Middlesboro, KY Homes

• 

  

  

  /23

  Est $137,681

  Not Listed For Sale

  716 Ilchester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1930

  716 Ilchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /2

  $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, attached

  Kevin Carroll Backwoods Realty & Development

  523 N 30th St, Middlesboro, KY 40965
• 

  

  

  /23

  $150,000

  Sold Jun 04, 2026

  359 Beans Fork Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 1920

  Last Sold Summary

  • $158/SF
  • 61 Days On Market

  Current Estimated Value $160,015

  Last Listing Agent Misti McGrath Realty Group

  359 Beans Fork Rd, Middlesboro, KY 40965
• 

  

  

  /49

  Est $250,945

  Not Listed For Sale

  715 Worchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1985

  715 Worchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Janice Pratt AAA Realty, Inc.
• 

  

  

  /23

  $199,000

  • 3 Beds
  • 1 Bath
  • 1,480 Sq Ft

  1102 W Chester Ave, Middlesboro, KY 40965

  Just listed 1480 sq ft historical spilt level home at 1102 W Chester Ave Middlesboro Ky. This home is in walking distance from downtown. It has three bedrooms and one bath and a large den with a beautiful fireplace. The eat in kitchen is right off the den area. There is a covered screened in porch just off the dinning area.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  1102 W Chester Ave, Middlesboro, KY 40965
• 

  

  /4

  $130,000

  Sold Aug 25, 2026

  1577 Beans Fork Rd, Middlesboro, KY 40965

  • Land
  • 1.02 Acres
  • $127,451 per Acre

  Last Sold Summary

  • 420% Above List Price
  • 50 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  1577 Beans Fork Rd, Middlesboro, KY 40965
• 

  

  /16

  Est $139,781

  Not Listed For Sale

  507 Worchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,368 Sq Ft
  • Built 1918

  507 Worchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /13

  $35,000

  Pending

  • Land
  • 12,196 Sq Ft
  • $125,000 per Acre

  904-A E Cumberland Ave, Middlesboro, KY 40965

  Almost 1/2 acre in the Middlesboro city limits with a nice garage. The 1,292 sf garage has been well maintained. is already connected to electric service and public water is available. The land has been surveyed and would be the perfect place to start your own service garage, woodworking shop, or for storage. Commercial electric garage door opener and already has heat. Don't let this pass you by!

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  904-A E Cumberland Ave, Middlesboro, KY 40965
• 

  

  /48

  $324,900

  Sold Apr 17, 2026

  805 Worchester Ave, Middlesboro, KY 40965

  • 5 Beds
  • 3 Baths
  • 2,250 Sq Ft
  • Built 1942

  Last Sold Summary

  • 7% Below List Price
  • $144/SF
  • 169 Days On Market

  Current Estimated Value $323,836

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  805 Worchester Ave, Middlesboro, KY 40965
• 

  

  /48

  Est $405,078

  Not Listed For Sale

  515 Worchester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 3.5 Baths
  • 4,300 Sq Ft
  • Built 1992

  515 Worchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /10

  $299,000

  • 6 Beds
  • 4 Baths
  • 3,594 Sq Ft

  312 W Chester Ave, Middlesboro, KY 40965

  Multi-unit rental property for sale. This instant money-maker has 4 apartments, all of which are rented. Tenants pay all utilities. Now is the perfect time to invest in rental property. Right now, there is no risk of your apartments sitting empty-schedule an appointment today before someone else realizes the potential in these units. Don't wait!

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  312 W Chester Ave, Middlesboro, KY 40965
• 

  

  /17

  $222,500

  Sold May 22, 2026

  810 Worchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Below List Price
  • $111/SF
  • 6 Days On Market

  Current Estimated Value $218,260

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  810 Worchester Ave, Middlesboro, KY 40965
• 

  

  /15

  Est $108,871

  Not Listed For Sale

  106 Ellenwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft
  • Built 1970

  106 Ellenwood Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Dawn Risner Turn Key Realty
• 

  

  /3

  $125,000

  $50K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft

  120 Redwood Rd Unit A & B, Middlesboro, KY 40965

  Great investment opportunity with this one. Built in 2000 per appraisal, this property offers a total of 1,664 square feet and is currently occupied by reliable, long-term tenants. Each unit features 2 bedrooms and 1 bathroom, providing comfortable living space for residents. The address, listed as 102 A&B Redwood Road, originates from a previous appraisal. The property is confirmed per the

  Megan Stanaford Black Diamond Realty

  120 Redwood Rd Unit A & B, Middlesboro, KY 40965
• 

  

  /32

  $173,675

  Sold Mar 27, 2026

  140 Hickory Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • Built 2009

  Last Sold Summary

  • 5% Above List Price
  • 15 Days On Market

  Current Estimated Value $192,025

  Last Listing Agent SARAH RICHARDS RE/MAX Preferred Group

  140 Hickory Ln, Middlesboro, KY 40965
• 

  

  /34

  Est $199,147

  Not Listed For Sale

  127 Cawood Ln, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,163 Sq Ft
  • Built 1976

  127 Cawood Ln, Middlesboro, KY 40965

  Last Sold Summary

  • 234 Days On Market

  Last Listing Agent Cookie Russell Realty Network, Inc
• 

  

  /20

  $229,500

  • 6 Beds
  • 6 Baths
  • 2,700 Sq Ft

  623 N 20th St, Middlesboro, KY 40965

  Excellent investment opportunity with a strong ~9% cap rate at asking price! This unique 4-unit property offers incredible versatility-perfect as a pure cash-flowing asset or an ideal opportunity to live in one unit while renting out the other three. The property consists of four fully occupied units: a main multi-family building featuring one 2-bedroom unit and two 1-bedroom units, plus a

