Middlesboro, KY Homes for Sale

• 

  

  

  /4

  $200,000

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  3008 State Highway 441, Middlesboro, KY 40965

  This Newly Remodeled home is located just minutes away from downtown Middlesboro and the Historic Cumberland Gap National Park, It features new floors, kitchen, bathrooms and a newly designed up stairs. Don't miss your chance to own this beautiful home. (inside Pictures coming soon)

  Brad Cawood Turn Key Realty

  3008 State Highway 441, Middlesboro, KY 40965
• 

  

  

  /24

  $199,900

  • 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
• 

  

  

  /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
• 

  

  

  /17

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  5 Abbey Ln, Middlesboro, KY 40965

  Tired of living in a house where you don't know your neighbors and feel like you can't enjoy your neighborhood? You can change all that with this 3 bedroom, 2 bath HOME in Ambleside subdivision. Have a problem with stairs? Not anymore. Two of the bedrooms and one bath are on the 2nd floor, but one bedroom and bath are on the first level. Nice open concept living room/dining room. You can enjoy

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  5 Abbey Ln, Middlesboro, KY 40965
• 

  

  

  /21

  $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
• 

  

  /28

  $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.

  Beth Combs Turn Key Realty

  164 Walker Ln, Middlesboro, KY 40965
• 

  

  /16

  $159,000

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  428 Wilderness Rd, Middlesboro, KY 40965

  Beautiful house located in Middlesboro Kentucky minutes away from Lincoln Memorial University and Cumberland Gap National Park. This home features beautiful hardwood floors, a great yard and even a garage. Don't miss the chance to own this wonderful home.

  Brad Cawood Turn Key Realty

  428 Wilderness Rd, Middlesboro, KY 40965
• 

  

  /57

  $319,900

  • 3 Beds
  • 2.5 Baths
  • 2,512 Sq Ft

  440 Sams Mountain, Middlesboro, KY 40965

  This is a very nice private home. Comes with lot 10-11. Open concept with a lot of windows to let the sun light in, master on the main level, 2 car garage, wood deck, large kitchen with a long island with a flat gas range, with bar stools. This is a must see!! Close to town but in a quiet area. Don't wait call today for your showing!BUYER TO VERIFY SQUARE FOOTAGE!!

  Steve Mason REMAX PROFESSIONAL'S

  440 Sams Mountain, Middlesboro, KY 40965
• 

  

  /24

  $284,900

  • 3 Beds
  • 2 Baths
  • 2,096 Sq Ft

  10 Thaxted Ln, Middlesboro, KY 40965

  HIDDEN GEM! This beautiful one level home is located in Middlesboro, just outside the city limits in a private area in Ambleside subdivision. This home has 2096 sf of living space, all on one level, with 3 bedrooms and 2 full baths. There is a spacious kitchen with custom cabinets and steel appliances which stay with the house. The stove has a convection oven and the refrigerator has French

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  10 Thaxted Ln, Middlesboro, KY 40965
• 

  

  /15

  $205,000

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft

  708 Ilchester Ave, Middlesboro, KY 40965

  Newly renovated 3 bedroom, 2 bath house located in a great neighborhood in Middlesboro, Ky. Within minutes of Lincoln Memorial university.

  Michael Hensley REMAX PROFESSIONAL'S

  708 Ilchester Ave, Middlesboro, KY 40965
• 

  

  /43

  $209,900

  • 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. This home has a large dinning room with the kitchen having plenty of cabinets for storage. There is a walk-in pantry and a separate laundry room. Three (3) bedrooms and two (2) full

  Janice Pratt AAA Realty, Inc.

  1315 Winchester Ave, Middlesboro, KY 40965
• 

  

  /18

  $189,000

  • 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

  409 Meadow Ln, Middlesboro, KY 40965
• 

  

  /11

  $190,000

  • 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

  Aaron Rose Realty Network, Inc

  105 Mudlick Rd, Middlesboro, KY 40965
• 

  

  /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
• 

  

  /24

  $185,000

  • 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
• 

  

  /16

  $187,900

  • 3 Beds
  • 2 Baths
  • 1,404 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 with an adjoining dining room and a galley kitchen. This home also offers a one car attached garage and additional parking in the driveway. Only minutes away from shopping, groceries, gas stations, and other amenities.

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  106 S 38th St, Middlesboro, KY 40965
• 

  

  /17

  $157,000

  • 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.

  Nicole Goins Heartland Real Estate, LLC

  1005 Hollywood Dr, Middlesboro, KY 40965
• 

  /2

  $185,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft

  414 SE North 24th St, Middlesboro, KY 40965

  Located just minutes from historic downtown Middlesboro, KY, this all-brick, one-level home offers a unique opportunity for multi-generational living or investment income. Each side features 2 bedrooms and 1 bathroom, with separate living spaces—ideal for hosting guests, rental potential, or two families sharing one property. Enjoy the convenience of off-street parking and a versatile layout that

  Beth Combs Turn Key Realty

  414 SE North 24th St, Middlesboro, KY 40965
• 

  /2

  $185,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,024 Sq Ft

  919 W Rochester Ave, Middlesboro, KY 40965

  Looking for a home and an investment opportunity? This property offers two separate living spaces under one roof�each featuring 2 bedrooms and 1 bath. Ideal for multi-generational living or rental income. Enjoy a spacious backyard and a convenient location just minutes from downtown Middlesboro, KY.

