Middlesboro, KY Homes for Sale

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  /16

  $145,000

  • 3 Beds
  • 2 Baths
  • 648 Sq Ft

  138 Robinson Ln, Middlesboro, KY 40965

  Check out this charming 3-bedroom, 2-bath home featuring a spacious covered porch, updated master bathroom, fenced backyard, and beautiful tile and hardwood flooring throughout. Conveniently located just minutes from historic downtown Middlesboro, KY.

  Beth Combs Turn Key Realty

  138 Robinson Ln, Middlesboro, KY 40965
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  /20

  $120,000

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977

  Looking for 11 acres of clean-cut acreage, Peacefull, quite ready to build your dream home. Public water and electric on the property. Hard to find land like this. Seller has already cut a nice wide road to the top.

  Steve Mason REMAX PROFESSIONAL'S

  TBD Rt 516 Old Cross Rd, Pineville, KY 40977
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  /17

  $49,900

  • 3 Beds
  • 1 Bath
  • 1,139 Sq Ft

  103 Nutwood Rd, Middlesboro, KY 40965

  Attention investors and DIY enthusiasts! Multiple exit strategies: finish this remodel then either flip, rent or move in! Home being sold as is. Cash preferred but will consider financed all offers. Seller is assisted by an Attorney in Fact. Do not knock on door or approach house without prior communication.

  Dustin Hepburn

  103 Nutwood Rd, Middlesboro, KY 40965
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  /36

  $172,000

  • 3 Beds
  • 2 Baths
  • 934 Sq Ft

  45 Fourmile Run Rd, Middlesboro, KY 40965

  Newly Remodeled, move-in ready home. This home is nestled in the heart of Middlesboro on a .489 acre lot. This home has 3 bedrooms and 2 newly renovated bathrooms. The washer and dryer will stay with home. This quiet cozy home has a log cabin look with a large covered front porch. I also has a carport or breezeway to get to the garage. This home also has a fenced in chicken coop. All the

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  45 Fourmile Run Rd, Middlesboro, KY 40965
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  /18

  $164,900

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  114 W Rochester Ave, Middlesboro, KY 40965

  Charming Fully Remodeled Brick Ranch - Move-In Ready! Welcome home to this beautifully updated 3-bedroom, 2-bath brick ranch situated on a large lot just minutes from downtown Middlesboro. Step inside to discover a completely remodeled interior featuring brand-new laminate flooring throughout, a stunning new kitchen with modern cabinetry and appliances, and two fully updated bathrooms. This home

  Michael Hensley REMAX PROFESSIONAL'S

  114 W Rochester Ave, Middlesboro, KY 40965
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  /50

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  4921 W Cumberland Ave, Middlesboro, KY 40965

  Charming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beautifully maintained 3-bedroom, 2-bathroom home located close to shopping, restaurants, schools, and parks — everything you need is just minutes away! Inside, you'll find a warm and inviting layout featuring hardwood and vinyl flooring, offering both style and durability. The spacious living areas are perfect

  Dustin Daniels Mountain Realty

  4921 W Cumberland Ave, Middlesboro, KY 40965
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  /16

  $180,000

  • 3 Beds
  • 1 Bath
  • 792 Sq Ft

  918 E Cumberland Ave, Middlesboro, KY 40965

  This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and one bath with a large kitchen and large living room. This home needs some attention but has a lot of potential. The downstairs could be used as apartment or extra living space. There is another home on the property and might be possible to repair.

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  918 E Cumberland Ave, Middlesboro, KY 40965
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  /5

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  280 Parker Ln, Middlesboro, KY 40965

  Beautiful and practically brand new! This 3 bedroom 2 bath home is perfect for a sweet family! From the ground up, this home is only 3 years old. All appliances included, very well taken care of. You HAVE to see this one!!

