Middlesboro, KY Homes for Sale under $300,000

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  /40

  $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
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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

  Kevin Carroll Backwoods Realty & Development

  515 Englewood Rd, Middlesboro, KY 40965
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  /30

  $229,000

  $11K 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
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  /28

  $155,000

  $34K 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
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  /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 Backwoods Realty & Development

  815 Dorchester Ave, Middlesboro, KY 40965
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  /13

  $55,000

  $20K 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
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  /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
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  /31

  $158,000

  $24K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  180 Stevenson Bridge Rd, Middlesboro, KY 40965

  Escape to the peace and beauty of country living at 180 Stevenson Branch Rd, Middlesboro, KY. Nestled on approximately 2 acres just minutes from historic downtown Middlesboro, this charming rustic cabin offers the perfect combination of privacy, character, and convenience. Enjoy quick access to shopping, restaurants, medical facilities, banks, and everyday amenities while coming home to a

  Kevin Carroll Backwoods Realty & Development

  180 Stevenson Bridge Rd, Middlesboro, KY 40965
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  /35

  $179,900

  $7K PRICE DROP

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

  1200 W Chester Ave, Middlesboro, KY 40965

  Charming Home for Sale in Middlesboro, KY - 1200 W Chester Ave Welcome to this inviting home located in the heart of Middlesboro! Situated on a spacious corner lot at 1200 W Chester Avenue, this property offers comfort, convenience, and small-town charm—all in one. Comfortable living spaces with plenty of natural light. Functional kitchen with ample cabinet storage Generous yard—perfect for

  Megan Stanaford Black Diamond Realty

  1200 W Chester Ave, Middlesboro, KY 40965
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  /20

  $169,900

  • 2 Beds
  • 1 Bath
  • 853 Sq Ft

  371 Eagle Ln, Middlesboro, KY 40965

  Looking for a nice home that is USDA, FHA, or VA approved? We have just what you have been looking for--hurry before it's gone! Move-in ready home only 15 years old iwth 2 bedrooms 1 bath, utility room large living room and kitchen with stove, refrigerator, dishwasher, washer and dry, which all go with the sale. Don't miss this opportunity to own a house perfect for raising your family.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  371 Eagle Ln, Middlesboro, KY 40965
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  /29

  $279,000

  $20K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,068 Sq Ft

  207 Arthur Heights, Middlesboro, KY 40965

  CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  207 Arthur Heights, Middlesboro, KY 40965
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  /72

  $165,000

  $20K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 2,430 Sq Ft

  713 Exeter Ave, Middlesboro, KY 40965

  Welcome to the stunning 713 Exeter Ave located in the lovely town of Middlesboro KY, less than 5 minutes to downtown Middlesboro, 15 minutes from LMU, & super close to Norris Lake. This home makes a perfect residence for anyone looking in the area and would make a great rental property as well! This home offers ample space with 4 bedrooms on the main level and tons of potential for a loft or 2

  Victoria Allen Century 21 Virginia Wilder Real Estate

  713 Exeter Ave, Middlesboro, KY 40965
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  /4

  $24,000

  $1K PRICE DROP

  • Land
  • 7,492 Sq Ft
  • $139,535 per Acre

  109 Bloomsbury Ave, Middlesboro, KY 40965

  50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

  Megan Stanaford Black Diamond Realty

  109 Bloomsbury Ave, Middlesboro, KY 40965
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  /2

  $182,000

  • 2 Beds
  • 2 Baths
  • 1,608 Sq Ft

  414 S 24th St, Middlesboro, KY 40965

  Prime commercial opportunity at 414 S 24th Street in Middlesboro, KY! This versatile property offers excellent visibility and accessibility in a well-established area, just minutes from historic downtown Middlesboro and major routes. Ideal for office space, retail, professional services, or an investment property with strong potential in Bell County. Spacious layout, solid construction, and

  Beth Combs Backwoods Realty & Development

  414 S 24th St, Middlesboro, KY 40965
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  /30

  $269,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  127 Alpine Rd, Middlesboro, KY 40965

  This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  127 Alpine Rd, Middlesboro, KY 40965
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  /32

  $270,000

  $29K PRICE DROP

  • 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 main

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  113 Hollywood Dr, Middlesboro, KY 40965

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