  Beth Combs Turn Key Realty

  919 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /15

  $160,000 Sold Jul 14, 2025

  • 1,040 Sq Ft
  • $154/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2008

  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
• 

  

  /17

  $160,000 Sold Jul 03, 2025

  • 800 Sq Ft
  • $200/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2018

  524 E Lothbury Ave, Middlesboro, KY 40965

  This Charming 2 bedroom, 1 bath home was built in 2018 and is located in a fantastic neighborhood that is convenient to shopping and Lincoln Memorial University. Perfect home for a first-time home buyer or someone wanting to just have a smaller, low maintenance home. All information is believed to be accurate but is to be verified by buyer or buyer's agent.

  Michael Hensley REMAX PROFESSIONAL'S

  524 E Lothbury Ave, Middlesboro, KY 40965
• 

  

  /10

  $186,000 Sold May 28, 2025

  • 1,899 Sq Ft
  • $98/SF
  • 52 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1964

  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)

  Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  806 Manchester Ave, Middlesboro, KY 40965
• 

  

  /15

  $170,000 Sold May 19, 2025

  • 2,073 Sq Ft
  • $82/SF
  • 0 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1947

  1002 W Chester Ave, Middlesboro, KY 40965

  4 Bedroom 1 bath brick, one and a half story home on a large level lot.4 year old roof, 2 year old HVAC, new appliances, HARDWOOD FLOORS, formal dining room with additional laundry room.Ready for new owners! First time home buyers, investors, upsizers, and downsizers are all welcome!Buyer/agent to verify all information.

  Misti McGrath Realty Group

  1002 W Chester Ave, Middlesboro, KY 40965
• 

  

  /16

  $205,000 Sold May 12, 2025

  • 1,900 Sq Ft
  • $108/SF
  • 17 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1992

  286 Tiwani Ridge Rd, Middlesboro, KY 40965

  Come on home to the mountains!Main suite upstairs with an additional 2 bedrooms and bath with a jetted tub on the same level. Surrounded by peaceful woods and very few neighbors.2 car garage, beautiful kitchen and the staircase is picture perfect!Buyer to verify all information

  Misti McGrath Realty Group

  286 Tiwani Ridge Rd, Middlesboro, KY 40965
• 

  

  /34

  $169,000 Sold May 09, 2025

  • 2,163 Sq Ft
  • $78/SF
  • 234 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1976

  127 Cawood Ln, Middlesboro, KY 40965

  Tri level home with 4 bedrooms 2 baths, one upstairs and one downstairs. , lots of storage buildings, living room and family room downstairs both have fireplaces, covered back patio, paved/concreted driveway. Within 10 minutes to schools, shopping and 2 colleges, brick and siding, upper covered porch, back wooden covered porch, concrete sidewalks, front bay window, 2 storage sheds and 1 large

  Cookie Russell Realty Network, Inc

  127 Cawood Ln, Middlesboro, KY 40965
• 

  

  /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
• 

  

  /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
• 

  

  /5

  $55,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  510 W Chester Ave, Middlesboro, KY 40965

  Excellent location on this fixer upper in Middlesboro. 3 bed 1 bath, oversized kitchen with a nice level yard.Buyer/buyers agent to verify all information

  Misti McGrath Realty Group

  510 W Chester Ave, Middlesboro, KY 40965
• 

  

  /54

  $425,000

  • 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

  Megan Stanaford Black Diamond Realty

  119 Wagon Hollow Rd, Middlesboro, KY 40965
• 

  

  /5

  $22,500

  • Land
  • 0.36 Acre
  • $62,500 per Acre

  526 Balmoral Rd, Middlesboro, KY 40965

  Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

  Megan Stanaford Black Diamond Realty

  526 Balmoral Rd, Middlesboro, KY 40965
• 

  /2

  $10,500

  • Land
  • 0.40 Acre
  • $26,250 per Acre

  4163 441, Middlesboro, KY 40965

  This is a rare vacant lot on the beltline in Middlesboro. Electric and sewer on site.

  David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  4163 441, Middlesboro, KY 40965
• 

  

  /45

  $100,000

  • 6 Beds
  • 4 Baths
  • 2,520 Sq Ft

  416 Winchester Ave, Middlesboro, KY 40965

  Come check out 416 Winchester Ave Middlesboro KY. This property could be utilized as apartments or as one large unit. Parking allows for 4 vehicles out front and the driveway allows for a couple more. Level lot, tons of space. Public records show the building being built in 1891, there is a metal roof that's approximately a year old, hardwood flooring throughout with a mix of some vinyl flooring.

  Megan Stanaford Black Diamond Realty

  416 Winchester Ave, Middlesboro, KY 40965
• 

  /2

  $17,000

  • Land
  • 1.14 Acres
  • $14,912 per Acre

  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
• 

  

  /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
• 

  

  /7

  $27,500

  • 3 Beds
  • 1 Bath
  • 2,470 Sq Ft

  524 Avondale Ave, 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 offers preferred but will consider financed all offers.

  Dustin Hepburn

  524 Avondale Ave, Middlesboro, KY 40965
• 

  

  /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
• 

  

  /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
• 

  

  /66

  $329,900

  • 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
• 

  

  /16

  $29,900

  • Land
  • 2.32 Acres
  • $12,888 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
• 

  

  /36

  $249,900

  • 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

Showing Results 1 - 40, Page 1 of 4