Middlesboro, KY Homes

• 

  

  

  /10

  $293,000

  Sold Feb 06, 2026

  314 Picadilly Ct, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 2,576 Sq Ft
  • Built 1999

  Last Sold Summary

  • $114/SF
  • 9 Days On Market

  Current Estimated Value $312,774

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

  314 Picadilly Ct, Middlesboro, KY 40965
• 

  

  

  /19

  Est $94,635

  Not Listed For Sale

  422 Sherwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,136 Sq Ft
  • Built 1900

  422 Sherwood Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 8 Days On Market
• 

  

  

  /16

  $69,900

  $10K PRICE DROP

  • 2,256 Sq Ft

  417-A&B Avondale Ave, Middlesboro, KY 40965

  Has the up stairs new flooring some new windows roof 7 years old hot water 7 years old new gutters with gutter guards. Bring your vision and bring this fixer upper back to life. Great duplex for rental or 2 families, Walking distances to everything. Live in one and rent one out. Check it out.

  Nancy Maiden Mountain Realty

  417-A&B Avondale Ave, Middlesboro, KY 40965
• 

  

  

  /15

  $175,000

  Sold Jan 13, 2026

  708 Ilchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Built 1980

  Last Sold Summary

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

  Current Estimated Value $180,515

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  708 Ilchester Ave, Middlesboro, KY 40965
• 

  

  

  /26

  Est $154,992

  Not Listed For Sale

  431 Bellwood Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1934

  431 Bellwood Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 17 Days On Market
• 

  

  /24

  $155,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  1807 Winchester Ave, Middlesboro, KY 40965

  Three-bedroom traditional brick ranch home. Located on a level lot convenient to the local hospital and downtown Middlesboro.

  Michael Hensley REMAX PROFESSIONAL'S

  1807 Winchester Ave, Middlesboro, KY 40965
• 

  

  /18

  $168,000

  Sold Apr 22, 2026

  409 Meadow Ln, Middlesboro, KY 40965

  • 4 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $150/SF
  • 29 Days On Market

  Current Estimated Value $167,944

  Last Listing Agent Brad Cawood Turn Key Realty

  409 Meadow Ln, Middlesboro, KY 40965
• 

  

  /21

  Est $203,307

  Not Listed For Sale

  104 Hollywood Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1955

  104 Hollywood Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 284 Days On Market
• 

  

  /5

  $15,000

  $5K PRICE DROP

  • Land
  • 5,662 Sq Ft
  • $115,385 per Acre

  118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965

  Unrestricted lot in a good location in Middlesboro. Has old home on the property that does not hold any value and would need to be disposed of.

  Michael Hensley REMAX PROFESSIONAL'S

  118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965
• 

  

  /17

  $239,500

  Sold Nov 19, 2025

  5 Abbey Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $196/SF
  • 86 Days On Market

  Current Estimated Value $207,495

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  5 Abbey Ln, Middlesboro, KY 40965
• 

  

  /14

  Est $110,922

  Not Listed For Sale

  1111 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,568 Sq Ft
  • Built 1955

  1111 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 194 Days On Market
• 

  /2

  $15,000

  $5K PRICE DROP

  • Land
  • 5,488 Sq Ft
  • $119,048 per Acre

  205 Exeter Ave, Middlesboro, KY 40965

  Great lot, city utilities available.

  Megan Stanaford Black Diamond Realty

  205 Exeter Ave, Middlesboro, KY 40965
• 

  

  /48

  $275,000

  Sold Nov 03, 2025

  109 Hollywood Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 3,544 Sq Ft

  Last Sold Summary

  • 11% Below List Price
  • $78/SF
  • 159 Days On Market

  Current Estimated Value $280,458

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

  109 Hollywood Dr, Middlesboro, KY 40965
• 

  

  /39

  Est $265,402

  Not Listed For Sale

  807 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2024

  807 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 95 Days On Market
• 

  

  /9

  $159,900

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  908 Manchester Ave, Middlesboro, KY 40965

  This three-bedroom, two-bath home at 908 Manchester has been thoughtfully updated with a brand new metal roof, fresh HVAC system, and energy-efficient windows. At fourteen hundred square feet on a nice lot, it's move-in ready and priced to sell. It's in a quiet neighborhood, super close to schools, and offers great value in the Middlesboro market. Perfect for families or anyone wanting

  Jonathan Evans Action Realty

  908 Manchester Ave, Middlesboro, KY 40965
• 

  

