Middlesboro, KY Homes for Sale under $300,000

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  /18

  $93,500

  $32K PRICE DROP

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

  123 Cawood Ln, Middlesboro, KY 40965

  Large 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
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  /14

  $50,000

  • 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

  $59,900

  • Land
  • 4.24 Acres
  • $14,127 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
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  /4

  $159,000

  $5K PRICE DROP

  • 700 Sq Ft

  1801 Exeter Ave, Middlesboro, KY 40965

  2 HOMES with one FULLY remodeled home in back 2 bedroom 1 bath Cute as a button! Home on corner lot needs work but would be a very smart investment. With access to ATV friendly roads, close to stores and hospital.1801 Exeter and 1801 1/2 Exeter

  Misti McGrath Realty Group

  1801 Exeter Ave, Middlesboro, KY 40965
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  /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
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  /18

  $135,000

  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
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  /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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  /9

  $260,000

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

  2802 W Cumberland Ave, Middlesboro, KY 40965

  Exceptional and holy smokes what style! 3-bedroom 1.5 bath home on a Cumberland Avenue corner lot. The rebirth of this home and the current owners have turned this home into an absolute DREAM!Very light yard maintenance so you can spend all your time on the front porch watching the world go by or in front of the gorgeous fireplace, let's go see!

  Misti McGrath Realty Group

  2802 W Cumberland Ave, Middlesboro, KY 40965
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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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  /37

  $297,500

  $53K 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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  /46

  $125,000

  • 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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  /15

  $59,000

  • 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
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  /40

  $232,500

  $17K 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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  /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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  /15

  $149,500

  • 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

  $134,000

  $1K 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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  /36

  $285,000

  00 Highway 217 & 1344, Middlesboro, KY 40965

  UNIQUE OPPORTUNITY PROPERTY. This property offers plenty of potential. Formerly Shillelagh garage and swimming hole, this property has above the ground fuel tanks that could provide ATV's, Side-by-side, farm equipment fuel for work or entertainment. There are Off-road trails for ATV enthusiasts to enjoy the endless trails. These 9.613 surveyed acres can be used for residential, commercial

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  00 Highway 217 & 1344, Middlesboro, KY 40965
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  /27

  $89,900

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  816 W Chester Ave, Middlesboro, KY 40965

  Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

  James Martin Century 21 Pinnacle

  816 W Chester 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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  /14

  $150,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  422 Wilderness Rd, Middlesboro, KY 40965

  Super cute starter home with 2 beds and 1 full bath. Recently remodeled with excellent updates.The backyard is an oasis with additional building with electricity. Starter home, income producing property, downsizing or whatever fits your needs, this home has it!

  Misti McGrath Realty Group

  422 Wilderness Rd, 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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  /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
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  /22

  $99,999

  $19K 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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  /12

  $85,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  310 Barkley Dr, Middlesboro, KY 40965

  2 bed, 1 bath, manufactured home sitting on a large level lot. Conveniently located to shopping and Harrogate, TN.

  Michael Hensley REMAX PROFESSIONAL'S

  310 Barkley 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
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  /4

  $19,000

  $6K PRICE DROP

  • Land
  • 1.02 Acres
  • $18,627 per Acre

  1577 Beans Fork Rd, Middlesboro, KY 40965

  OVER 1 ACRE AND NO RESTRICTIONS!!! Live peaceful, level and free on your own land.Bring your own home or build your own home, in the quiet top of Beans Fork.Utilities available All reasonable offers entertained Home on land holds zero value, please do not enter without agent

  Misti McGrath Realty Group

  1577 Beans Fork Rd, Middlesboro, KY 40965
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  /3

  $125,000

  $50K PRICE DROP

  • 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
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  /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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  /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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  /20

  $215,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,652 Sq Ft

  116 N Petersborough Ave, Middlesboro, KY 40965

  Exceptional 3 bedrooms, 1 bath home in the heart of Middlesboro. Located just off Cumberland Ave on 30th St, this home's location is what you have been looking for--within walking distance of downtown, schools, and the hospital. Just down the street from the T-ball field and the city pool. With hardwood floors throughout and beautiful wood trim, this house is waiting for a family to make it a

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  116 N Petersborough Ave, Middlesboro, KY 40965
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  /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
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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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  /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
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  /9

  $154,900

  $5K 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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  /34

  $175,000

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  64 Dunlap Hollow Rd, Middlesboro, KY 40965

  This home is turnkey and ready to move right in; it has been well maintained over the years. This home has 4 Bedrooms, 2 Full Baths, Dining Room and a Kitchen that comes with Range, Refrigerator, Dishwasher and Microwave plus the laundry room has a washer and dryer set that will stay with home. Step out the back door and just a few steps up the hill is a wonderful workshop and a storage shed.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  64 Dunlap Hollow Rd, Middlesboro, KY 40965
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  /3

  $35,000

  • Land
  • 14,853 Sq Ft
  • $102,639 per Acre

  2107 Winchester Ave, Middlesboro, KY 40965

  PRIME LOCATION, NO FLOOD ZONE! Discover the ultimate blank canvas within the city limits. This fully cleared, level, and build ready lot offers an exceptional opportunity to build your dream home, or next investment project. Situated entirely outside the FEMA flood zone, this lot offers peace of mind and reduced insurance costs. All city utilities are ready for connection. This lot would always

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  2107 Winchester Ave, Middlesboro, KY 40965

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