Middlesboro KY Real Estate & Homes for Sale

33 Properties Found

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Beds:
5
Baths:
3.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
26006775
Type:
Single Family
Subdivision:
Rural
Lot size:
1.17 Acres
Year built:
2025
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
View additional info

ADDITIONAL INFORMATION

Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed bathrooms throughout. The heart of the home is a large, well-appointed kitchen, ideal for cooking, gathering, and entertaining. You'll also appreciate the oversized laundry room, adding convenience and extra storage. Enjoy outdoor living with a nice back deck, perfect for relaxing or hosting guests. A front deck is currently being completed, adding even more curb appeal and outdoor space. Additional features include: City water and sewer. Expansive lot with room to roam. This property combines comfort, space, and value in a peaceful setting. Call today to schedule your private showing—this one won't last long!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,320
Status:
Active
MLS#:
26005639
Type:
Single Family
Subdivision:
Windermere
Lot size:
0.3 Acres
Year built:
1994
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
View additional info

ADDITIONAL INFORMATION

Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is highlighted by a charming fireplace—perfect for gathering on cooler evenings. The eat-in kitchen offers a warm and functional space for everyday meals. Step outside to enjoy a large backyard complete with a swimming pool, an expansive deck, and a screened-in area attached to the deck—perfect for relaxing without worrying about pests while still enjoying the outdoors. Whether you're hosting guests or unwinding after a long day, this outdoor space has it all. With its flexible layout, multiple living spaces, and great indoor and outdoor amenities, this home has something for everyone. Don't miss your chance to make it yours!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,146
Status:
Active
MLS#:
1330109
Type:
Single Family
Lot size:
0.58 Acres
Year built:
1991
A broker reciprocity listing Courtesy: Backwoods Realty & Development 423-419-5742
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:
3.00
Sq.Ft.:
2,210
Status:
Active
MLS#:
1329448
Type:
Single Family
Lot size:
0.75 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Backwoods Realty & Development 423-419-5742
View additional info

ADDITIONAL INFORMATION

Discover the perfect blend of peaceful living and everyday convenience in this unique, nature-surrounded home located right in town. Set on approximately 0.75 acres, this property offers privacy, scenic surroundings, and abundant natural light through dramatic floor-to-ceiling windows overlooking the wooded landscape and spacious yard. Inside, the home showcases warm character with vaulted wood ceilings, exposed beams, hardwood floors, and a striking custom spiral staircase that creates a true centerpiece. The open kitchen and living area feature custom cabinetry, stainless steel appliances, and seamless flow, ideal for both daily living and entertaining. The main level includes a spacious owner's suite with a luxury bath featuring a jacuzzi tub, walk-in shower, and private balcony access, perfect for enjoying peaceful mountain and nature views. A second bedroom, full guest bath, and access to the rear deck and fenced yard complete the main floor. Upstairs, the loft bedroom provides flexible space for sleeping, office, or retreat. The walk-out finished basement offers additional living space with a full bath, laundry area, and multiple possibilities including recreation, guest quarters, or home office. A heated and cooled converted garage with built-in shelving provides excellent storage or workspace. Recent updates include beautiful hardwood flooring, smart HVAC system, and a lifetime warranty metal roof. Outdoor features include a large storage shed and expansive yard ideal for enjoying wildlife, relaxing, or entertaining. This rare property combines charm, space, and setting—schedule your private showing today to experience it for yourself.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,016
Status:
Active
MLS#:
1328317
Type:
Single Family
Subdivision:
Vista Venado
Lot size:
0.94 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
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ADDITIONAL INFORMATION

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 dishwasher, a new refrigerator, a new cook stove and a new built in microwave. There are lots of cabinets and a pantry. The main floor also has a half bathroom. The upstairs has 3 bedrooms and 2 full bathrooms, laundry room and a computer/study room that leads out to the balcony. This home has central gas heat and central air. Lots of windows to enjoy the amazing mountain views. There is a wonderful view overlooking the city of Middlesboro. The new laminate flooring throughout this home is waterproof. City water, the driveway was paved November 2024, this home is move in ready with possession at closing, there is a balcony upstairs and a wrapped deck on the main level with a natural gas connection for your gas grill, never worry about running out of gas in those propane tanks again! Internet available. This home is located in the county yet less than 5 minutes to downtown Middlesboro.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,908
Status:
Active
MLS#:
1326276
Type:
Single Family
Lot size:
0.16 Acres
Year built:
1949
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,296
Status:
Active
MLS#:
1316842
Type:
Single Family
Lot size:
0.18 Acres
Year built:
1948
A broker reciprocity listing Courtesy: Realty Network, Inc 423-869-3121
View additional info

ADDITIONAL INFORMATION

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 convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!

Beds:
7
Baths:
5.00
Sq.Ft.:
6,276
Status:
Active
MLS#:
1290184
Type:
Single Family
Lot size:
2.9 Acres
Year built:
1923
A broker reciprocity listing Courtesy: Backwoods Realty & Development 423-419-5742
View additional info

ADDITIONAL INFORMATION

A One-of-a-Kind Dream Home with Spectacular Views! This stunning home offers breathtaking views from every window and boasts 7 spacious bedrooms, 3 full bathrooms, and 2 half bathrooms—plenty of room for the entire family! Step inside and be captivated by the grand staircase and an incredible private library, perfect for quiet moments or working from home. The walkout basement is ready to be finished to your specifications, allowing you to create the ultimate entertainment space, home gym, or guest suite. As an added bonus, the price includes an extra buildable lot, giving you even more possibilities for expansion or investment. Don't miss out on this rare opportunity to own a truly unique home. Schedule your showing today!

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26–33 of 33 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

    $170,000
    16.7%
    change since last quarter
  • # Active listings

    56
    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