Homes for Sale in 40965

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  /18

  $125,000

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

  123 Cawood Ln, Middlesboro, KY 40965

  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 mudroom/workshop provides

  

  Dustin Daniels

  Mountain Realty

  (606) 717-1149

  123 Cawood Ln, Middlesboro, KY 40965
• 

  

  

  /46

  $325,000

  • 4 Beds
  • 2.5 Baths
  • 2,488 Sq Ft

  1015 Old Wilson Ln, Middlesboro, KY 40965

  Super nice four bedroom, two and 1/2 bath, 2488 sq ft with hardwood floors on a level lot in Middlesboro. Welcome to a home designed for the way you live. This stunning split level residence offers the perfect architectural solution for those seeking distinct spaces without sacrificing an open feel. This home offers privacy and distinct zones for living, working and relaxing.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  1015 Old Wilson Ln, Middlesboro, KY 40965
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  /31

  $185,000

  $23K PRICE DROP

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

  23 Castleford Way, Middlesboro, KY 40965

  Back on the market at no fault of the seller! Located in the desirable Ambleside subdivision, this beautifully maintained and tastefully decorated two-story home features soft, calming paint colors, gorgeous luxury vinyl flooring, and a warm, welcoming feel throughout. This charming home offers 3 spacious bedrooms and 1.5 bathrooms. The main level includes a comfortable living room, formal dining

  Beth Combs Turn Key Realty

  23 Castleford Way, Middlesboro, KY 40965
• 

  

  

  /11

  $225,000

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

  2621 W 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 W Cumberland Ave, Middlesboro, KY 40965
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  /40

  $239,000

  $10K 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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  /21

  $219,900

  $30K 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
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  /29

  $259,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  206 Summit Dr, Middlesboro, KY 40965

  Beautiful move-in ready renovated Property. Home features four bedrooms 2 1/2 baths. kitchen features soft closed custom cabinets, kitchen island and stainless steel appliances. Laminated floors throughout the home. Enjoy your coffee on screened in back porch. Storage building for your tools, lawnmower etc..Property is located within minutes from Lmu main campus, Shopping, restaurants, and

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  206 Summit Dr, 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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  /67

  $180,000

  $5K 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
• 

  

  /20

  $399,000

  • 3 Beds
  • 3 Baths
  • 3,397 Sq Ft

  103 Kingsbury Woods Rd, Middlesboro, KY 40965

  Rare opportunity to own a premier golf course property on Hole #2 at the Middlesboro Golf Course—one of only four homes situated directly on the course. Perfectly positioned on a generous 0.67-acre lot, this spacious residence offers a grand total living space, including a finished basement, providing plenty of room to live, entertain, and relax. With three bedrooms and three full baths, the home

  Anthony Gigilo ListWithFreedom.com

  103 Kingsbury Woods Rd, Middlesboro, KY 40965
• 

  

  /30

  $125,000

  • 4 Beds
  • 2 Baths
  • 2,592 Sq Ft

  316 Exeter Ave, Middlesboro, KY 40965

  Looking for an older home to bring back to life. This home has all the old wood trim. big rooms with fireplaces in most of the rooms, this home comes with an extra building lot and a garage/ carport also. Call Now!!

  Steve Mason REMAX PROFESSIONAL'S

  316 Exeter Ave, Middlesboro, KY 40965
• 

  

  /3

  $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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  /5

  $855,000

  • 2 Beds
  • 2 Baths
  • 15,119 Sq Ft

  725 19th St, Middlesboro, KY 40965

  Prime Multifamily Investment Opportunity Presenting a well-established commercial apartment building in the heart of Middlesboro, Kentucky. Built in 1990, this single-story property offers approximately 15,225 square feet of space ideally suited for residential rental units, providing stable cash flow in a convenient location. Strategically positioned on N 19th Street, the building benefits from

  Beth Combs Turn Key Realty

  725 19th St, Middlesboro, KY 40965
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  /4

  $164,000

  • 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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  /2

  $85,000

  $14K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  923 Winchester Ave, Middlesboro, KY 40965

  This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  923 Winchester Ave, Middlesboro, KY 40965
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  /17

  $139,900

  $20K 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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  /2

  $20,000

  $5K PRICE DROP

  • Land
  • 13,068 Sq Ft
  • $66,667 per Acre

  2503 Exeter Ave, Middlesboro, KY 40965

  Level, city, corner Lot available for building or doublewide placement!Buyer/agent to verify all information

  Misti McGrath Realty Group

  2503 Exeter Ave, Middlesboro, KY 40965
• 

  

  /11

  $49,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  6, Middlesboro, KY 40965

  Don't miss out on your chance to own this slightly used 2025 3 bedroom 2 bath home in the heart of Middlesboro. Located in a family friendly community that values affordability with space rent at $175. Available for showings now!

