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 2025 Lexington Bluegrass Multiple Listing Service. All rights reserved.

Middlesboro KY Real Estate & Homes for Sale

39 Properties Found

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,684
Status:
NEW LISTING
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:
3
Baths:
2.00
Sq.Ft.:
1,296
Status:
NEW LISTING
MLS#:
25013288
Type:
Single Family
Subdivision:
Rural
Lot size:
0.32 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
View additional info

ADDITIONAL INFORMATION

COZY RANCHER NESTLED IN THE HEART OF MIDDLESBORO! This gem is in Ambleside! This cozy rancher has 1296 square feet with lots of storage space. The open floor plan makes family time and entertaining even more enjoyable. The main bedroom has two closets and a custom shower. The extended ceilings add character to this home. There is laminate and Vinyl floors throughout the home, closet space at the end of the hall and entrance way closet for extra storage. The kitchen has updated appliances. There is crown molding throughout the home and cozy gas fireplace in the living room. Enjoy your morning coffee or cuddle on the swing of the large front porch. The beautiful landscaping is added curb appeal to the wonderful ranch home. There is a nice flat backyard with a deck and privacy fence. This home would be a great starter home or just as sweet as a forever home. Call today for a showing.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,120
Status:
NEW LISTING
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:
3
Baths:
2.00
Sq.Ft.:
1,221
Status:
NEW LISTING
MLS#:
25013090
Type:
Single Family
Subdivision:
Rural
Lot size:
0.31 Acres
Year built:
1986
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
View additional info

ADDITIONAL INFORMATION

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 your neighborhood sitting on your covered front porch or sitting on your covered patio in your fenced-in back yard. Make an appointment today. We'll be glad to welcome you home.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,064
Status:
NEW LISTING
MLS#:
1305018
Type:
Single Family
Lot size:
0.4 Acres
Year built:
1960
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Fenced in 3 bed 1 bath home on an excellent lot! New plumbing, new gas furnace. HUGE bathroom with double shower. Great opportunity for investors!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,456
Status:
Active
MLS#:
1303280
Type:
Single Family
Lot size:
3 Acres
Year built:
2007
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

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 orchard! Buyer/Buyers agent to verify all information

Beds:
4
Baths:
2.00
Sq.Ft.:
1,568
Status:
Active
MLS#:
25011716
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.41 Acres
Year built:
2020
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
View additional info

ADDITIONAL INFORMATION

Great property for anyone at any stage in life. Move in ready! 4 bedroom, 2 bathroom manufactured home built in 2020 sitting on 0.41 of an acre, per public records. Easy access to shopping, 10 minutes to LMU's main campus in Harrogate TN.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,040
Status:
Active
MLS#:
25011542
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.31 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
View additional info

ADDITIONAL INFORMATION

This 1040 SqFt modular home could be a great starter home. Its a two bedroom with a bonus room that could be used for a third bedroom. This property has a nice level yard and is fenced in in the back with a outside building thats been finished out for an office with heat and ac.

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.:
996
Status:
Active
MLS#:
1302435
Type:
Single Family
Lot size:
3.89 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Realty Network, Inc 423-869-3121
View additional info

ADDITIONAL INFORMATION

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 living or a peaceful retreat. Recent updates include a brand new heating and air conditioning system with a 10-year warranty, and a new refrigerator with a 3-year Lowe's warranty—ensuring comfort and reliability for years to come. The roof is approximately 10 years old, and the crawl space features a moisture barrier for added protection and peace of mind. Enjoy morning coffee or evening sunsets while soaking in the natural beauty that surrounds you. Located just minutes from area lakes and endless opportunities for hiking, fishing, and outdoor adventure, this home offers the best of both worlds—rural charm and modern convenience. Don't miss this opportunity to own your own slice of mountain-view paradise!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,296
Status:
Active
MLS#:
1302185
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

This Property comes with Parcel ID:057-34-00-036.00 also. Which consist of around 3 acres and 1 livable structure of about 1000 sq foot. It is located just mins away from downtown Middlesboro and the LMU Campus.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
1301589
Type:
Single Family
Lot size:
0.4 Acres
Year built:
1996
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

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.

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:
3
Baths:
2.00
Sq.Ft.:
648
Status:
Active
MLS#:
1301207
Type:
Single Family
Lot size:
0.2 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

Check out this charming 3-bedroom, 2-bath home featuring a spacious covered porch, updated master bathroom, fenced backyard, and beautiful tile and hardwood flooring throughout. Conveniently located just minutes from historic downtown Middlesboro, KY.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,040
Status:
Active
MLS#:
1301087
Type:
Single Family
Lot size:
0.27 Acres
Year built:
2012
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

