Middlesboro, KY Homes

• 

  

  

  /15

  $39,900

  • Land
  • 3.69 Acres
  • $10,813 per Acre

  Lot 103 Doe's Crossing, Middlesboro, KY 40965

  This beautiful property has 3.691 Acres. Enjoy the wildlife that strolls over from the National Park that joins this property. Water and electric and natural gas available. You can build your dream home with a minimum SF of 1,500. Enjoy natures beauty all around yet close to downtown Middlesboro. Gorgeous views!

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  Lot 103 Doe's Crossing, Middlesboro, KY 40965
• 

  

  

  /40

  $249,900

  Sold Aug 07, 2026

  913 Doncaster St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1998

  Last Sold Summary

  • $186/SF
  • 61 Days On Market

  Current Estimated Value $249,055

  Last Listing Agent Janice Pratt Fathom Realty TN LLC

  913 Doncaster St, Middlesboro, KY 40965
• 

  

  

  /39

  Est $272,204

  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

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S
• 

  

  

  /17

  $19,900

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  13 Duncan Ln, Middlesboro, KY 40965

  Manufactured home with 3 bedrooms and 2 bathrooms. Situated on a 0.36 acre lot built in 2000. Please be advised that any offers on this property require a minimum Earnest Money Deposit of 1% of the Purchase Price or $1,000, whichever is greater. Purchasers may use any lender they choose to finance the purchase of a property. However, the seller requires that all non-cash offers must be

  James Martin Century 21 Pinnacle

  13 Duncan Ln, Middlesboro, KY 40965
• 

  

  

  /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 $335,750

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

  314 Picadilly Ct, Middlesboro, KY 40965
• 

  

  /28

  Est $215,412

  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

  Last Listing Agent Beth Combs Turn Key Realty
• 

  /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
• 

  

  /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 $193,728

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  708 Ilchester Ave, Middlesboro, KY 40965
• 

  

  /10

  Est $124,157

  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

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

  

  /9

  $142,500

  $17K PRICE DROP

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

  908 Manchester Ave, Middlesboro, KY 40965

  MOTIVATED SELLER 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

  Jonathan Evans Action Realty

  908 Manchester 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 $172,220

  Last Listing Agent Brad Cawood Turn Key Realty

  409 Meadow Ln, Middlesboro, KY 40965
• 

  

  /28

  Est $218,892

  Not Listed For Sale

  908 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1955

  908 W Chester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 131 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /34

  $159,000

  $16K PRICE DROP

  • 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
• 

  

  /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 $232,108

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  5 Abbey Ln, Middlesboro, KY 40965
• 

  

  /15

  Est $201,402

  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

  Last Listing Agent Misti McGrath Realty Group
• 

  

  /3

  $29,000

  $6K PRICE DROP

  • Land
  • 14,853 Sq Ft
  • $85,044 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
• 

  

  /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 $290,736

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

  109 Hollywood Dr, Middlesboro, KY 40965
• 

  

  /15

  Est $190,726

  Not Listed For Sale

  1200 W Chester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,028 Sq Ft
  • Built 1958

  1200 W Chester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent Blake Ramey Century 21 Virginia Wilder Real Estate
• 

  

  /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
• 

  

  /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 $185,002

  Last Listing Agent Brad Cawood Turn Key Realty

  3008 State Highway 441, Middlesboro, KY 40965
• 

  

  /18

  Est $218,866

  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

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /42

  $315,000

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,664 Sq Ft

  926 Doncaster Ave, Middlesboro, KY 40965

  Looking for a HOME and not just another house? This is it! With 5 bedrooms, 2 baths, a bonus room to use as a den or rec room, and even special features like a light equipped with a built-in blue tooth speaker in the master bathroom. This home was built with 'family living' in mind. The kitchen is equipped with a new island/breakfast bar that seats six and blends seamlessly with the dining area.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  926 Doncaster Ave, 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 $187,509

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

  106 S 38th St, Middlesboro, KY 40965
• 

  

  /28

  Est $161,001

  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

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real
• 

  

  /30

  $200,000

  $40K PRICE DROP

  • 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
• 

  /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
• 

  /2

  Est $219,153

  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

  $149,900

  $39K 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
• 

  

  /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 $333,240

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  3306 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /22

  Est $224,047

  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

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /15

  $159,900

  $15K 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 Backwoods Realty & Development

  815 Dorchester Ave, 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 $305,285

  Last Listing Agent Blake Ramey Century 21 Virginia Wilder Real Estate

  832 N 25th St, Middlesboro, KY 40965
• 

  

  /22

  Est $332,094

  Not Listed For Sale

  123 Twin Acres Rd, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 3,338 Sq Ft
  • Built 1987

  123 Twin Acres Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Ann Robinson Mountain Realty
• 

  

  /13

  $45,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  918 E Cumberland Ave, Middlesboro, KY 40965

  Old home needs work with an attached older home that needs to be torn down. Great Location on Cumberland Ave behind Food City

  Steve Mason REMAX PROFESSIONAL'S

  918 E Cumberland Ave, 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 $110,128

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  101 Earle Ln, Middlesboro, KY 40965
• 

  

  /19

  Est $165,396

  Not Listed For Sale

  1408 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1933

  1408 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 66 Days On Market

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

  

  /15

  $135,000

  $7K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,404 Sq Ft

  708 W Chester Ave, Middlesboro, KY 40965

  Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.

  Michael Hensley REMAX PROFESSIONAL'S

  708 W Chester Ave, Middlesboro, KY 40965
• 

  

  /18

  $175,000

  Sold Dec 31, 2025

  114 W Rochester Ave, Middlesboro, KY 40965

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

  Last Sold Summary

  • $174/SF
  • 15 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  114 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /10

  Est $111,487

  Not Listed For Sale

  1619 Winchester Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1.5 Baths
  • 1,364 Sq Ft
  • Built 1940

  1619 Winchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 178 Days On Market

  Last Listing Agent Misti McGrath Realty Group
• 

  

  /10

  $79,000

  Pending

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  1614 Exeter Ave, Middlesboro, KY 40965

  Cozy two bedroom, one bath fixer upper located in Middlesboro, KY. Perfect home for an investor or someone who loves to flip houses and add their own personal touch. One car garage adds extra storage. The home also comes with an extra lot at 1612 Exeter Ave. The lot currently has a home sitting on it that is not livable and currently being used for storage. Beautiful level lot. Call Jennifer

  Jennifer Moyers Action Realty

  1614 Exeter Ave, Middlesboro, KY 40965

Showing Results 161 - 200, Page 5 of 18