Middlesboro KY Real Estate & Homes for Sale

37 Properties Found

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Beds:
3
Baths:
4.00
Sq.Ft.:
2,349
Status:
Active
MLS#:
1309393
Type:
Single Family
Lot size:
0.32 Acres
Year built:
1945
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

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 a custom daybed swing, or fire up the natural gas grill in the outdoor cooking area designed for effortless entertaining. Inside, you'll find rich hardwood flooring throughout and a warm, inviting layout. The primary suite is a true escape, complete with an ensuite bathroom and a relaxing jacuzzi-style tub. Additional features include a one-car garage with a built-in workshop area, extra storage throughout the home, a storage shed, and privacy fencing around the backyard. Located just minutes from the heart of historic downtown Middlesboro, you'll enjoy close proximity to charming shops, dining, and local attractions. Don't miss your chance to own this rare combination of charm, space, and lifestyle!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,210
Status:
Active
MLS#:
1309140
Type:
Single Family
Lot size:
0.75 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

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 living room or balcony. Recently updated, the home boasts beautiful hardwood floors, custom cabinetry, a lifetime warranty metal roof, and a smart HVAC system. Inside, a vaulted wooden ceiling and a striking wooden spiral staircase enhance the home's unique character. The main level includes a generous owner's suite with a luxurious bath featuring a walk-in shower and jacuzzi tub, as well as a balcony with stunning mountain views. A second bedroom with access to the back deck and fenced yard, along with a full guest bath, complete the main floor. The lower level offers expansive living space with a full bath, washer, dryer, and potential for additional living areas. A converted garage provides heated and cooled space with built-in shelves for storage, complemented by a large shed on the property for additional storage needs. Don't miss out on this hidden treasure—schedule your viewing today to experience the charm and comfort this home has to offer!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,512
Status:
Active
MLS#:
1307361
Type:
Single Family
Subdivision:
Sams Mountain
Lot size:
0.62 Acres
Year built:
2013
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
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ADDITIONAL INFORMATION

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!!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,976
Status:
Active
MLS#:
1306495
Type:
Single Family
Lot size:
92 Acres
Year built:
1966
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

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, large living room, kitchen with breakfast bar that extends to dining room with brick fireplace (sellers do not use fireplace) and a laundry room. This home has baseboard electric heat and duct work for a heat pump, nice decking around home that leads to the second home. Second home has a large living room, kitchenette, laundry area, one full bathroom, and a large bedroom with doors leading to the deck, home has central heat and air, and it comes with lots of windows letting in nature's beauty. There is a back entrance to the upstairs with an unfinished attic with electricity in the attic. There is a Generac generator that provides backup power to both homes. Main house has new water heater installed in 2024. Wildlife is in an abundance on this property including bear, deer, turkey and many others. This property has two septic systems, public water to each home. Concrete sidewalk to main house, paved driveway shared by both homes. If total seclusion is what you are looking for, this is it!! Property has never been timbered, coal minerals convey with property, long private driveway leading to homes tucked away, there is a pond on property. This property is about 1.5 miles from the Cumberland Gap National Park Visitors Center and is about close to 25E and is about 2 minutes from Food City and downtown including Appalachian Regional Hospital. There are multiple potential uses for this amazing property.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,684
Status:
Active
MLS#:
1305513
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1952
A broker reciprocity listing Courtesy: AAA Realty, Inc. 423-489-9744
View additional info

ADDITIONAL INFORMATION

MIDDLESBORO KENTUCKY This 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 bathrooms. Showers have been updated with new hardware. Each bedroom has a walk-in closet with built-ins. The master bedroom has two (2) closets. When entering in from the front door you will notice a nice foyer with two (2) 2-inch wooden motorized blinds. New central heating and air unit; tile floor with new carpet. You will enjoy the large outside deck with a heated pool with lights starting at 3' going to 9' deep. the pool comes with custom cover to fit and has a cholerine filter. There is a new salt water filter to convert to salt water. There is a pool shed with a commode. There is a barn and has a separate covered area for a boat or vehicle. This home has a very private back yard with a block wall and new vinyl fencing. The home is located in a prime location; five (5) blocks from the hospital and minutes to LMU and Walmart.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
1305300
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

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.