  Misti McGrath Realty Group

  280 Parker Ln, Middlesboro, KY 40965
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  /30

  $205,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  140 Chasteen Dr, Middlesboro, KY 40965

  If you have been looking for a home to call your own, don't miss out on this lovely home with a white picket fence. A spacious 1,800 sf home with 3 bedrooms and 2 bathrooms on a large lot with a fenced-in back yard. You will love the kitchen with granite countertops and the laminate and tile flooring throughout. Don't let this one get away. We'll be happy to show you how this home can be your

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  140 Chasteen Dr, Middlesboro, KY 40965
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  /11

  $112,000 Pre-Foreclosure

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  903 Ilchester Ave, Middlesboro, KY 40965

  Great potential for a starter home or investment. Does need some work. Close to LMU, Cumberland National Park, Middlesboro Country Club, and local restaurants.

  Blake Ramey Century 21 Virginia Wilder Real Estate

  903 Ilchester Ave, Middlesboro, KY 40965
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  /37

  $249,000

  • 4 Beds
  • 3 Baths
  • 1,966 Sq Ft

  6 Hampton Ct, Middlesboro, KY 40965

  Beautiful split foyer home in Ambleside. The view from the front window is amazing. This well-maintained home has a primary bedroom and bath on both the floors. The kitchen is spacious with all custom built cabinets, a built-in pantry, and a breakfast bar. There are 3 bedrooms on the main floor with 2 baths. The large living room overlooks the community and a beautiful view of the mountains.

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  6 Hampton Ct, Middlesboro, KY 40965
• 

  

  /22

  $115,000

  • 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

  Aaron Rose Realty Network, Inc

  252 Chasteen Dr, Middlesboro, KY 40965
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  /35

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  807 Exeter Ave, Middlesboro, KY 40965

  New custom built home in the heart of Middlesboro. This home features three (3) bedrooms and two (2) bathrooms. Walking up to the home you are immediately greeted with a covered front porch constructed using composite decking and adorned with large columns. As you enter this home you are met with a spacious living room/kitchen/dinning room designed in an open concept style. Kitchen is

  Janice Pratt AAA Realty, Inc.

  807 Exeter Ave, Middlesboro, KY 40965
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  /53

  $245,000

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  129 Lower Gibson Ln, Middlesboro, KY 40965

  🏡 The Chateau on the Creek - Home for Sale in Middlesboro, KY (Bell County)Welcome to The Chateau on the Creek, a beautifully updated 3-bedroom, 2.5-bathroom home in Middlesboro, KY (Bell County). Offering 1,856 sq. ft. of living space, a detached garage, and a backyard oasis, this move-in ready property combines timeless charm with modern updates.The exterior has been

  Michael Hensley REMAX PROFESSIONAL'S

  129 Lower Gibson Ln, Middlesboro, KY 40965
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  /48

  $349,900

  • 5 Beds
  • 3 Baths
  • 2,250 Sq Ft

  805 Worchester Ave, Middlesboro, KY 40965

  This home has been brought back beyond its Glory!! Completely remodeled from the sub flooring to the roof. This 5 bds, 3 full baths,new kitchen w/Quartz counter tops, marble back splash, stainless appliances, new LVP flooring, Breath taking bathrooms, master on the main, 3 bdrms upstairs with a full bath 2 HVAC units. 2 car garage w new garage doors. IT'S A MUST SEE!!

  Steve Mason REMAX PROFESSIONAL'S

  805 Worchester Ave, Middlesboro, KY 40965
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  /2

  $17,500

  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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  /3

  $110,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  413 S 26th St, Middlesboro, KY 40965

  Cute little 2-bedroom 1 bath house with great size backyard for family gathering. This house is in a great location convenient to schools, shopping, and walking the town.

  Lisa Stacy-Gibbs Turn Key Realty

  413 S 26th St, Middlesboro, KY 40965
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  /5

  $75,000

  • 2 Beds
  • 1 Bath
  • 1,456 Sq Ft

  1720 Exeter Ave, Middlesboro, KY 40965

  Super cute house with a great lay out! Fenced in corner lot, excellent outdoor space with oversized garage, a little tlc and this home will shine!

