Middlesboro, KY Homes

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  /18

  $135,000

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  413 S 26th St, Middlesboro, KY 40965

  This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from downtown Middlesboro and the Cumberland Gap National Park. This home has had some great improvements such as a new roof and new windows installed. don't miss your opportunity to call this your own.

  Brad Cawood Turn Key Realty

  413 S 26th St, Middlesboro, KY 40965
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• 

  

  

  /15

  $145,000

  Sold Nov 25, 2025

  192 Owens Ln, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,600 Sq Ft
  • Built 1982

  Last Sold Summary

  • 12% Below List Price
  • $56/SF
  • 8 Days On Market

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  192 Owens Ln, Middlesboro, KY 40965
• 

  

  

  /49

  Est $207,597

  Not Listed For Sale

  412 Wilderness Rd, Middlesboro, KY 40965

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

  412 Wilderness Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Dustin Daniels Mountain Realty
• 

  

  

  /11

  $10,000

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,216 Sq Ft

  142 7th St, Middlesboro, KY 40965

  Neely Gray VMF Homes

  142 7th St, Middlesboro, KY 40965
• 

  

  /2

  $70,000

  Sold Jul 08, 2026

  923 Winchester Ave, Middlesboro, KY 40965

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Built 1940

  Last Sold Summary

  • 29% Below List Price
  • $88/SF
  • 159 Days On Market

  Current Estimated Value $77,231

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  923 Winchester Ave, Middlesboro, KY 40965
• 

  

  /21

  Est $432,738

  Not Listed For Sale

  2004 Twin Fawn Trail, Middlesboro, KY 40965

  • 5 Beds
  • 2.5 Baths
  • 2,742 Sq Ft
  • Built 2002

  2004 Twin Fawn Trail, Middlesboro, KY 40965

  Last Sold Summary

  • 205 Days On Market

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

  

  /37

  $267,500

  $83K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,195 Sq Ft

  717 S 27th St, Middlesboro, KY 40965

  This open floor plan home is waiting for your large family. This home features 5 bedrooms and 4 full baths, cathedral ceilings, a rock fireplace in the living room, and a full, unfinished basement just waiting for you to make more living space. Located in downtown with an out-of-town feel, get in to see this home now. *Buyer to verify acreage and septic.

  Barry Turner RE/MAX LakeTime Realty London

  717 S 27th St, Middlesboro, KY 40965
• 

  

  /57

  $279,000

  Sold Feb 27, 2026

  440 Sams Mountain, Middlesboro, KY 40965

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft
  • Built 2013

  Last Sold Summary

  • 14% Below List Price
  • $111/SF
  • 3 Days On Market

  Last Listing Agent Steve Mason REMAX PROFESSIONAL'S

  440 Sams Mountain, Middlesboro, KY 40965
• 

  

  /6

  Est $94,068

  Not Listed For Sale

  615 Evans Dr, Middlesboro, KY 40965

  • 3 Beds
  • Built 1975

  615 Evans Dr, Middlesboro, KY 40965

  Last Sold Summary

  • 156 Days On Market

  Last Listing Agent Chip Stephens South Fork Realty
• 

  

  /11

  $214,999

  $10K PRICE DROP Pending

  • 3 Beds
  • 1.5 Baths
  • 3,948 Sq Ft

  2621 Cumberland Ave, Middlesboro, KY 40965

  Opportunities are built on the right properties and this could be the one! The potential of this home is limitless. a home with instant equity to put your finishing touches on!

  Kelsey Kelley Keller Williams Legacy Group

  2621 Cumberland Ave, Middlesboro, KY 40965
• 

  /2

  $12,000

  Sold Jul 09, 2026

  2503 Exeter Ave, Middlesboro, KY 40965

  • Land
  • 13,068 Sq Ft
  • $40,000 per Acre

  Last Sold Summary

  • 52% Below List Price
  • 110 Days On Market

  Current Estimated Value $128,000

  Last Listing Agent Misti McGrath Realty Group

  2503 Exeter Ave, Middlesboro, KY 40965
• 

  

  /31

  Est $145,627

  Not Listed For Sale

  135 Highpoint Rd, Middlesboro, KY 40965

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

  135 Highpoint Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 161 Days On Market

  Last Listing Agent Janice Pratt AAA Realty, Inc.
• 

  

  /20

  $189,000

  Pending

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1208 Hwy 217 Hwy Unit 217, Middlesboro, KY 40965

  Here is your opportunity to own a home in a desirable community. Approximately 11 acres in the Hutch or Clear Fork area of Bell County. Property has lots of good fencing. The home on the property is in fair condition and may need to be upgraded or remodeled. This is a rare opportunity to have a home in the country that so many dream of. Call me today and come check out this Beautiful Property!!!!