Beds:
6
Baths:
4.00
Sq.Ft.:
4,033
Status:
Active
MLS#:
25011376
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.71 Acres
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

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, minutes from downtown, short drive to Cumberland Gap National Park.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
1301528
Type:
Single Family
Lot size:
2 Acres
Year built:
1939
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

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 by nature, this rustic 3-bedroom, 1-bath cabin offers the perfect retreat. The home sits on a spacious lot with a large, level backyard, ideal for gardening or outdoor gatherings. Mature trees offer privacy, and the peaceful setting invites relaxation. Step inside to a warm, cabin-style interior featuring hardwood floors throughout, stainless steel appliances, and a cozy ambiance highlighted by two pallet stoves. The home also includes an updated kitchen, washer and dryer, and a durable metal roof built to last. Enjoy your mornings or evenings on the covered front porch, surrounded by blooming plants and the sounds of nature. Additional features include a 1-car garage, covered carport, workshop, and storage building—perfect for hobbies, tools, or extra space. The unfinished basement provides even more potential to make this property your own, with just a few personal touches, this charming home can become your ideal escape—whether full-time or a weekend getaway.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,146
Status:
Active
MLS#:
1299951
Type:
Single Family
Lot size:
0.58 Acres
Year built:
1991
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

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, attached living space—ideal for extended family or rental income. The guest quarters offer 2 bedrooms, 2 bathrooms, a full kitchen, living room, laundry area, and private entry—essentially two homes in one! Located just minutes from two local colleges and close to shopping and dining, this move-in-ready property is a rare opportunity for multi-generational living or income potential. With numerous upgrades throughout, this spacious home could be the dream property you've been waiting for!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,344
Status:
Active
MLS#:
1293786
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

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 yard, covered front porch.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,144
Status:
Active
MLS#:
1284881
Type:
Single Family
Lot size:
0.7 Acres
Year built:
1955
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

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 homebuyer or a small family, with its spacious yard perfect for pets, children, or anyone seeking the privacy of their own backyard. The home is equipped with vinyl and tile flooring.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,174
Status:
Active
MLS#:
1277166
Type:
Single Family
Lot size:
0.34 Acres
Year built:
1956
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

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 main suite has a beautiful walk-in shower with overhead sky-lights for natural lighting. Also in the main suit has a walk-in closet. There is a galley kitchen with built-in appliances. The basement can be an in-law suite with a studio apartment set-up and full kitchen. This is a charming home! Schedule an appointment today!

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26–37 of 37 properties displayed
Andrea D. Conner, License 344441, Xome Inc., License 262361, [email protected], 844-400-XOME (9663), 751 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Real Estate listings held by other brokerage firms are marked with the name of the listing broker. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright 2026 Knoxville Area Association of Realtors. All rights reserved.

Andrea D. Conner, License 221773, Xome Inc., License 239054, [email protected], 844-400-XOME (9663), 1795 Alysheba Way, Suite 102, Lexington, KY 40509


The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Lexington Bluegrass Multiple Listing Service. The Broker providing this data believes them to be correct but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2026 Lexington Bluegrass Multiple Listing Service. All rights reserved.



Middlesboro Real Estate

Middlesboro is located in Kentucky.

Middlesboro Weather

Middlesboro Map

Middlesboro Real Estate Market Conditions

  • Median sales price

    $180,000
    -3276800%
    change since last quarter
  • # Active listings

    48
    30-day change

Middlesboro Schools and Demographics

Education near Middlesboro, KY

City County
High School Graduates N/A N/A
College Degree - 2 year N/A N/A
College Degree - 4 year N/A N/A
Graduate Degree N/A N/A
Expenditures per Student N/A N/A
Students per Teacher N/A N/A

Elementary Schools near Middlesboro, KY

Grades Students P/T Ratio ZIP
Bell Central School Center PK - 08 628 13.2 40965
East End Intermediate School PK - PK 88 44 40965
Frakes School Center PK - 08 156 15.6 40940
Lone Jack School Center PK - 08 217 16.7 40939
Middlesboro Elementary School KG - 04 459 14.3 40965
Page School Center PK - 08 421 17.5 40977
Yellow Creek School Center PK - 08 583 18.2 40965

Middle Schools near Middlesboro, KY

Grades Students P/T Ratio ZIP
Middlesboro Middle School 05 - 08 374 16.3 40965
Pineville Elementary School PK - 06 312 14.2 40977
Pineville High School 07 - 12 245 13.2 40977

High Schools near Middlesboro, KY

Grades Students P/T Ratio ZIP
Bell County High School 09 - 12 815 19.9 40977
Middlesboro High School 09 - 12 391 16.3 40965

Ungraded Schools near Middlesboro, KY

Grades Students P/T Ratio ZIP
* Bell County Alternative School 07 - 12 24 6.9 40977
* Middlesboro Alternative School 09 - 12 39 53.2 40965
Bell County Area Technology Center UG - UG 0 40977
Cumberland Tech - Southeast Campus UG - UG 0 40965
Cumberland Technical College UG - UG 0 40977
Cumberland Valley Health Tech Center UG - UG 0 40977
Pineville Independent School PK - 12 516 16.1 40977
Southeast Tech UG - UG 0 40965

Demographics near Middlesboro, KY

City County
Neighborhood Type
Population N/A N/A
Population Density N/A N/A
Median Age N/A N/A
People per Household N/A N/A
Median Household Income N/A N/A
Average Income per Capita N/A N/A

Real estate near Middlesboro