  Derek Eisenberg Continental Real Estate Group

  623 N 20th St, Middlesboro, KY 40965
• 

  /2

  $8,000

  Sold Nov 18, 2025

  4163 441, Middlesboro, KY 40965

  • Land
  • 17,424 Sq Ft
  • $20,000 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 82 Days On Market

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

  4163 441, Middlesboro, KY 40965
• 

  

  /16

  Est $88,195

  Not Listed For Sale

  309 Oakwood Rd, Middlesboro, KY 40965

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

  309 Oakwood Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors
• 

  

  /26

  $250,000

  $19K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,750 Sq Ft

  119 S 20th St, Middlesboro, KY 40965

  New on the market, this multipurpose commercial historical property could be your own personal residential space. With 1,750 square feet total, completely refinished, new water lines, sewer lines from the house to the street, new floors, new steel tubs, exhaust fans, new plumbing and water heater, new deck, LED lighting, real tile backsplashes over the kitchen counters and tubs. Two bedrooms

  Tina Eades Kentucky Homes and Land LLC

  119 S 20th St, Middlesboro, KY 40965
• 

  /2

  $167,000

  Sold Sep 15, 2025

  919 W Rochester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,024 Sq Ft
  • Built 2010

  Last Sold Summary

  • 10% Below List Price
  • $83/SF
  • 4 Days On Market

  Current Estimated Value $187,308

  Last Listing Agent Beth Combs Turn Key Realty

  919 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /24

  Est $143,531

  Not Listed For Sale

  205 Oakwood Rd, Middlesboro, KY 40965

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft
  • Built 1947

  205 Oakwood Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S
• 

  

  /34

  $359,500

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2909 W Cumberland Ave, Middlesboro, KY 40965

  This beautiful brick has touches of class to enjoy for a lifetime. With all the beauty of her old style from big rooms, original cherry doors 9 1/2 foot ceilings and original hardwood floors. A fabulous front porch, a 2 car garage with a spacious and playful backyard. On the inside you will enjoy a kitchen that sparkles white with stainless steel appliances and a grand island for cooking and

  Lisa Stacy-Gibbs Backwoods Realty & Development

  2909 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /20

  $187,000

  Sold Aug 20, 2026

  116 N Petersborough Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,652 Sq Ft
  • Built 1930

  Last Sold Summary

  • 17% Below List Price
  • $113/SF
  • 76 Days On Market

  Current Estimated Value $211,604

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  116 N Petersborough Ave, Middlesboro, KY 40965
• 

  

  /27

  Est $301,610

  Not Listed For Sale

  103 Sherwood Rd, Middlesboro, KY 40965

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 1965

  103 Sherwood Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 127 Days On Market

  Last Listing Agent Ann Robinson Mountain Realty
• 

  

  /18

  $135,000

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  2002 Winchester Ave, Middlesboro, KY 40965

  CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  2002 Winchester Ave, Middlesboro, KY 40965
• 

  

  /20

  $108,000

  Sold Dec 19, 2025

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977

  • Land
  • 11 Acres
  • $9,818 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 6 Days On Market

  Current Estimated Value $120,000

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977
• 

  

  /38

  Est $170,107

  Not Listed For Sale

  504 Manchester Ave, Middlesboro, KY 40965

  • 4 Beds
  • 3 Baths
  • 2,182 Sq Ft
  • Built 1940

  504 Manchester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 179 Days On Market

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

  /2

  $595,000

  $105K PRICE INCREASE

  • 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 Backwoods Realty & Development

  142 Edgewood Rd, Middlesboro, KY 40965
• 

  

  /32

  $231,000

  Sold Oct 22, 2025

  825 S 28th St, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 2004

  Last Sold Summary

  • 14% Below List Price
  • $114/SF
  • 151 Days On Market

  Current Estimated Value $238,971

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  825 S 28th St, Middlesboro, KY 40965
• 

  

  /19

  Est $91,922

  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

  Last Listing Agent Brad Cawood Turn Key Realty
• 

  

  /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
• 

  

  /24

  $152,500

  Sold Jul 21, 2026

  1807 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Below List Price
  • $138/SF
  • 15 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  1807 Winchester Ave, Middlesboro, KY 40965
• 

  

  /26

  Est $158,221

  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

  Last Listing Agent Lawrence McGeorge Tri State Realty Inc of KY DBA Re/Max Professionals
• 

  

  /22

  $229,000

  • 4 Beds
  • 2 Baths
  • 1,544 Sq Ft

  812 Worchester Ave, Middlesboro, KY 40965

  Isn't she lovely?! Located right in the middle of Middlesboro Ky. 4 bedroom 2 bath home with a beautiful kitchen! Yard space for all the things on a quiet street. Excellent home to check out today!

  Misti McGrath Realty Group

  812 Worchester Ave, Middlesboro, KY 40965
• 

  /2

  $32,500

  Sold Mar 19, 2026

  0 Windermere, Middlesboro, KY 40965

  • Land
  • 29,185 Sq Ft
  • $48,507 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 41 Days On Market

  Last Listing Agent Misti McGrath Realty Group

  0 Windermere, Middlesboro, KY 40965
• 

  

  /21

  Est $203,790

  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

  Last Listing Agent Lisa Davenport REMAX PROFESSIONAL'S
• 

  

  /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
• 

  

  /10

  $90,000

  Sold Nov 19, 2025

  234 S 46th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 2013

  Last Sold Summary

  • 17% Below List Price
  • $97/SF
  • 47 Days On Market

  Current Estimated Value $93,533

  Last Listing Agent Misti McGrath Realty Group

  234 S 46th St, Middlesboro, KY 40965
• 

  

  /14

  Est $147,104

  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

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

Showing Results 121 - 160, Page 4 of 18