  Misti McGrath Realty Group

  1720 Exeter Ave, Middlesboro, KY 40965
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  /38

  $369,900

  • 4 Beds
  • 2.5 Baths
  • 3,885 Sq Ft

  2702 Cumberland Ave, Middlesboro, KY 40965

  Don't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner lot. This 3,800 sq ft turn of the century home, that has been completely updated, boasts 4 bedrooms, 2 full baths and 1 half bath. On the primary level you'll find a covered front porch, sun room, large living room, and oversized dedicated dining area. Off of the dining room, you'll find a massive kitchen

  Darrell Lewis DIY Flat Fee.com

  2702 Cumberland Ave, Middlesboro, KY 40965
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  /20

  $269,500

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  220 Windermere Dr, Middlesboro, KY 40965

  BEAUTIFUL MOVE IN READY HOME IN AMBLESIDE. Discover your next home in Ambleside, a tranquil subdivision in the heart of Middlesboro outside the city limits. With the beautiful landscaped yard that offers a warm, inviting atmosphere. Enjoy the peaceful suburban setting with the convenience of nearby amenities including shopping, dining, parks and entertainment. This home has 3 bedrooms with the

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  220 Windermere Dr, Middlesboro, KY 40965
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  /30

  $169,000

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  3008 State Highway 441, Middlesboro, KY 40965

  This Newly Remodeled home is located just minutes away from downtown Middlesboro and the Historic Cumberland Gap National Park, It features new floors, kitchen, bathrooms and a newly designed up stairs. Don't miss your chance to own this beautiful home. Seller will install privacy fence with acceptable offer.

  

  Brad Cawood

  Turn Key Realty

  (606) 288-6047

  3008 State Highway 441, 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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  /2

  $7,500

  • Land
  • 0.2 Acre
  • $37,500 per Acre

  0 Wells Camp Rd, Middlesboro, KY 40965

  Lot off of Wells Camp road just outside of Middlesboro KY. Electric available, no other utilities have been installed to sellers knowledge. Buyer to do their own due diligence and verification pertaining to the property.

  Megan Stanaford Black Diamond Realty

  0 Wells Camp Rd, Middlesboro, KY 40965
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  /52

  $569,999

  • 5 Beds
  • 4 Baths
  • 4,331 Sq Ft

  850 Big Buck Ln, Middlesboro, KY 40965

  First Time on The Market this gorgeous contemporary home was custom built in 2022 with approximately 4,331 SF including the 2 car attached garage. This home has 3 'En Suites' plus 2 more bedrooms for a total of 5 bedrooms and 4 full bathrooms. The unique ceilings were designed just for this home! You will find the large living room to be relaxing with a built-in electric fireplace. The custom

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  850 Big Buck Ln, Middlesboro, KY 40965
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  /4

  $49,900

  • Land
  • 0.34 Acre
  • $146,765 per Acre

  1107 Winchester Ave, Middlesboro, KY 40965

  Large building lot in Middlesboro. Zoned R-2 Residential, the lot has plenty of room to build a home. It's rare to find a lot in Middlesboro that is level and ready for building.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  1107 Winchester Ave, Middlesboro, KY 40965
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  /28

  $229,900

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  1203 Winchester Ave, Middlesboro, KY 40965

  Beautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal living room with hardwood floors and a gas fireplace. The dining area is right off the galley kitchen, which has a door leading onto the carpeted porch-perfect for entertaining or cooking outside. There is easy access from the carport right into the large open den/family room. Also on the main level there is

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  1203 Winchester Ave, Middlesboro, KY 40965
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  /12

  $100,000

  • 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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  /19

  $85,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  101 Earle Ln, Middlesboro, KY 40965

  Three bedroom, 2 bath home located on a large level yard in a great location in Middlesboro, Ky. Convenient to shopping, Hosptial, and Lincoln Memorial University.

