Middlesboro, KY Homes for Sale

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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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  /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

  (606) 713-0736

  4921 W Cumberland Ave, 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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  /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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  /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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  /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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  /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

  $70,000

  • 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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  /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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  /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

  $99,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  923 Winchester Ave, Middlesboro, KY 40965

  This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  923 Winchester Ave, 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,

  Beth Combs Turn Key Realty

  523 N 30th St, Middlesboro, KY 40965
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  /11

  $112,000

  • 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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  /34

  $165,000

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  123 Upper Gibson Ln, Middlesboro, KY 40965

  Cozy 3 bedroom, 1 bathroom home sitting on a surveyed acre with detached 1 car garage that has room for a workshop, storage, crafting etc. The yard is level with a gentle slope on the front edge of the property. There is right of way access to the creek as well. Inside the home, you'll find a large living room and 3 nice sized bedrooms. The kitchen is adequate as well as the dining area. Front

  Megan Stanaford Black Diamond Realty

  123 Upper Gibson Ln, 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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  /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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  /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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  /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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  /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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  /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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  /16

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft

  140 Wellington Dr, Middlesboro, KY 40965

  Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

  Janice Pratt AAA Realty, Inc.

  140 Wellington Dr, 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
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  /52

  $198,500

  • 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

  $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
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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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  /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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  /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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  /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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  /32

  $240,000

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  11 Castleford Way, Middlesboro, KY 40965

  Renovated and truly move in ready! Proudly owned by just one owner, this home shows exceptional care from the moment you step inside. Fresh paint, new luxury vinyl and laminate flooring, and thoughtful updates throughout create a clean, modern feel. The kitchen shines with new granite countertops, an updated sink and faucet, and finishes that pair beautifully with the existing cabinetry. Down the

  Jennifer Ware Kentucky Land and Home

  11 Castleford Way, Middlesboro, KY 40965
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  /6

  $24,900

  • 3 Beds
  • 2 Baths

  13 Duncan Ln, Middlesboro, KY 40965

  Charming 3-bedroom, 2-bath manufactured home situated on an approx. 0.32-acre corner lot. The home offers a practical layout with good flow and a spacious yard

  Beth Combs Turn Key Realty

  13 Duncan Ln, Middlesboro, KY 40965
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  /40

  $525,000

  • 5 Beds
  • 2.5 Baths
  • 2,542 Sq Ft

  2004 Twin Fawn Trail, Middlesboro, KY 40965

  This gorgeous cape cod home sits on 4.4 acres with deer visiting often. This home has 5 bedrooms, 2.5 bathrooms, formal living room with fireplace, family room (could be used as formal dining room) a second fireplace in the sunroom, amazing kitchen with island, the kitchen counter tops are granite, the stainless-steel appliances stay, which include double wall ovens, gas range with gas oven

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  2004 Twin Fawn Trail, Middlesboro, KY 40965
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  /16

  $19,900

  • Land
  • 2.32 Acres
  • $8,578 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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  /10

  $293,000

  • 4 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  314 Picadilly Ct, Middlesboro, KY 40965

  Spacious home located in Ambleside subdivision. This home has 4 bedrooms and 2 1/2 bathrooms. The home was completely remodeled approximately 2 years ago, with a new roof, new flooring throughout, and a completely updated kitchen. HVAC system replaced in January 2025. Don't let this one get past you, make it a must see!

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  314 Picadilly Ct, Middlesboro, KY 40965
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  /22

  $109,000

  • 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 easily

  Aaron Rose Realty Network, Inc

  252 Chasteen Dr, 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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  /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

  $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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  /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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  /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. The lot's are restricted to on site stick built homes. 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
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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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