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

35 Properties Found

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Beds:
3
Baths:
1.00
Sq.Ft.:
1,100
Status:
NEW LISTING
MLS#:
1301631
Type:
Single Family
Lot size:
0.3 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Step into investing with this 3 bedroom 1 bath with new roof and hvac. Hardwood flooring and a wood fireplace. Currently an income producing property! Call me to see!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,900
Status:
NEW LISTING
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:
NEW LISTING
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:
NEW LISTING
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:
NEW LISTING
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:
NEW LISTING
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.:
1,040
Status:
Active
MLS#:
25009885
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.27 Acres
Year built:
2012
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
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.:
n/a
Status:
Active
MLS#:
25009529
Type:
Single Family
Subdivision:
Rural
Lot size:
0.2 Acres
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:
2
Baths:
1.00
Sq.Ft.:
850
Status:
Active
MLS#:
25009132
Type:
Single Family
Subdivision:
Rural
Lot size:
0.28 Acres
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
View additional info

ADDITIONAL INFORMATION

Are you ready for your very own home? Come check out this adorable, remodeled, cottage style home featuring 2 bedrooms and 1 cozy bathroom. Pretty kitchen and nice living room. Bell County Ky PVA measuring tool shows the lot size is 0.279 of an acre. Nice wide driveway and covered parking area. This space would make a nice outdoor sitting area. Level yard, close to shopping and 10 minutes to LMU's main campus, 15 minutes to the Vet school. Schedule your appointment to view this lovely cottage!

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:
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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,408
Status:
Active
MLS#:
1292147
Type:
Single Family
Lot size:
0.33 Acres
Year built:
1971
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

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. It has a galley kitchen with a formal dining room. There is a den that extends from the dining area for more space for entertaining. This home also offers a one car attached garage and additional parking in the driveway. There is a guest bath with a tub and shower. The main bedroom has a full bath as well with a shower. This home is cozy with 1404 square feet. Only minutes away from shopping, groceries, gas stations, and other amenities.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,064
Status:
Active
MLS#:
25004051
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.5 Acres
Year built:
1960
A broker reciprocity listing Courtesy: Shawn Rogers Realty, Inc 606-215-3138
View additional info

ADDITIONAL INFORMATION

Motivated sellers, say 'bring us an offer!' All debris in and around home to be removed prior to closing. Solidly built home with some updates, including all plumbing updated, some new windows installed, some new windows purchased and to remain for new owner. 2 bedrooms plus a bonus room that can be used as a bedroom, just doesn't have a closet. Large bathroom, updated kitchen, and a wide hallway. Large yard, completely fenced, and entirely flat. NOT in flood zone 5-6 year old water heater. City sewer & Trash pickup. Close to 2 colleges, hospital, and stores.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,974
Status:
Active
MLS#:
1291613
Type:
Single Family
Subdivision:
Ambleside
Lot size:
0.6 Acres
Year built:
1984
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

This newly renovated 3 bed ,2.5 bath, home is a must see for anyone. The spacious back patio is perfect for entertaining complete with a beautiful hot tub building. This home has 2 car garage ,new flooring, counter tops, appliances and much much more. Located just outside the city Limits but just mins away from 25E and downtown Middlesboro.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,016
Status:
Active
MLS#:
1288966
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
View additional info

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:
2
Baths:
1.00
Sq.Ft.:
1,204
Status:
Active
MLS#:
1287980
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1930
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

Beds:
2
Baths:
1.00
Sq.Ft.:
1,008
Status:
Active
MLS#:
1288008
Type:
Single Family
Lot size:
0.04 Acres
Year built:
1924
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Great opportunity for investors! Cabin style home, newly remodeled, new paint, new flooring, new split units for cheaper electricity bills with a massive garage, on an OVERSIZED LOT. PERFECT opportunity for an airbnb with plenty of parking for trailers and side by sides with access to trailheads! Lets go see it!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,349
Status:
Active
MLS#:
1287518
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

This adorable spacious three-bedroom, four-bathroom home offers plenty of living space for you and your family. Enjoy the inground pool, a pool room with a shower, and an outdoor bathroom. The screened-in porch includes a large daybed swing, while the natural gas grilling area is perfect for entertaining. The property also boasts a storage shed, privacy fencing, and hardwood flooring throughout. The primary bedroom includes an ensuite bathroom with a luxurious jacuzzi-style bathtub. Additional highlights include a one-car garage with a workshop area and extra storage throughout the home. Located just minutes from downtown historic Middlesboro, KY, you'll have easy access to a variety of shops and restaurants.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,439
Status:
Active
MLS#:
24026218
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.43 Acres
Year built:
2011
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
View additional info

ADDITIONAL INFORMATION

Really nice manufactured home ready to move in with several improvements. The owner has put new flooring down and painted the interior. This home is minutes from downtown yet is very private. There's three bedrooms and two baths. The large den has a fireplace and plenty of room for the whole family.

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.

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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 Real Estate

Middlesboro is located in Kentucky.

Middlesboro Weather

Middlesboro Map

Middlesboro Real Estate Market Conditions

  • Median sales price

    $87,000
    -3276800%
    change since last quarter
  • # Active listings

    53
    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