Middlesboro KY Real Estate & Homes for Sale

36 Properties Found

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Beds:
4
Baths:
3.00
Sq.Ft.:
3,885
Status:
Active
MLS#:
25500647
Type:
Single Family
Subdivision:
Brush Mountain Phrase 1
Lot size:
0.32 Acres
Year built:
1919
A broker reciprocity listing Courtesy: DIY Flat Fee.com 888-601-3771
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ADDITIONAL INFORMATION

Don't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner lot. This 3,800 sq ft turn of the century home, that has been completely updated, boasts 4 bedrooms, 2 full baths and 1 half bath. On the primary level you'll find a covered front porch, sun room, large living room, and oversized dedicated dining area. Off of the dining room, you'll find a massive kitchen with a huge island and bar stools ready to host dinner parties. Also on the primary level you will find the primary suite with attached full bathroom. Off of the kitchen there is also a half bath for guests. On the second level of the home, you'll find 3 more great sized bedrooms and a full bathroom with ample storage in the floored attic space. In the finished basement you will find an open concept ready for your imagination: home gym, theatre, office, bonus room, etc. Out back you will find a huge fenced in yard ready for entertaining with a storage building and lean-to attached. This home was completely remodeled in 2021-2022 to include new electrical, new plumbing, new fixtures, appliances, roof, gutters, new HVAC units, and more! Come see this once in a lifetime opportunity.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
25018632
Type:
Farm
Subdivision:
Rural
Lot size:
9.61 Acres
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
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ADDITIONAL INFORMATION

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 or farmland. The garage has electricity and plumbing for a restroom. There are 2 small cabins that were used as changing areas for the local swimmers in the community. With no restrictions these 9 acres could be converted to a camp site with tents or for camper parking for vacationers to enjoy the nature. The 2 ponds could be used for livestock, swimming or stock them with fish to build your own favor fishing hole. The property is boarded by a stream. This property is only minutes from Boone's Ridge Wildlife Preserve. This property has also had an environmental Assessment done on the property. For additional information of the study, contact information will be provided to the buyer by the seller. This diamond in the rough could be the gem you have been searching for

Beds:
4
Baths:
3.00
Sq.Ft.:
2,456
Status:
Active
MLS#:
1311840
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1966
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

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 a bonus room with a 1/2 bath that could be used as a home office, 2 bedrooms, and 1 full bath. The upstairs has 2 bedrooms and a full bath. The home sits on a nice level lot and has plenty of privacy. The lot next door is for sale separately.

Beds:
2
Baths:
1.00
Sq.Ft.:
910
Status:
Active
MLS#:
1311219
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1981
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
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ADDITIONAL INFORMATION

2 bed, 1 bath, manufactured home sitting on a large level lot. Conveniently located to shopping and Harrogate, TN.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,560
Status:
Active
MLS#:
1310085
Type:
Single Family
Lot size:
0.9 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
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ADDITIONAL INFORMATION

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, refrigerator stay with home, laundry area, covered front and back porch, central gas heat and central air, double pane tilt windows, metal roof approximately 3 years old, home has vinyl siding that is less than 2 years old, high crawl space large enough to stand with dirt floor, great place for storage; internet available, natural gas, located in the county yet approximately a mile from Walmart. City water, septic system, city sewer and fenced yard

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 a new heat pump that was installed in 2025, 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:
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
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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:
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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26–36 of 36 properties displayed
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.
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.



Middlesboro 40965 Real Estate

Middlesboro is located in Kentucky. Middlesboro 40965 is less family-centric than the surrounding county with 25.04% of the households containing married families with children. The county average for households married with children is 26.4%.

Middlesboro Weather

Middlesboro Map

Middlesboro Real Estate Market Conditions

  • Median sales price

    $175,000
    16.7%
    change since last quarter
  • # Active listings

    46
    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 40965

Zip Code City
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