Middlesboro, KY Homes for Sale

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  /30

  $188,000

  • 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. (inside Pictures coming soon)

  

  Brad Cawood

  Turn Key Realty

  (606) 288-6047

  3008 State Highway 441, Middlesboro, KY 40965
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  /18

  $189,000

  • 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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  /38

  $398,500

  • 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

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  220 Windermere Dr, Middlesboro, KY 40965
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  /34

  $249,900

  • 4 Beds
  • 2.5 Baths
  • 2,455 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. There is a gas fireplace that could be a dining room or an extension of the living room. The dining area is right off the galley kitchen with a door leading onto the carpeted porch easy for entertaining or cooking outside. There is easy access from the carport right into

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  1203 Winchester Ave, 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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  /17

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  5 Abbey Ln, Middlesboro, KY 40965

  Tired of living in a house where you don't know your neighbors and feel like you can't enjoy your neighborhood? You can change all that with this 3 bedroom, 2 bath HOME in Ambleside subdivision. Have a problem with stairs? Not anymore. Two of the bedrooms and one bath are on the 2nd floor, but one bedroom and bath are on the first level. Nice open concept living room/dining room. You can enjoy

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  5 Abbey Ln, 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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  /57

  $299,900

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft

  440 Sams Mountain, Middlesboro, KY 40965

  This is a very nice private home. Comes with lot 10-11. Open concept with a lot of windows to let the sun light in, master on the main level, 2 car garage, wood deck, large kitchen with a long island with a flat gas range, with bar stools. This is a must see!! Close to town but in a quiet area. Don't wait call today for your showing!BUYER TO VERIFY SQUARE FOOTAGE!!

  Steve Mason REMAX PROFESSIONAL'S

  440 Sams Mountain, Middlesboro, KY 40965
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  /66

  $329,900

  • 6 Beds
  • 3.5 Baths
  • 4,033 Sq Ft

  832 N 25th St, Middlesboro, KY 40965

  beautiful and spacious home located within the city limits of Middlesboro. this property consists of a main home and a separate apartment.The main home has four beds and 3 baths (2 full and 1 half). It has potential for a home office, home library, etc. The apartment that sits above the garage provides a unique income producing opportunity. It has 2 bedrooms and 1 full bath. Great location,

  Blake Ramey Century 21 Virginia Wilder Real Estate

  832 N 25th St, Middlesboro, KY 40965
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  /36

  $230,000

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

  4921 W Cumberland Ave, Middlesboro, KY 40965

  Nice Ranch style home with an oversized 1 car garage with a 2-car carport attached, 3 bd, 2 full baths, large dining / kitchen area, laundry room, comes with 2 storage buildings This is a very nice home. Ready to move in and no work to be done. Close to main town or hit the woods with your side by side.

  Steve Mason REMAX PROFESSIONAL'S

  4921 W Cumberland Ave, Middlesboro, KY 40965
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  /27

  $299,900

  • 3 Beds
  • 2 Baths
  • 2,270 Sq Ft

  900 Twin Fawn Trail, Middlesboro, KY 40965

  In the beautiful hills of Vista Venado lies the gorgeous 3 bedroom and 2 bath 900 Twin Fawn Trail.From the trey ceilings to the marble flooring, to the jetted tub this home is breathtaking! Your HOA fee of $20/month gives you unlimited water with very light restrictions. Massive patio for all your entertaining. Brand new french drain system.Quiet neighborhood perfect for evening

  Misti McGrath Realty Group

  900 Twin Fawn Trail, Middlesboro, KY 40965
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  /32

  $249,900

  • 4 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  825 S 28th St, Middlesboro, KY 40965

  Beautiful, split foyer home with 4 bedrooms and 2 1⁄2 bathrooms. The upstairs features a kitchen with plenty of space for storage, updated appliances, and tile floors. This home allows the natural light to shine through in all the rooms. The dining room and living room are open for entertainment or a growing family. The primary bedroom and bath are on the main floor. The guest bath is

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  825 S 28th St, Middlesboro, KY 40965
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  /41

  $259,900

  • 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

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  301 Doe's Crossing, Middlesboro, KY 40965
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  /25

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft

  505 S South 38th St, Middlesboro, KY 40965

  Located in Middlesboro, KY, this property is conveniently close to the hospital, schools, banks, shopping, and downtown historic Middlesboro, where you'll find charming boutiques and excellent dining options. This 2-bedroom, 2-bathroom brick home features an unfinished basement and sits on nearly an acre of land. Currently generating rental income, it also makes a great option for a first-time