  Michael Hensley REMAX PROFESSIONAL'S

  101 Earle Ln, Middlesboro, KY 40965
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  /24

  $185,000

  • 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,

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  63 Old Pineville Pike, Middlesboro, KY 40965
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  /15

  $299,000

  • 3 Beds
  • 4 Baths
  • 2,349 Sq Ft

  915 E Lothbury Ave, Middlesboro, KY 40965

  Charming & Spacious Home with Poolside Living in Historic Middlesboro! This 3-bedroom, 4-bath home offers an abundance of space, comfort, and entertainment features for the whole family. Step outside to your own private retreat featuring a inground pool, a dedicated pool room with its own shower, and a convenient outdoor bathroom—ideal for summer gatherings. Unwind on the screened-in porch with

  Beth Combs Turn Key Realty

  915 E Lothbury Ave, Middlesboro, KY 40965
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  /21

  $279,900

  • 3 Beds
  • 3 Baths
  • 2,210 Sq Ft

  515 Englewood Rd, Middlesboro, KY 40965

  Explore this charming home offering a blend of tranquility and convenience! Nestled in town yet surrounded by nature, this rare gem features a spacious walk-out finished basement and an open kitchen/living room with stainless steel appliances. Loft bedroom.Enjoy panoramic views from the expansive glass windows overlooking the .75-acre yard, perfect for daily wildlife sightings from your

  Beth Combs Turn Key Realty

  515 Englewood Rd, Middlesboro, KY 40965
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  /54

  $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 makes 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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  /2

  $17,000

  0 Home Run Rd, Middlesboro, KY 40965

  Take a look at this beautiful land with 1.14 acres located in city limits of Middlesboro, KY. Doublewide homes welcome, it is unrestricted and has city water, city sewer and electric available! Sits fronting a paved street and is close to downtown Middlesboro.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  0 Home Run Rd, Middlesboro, KY 40965
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  /48

  $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

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  259 Watson Ln, Middlesboro, KY 40965
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  /2

  $139,900

  • Land
  • 14.46 Acres
  • $9,675 per Acre

  0 Hwy 217 Unit 1306328, Middlesboro, KY 40965

  LOTS AND ACREAGE FIVE (5) BUILDING LOTS. 14.46 ACRESON KY-217. ROLLING LANDSCAPE WITH BEAUTIFUL COUNTRY MOUNTAIN VIEW.

  Janice Pratt AAA Realty, Inc.

  0 Hwy 217 Unit 1306328, Middlesboro, KY 40965
• 

  

  /15

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft

  708 Ilchester Ave, Middlesboro, KY 40965

  Newly renovated 3 bedroom, 2 bath house located in a great neighborhood in Middlesboro, Ky. Within minutes of Lincoln Memorial university.

  Michael Hensley REMAX PROFESSIONAL'S

  708 Ilchester Ave, Middlesboro, KY 40965
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  /43

  $209,900

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  1315 Winchester Ave, Middlesboro, KY 40965

  MIDDLESBORO KENTUCKYThis home is perfect for entertaining. It sits on a corner lot with plenty of accessible parking. There is a disability ramp if one is needed. Large living room with a gas fireplace. This home has a large dinning room with the kitchen having plenty of cabinets for storage. There is a walk-in pantry and a separate laundry room. Three (3) bedrooms and two (2) full

  Janice Pratt AAA Realty, Inc.

  1315 Winchester Ave, Middlesboro, KY 40965
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  /18

  $184,900

  • 4 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  409 Meadow Ln, Middlesboro, KY 40965

  This 4 bedroom home is located just minutes away from Downtown Middlesboro KY. With upgraded kitchen and new floors this house is a hidden gem.

  

  Brad Cawood

  Turn Key Realty

  (606) 729-0510

  409 Meadow Ln, Middlesboro, KY 40965
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  /21

  $190,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  626 S 22nd St, Middlesboro, KY 40965

  Wonderfully maintained home sitting on 12 beautiful flat, and cleared lots at the dead end of 22nd St.VERY private and perfectly seated home makes you feel like you're away from everything while being close to town. Lots of landscaping providing extra privacy. Room to build more homes, investment properties, or keep it all to yourself for gardening in the fertile soil or have a mini

  Misti McGrath Realty Group

  626 S 22nd St, Middlesboro, KY 40965
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  /13

  $349,900

  • Land
  • 1.69 Acres
  • $207,041 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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