Middlesboro, KY Homes

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  /9

  $139,000

  • Land
  • 5.33 Acres
  • $26,079 per Acre

  312 Blakely Ln, Middlesboro, KY 40965

  Rare find! 5.33 undeveloped acres in Middlesboro on Blakely Lane, off Cumberland Ave. Zoned R-1. Land is mostly level with a drop to the creek behind. Portion near the creek is in the floor plain. Several building sites on the land above the flood plain. Easy access to Cumberland Ave yet away from the noise and traffic.

  Ann Robinson Action Realty

  312 Blakely Ln, Middlesboro, KY 40965
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  /14

  $153,500 Sold Mar 21, 2025

  141 Maxwelton Heights, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1965

  Last Sold Summary

  • 10% Above List Price
  • $77/SF
  • 131 Days On Market

  Current Estimated Value $195,209

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  141 Maxwelton Heights, Middlesboro, KY 40965
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  /24

  Est $133,008 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  205 Oakwood Rd, Middlesboro, KY 40965

  205 Oakwood Rd, Middlesboro, KY 40965
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  /2

  $490,000 Pending

  • 7 Beds
  • 5 Baths
  • 6,276 Sq Ft

  142 Edgewood Rd, Middlesboro, KY 40965

  A One-of-a-Kind Dream Home with Spectacular Views!This stunning home offers breathtaking views from every window and boasts 7 spacious bedrooms, 3 full bathrooms, and 2 half bathrooms—plenty of room for the entire family!Step inside and be captivated by the grand staircase and an incredible private library, perfect for quiet moments or working from home. The walkout basement is

  Lisa Stacy-Gibbs Turn Key Realty

  142 Edgewood Rd, Middlesboro, KY 40965
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  /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

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

  314 Picadilly Ct, Middlesboro, KY 40965
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  /27

  Est $283,199 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  103 Sherwood Rd, Middlesboro, KY 40965

  103 Sherwood Rd, Middlesboro, KY 40965
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  /16

  $79,900

  • 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.

  Nancy Maiden Mountain Realty

  417-A&B Avondale Ave, Middlesboro, KY 40965
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  /21

  $177,000 Sold May 05, 2025

  104 Hollywood Dr, Middlesboro, KY 40965

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

  Last Sold Summary

  • 23% Below List Price
  • $118/SF
  • 284 Days On Market

  Current Estimated Value $214,317

  Last Listing Agent Lisa Davenport REMAX PROFESSIONAL'S

  104 Hollywood Dr, Middlesboro, KY 40965
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  /38

  Est $143,471 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,182 Sq Ft

  504 Manchester Ave, Middlesboro, KY 40965

  504 Manchester Ave, Middlesboro, KY 40965
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  /5

  $15,000

  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
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  /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

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  708 Ilchester Ave, Middlesboro, KY 40965
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  /19

  Est $89,817 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,136 Sq Ft

  422 Sherwood Rd, Middlesboro, KY 40965

  422 Sherwood Rd, Middlesboro, KY 40965
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  /2

  $40,000

  0 Windermere, Middlesboro, KY 40965

  Here is your chance to own land in AMBLESIDE!! I heard a rumor they aren't making any more! 2 lots listed together for $40k or seller is willing to separate the property for qualified, serious buyers.Seller is willing to have property cleared for buyer. In county with city sewer and water!

  Misti McGrath Realty Group

  0 Windermere, Middlesboro, KY 40965
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  /31

  $290,000 Sold Jun 16, 2025

  135 Highpoint Rd, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1950

  Last Sold Summary

  • 93% Above List Price
  • $242/SF
  • 161 Days On Market

  Current Estimated Value $161,396

  Last Listing Agent Janice Pratt Fathom Realty TN LLC

  135 Highpoint Rd, Middlesboro, KY 40965
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  /26

  Est $148,239 Not Listed For Sale

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

  431 Bellwood Rd, Middlesboro, KY 40965

  431 Bellwood Rd, Middlesboro, KY 40965
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  /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

  Beth Combs Turn Key Realty

  515 Englewood Rd, Middlesboro, KY 40965
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  /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 $245,545

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  5 Abbey Ln, Middlesboro, KY 40965
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  /14

  Est $85,642 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,568 Sq Ft

  1111 Exeter Ave, Middlesboro, KY 40965

  1111 Exeter Ave, Middlesboro, KY 40965
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  /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,

  Beth Combs Turn Key Realty

  523 N 30th St, Middlesboro, KY 40965
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  /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 $296,838

