

  • 8% Below List Price
  • $38/SF
  • 93 Days On Market

  Current Estimated Value $94,588

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  309 Oakwood Rd, Middlesboro, KY 40965
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  /18

  Est $76,611 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 920 Sq Ft

  401 S 20th St, Middlesboro, KY 40965

  401 S 20th St, Middlesboro, KY 40965
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  /17

  $159,900

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  405 S 37th St, Middlesboro, KY 40965

  Looking for a home to raise your family? Don't let this one go by! Spacious 4 bedrooms, 2 bath home with a fenced in yard, this one is just the right size for a growing family. Just minutes from the hospital and schools, yet tucked away on a side street with little traffic. Let us show you your new home today! Schedule a showing before it's gone.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  405 S 37th St, Middlesboro, KY 40965

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