  Beth Combs Turn Key Realty

  505 S South 38th St, Middlesboro, KY 40965
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  /2

  $20,000

  • Land
  • 0.13 Acre
  • $153,846 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

  $165,000

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  4605 W Cumberland Ave, Middlesboro, KY 40965

  One level ranch style home with 3 bedrooms, 2 bathrooms, living room, eat in kitchen, laundry room, central heat and air, nice level yard, paved driveway covered front porch, high speed internet available, double pane windows, public water and public sewer, hardwood floors, storage shed, range, refrigerator, washer and dryers stay with home, This home is less than half a mile from hospital.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  4605 W Cumberland Ave, 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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  /10

  $108,000

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  234 S 46th St, Middlesboro, KY 40965

  NO RESTRICTIONS! Right outside city limits (with city amenities but no taxes) and close to trailheads you'll find this newly renovated, VERY NICE, single wide with 3 bedrooms and 2 baths, 3 porches, nice level land with a firepit and the mountains in your back yard!Perfect for a rental property or air bnb or your own place to call home!

  Misti McGrath Realty Group

  234 S 46th St, Middlesboro, KY 40965
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  /18

  $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

  $20,000

  • Land
  • 0.28 Acre
  • $71,429 per Acre

  Lot #1 Bellwood Rd, Middlesboro, KY 40965

  Build Lot within Middlesboro City Limits. Limited restrictions. Can be used for a lot for a double-wide Manufactured home with city guidelines.

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  Lot #1 Bellwood Rd, Middlesboro, KY 40965
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  /52

  $599,000

  • 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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  /14

  $115,000

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  209 Dalewood Rd, Middlesboro, KY 40965

  Great property for anyone at any stage in life. Move in ready! 4 bedroom, 2 bathroom manufactured home built in 2020 sitting on 0.41 of an acre, per public records. Easy access to shopping, 10 minutes to LMU's main campus in Harrogate TN.

  Megan Stanaford Black Diamond Realty

  209 Dalewood Rd, Middlesboro, KY 40965
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  /12

  $105,000

  • 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

  $98,000

  • 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

  $199,900

  • 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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  /54

  $300,000

  • 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

  Megan Stanaford Black Diamond Realty

  119 Wagon Hollow Rd, Middlesboro, KY 40965
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  /5

  $22,500

  • Land
  • 0.36 Acre
  • $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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  /2

  $10,500

  • Land
  • 0.4 Acre
  • $26,250 per Acre

  4163 441, Middlesboro, KY 40965

  This is a rare vacant lot on the beltline in Middlesboro. Electric and sewer on site.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  4163 441, Middlesboro, KY 40965
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  /45

  $100,000

  • 6 Beds
  • 4 Baths
  • 2,520 Sq Ft

  416 Winchester Ave, Middlesboro, KY 40965

  Come check out 416 Winchester Ave Middlesboro KY. This property could be utilized as apartments or as one large unit. Parking allows for 4 vehicles out front and the driveway allows for a couple more. Level lot, tons of space. Public records show the building being built in 1891, there is a metal roof that's approximately a year old, hardwood flooring throughout with a mix of some vinyl flooring.

  Megan Stanaford Black Diamond Realty

  416 Winchester Ave, 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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  /15

  $199,000

  • 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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  /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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  /11

  $184,999

  • 3 Beds
  • 1 Bath
  • 996 Sq Ft

  105 Mudlick Rd, Middlesboro, KY 40965

  Charming 3-Bedroom Ranch on 3.89 Scenic Acres!Welcome to this delightful 3-bedroom, 1-bath ranch-style home nestled on 3.89 picturesque acres with stunning mountain views. This inviting property offers the perfect blend of peaceful country living and convenient access to town, schools, shopping, and outdoor recreation.Step inside to find a cozy yet spacious layout, ideal for family

  Aaron Rose Realty Network, Inc

  105 Mudlick Rd, Middlesboro, KY 40965
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  /16

  $29,900

  • Land
  • 2.32 Acres
  • $12,888 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
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  /31

  $179,900

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  180 Stevenson Bridge Rd, Middlesboro, KY 40965

  Charming Rustic Cabin with Modern Comforts on 2 Acres Welcome to 180 Stevenson Branch Rd in Middlesboro, KY—where country charm meets convenience. Just minutes from historic downtown Middlesboro, you'll enjoy easy access to quaint shops, local restaurants, major retailers, medical offices, banks, and hospitals—all while savoring the serenity of rural living. Nestled on a hillside and surrounded

  Beth Combs Turn Key Realty

  180 Stevenson Bridge Rd, Middlesboro, KY 40965

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