  /30

  $168,700

  Sold Jan 21, 2026

  3008 State Highway 441, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Built 1900

  Last Sold Summary

  • 16% Below List Price
  • $94/SF
  • 104 Days On Market

  Current Estimated Value $175,712

  Last Listing Agent Brad Cawood Turn Key Realty

  3008 State Highway 441, Middlesboro, KY 40965
• 

  

  /28

  Est $204,000

  Not Listed For Sale

  815 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1969

  815 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 163 Days On Market
• 

  

  /34

  $175,000

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  64 Dunlap Hollow Rd, Middlesboro, KY 40965

  This home is turnkey and ready to move right in; it has been well maintained over the years. This home has 4 Bedrooms, 2 Full Baths, Dining Room and a Kitchen that comes with Range, Refrigerator, Dishwasher and Microwave plus the laundry room has a washer and dryer set that will stay with home. Step out the back door and just a few steps up the hill is a wonderful workshop and a storage shed.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  64 Dunlap Hollow Rd, Middlesboro, KY 40965
• 

  

  /16

  $180,000

  Sold Oct 21, 2025

  106 S 38th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1971

  Last Sold Summary

  • 20% Below List Price
  • $128/SF

  Current Estimated Value $179,005

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

  106 S 38th St, Middlesboro, KY 40965
• 

  

  /18

  Est $166,919

  Not Listed For Sale

  1212 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,206 Sq Ft
  • Built 1930

  1212 Winchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 151 Days On Market
• 

  

  /3

  $35,000

  • Land
  • 14,853 Sq Ft
  • $102,639 per Acre

  2107 Winchester Ave, Middlesboro, KY 40965

  PRIME LOCATION, NO FLOOD ZONE! Discover the ultimate blank canvas within the city limits. This fully cleared, level, and build ready lot offers an exceptional opportunity to build your dream home, or next investment project. Situated entirely outside the FEMA flood zone, this lot offers peace of mind and reduced insurance costs. All city utilities are ready for connection. This lot would always

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  2107 Winchester Ave, Middlesboro, KY 40965
• 

  /2

  $6,000

  Sold Dec 31, 2025

  lot 34 Brush Mountain Cir, Miracle, KY 40856

  • Land
  • 2.58 Acres
  • $2,326 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 141 Days On Market

  Last Listing Agent Megan Stanaford Black Diamond Realty

  lot 34 Brush Mountain Cir, Miracle, KY 40856
• 

  

  /10

  Est $123,321

  Not Listed For Sale

  1102 Winchester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1800

  1102 Winchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 33 Days On Market
• 

  

  /19

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  913 Doncaster St, Middlesboro, KY 40965

  This home is located in the city of Middlesboro minutes away from the hospital, close to downtown. Walmart, LMU are minutes away. It's located in a very safe neighborhood. The home includes a 364' single care garage.

  Janice Pratt Fathom Realty TN LLC

  913 Doncaster St, Middlesboro, KY 40965
• 

  

  /33

  $340,000

  Sold May 18, 2026

  3306 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,126 Sq Ft
  • Built 1976

  Last Sold Summary

  • 3% Below List Price
  • $160/SF
  • 1 Day On Market

  Current Estimated Value $335,582

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  3306 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /15

  Est $199,058

  Not Listed For Sale

  1002 W Chester Ave, Middlesboro, KY 40965

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

  1002 W Chester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 0 Days On Market
• 

  

  /20

  $279,000

  • 3 Beds
  • 3 Baths
  • 2,210 Sq Ft

  515 Englewood Rd, Middlesboro, KY 40965

  Discover the perfect blend of peaceful living and everyday convenience in this unique, nature-surrounded home located right in town. Set on approximately 0.75 acres, this property offers privacy, scenic surroundings, and abundant natural light through dramatic floor-to-ceiling windows overlooking the wooded landscape and spacious yard. Inside, the home showcases warm character with vaulted wood

  Kevin Carroll Backwoods Realty & Development

  515 Englewood Rd, Middlesboro, KY 40965
• 

  

  /66

  $305,000

  Sold May 14, 2026

  832 N 25th St, Middlesboro, KY 40965

  • 6 Beds
  • 3.5 Baths
  • 4,033 Sq Ft

  Last Sold Summary

  • 10% Below List Price
  • $76/SF
  • 278 Days On Market

  Current Estimated Value $312,609

  Last Listing Agent Blake Ramey Century 21 Virginia Wilder Real Estate

  832 N 25th St, Middlesboro, KY 40965
• 

  