  Danny Wilson Coldwell Banker Bisceglia Realty & Auction Co

  1208 Hwy 217 Hwy Unit 217, Middlesboro, KY 40965
• 

  

  /29

  $155,000

  Sold Jul 27, 2026

  1425 Highway 441, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,242 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Below List Price
  • $125/SF
  • 30 Days On Market

  Current Estimated Value $164,700

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  1425 Highway 441, Middlesboro, KY 40965
• 

  

  /15

  Est $199,732

  Not Listed For Sale

  810 S 28th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 2008

  810 S 28th St, Middlesboro, KY 40965

  Last Sold Summary

  • 19 Days On Market

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

  

  /7

  $189,000

  Pending

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1208 Kentucky 217, Middlesboro, KY 40965

  Here is your opportunity to own a home in a desirable community. Approximately 11 acres in the Hutch or Clear Fork area of Bell County. Property has lots of good fencing This is a rare opportunity to have a home in the country that so many dream. Come check out this Beautiful Property!!!!

  Danny Wilson Coldwell Banker Bisceglia Realty & Auction Co

  1208 Kentucky 217, Middlesboro, KY 40965
• 

  

  /10

  $245,000

  Sold Aug 07, 2026

  2802 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,304 Sq Ft
  • Built 1924

  Last Sold Summary

  • 6% Below List Price
  • $188/SF
  • 13 Days On Market

  Current Estimated Value $215,311

  Last Listing Agent Misti McGrath Realty Group

  2802 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /20

  Est $229,032

  Not Listed For Sale

  1013 Doncaster Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1996

  1013 Doncaster Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Misti McGrath Realty Group
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  /12

  $215,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  209 S 19th St, Middlesboro, KY 40965

  209 S. 19th Street, Middlesboro, KY 40965 Beautiful 2022 manufactured home offering approximately 1,352 sq. ft. of comfortable living space with 3 bedrooms and 2 bathrooms. The home is situated in a private setting while still conveniently located within town. Features include city utilities and a concrete block foundation. The PVA reflects approximately 0.50 acre; buyer to verify acreage and all

  Megan Stanaford Black Diamond Realty

  209 S 19th St, Middlesboro, KY 40965
• 

  

  /34

  $130,000

  Sold May 06, 2026

  123 Upper Gibson Ln, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft
  • Built 1945

  Last Sold Summary

  • 21% Below List Price
  • $119/SF
  • 20 Days On Market

  Current Estimated Value $132,099

  Last Listing Agent Megan Stanaford Black Diamond Realty

  123 Upper Gibson Ln, Middlesboro, KY 40965
• 

  

  /23

  Est $246,711

  Not Listed For Sale

  1009 W Rochester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,206 Sq Ft
  • Built 1992

  1009 W Rochester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Misti McGrath Realty Group
• 

  

  /46

  $105,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,456 Sq Ft

  1720 Exeter Ave, Middlesboro, KY 40965

  Welcome to 1720 Exeter Avenue, this adorable fixer has tons of potential with 2 living areas, a detached garage, brand new metal roof, and a fully fenced yard! Less than 5 minutes to schools and hospital, and only 15 minutes from LMU Harrogate main campus. Offered at a great price! Call or text today to schedule a showing!

  Victoria Allen Century 21 Virginia Wilder Real Estate

  1720 Exeter Ave, Middlesboro, KY 40965
• 

  

  /34

  $310,000

  Sold Mar 24, 2026

  409 Fairview Rd, Middlesboro, KY 40965

  • 4 Beds
  • 3.5 Baths
  • 2,684 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $115/SF
  • 29 Days On Market

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real

  409 Fairview Rd, Middlesboro, KY 40965
• 

  

  /6

  Est $245,079

  Not Listed For Sale

  205 Fairview Rd, Middlesboro, KY 40965

  • Studio
  • 1,616 Sq Ft
  • Built 1976

  205 Fairview Rd, Middlesboro, KY 40965

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Misti McGrath Realty Group
• 

  

  /15

  $59,000

  Pending

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  518 S 43rd St, Middlesboro, KY 40965

  Two bedroom, 1 bath home located in a great neighborhood. Large bedrooms, living room, and kitchen. Don't miss the opportunity to make this home your own.

