Middlesboro, KY Homes for Sale

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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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  /16

  $160,000

  • 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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  /17

  $159,900

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  405 S 37th St, Middlesboro, KY 40965

  Looking for a home to raise your family? Don't let this one go by! Spacious 4 bedrooms, 2 bath home with a fenced in yard, this one is just the right size for a growing family. Just minutes from the hospital and schools, yet tucked away on a side street with little traffic. Let us show you your new home today! Schedule a showing before it's gone.

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  405 S 37th St, Middlesboro, KY 40965
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  /53

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  129 Lower Gibson Ln, Middlesboro, KY 40965

  🏡 The Château on the Creek - Home for Sale in Middlesboro, KY (Bell County) Welcome to The Château 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 completely redone

  Michael Hensley REMAX PROFESSIONAL'S

  129 Lower Gibson Ln, Middlesboro, KY 40965
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  /10

  $197,000

  • 3 Beds
  • 1.5 Baths
  • 1,238 Sq Ft

  1200 W Chester Ave, Middlesboro, KY 40965

  Have you been looking for a cozy home on a quiet, family-friendly street to raise your family? You need to put this one on your ''must see'' list. Newly remodeled with new floors, new lights, new windows, new doors, and new fencing! With 3 bedrooms and 1 and 1/2 baths, this home is the perfect starter home. The fenced in yard is flat with lots of room for kids--don't miss out on this one.

  Patsy Barnett Coldwell Banker Bisceglia Real

  1200 W Chester Ave, 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 complete

  Janice Pratt Fathom Realty TN LLC

  807 Exeter Ave, Middlesboro, KY 40965
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  /40

  $249,000

  • 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 a

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  301 Doe's Crossing, Middlesboro, KY 40965
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  /21

  $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 Fathom Realty TN LLC

  140 Wellington Dr, 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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  /32

  $164,900

  • 3 Beds
  • 2 Baths

  140 Hickory Ln, Middlesboro, KY 40965

  3-bedroom, 2-bath home situated on a spacious 0.66-acre lot, offering the perfect blend of privacy and convenience. Located just minutes from all the amenities Middlesboro has to offer, this property provides easy access to shopping, dining, schools, and highways. Enjoy the generous outdoor space with plenty of room for gardening, entertaining, or future improvements. A great opportunity for

  SARAH RICHARDS RE/MAX Preferred Group

  140 Hickory Ln, Middlesboro, KY 40965
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  /21

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  908 W Chester Ave, Middlesboro, KY 40965

  This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment behind the house. The apartment is open space with 1 bdrm and a full bath. Apartment is rented. Metal roof, vinyl siding and windows, hardwood, laminate & tile floors. Privacy and a chain link fenced in back yard, 2 storage buildings, level back yard.

  Steve Mason REMAX PROFESSIONAL'S

  908 W Chester Ave, Middlesboro, KY 40965
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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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  /8

  $210,000

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  280 Parker Ln, Middlesboro, KY 40965

  Beautiful and practically brand new! This 3 bedroom 2 bath home is perfect for a sweet family! From the ground up, this home is only 3 years old. All appliances included, very well taken care of. You HAVE to see this one!!

  Misti McGrath Realty Group

  280 Parker 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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  /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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  /5

  $30,000

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965

  LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965
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  /15

  $68,000

  • 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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  /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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  /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

  $155,000

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  123 Upper Gibson Ln, Middlesboro, KY 40965

  Schedule to see this cozy home that has 2 traditional bedrooms with closets and one room that's used as a bedroom that doesn't have a closet but an armoire is an easy solution. One nice sized bathroom as well. The home is sitting on a surveyed acre with a 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

  Megan Stanaford Black Diamond Realty

  123 Upper Gibson Ln, Middlesboro, KY 40965
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  /27

  $24,900

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  13 Duncan Ln, Middlesboro, KY 40965

  This property is now under auctionterms. All Bids must be submitted during the auction via the property service listing page at This sale is subject to a 5% or $2,500 minimum buyer s premium pursuant to the auction Terms & Conditions. All bids will be subject toseller approval (minimums may apply). This property is now under auction terms. All Bids must be submitted during the auction

  Beth Combs Turn Key Realty

  13 Duncan Ln, 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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  /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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  /27

  $119,900

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  816 W Chester Ave, Middlesboro, KY 40965

  Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

  James Martin Century 21 Pinnacle

  816 W Chester Ave, 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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  /51

  $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 make 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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  /36

  $279,000

  • 4 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  206 Summit Dr, Middlesboro, KY 40965

  Beautiful move-in ready renovated Property. Home features four bedrooms 2 1/2 baths. kitchen features soft closed custom cabinets, kitchen island and stainless steel appliances. Laminated floors throughout the home. Enjoy your coffee on screened in back porch. Storage building for your tools, lawnmower etc..Property is located within minutes from Lmu main campus, Shopping, restaurants, and

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  206 Summit Dr, Middlesboro, KY 40965
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  /32

  $235,200

  • 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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  /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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  /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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  /23

  $150,000

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  359 Beans Fork Rd, Middlesboro, KY 40965

  I love a good sunroom, don't you? Recently updated 2-bedroom 1 bath home is move in ready! Extra-large fenced in level yard with a garage perfect for tinkering!Electric and plumbing included in the updates. You won't find a home like this in this price range! Come see for yourself!

  Misti McGrath Realty Group

  359 Beans Fork Rd, Middlesboro, KY 40965
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  /48

  $339,900

  • 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. Also, a fenced in back yard!! NOT IN THE

  Steve Mason REMAX PROFESSIONAL'S

  805 Worchester Ave, Middlesboro, KY 40965
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  /52

  $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 upstairs,

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  259 Watson Ln, Middlesboro, KY 40965
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  /9

  $139,000

  • Land
  • 5.33 Acres
  • $26,079 per Acre

  312 Blakely Ln, Middlesboro, KY 40965

  Rare find! 5.33 undeveloped acres in Middlesboro on Blakely Lane, off Cumberland Ave. Zoned R-1. Land is mostly level with a drop to the creek behind. Portion near the creek is in the floor plain. Several building sites on the land above the flood plain. Easy access to Cumberland Ave yet away from the noise and traffic.

  Ann Robinson Action Realty

  312 Blakely Ln, Middlesboro, KY 40965
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  /16

  $79,900

  • 2,256 Sq Ft

  417-A&B Avondale Ave, Middlesboro, KY 40965

  Has the up stairs new flooring some new windows roof 7 years old hot water 7 years old new gutters with gutter guards. Bring your vision and bring this fixer upper back to life.

  Nancy Maiden Mountain Realty

  417-A&B Avondale Ave, Middlesboro, KY 40965
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  /5

  $15,000

  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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