  /18

  Est $225,098

  Not Listed For Sale

  811 Gloucester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,661 Sq Ft
  • Built 1965

  811 Gloucester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 0 Days On Market
• 

  

  /30

  $240,000

  • 3 Beds
  • 1.5 Baths
  • 2,154 Sq Ft

  116 Edgewood Rd, Middlesboro, KY 40965

  Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, space, and convenience at 116 Edgewood Road in Middlesboro. This spacious 2,154-square-foot home offers 3 bedrooms and 2 full bathrooms, nestled on approximately 0.75 acres while remaining within walking distance of downtown amenities. Step inside to find a versatile floor plan with multiple living areas and

  Megan Stanaford Black Diamond Realty

  116 Edgewood Rd, Middlesboro, KY 40965
• 

  

  /19

  $87,000

  Sold Jan 20, 2026

  101 Earle Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1970

  Last Sold Summary

  • 17% Below List Price
  • $79/SF
  • 111 Days On Market

  Current Estimated Value $98,843

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  101 Earle Ln, Middlesboro, KY 40965
• 

  

  /28

  Est $151,641

  Not Listed For Sale

  808 Manchester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 2 Baths
  • 1,237 Sq Ft
  • Built 1946

  808 Manchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 31 Days On Market
• 

  

  /13

  $455,000

  • 5 Beds
  • 4 Baths
  • 3,146 Sq Ft

  523 N 30th St, Middlesboro, KY 40965

  Spacious All-Brick Home with Attached Guest Quarters - Prime Location! This beautifully maintained, all-brick home offers exceptional flexibility and space, featuring a main residence with 3 bedrooms, 2 bathrooms, a bonus room perfect for a home office, rec room, or additional sleeping area, and two laundry rooms for added convenience.In addition, the property includes a fully separate,

  Kevin Carroll Backwoods Realty & Development

  523 N 30th St, Middlesboro, KY 40965
• 

  

  /16

  $147,000

  Sold Oct 27, 2025

  428 Wilderness Rd, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1960

  Last Sold Summary

  • 8% Below List Price
  • $111/SF
  • 64 Days On Market

  Current Estimated Value $146,367

  Last Listing Agent Brad Cawood Turn Key Realty

  428 Wilderness Rd, Middlesboro, KY 40965
• 

  /2

  Est $215,355

  Not Listed For Sale

  806 Manchester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 2 Baths
  • 1,899 Sq Ft
  • Built 1964

  806 Manchester Ave, Middlesboro, KY 40965
• 

  

  /28

  $165,000

  $24K PRICE DROP

  4607 W Cumberland Ave, Middlesboro, KY 40965

  This is a great opportunity to own investment property or live in one unit and rent the other unit to make mortgage payment, each unit has 1 bedroom, 1 full bathroom, living room, eat-in kitchen and laundry area; each unit comes with range, refrigerator, washer and dryer. Apartments sit on level lot, paved driveway, public water and public sewer, each unit has a heat pump, decks have been stained

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  4607 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /6

  $60,000

  Sold Sep 03, 2025

  515 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1940

  Last Sold Summary

  • $55/SF
  • 17 Days On Market

  Current Estimated Value $69,047

  Last Listing Agent Misti McGrath Realty Group

  515 Winchester Ave, Middlesboro, KY 40965
• 

  

  /22

  Est $222,470

  Not Listed For Sale

  811 Manchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • Built 1970

  811 Manchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 54 Days On Market
• 

  

  /15

  $169,000

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  815 Dorchester Ave, Middlesboro, KY 40965

  Welcome to Historic Middlesboro KY - Beautifully Renovated Home with Stunning Mountain Views! Situated on an easy-to-maintain 0.29-acre lot, this charming home in the heart of Middlesboro KY JUST MINUTES FROM ONE OF THE OLDEST GOLF COURSES--This House blends historic charm with modern updates. Enjoy breathtaking views of the Cumberland Mountains, Cumberland Gap National Park, and the iconic

  Lisa Stacy-Gibbs Turn Key Realty

  815 Dorchester Ave, Middlesboro, KY 40965
• 

  

  /20

  $60,000

  Sold Apr 03, 2026

  72 Happy Hollow Hill Rd, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 2007

  Last Sold Summary

  • 25% Below List Price
  • $32/SF
  • 18 Days On Market

  Current Estimated Value $60,000

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  72 Happy Hollow Hill Rd, Middlesboro, KY 40965

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