Middlesboro, KY Homes for Sale

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  /30

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft

  238 Windermere Dr, Middlesboro, KY 40965

  BEATUIFUL AMBLESIDE HOME! This home is nestled in the beautiful Ambleside subdivision with 3 bedrooms and 2 baths. The main living space has a main suite including a walk-in closet, 2 bedrooms, guest bath, kitchen, living room, dining room and laundry room. There are hardwood flooring and carpet throughout the home with vinyl in the kitchen and baths. There is a laundry room on the main floor

  Sheila Durham Coldwell Banker Bisceglia Real

  238 Windermere Dr, Middlesboro, KY 40965
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  /36

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  709 Balmoral Rd, Middlesboro, KY 40965

  HAVE IT ALL IN THE HEART OF BEAUTIFUL MIDDLESBORO KY!! Check out this gorgeous home with all the bells a whistles! Features include: 4 bedrooms, 2 bathrooms, 2 living rooms, brick fireplace with buck stove insert, laundry room, laminate flooring, spacious kitchen, huge level yard, above ground swimming pool, large back deck perfect for entertaining with covered outdoor kitchen, 2 car attached

  D.J Wilder Century 21 Virginia Wilder Real Estate

  709 Balmoral Rd, Middlesboro, KY 40965
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  /22

  $289,900

  • 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 living

  Beth Combs Turn Key Realty

  515 Englewood Rd, Middlesboro, KY 40965
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  /66

  $340,000

  • 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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  /11

  $199,000

  • 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 living or a

  Aaron Rose Realty Network, Inc

  105 Mudlick Rd, Middlesboro, KY 40965
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  /36

  $267,500

  • 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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  /24

  $195,000

  • 3 Beds
  • 1 Bath
  • 2,000 Sq Ft

  515 N 25th St, Middlesboro, KY 40965

  Cute as I'll get out! And no, I don't mean cute as in little either. This one packs a big punch so don't just do a drive-by, you MUST see inside!3 bedrooms with multiple bonus rooms and extra, extra storage space. Charming character and the quality of yesteryear, you'll feel the comfort just walking through the door. Let's go!Buyer/Agent to verify all information

  Misti McGrath Realty Group

  515 N 25th St, Middlesboro, KY 40965
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  /20

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  106 S 38th St, Middlesboro, KY 40965

  Well-kept Brick Ranch Home. This home is conveniently located in the heart of the city limits. The 3 bedroom 2 bath home has a spacious living room. It has a galley kitchen with a formal dining room. There is a den that extends from the dining area for more space for entertaining. This home also offers a one car attached garage and additional parking in the driveway. There is a guest bath with

  Sheila Durham Coldwell Banker Bisceglia Real

  106 S 38th St, Middlesboro, KY 40965
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  /24

  $199,900

  • 3 Beds
  • 1 Bath
  • 1,661 Sq Ft

  811 Gloucester Ave, Middlesboro, KY 40965

  This 3 bedroom, 1 bath brick home is located on a quiet dead-end street in the heart of historic Middlesboro, Ky. With a large level fenced in back yard and a wooded area to your right, you will have plenty of privacy. The interior includes large bedrooms, a dining room, and a large living room area.

  Michael Hensley REMAX PROFESSIONAL'S

  811 Gloucester Ave, Middlesboro, KY 40965
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  /16

  $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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  /38

  $235,000

  • 2 Beds
  • 1 Bath
  • 2,031 Sq Ft

  512 N 25th St, Middlesboro, KY 40965

  This charming home in a residential area downtown Middlesboro. Relax on the perfect porch or enjoy the level backyard with patio and pergola to offer shade and enjoy the beautiful sunsets. This exquisite 2-bedroom 1 bath home has original hardwood floors and amazing character with its wide trim all while having new modern double pane lifetime windows. After a long day you can relax in your new

  Lisa Stacy-Gibbs Turn Key Realty

  512 N 25th St, 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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  /7

  $89,900

  • 3 Beds
  • 1 Bath
  • 2,000 Sq Ft

  1197 Beans Fork 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.

  Darrell Lewis DIYFlatFee.Com

  1197 Beans Fork Rd, Middlesboro, KY 40965
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  /14

  $118,000

  • 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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  /18

  $98,500

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  600 S 38th St, Middlesboro, KY 40965

  This 1040 SqFt modular home could be a great starter home. Its a two bedroom with a bonus room that could be used for a third bedroom. This property has a nice level yard and is fenced in in the back with a outside building thats been finished out for an office with heat and ac.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  600 S 38th St, 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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  /15

  $150,000

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  810 S 28th St, Middlesboro, KY 40965

  This beautiful 3 bed 2 bath home in Middlesboro is in a great neighborhood and close to all downtown amenities. Bathrooms are currently being completely remodeled and near finished. This home is perfect for a family to be in a safe neighborhood with a big yard and fenced in back yard.

