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Middlesboro, KY Houses for Sale

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  • /41

    $269,000

    • 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

    Agent Photo

    Virginia Wilder

    Century 21 Virginia Wilder Real Estate

    (606) 404-4782

    301 Doe's Crossing, Middlesboro, KY 40965
  • /22

    $105,000

    • 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. It won't last long at this price!

    Agent Photo

    Virginia Wilder

    Century 21 Virginia Wilder Real Estate

    (606) 731-0781

    252 Chasteen Dr, Middlesboro, KY 40965
  • /29

    $269,900

    • 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 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
  • /22

    $285,000

    • 4 Beds
    • 2 Baths
    • 3,338 Sq Ft

    123 Twin Acres Rd, Middlesboro, KY 40965

    You'll have it all in this beautiful ranch style home on Twin Acres Rd. Living room, dining, kitchen, breakfast, den with fireplace, 4 bedrooms, 2 full baths, bonus room, and large sunroom overlooking the backyard. Level yard, partially fenced, easy care brick construction, 2 car attached garage, patio, covered front porch, storage room. Great location... convenient to shopping, schools, and

    Ann Robinson Action Realty

    123 Twin Acres Rd, Middlesboro, KY 40965
  • /24

    $289,900

    • 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
  • /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
  • /33

    $305,000

    • 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
  • /20

    $214,900

    • 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
  • /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
  • /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
  • /46

    $229,900

    • 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 and a large dining room. Kitchen has plenty of cabinets for storage, a walk-in pantry and a separate laundry room. Three (3) bedrooms with two (2) full bathrooms. Showers have been

    Janice Pratt AAA Realty, Inc.

    1315 Winchester Ave, Middlesboro, KY 40965
  • /17

    $94,900

    • 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
  • /24

    $199,900

    • 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
  • /27

    $159,900

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

    109 N 30th St, Middlesboro, KY 40965

    Sweet little cottage located just off Cumberland Valley in Middlesboro City Limits with easy access to Lincoln Memorial University, downtown, Harrogate TN, Cumberland Gap Nat'l Park and more! This residence has been updated in recent years entirely. Exterior vinyl, windows & shingles have been replaced, as well as kitchen cabinets, appliances, & fixtures. The combination Living/Dining/Kitchen

    Tim Smith Sallie Davidson, Realtors

    109 N 30th St, Middlesboro, KY 40965
  • /7

    $114,900

    • 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
  • /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
  • /12

    $189,500

    • 2 Beds
    • 2 Baths
    • 1,899 Sq Ft

    806 Manchester Ave, Middlesboro, KY 40965

    Beautiful 2 bedrooms, 2 bathrooms (master bath is extra large) home in great neighborhood. Home offers a large bonus/sun room, beautiful cream-colored kitchen cabinets, tile and hardwood flooring. Don't let this one get away! Is super clean and in move-in condition. (Age is estimated and square footage to be verified)

    Patsy Barnett Coldwell Banker Bisceglia Real

    806 Manchester Ave, Middlesboro, KY 40965
  • /35

    $89,900

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft

    1809 Exeter Ave, Middlesboro, KY 40965

    Motivated sellers, say 'bring us an offer!'All debris in and around home to be removed prior to closing.Solidly built home with some updates, including all plumbing updated, some new windows installed, some new windows purchased and to remain for new owner.2 bedrooms plus a bonus room that can be used as a bedroom, just doesn't have a closet.Large bathroom, updated

    Billy Hibbitts Shawn Rogers Realty, Inc

    1809 Exeter Ave, Middlesboro, KY 40965
  • /31

    $279,900

    • 3 Beds
    • 2.5 Baths
    • 1,974 Sq Ft

    9 Ennismore Dr, Middlesboro, KY 40965

    This newly renovated 3 bed ,2.5 bath, home is a must see for anyone. The spacious back patio is perfect for entertaining complete with a beautiful hot tub building. This home has 2 car garage ,new flooring, counter tops, appliances and much much more. Located just outside the city Limits but just mins away from 25E and downtown Middlesboro.

    Brad Cawood Turn Key Realty

    9 Ennismore Dr, Middlesboro, KY 40965
  • /3

    $145,000

    • 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
  • /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
  • /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
  • /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
  • /44

    $315,000

    • 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
  • /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

    Beth Combs Turn Key Realty

    515 Englewood Rd, Middlesboro, KY 40965
  • /23

    $169,900

    • 4 Beds
    • 2 Baths
    • 1,689 Sq Ft

    501 N 25th St, Middlesboro, KY 40965

    'PRICE REDUCED' ATTENTION INVESTOR'S !!!! The Home can be easily converted into a Duplex and the Garage made into a rental unit to make this a Great income producing property!!!! Motivated Seller!!! Don't miss out on this opportunity!!!! This garage has two overhead cranes so you can do almost any repair job you need to on your car or truck. This garage is one of a kind. Come and see. Located

    Danny Wilson Coldwell Banker Bisceglia Realty & Auction Co

    501 N 25th St, Middlesboro, KY 40965
  • /28

    $440,000

    • 5 Beds
    • 4 Baths
    • 3,874 Sq Ft

    101 Kim Ln, Middlesboro, KY 40965

    Don't miss out on this hidden gem in the city limits of Middlesboro. This house has it all-over 3,800 sf of living space with 5 bedrooms and 4 bathrooms, a 3 car attached garage and 1 car detached garage. Built in 2005, the owners spared no expense to have all the space you need. House is fully furnished. With a lovely manicured lawn, this house could be what you have been looking for---call

    Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

    101 Kim Ln, Middlesboro, KY 40965
  • /26

    $550,000

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

    1015 Old Wilson Ln, Middlesboro, KY 40965

    FIRST TIME ON THE MARKET!This wonderful split foyer is in the city limits and has additional options. This 4 bedroom home has a spacious den, a family room and dining room. This home has been updated over the years with hardwood and title floors. The den is opened to dining and kitchen area for easy entertaining and has sliding glass doors for easy access to the back patio. There is an

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    1015 Old Wilson Ln, Middlesboro, KY 40965
  • /18

    $110,000

    • 2 Beds
    • 1 Bath
    • 1,204 Sq Ft

    3575 Highway 441, Middlesboro, KY 40965

    Sheila Durham Coldwell Banker Bisceglia Real

    3575 Highway 441, Middlesboro, KY 40965
  • /65

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 3,759 Sq Ft

    495 Highway Unit 1534, Pineville, KY 40977

    This is your dream home nestled in the beautiful mountains of Southeastern Kentucky! With a little over 3,700 Square feet between the finished basement, the first, and second floors, this home provides you with a spacious place to relax. The large windows in the living room and kitchen area give plenty of natural light inside the home during the day. Kitchen cabinets are soft close and lower

    Blake Ramey Century 21 Virginia Wilder Real Estate

    495 Highway Unit 1534, Pineville, KY 40977
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