Middlesboro, KY Homes 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

  

  Virginia Wilder

  Century 21 Virginia Wilder Real Estate

  (606) 404-4782

  301 Doe's Crossing, Middlesboro, KY 40965
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  /13

  $24,000

  • Land
  • 1.46 Acres
  • $16,438 per Acre

  Lot 13 Venado Dr, Middlesboro, KY 40965

  This beautiful tract of land has 1.4658 acres and is ready for your build your home! Corner lot; water and electric and natural gas available, buyer will need to have septic system installed; this wonderful subdivision has wildlife and natures beauty all around yet close to downtown Middlesboro; Paved county street along property on two sides; great views!

  

  Virginia Wilder

  Century 21 Virginia Wilder Real Estate

  (606) 612-7466

  Lot 13 Venado Dr, Middlesboro, KY 40965
• 

  

  /2

  $19,500

  • Land
  • 1.14 Acres
  • $17,105 per Acre

  0 Home Run Rd, Middlesboro, KY 40965

  1.14 acres located in city limits of Middlesboro, KY. This unrestricted property has city water, city sewer and electric available.

  

  Virginia Wilder

  Century 21 Virginia Wilder Real Estate

  (606) 603-2970

  0 Home Run Rd, 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!

  

  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
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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

  $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
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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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  /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
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  /14

  $125,000

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

  209 Dalewood Rd, Middlesboro, KY 40965

  Property will be available for showings on April 19th, 20254 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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  /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
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  /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
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  /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
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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. Call for a showing.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  0 Highway 217 Unit 25005121, Middlesboro, 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
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  /33

  $140,000

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  2817 Ky 441, Middlesboro, KY 40965

  This charming 3-bedroom, 2-bathroom manufactured home in Middlesboro offers a spacious open and split floor plan, perfect for modern living. The layout provides ample privacy with the master suite separated from the two additional bedrooms. The open living and dining areas create an inviting atmosphere, ideal for entertaining or relaxing with family. With plenty of natural light, modern finishes,

  Sallye Broyles RE/MAX LakeTime Realty

  2817 Ky 441, 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
• 

  

  /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
• 

  

  /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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  /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

  $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
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  /16

  $1,250,000

  • Land
  • 65 Acres
  • $19,278 per Acre

  423 N 10th St, Middlesboro, KY 40965

  64.89 acres within the city limits of Middlesboro, KY with a family farm house included. Zoned commercial, property is within a mile of Cumberland Gap National Park and less than 3 miles from LMU in Harrogate, TN. Just minutes from US Hwy 25E and the main business district in Middlesbotro, KY, including Walmart and the Middlesboro Mall, makes it an ideal location for a hotel or other commercial

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  423 N 10th St, Middlesboro, KY 40965
• 

  

  /20

  $140,000

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft

  112 Parker Ln, Middlesboro, KY 40965

  Really nice manufactured home ready to move in with several improvements. The owner has put new flooring down and painted the interior. This home is minutes from downtown yet is very private. There's three bedrooms and two baths. The large den has a fireplace and plenty of room for the whole family.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  112 Parker Ln, Middlesboro, KY 40965
• 

  

  /19

  $1,200,000

  • Land
  • 3.76 Acres
  • $319,149 per Acre

  3066 Us Highway 25 E, Middlesboro, KY 40965

  Unlimited possibilities! Located on Hwy US-25E, this 3.76 ac tract of land is prime for development. Located right next to Casey's gas station/truck stop, it would be the perfect place to put a diner, a motel, or a car wash. Hwy 25E serves as an arterial expressway for long-distance travelers and truckers connecting central Appalachia to the Great Lakes and Eastern Seaboard regions of the U.S.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  3066 Us Highway 25 E, Middlesboro, KY 40965
• 

  

  /13

  $1,200,000

  • Land
  • 3.20 Acres
  • $375,000 per Acre

  2794 Us Highway 25 E, Middlesboro, KY 40965

  3.20 acres fronting on US HWY 25E in Middlesboro, KY. This property used to be the ''Highway Oil'' property with 596 feet of highway frontage. Currently has a 3500 sf brick house and an ''office'' that was used when the property served as a car lot-both structures are in poor shape and are not considered fit for residential purposes. This type of ''family owned'' property doesn't come available

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  2794 Us Highway 25 E, 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
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  /7

  $45,000

  • Land
  • 3.16 Acres
  • $14,241 per Acre

  19 Venado Dr, Middlesboro, KY 40965

  Come check out these beautiful lots with breathtaking views in one of the nicest neighborhoods in all of southeast KY. (Outline of property on pics is a rough estimate. Lots are 18&19)

  Ben Madon Coldwell Banker Bisceglia Realty & Auction Co

  19 Venado Dr, 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
• 

  

  /12

  $25,000

  • Land
  • 1.27 Acres
  • $19,685 per Acre

  9999 Sams Mountain Rd, Middlesboro, KY 40965

  Nice large lots on Sam's Mountain just north of Middlesboro Ky. Lots 12 and 13 are on the market. On the left side of the road as you go around the curve near the top. The lots are wooded and most of this parcel is flat. This is a once in a lifetime sale. Schedule your appointment to look at this property today!

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  9999 Sams Mountain Rd, Middlesboro, KY 40965
• 

  

  /16

  $1,250,000

  • Land
  • 65 Acres
  • $19,278 per Acre

  423 N 10th St, Middlesboro, KY 40965

  64.89 acres within the city limits of Middlesboro, KY with a family farm house included. Zoned commercial, property is within a mile of Cumberland Gap National Park and less than 3 miles from LMU in Harrogate, TN. Just minutes from US Hwy 25E and the main business district in Middlesboro, KY, including Walmart and the Middlesboro Mall, makes it an ideal location for a hotel or other commercial

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  423 N 10th St, Middlesboro, KY 40965

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