  Ben Madon Coldwell Banker Bisceglia Realty & Auction Co

  810 S 28th St, Middlesboro, KY 40965
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  /15

  $115,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  921 Winchester Ave, Middlesboro, KY 40965

  This country style home has 2 bedrooms with optional 3rd bedroom, 2 bathrooms, living room, dining room, kitchen, and large laundry room, central heat and air is about 6 years old, insulated windows are about 10 years old, seller is installing new cook stove and refrigerator, home has city water and city sewer, high speed internet available, concrete driveway, storage shed stays with home. Level

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  921 Winchester Ave, Middlesboro, KY 40965
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  /4

  $89,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  3028 Highway 441, Middlesboro, KY 40965

  This Property comes with Parcel ID:057-34-00-036.00 also. Which consist of around 3 acres and 1 livable structure of about 1000 sq foot. It is located just mins away from downtown Middlesboro and the LMU Campus.

  Brad Cawood Turn Key Realty

  3028 Highway 441, Middlesboro, KY 40965
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  /31

  $182,050

  • 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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  /16

  $160,000

  • 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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  /23

  $179,900

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  164 Walker Ln, Middlesboro, KY 40965

  Charming 3 Bedroom, 2 Bath Home - Fully Updated and Move-In Ready! Renovations and upgrades installed in 2023, this beautifully maintained home offers numerous upgrades throughout. Enjoy brand-new 12 ml vinyl plank flooring, solid wood soft-close kitchen cabinets, new countertops, a modern kitchen sink and fixtures, and a full suite of new stainless steel appliances—including washer and dryer.

  Michael Hensley REMAX PROFESSIONAL'S

  164 Walker Ln, Middlesboro, KY 40965
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  /27

  $339,000

  • 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 walks. Let's go

  Misti McGrath Realty Group

  900 Twin Fawn Trail, Middlesboro, KY 40965
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  /25

  $140,000

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  422 Wilderness Rd, Middlesboro, KY 40965

  Available now! Are you ready for your very own home? Come check out this adorable, remodeled, cottage style home featuring 2 bedrooms and 1 cozy bathroom. Pretty kitchen and nice living room. Bell County Ky PVA measuring tool shows the lot size is 0.279 of an acre. Nice wide driveway and covered parking area. This space would make a nice outdoor sitting area. Level yard, close to shopping and 10

  Megan Stanaford Black Diamond Realty

  422 Wilderness Rd, Middlesboro, KY 40965
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  /31

  $458,000

  • 5 Beds
  • 4 Baths
  • 3,146 Sq Ft

  523 N 30th St, Middlesboro, KY 40965

  Spacious All-Brick Home with Attached Guest Quarters - Prime Location! This beautifully maintained, all-brick home offers exceptional flexibility and space, featuring a main residence with 3 bedrooms, 2 bathrooms, a bonus room perfect for a home office, rec room, or additional sleeping area, and two laundry rooms for added convenience.In addition, the property includes a fully separate, attached

  Beth Combs Turn Key Realty

  523 N 30th St, Middlesboro, KY 40965
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  /29

  $260,000

  • 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 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 spacious

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  825 S 28th St, Middlesboro, KY 40965
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  /17

  $85,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  1813 Winchester Ave, Middlesboro, KY 40965

  Great opportunity for investors! Cabin style home, newly remodeled, new paint, new flooring, new split units for cheaper electricity bills with a massive garage, on an OVERSIZED LOT. PERFECT opportunity for an airbnb with plenty of parking for trailers and side by sides with access to trailheads! Lets go see it!

  Misti McGrath Realty Group

  1813 Winchester Ave, Middlesboro, KY 40965
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  /7

  $109,900

  • 2 Beds
  • 1 Bath
  • 1,236 Sq Ft

  112 Exeter Ave, De Soto, KY 40965

  Welcome to 112 Cumberland Ave, Middlesboro, KY—a delightful 2-bedroom, 1-bath home boasting 1,236 square feet of comfortable living space! Perfectly situated in a prime, convenient location, this charming residence is just steps away from Middlesboro's best shopping, dining, and entertainment. With the option for an additional bedroom, this home offers flexibility to suit your needs, whether for

  Jonathan Evans Action Realty

  112 Exeter Ave, De Soto, KY 40965
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  /24

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,989 Sq Ft

  4922 W Cumberland Ave, Middlesboro, KY 40965

  Looking for a place to call home? Don't miss out on this one! This 3 bedroom, 2 bath brick ranch is spacious and sits on a large lot within the city limits. Lovingly cared for, you can feel the memories made in this home and imagine the new ones you can make with your family. Even the basketball goal next to the detached garage will bring back memories of summer nights playing ball in the back