  Michael Hensley REMAX PROFESSIONAL'S

  518 S 43rd St, Middlesboro, KY 40965
• 

  

  /31

  $183,500

  Sold Jul 17, 2026

  23 Castleford Way, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Built 1986

  Last Sold Summary

  • 12% Below List Price
  • $170/SF
  • 25 Days On Market

  Current Estimated Value $181,539

  Last Listing Agent Beth Combs Backwoods Realty & Development

  23 Castleford Way, Middlesboro, KY 40965
• 

  

  /11

  Est $133,036

  Not Listed For Sale

  302 W Rochester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1975

  302 W Rochester Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Sharon Teaney Century 21 Virginia Wilder Real Estate
• 

  

  /40

  $229,500

  $20K PRICE DROP

  • 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
• 

  

  /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 $281,908

  Last Listing Agent Brad Cawood Turn Key Realty

  115 George Ann Dr, Middlesboro, KY 40965
• 

  

  /22

  Est $123,248

  Not Listed For Sale

  407 S 22nd St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • Built 1940

  407 S 22nd St, Middlesboro, KY 40965

  Last Sold Summary

  • 47 Days On Market

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

  

  /44

  $299,000

  • 4 Beds
  • 2 Baths
  • 2,032 Sq Ft

  400 Gloucester Ave, Middlesboro, KY 40965

  Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  400 Gloucester Ave, Middlesboro, KY 40965
• 

  

  /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 $567,667

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

  423 N 10th St, Middlesboro, KY 40965
• 

  

  /19

  Est $152,614

  Not Listed For Sale

  201 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 2015

  201 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 246 Days On Market

  Last Listing Agent Dustin Daniels Mountain Realty
• 

  

  /13

  $275,000

  $75K PRICE DROP

  • Land
  • 1.69 Acres
  • $162,722 per Acre

  321 W Chester Ave, Middlesboro, KY 40965

  1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Pharmacy, Banks, Theater, Auto Repair, Hotel-Motel, Bed & Breakfast, and Multi Family Copy of Middlesboro Zoning attached. All city utilities available.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  321 W Chester Ave, Middlesboro, KY 40965
• 

  

  /16

  $147,979

  Sold Feb 26, 2026

  138 Robinson Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 648 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $228/SF
  • 19 Days On Market

  Last Listing Agent Beth Combs Turn Key Realty

  138 Robinson Ln, Middlesboro, KY 40965
• 

  

  /18

  Est $84,799

  Not Listed For Sale

  401 S 20th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 920 Sq Ft
  • Built 1996

  401 S 20th St, Middlesboro, KY 40965

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Real
• 

  

  /16

  $142,500

  $7K PRICE DROP

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

  125 Cawood Ln, Middlesboro, KY 40965

  Cute as a button! This adorable cottage style home would make an excellent choice for a first home! Come see today!

  Misti McGrath Realty Group

  125 Cawood Ln, Middlesboro, KY 40965
• 

  

  /28

  $150,000

  Sold Mar 25, 2026

  2523 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 2022

  Last Sold Summary

  • 7% Above List Price
  • $89/SF
  • 3 Days On Market

  Current Estimated Value $159,025

  Last Listing Agent Jody Moore Threshold Real Estate Services

  2523 Exeter Ave, Middlesboro, KY 40965
• 

  

  /16

  Est $98,952

  Not Listed For Sale

  306 Exeter Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1920

  306 Exeter Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Dawn Risner Turn Key Realty
• 

  

  /41

  $120,000

  $15K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,844 Sq Ft

  215 S 21st St, Middlesboro, KY 40965

  Investment Opportunity - Fire-Damaged Home at 215 S. 21st Street, Middlesboro, KY Investor Special! This property at 215 S. 21st Street, Middlesboro, KY has sustained significant fire damage and is being offered as-is. This is an excellent opportunity for experienced investors, contractors, or buyers looking for a major renovation or potential rebuild project. Situated in an established

  Megan Stanaford Black Diamond Realty

  215 S 21st St, Middlesboro, KY 40965

Showing Results 41 - 80, Page 2 of 18