  Neely Gray VMF Homes

  6, Middlesboro, KY 40965
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  /24

  $159,000

  $41K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  63 Old Pineville Pike, Middlesboro, KY 40965

  Remodeled and gorgeous! This home has completely remodeled throughout with gorgeous kitchen and new bathrooms! This home was stripped down to the studs! Laminate floors are waterproof. The master bathroom has a double bowl sink, nice walk-in shower. There are 3 bedrooms and 2 full bathroom, large living room, kitchen with new farmhouse sink. The kitchen extends to dining room, range, refrigerator

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  63 Old Pineville Pike, 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
• 

  

  /3

  $135,000

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

  215 S 21st St, Middlesboro, KY 40965

  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

  $104,900

  $15K 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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  /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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  /19

  $44,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  406 W Rochester Ave, Middlesboro, KY 40965

  Cottage style, 3 bedroom 2 bathroom home with chain link fencing in the city limits of Middlesboro KY. PVA records show 0.18 of an acre, city water, city sewer. Home needs some work but would make a great permanent home or use as a rental. Close to LMU and all the beauty Southeastern KY offers! 5 minutes to the Cumberland Gap National Park, shopping and more! Buyer to verify all property

  Megan Stanaford Black Diamond Realty

  406 W Rochester Ave, Middlesboro, KY 40965
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  /2

  $15,000

  • Land
  • 1 Acre
  • $15,000 per Acre

  208 Deer Dr, Miracle, KY 40856

  Escape to the serenity of Brush Mountain Farms Phase 2 in Miracle, KY, and claim your own slice of paradise on this stunning 1 +/- acre lot, known as Lot 46. Nestled amidst breathtaking natural beauty, this expansive parcel of land presents an idyllic setting for building your dream home or vacation retreat.

  Will Childers WTC Realty LLC

  208 Deer Dr, Miracle, KY 40856
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  /17

  $245,000

  • 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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  /12

  $225,000

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

  908 W Chester Ave, Middlesboro, KY 40965

  This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment behind the house great for the mother-in-law. The apartment is open space with 1 bdrm and a full bath. Metal roof, vinyl siding and windows, hardwood, laminate & tile floors. Privacy and a chain link fenced in back yard, 2 storage buildings, level back yard. Great student home and rental!!

  Steve Mason REMAX PROFESSIONAL'S

  908 W Chester Ave, 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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  /33

  $499,000

  $26K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,542 Sq Ft

  2004 Twin Fawn Trail, Middlesboro, KY 40965

  This gorgeous cape cod home sits on 4.4 acres with deer visiting often. This home has 5 bedrooms, 2.5 bathrooms, formal living room with fireplace, family room (could be used as formal dining room) a second fireplace in the sunroom, amazing kitchen with island, the kitchen counter tops are granite, the stainless-steel appliances stay, which include double wall ovens, gas range with gas oven

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  2004 Twin Fawn Trail, Middlesboro, KY 40965
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  /16

  $19,900

  $10K PRICE DROP

  • Land
  • 2.32 Acres
  • $8,578 per Acre

  LOT 9 Brush Mountain Cir, Miracle, KY 40856

  Discover tranquility at Brush Mountain Farms in Bell County, KY—a 2.32-acre wooded retreat in a gated community. Enjoy peace, privacy, and wildlife, with hiking trails and a developing wildlife preserve (Boone's Ridge) visible from the property. Located just 15 minutes from Boones Ridge Wildlife Park and 20 minutes from Pineville and Middlesboro, offering easy access to town amenities. Ideal for

  Tabitha House CENTURY 21 Advantage Realty

  LOT 9 Brush Mountain Cir, Miracle, KY 40856
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /52

  $2,500,000

  • 3 Beds
  • 1.5 Baths
  • 1,976 Sq Ft

  259 Watson Ln, Middlesboro, KY 40965

  Offering for the first time on the market, this beautiful 92 acre property with 82 acres within city limits and 10 acres in the county. There is a beautiful hayfield and from that hayfield downtown Middlesboro can be seen as well as a view of the Pinnacle. This property comes with 2 homes. The main house has 3 bedrooms, 1 full bathroom and a half bathroom, foyer with staircase leading upstairs,

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  259 Watson Ln, Middlesboro, KY 40965
• 

  

  /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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