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. This year the crawlspace was professionally encapsulated with a transferable lifetime warranty and includes a commercial-grade dehumidifier for optimal moisture control. Updated PEX waterlines add peace of mind and efficiency. Outside, you'll find a 10x16 storage shed with an added loft, perfect for additional storage. The private yard creates a peaceful retreat, and the large picture window in the dining room offers the ideal spot for bird watching. This home is in excellent condition—stylish, updated, and completely move-in ready. Located just minutes from town, Lincoln Memorial University, Southeast College, the hospital, shops, and restaurants. Don't miss this one—it's truly a must-see!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,270
Status:
Active
MLS#:
1300789
Type:
Single Family
Subdivision:
Vista Venado
Lot size:
0.4 Acres
Year built:
2010
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

In the beautiful hills of Vista Venado lies the gorgeous 3 bedroom and 2 bath 900 Twin Fawn Trail. From the trey ceilings to the marble flooring, to the jetted tub this home is breathtaking! Your HOA fee of $20/month gives you unlimited water with very light restrictions. Massive patio for all your entertaining. Brand new french drain system. Quiet neighborhood perfect for evening walks. Let's go see today!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,044
Status:
Active
MLS#:
25009529
Type:
Single Family
Subdivision:
Rural
Lot size:
0.2 Acres
Year built:
1977
A broker reciprocity listing Courtesy: Huddleston Real Estate 606-528-5250
View additional info

ADDITIONAL INFORMATION

Charming Fixer-Upper: 3 Bed, 2 Bath Opportunity Awaits! This three-bedroom, two-bathroom diamond in the rough is brimming with potential and is ready for your personal touch. Nestled in a desirable neighborhood, this home offers a fantastic layout and ample space for family living. Endless Potential: Whether you're an investor looking for a project or a homeowner eager to create your dream space, this fixer-upper offers incredible potential. With some renovations and updates, you can transform this house into your ideal home. Don't miss out on this incredible opportunity to invest in a property that you can make your own. Schedule a showing today!

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:
4
Baths:
3.00
Sq.Ft.:
2,020
Status:
Active
MLS#:
1298148
Type:
Single Family
Subdivision:
Southwood Estates
Lot size:
0.45 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

Beautiful, split foyer home with 4 bedrooms and 2 ½ bathrooms. The upstairs features a kitchen with plenty of space for storage, updated appliances, and tile floors. This home allows the natural light to shine through in all the rooms. The dining room and living room are open for entertainment or a growing family. The primary bedroom and bath are on the main floor. The guest bath is spacious with a tub and shower combo. The main floor bedrooms are spacious with walk in closets. There is a bonus room downstairs that has been converted to a bedroom, a laundry room, and a half bath. From the downstairs, you can walk right into the 2 car garage. Whether you are a first time home owner or a family needing more space, this home maybe just what you been looking for.

Beds:
3
Baths:
1.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
1297570
Type:
Single Family
Lot size:
0.3 Acres
Year built:
1918
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

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

Beds:
2
Baths:
1.00
Sq.Ft.:
1,236
Status:
Active
MLS#:
25006450
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.18 Acres
Year built:
1955
A broker reciprocity listing Courtesy: Action Realty 606-248-7653
View additional info

ADDITIONAL INFORMATION

Welcome to 112 Cumberland Ave, Middlesboro, KY—a delightful 2-bedroom, 1-bath home boasting 1,236 square feet of comfortable living space! Perfectly situated in a prime, convenient location, this charming residence is just steps away from Middlesboro's best shopping, dining, and entertainment. With the option for an additional bedroom, this home offers flexibility to suit your needs, whether for a growing family, home office, or guest space. Move-in ready and brimming with potential.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,989
Status:
Active
MLS#:
1295519
Type:
Single Family
Lot size:
0.75 Acres
Year built:
1967
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

Looking for a place to call home? Don't miss out on this one! This 3 bedroom, 2 bath brick ranch is spacious and sits on a large lot within the city limits. Lovingly cared for, you can feel the memories made in this home and imagine the new ones you can make with your family. Even the basketball goal next to the detached garage will bring back memories of summer nights playing ball in the back while the sun sets and the street lights come on....Schedule a tour today--you deserve a house that you can make into a home.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,989
Status:
Active
MLS#:
25006370
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.75 Acres
Year built:
1967
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
View additional info

ADDITIONAL INFORMATION

: Looking for a place to call home? Don't miss out on this one! This 3 bedroom, 2 bath brick ranch is spacious and sits on a large lot within the city limits. Lovingly cared for, you can feel the memories made in this home and imagine the new ones you can make with your family. Even the basketball goal next to the detached garage will bring back memories of summer nights playing ball in the back while the sun sets and the street lights come on....Schedule a tour today--you deserve a house that you can make into a home.

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:
1.00
Sq.Ft.:
776
Status:
Active
MLS#:
1293374
Type:
Single Family
Lot size:
13.73 Acres
Year built:
1918
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

Unbelievable find in the city limits of Middlesboro. 13.7 acres inside the city limits with city water and public sewer. Property has two different homes and a barn. The address of the second home is 501 South 35th. street. Both homes need some TLC but are solid constructions. This property has potential for a small farm or development with several other home sites. Come take a look! Buyer to verify all information.

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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 2025 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




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

    $186,000
    16.7%
    change since last quarter
  • # Active listings

    55
    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