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  4922 W Cumberland Ave, Middlesboro, KY 40965
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  /32

  $299,000

  • 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 1476sq/ft 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

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  113 Hollywood Dr, Middlesboro, KY 40965
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  /33

  $297,500

  • 5 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  2410 Cumberland Ave, Middlesboro, KY 40965

  Remarkable Folk Victorian Historical Home. This home was built in 1908, redesigned for today's modern living, yet still encompassing the original charm. This home is nestled in the residential district of Cumberland Ave in Middlesboro. The inviting covered porch takes you back to the time that ''porch sitting'' in the evening was the thing to do and leads you into the entryway with tall

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  2410 Cumberland Ave, Middlesboro, KY 40965
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  /5

  $29,900

  • Land
  • 18 Acres
  • $1,656 per Acre

  0 Highway 217 Unit 25005121, Middlesboro, KY 40965

  18.005 acre lot at Brush Mountain Farms. This is a great property for a cabin. Great views with a walking trail nearby. This property is located in a gated community and has an HOA with restrictions. Call for a showing.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  0 Highway 217 Unit 25005121, Middlesboro, KY 40965
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  /22

  $119,000

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

  252 Chasteen Dr, Middlesboro, KY 40965

  This home has 3 bedrooms and 2 full bathrooms, living room, family room, 2 eat-in kitchens, 2 laundry hookups, attached storage shed, level lot with chain link fence, seller said it could be made into two apartments. Central heat and air, gas cook stove, natural gas, city water, city sewer. It is close to hospital. NEW ROOF It won't last long at this price!

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  252 Chasteen Dr, Middlesboro, KY 40965
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  /12

  $650,000

  • 2 Beds
  • 1 Bath
  • 776 Sq Ft

  516 S 34th St, Middlesboro, KY 40965

  Unbelievable find in the city limits of Middlesboro. 13.7 acres inside the city limits with city water and public sewer. Property has two different homes and a barn. The address of the second home is 501 South 35th. street. Both homes need some TLC but are solid constructions. This property has potential for a small farm or development with several other home sites. Come take a look! Buyer

  Michael Hensley REMAX PROFESSIONAL'S

  516 S 34th St, Middlesboro, KY 40965
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  /19

  $300,000

  • Land
  • 10 Acres
  • $31,217 per Acre

  00 Ky Hwy 217, Middlesboro, KY 40965

  BUSINESS OPPORTUNITY! This property has 9.613 surveyed acres with 2 garages and a storage shed. This unique property also has 2 ponds that could be stocked with fish. One pond was used as a public community swimming hole. Two of the cabins on the property served as restrooms and changing area. This property is surrounded by a stream. There is plenty of room to make a campground, RV parking

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  00 Ky Hwy 217, Middlesboro, KY 40965
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  /17

  $164,500

  • 3 Beds
  • 1 Bath
  • 1,110 Sq Ft

  1005 Hollywood Dr, Middlesboro, KY 40965

  Located in Middlesboro KY, you will find this 3 bedroom 1 bath ranch style home with a fully equipped kitchen, laundry room, carport. This property is located approximately 10 minutes from the main campus of LMU. This home requires a 24 hour notice prior to showing.

  Nicole Goins Heartland Real Estate, LLC

  1005 Hollywood Dr, 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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  /60

  $379,900

  • 5 Beds
  • 4 Baths
  • 2,943 Sq Ft

  717 S 27th St, Middlesboro, KY 40965

  Custom built home new in 2016 with beautiful mountain views. Main level has a large open concept den with stone fireplace and cathedral ceiling, kitchen, utility room, four bedrooms and three full bathrooms. Spacious Master Suite is upstairs and complete with two walk-in closets, full bathroom with walk-in shower and a garden tub. Large bonus room above the single car garage. Spacious back deck.

  Steve Mason REMAX PROFESSIONAL'S

  717 S 27th St, Middlesboro, KY 40965
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  /44

  $299,800

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

  915 E Lothbury Ave, Middlesboro, KY 40965

  This adorable spacious three-bedroom, four-bathroom home offers plenty of living space for you and your family. Enjoy the inground pool, a pool room with a shower, and an outdoor bathroom. The screened-in porch includes a large daybed swing, while the natural gas grilling area is perfect for entertaining. The property also boasts a storage shed, privacy fencing, and hardwood flooring throughout.

  Beth Combs Turn Key Realty

  915 E Lothbury Ave, Middlesboro, KY 40965

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