Middlesboro, KY Homes for Sale under $300,000

• 

  

  

  /18

  $70,000

  $55K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,426 Sq Ft

  123 Cawood Ln, Middlesboro, KY 40965

  Major Price Reduction!!Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back

  

  Dustin Daniels

  Mountain Realty

  123 Cawood Ln, Middlesboro, KY 40965
• 

  

  

  /14

  $35,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 728 Sq Ft

  105 Nutwood Rd, Middlesboro, KY 40965

  3 bed, 1 bath fixer-upper in Middlesboro, KY! Great investment opportunity—flip, rent, or make it your own. City water/sewer (per public record). Priced for potential—bring your ideas!

  Megan Stanaford Black Diamond Realty

  105 Nutwood Rd, Middlesboro, KY 40965
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  /28

  $39,900

  $20K PRICE DROP

  • Land
  • 4.24 Acres
  • $9,410 per Acre

  1197 Beans Fork Rd, Middlesboro, KY 40965

  Opportunity awaits on this 4.24-acre tract offering a peaceful setting with endless potential. The property was previously improved with a home that has recently been lost to fire, presenting a unique chance to start fresh and bring your vision to life. With utilities previously in place (buyer to verify), this parcel may offer a head start for rebuilding, whether you're considering a custom

  SARAH RICHARDS RE/MAX Preferred Group

  1197 Beans Fork Rd, Middlesboro, KY 40965
• 

  

  

  /16

  $60,000

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  712 Balmoral Rd, Middlesboro, KY 40965

  Investment opportunity with this 3 bedroom 1 bathroom home. Owner is relocating for work and must sell. The home is in progress of being renovated. Call for more info.

  Megan Stanaford Black Diamond Realty

  712 Balmoral Rd, Middlesboro, KY 40965
• 

  

  

  /5

  $30,000

  • Land
  • 1.26 Acres
  • $23,810 per Acre

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965

  LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965
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  /2

  $50,000

  • Land
  • 16,639 Sq Ft
  • $130,890 per Acre

  0000 Edgewood Rd, Middlesboro, KY 40965

  Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

  Megan Stanaford Black Diamond Realty

  0000 Edgewood Rd, Middlesboro, KY 40965
• 

  

  /18

  $110,000

  $25K PRICE DROP Pre-Foreclosure

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

  901 Exeter Ave, Middlesboro, KY 40965

  Hey Neighbors! If you've been looking for a solid property with room to build some serious sweat equity, you'll want to take a look at this one. Sitting on a spacious corner lot inside the Middlesboro city limits, this 1.5-story brick veneer home offers a massive 1,963 square feet of living space and sits on over half an acre 0.539 acres per (Bell County PVA). With a potential of 4 bedrooms, 2

  Russell Tribell Fathom Realty KY LLC

  901 Exeter Ave, Middlesboro, KY 40965
• 

  

  /17

  $129,900

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  405 S 37th St, Middlesboro, KY 40965

  Looking for a home to raise your family? Don't let this one go by! Spacious 4 bedrooms, 2 bath home with a fenced in yard, this one is just the right size for a growing family. Just minutes from the hospital and schools, yet tucked away on a side street with little traffic. Let us show you your new home today! Schedule a showing before it's gone.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  405 S 37th St, Middlesboro, KY 40965
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  /26

  $199,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,612 Sq Ft

  140 Wellington Dr, Middlesboro, KY 40965

  Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

  Janice Pratt Fathom Realty TN LLC

  140 Wellington Dr, Middlesboro, KY 40965
• 

  

  /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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  /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
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  /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
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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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /3

  $17,000

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  110 Danbury Ave, Middlesboro, KY 40965

  If you've been looking for a project here it is! Handyman special, would make a super cute flip! Or at this price you can buy it for just the land!Please do not go without an agent.Buyer/Buyers agent to confirm all information

  Misti McGrath Realty Group

  110 Danbury Ave, Middlesboro, KY 40965
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  /5

  $29,000

  • Land
  • 39,204 Sq Ft
  • $32,222 per Acre

  0 Bowling Rd Unit 1344123, Middlesboro, KY 40965

  0.9 Acres Partially cleared with wooded area in back for privacy. City limits. All utilities available. Perfect location for a home or two right next to the mountains!

  Misti McGrath Realty Group

  0 Bowling Rd Unit 1344123, Middlesboro, KY 40965
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  /51

  $250,000

  • 1,500 Sq Ft

  119 Wagon Hollow Rd, Middlesboro, KY 40965

  Welcome to the best of all worlds! One home and an operational store that fronts Highway 217. Several outbuildings and just over 20 acres make this the perfect property for homesteading as seller had livestock on the property at one time. The land is gently rolling to level, Pineville city water in place, spectrum internet and you're off the beaten path but just a 15 minute drive back into town.

  Megan Stanaford Black Diamond Realty

  119 Wagon Hollow Rd, Middlesboro, KY 40965
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  /3

  $28,000

  • Land
  • 7,405 Sq Ft
  • $164,706 per Acre

  14 Honeycutt Ln, Middlesboro, KY 40965

  COUNTY LOT, NO RESTRICTIONS!!!Flat and cleared lot in the county doesn't get much better than this!Previously home to a singlewide trailer means this location has all utilities including City water and septic.

  Misti McGrath Realty Group

  14 Honeycutt Ln, Middlesboro, KY 40965
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  /27

  $270,000

  • 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 1476 sf 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 suite

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  113 Hollywood Dr, Middlesboro, KY 40965
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  /17

  $230,000

  $15K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  156 Wellington Dr, Middlesboro, KY 40965

  Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is

  Megan Stanaford Black Diamond Realty

  156 Wellington Dr, Middlesboro, KY 40965
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  /5

  $22,500

  $8K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $62,500 per Acre

  526 Balmoral Rd, Middlesboro, KY 40965

  Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

  Megan Stanaford Black Diamond Realty

  526 Balmoral Rd, Middlesboro, KY 40965
• 

  

  /22

  $97,000

  $22K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  252 Chasteen Dr, Middlesboro, KY 40965

  Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily

  Aaron Rose Realty Network, Inc

  252 Chasteen Dr, Middlesboro, KY 40965
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  /16

  $295,000

  $15K PRICE DROP

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

  717 Highway 441, Middlesboro, KY 40965

  Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed

  Megan Stanaford Black Diamond Realty

  717 Highway 441, Middlesboro, KY 40965
• 

  

  /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
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  /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
• 

  

  /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
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  /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
• 

  

  /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
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  /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
• 

  

  /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
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  /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
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  /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
• 

  

  /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
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  /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
• 

  

  /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

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