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

  109 Hollywood Dr, Middlesboro, KY 40965
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  /13

  Est $105,439 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,963 Sq Ft

  901 Exeter Ave, Middlesboro, KY 40965

  901 Exeter Ave, Middlesboro, KY 40965
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  /2

  $189,000

  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
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  /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

  Last Listing Agent Brad Cawood Turn Key Realty

  3008 State Highway 441, Middlesboro, KY 40965
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  /28

  Est $185,935 Not Listed For Sale

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

  815 Exeter Ave, Middlesboro, KY 40965

  815 Exeter Ave, Middlesboro, KY 40965
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  /66

  $319,900

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

  832 N 25th St, Middlesboro, KY 40965

  beautiful and spacious home located within the city limits of Middlesboro. this property consists of a main home and a separate apartment.The main home has four beds and 3 baths (2 full and 1 half). It has potential for a home office, home library, etc. The apartment that sits above the garage provides a unique income producing opportunity. It has 2 bedrooms and 1 full bath. Great location,

  Blake Ramey Century 21 Virginia Wilder Real Estate

  832 N 25th St, Middlesboro, KY 40965
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  /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 $174,454

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

  106 S 38th St, Middlesboro, KY 40965
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  /18

  Est $146,217 Not Listed For Sale

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

  1212 Winchester Ave, Middlesboro, KY 40965

  1212 Winchester Ave, Middlesboro, KY 40965
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  /5

  $29,900

  • Land
  • 16.76 Acres
  • $1,784 per Acre

  0 Highway 217 Unit 25005121, Middlesboro, KY 40965

  16.7 acre lot at Brush Mountain Farms. This is a great property for a cabin. Great views with a walking trail nearby. This property is located in a gated community and has an HOA with restrictions. Call for a showing.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  0 Highway 217 Unit 25005121, Middlesboro, KY 40965
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  /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
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  /10

  Est $108,890 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft

  1102 Winchester Ave, Middlesboro, KY 40965

  1102 Winchester Ave, Middlesboro, KY 40965
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  /15

  $142,000

  • 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
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  /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

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  101 Earle Ln, Middlesboro, KY 40965
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  /7

  Est $84,630 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  2931 Cumberland Ave, Middlesboro, KY 40965

  2931 Cumberland Ave, Middlesboro, KY 40965
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  /38

  $359,000

  • 4 Beds
  • 2.5 Baths
  • 3,885 Sq Ft

  2702 Cumberland Ave, Middlesboro, KY 40965

  Don't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner lot. This 3,800 sq ft turn of the century home, that has been completely updated, boasts 4 bedrooms, 2 full baths and 1 half bath. On the primary level you'll find a covered front porch, sun room, large living room, and oversized dedicated dining area. Off of the dining room, you'll find a massive kitchen

  Darrell Lewis DIY Flat Fee.com

  2702 Cumberland Ave, Middlesboro, KY 40965
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  /27

  $145,000 Sold May 16, 2025

  109 N 30th St, Middlesboro, KY 40965

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

  Last Sold Summary

  • 15% Below List Price
  • $139/SF
  • 49 Days On Market

  Last Listing Agent Tim Smith Sallie Davidson, Realtors

  109 N 30th St, Middlesboro, KY 40965
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  /18

  Est $205,617 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,661 Sq Ft

  811 Gloucester Ave, Middlesboro, KY 40965

  811 Gloucester Ave, Middlesboro, KY 40965
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  /14

  $115,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  209 Dalewood Rd, Middlesboro, KY 40965

  Great property for anyone at any stage in life. Move in ready! 4 bedroom, 2 bathroom manufactured home built in 2020 sitting on 0.41 of an acre, per public records. Easy access to shopping, 10 minutes to LMU's main campus in Harrogate TN.

  Megan Stanaford Black Diamond Realty

  209 Dalewood Rd, Middlesboro, KY 40965
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  /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 $155,401

  Last Listing Agent Brad Cawood Turn Key Realty

  428 Wilderness Rd, Middlesboro, KY 40965
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  /43

  Est $271,025 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,765 Sq Ft

  1208 Gloucester Ave, Middlesboro, KY 40965

  1208 Gloucester Ave, Middlesboro, KY 40965
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  /32

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 3,174 Sq Ft

  113 Hollywood Dr, Middlesboro, KY 40965

  Beautiful Traditional Brick Ranch with Basement!This home has 1698sq/ft on the main floor with an additional 1476sq/ft in the basement. Nestled in the center of Middlesboro with a curved driveway and a 2 car carport with a storage unit between them. The home has two entrances from the carport for easy entry. There are two bonus rooms with a formal living room and formal dining area. The

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  113 Hollywood Dr, Middlesboro, KY 40965

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