Middlesboro KY Real Estate & Homes for Sale

40 Properties Found

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
NEW LISTING
MLS#:
1357060
Type:
Single Family
Lot size:
1.25 Acres
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

Welcome home to this beautifully updated 3-bedroom, 2-bathroom property offering approximately 1,600 square feet of comfortable living space. Recent improvements include a new roof, new HVAC system, new laminate flooring, and an updated kitchen featuring new cabinets and granite countertops. Outside, enjoy a large yard with beautiful mountain views, providing plenty of space for outdoor activities, entertaining, gardening, or simply relaxing and taking in the scenery. With its spacious layout, modern updates, and picturesque surroundings, this home offers a wonderful combination of comfort, style, and peaceful outdoor living.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,488
Status:
NEW LISTING
MLS#:
1356915
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Beautifully maintained with modern updates, lots of room to spread out, and an unbeatable location, this home is ready to raise its next family. Featuring 4 bedrooms 2.5 baths, gorgeous shiny kitchen with sliding glass doors taking you to the deck outside, this home would make a fabulous entertaining home. A formal living room with great natural lighting. A rock fireplace surrounded by a den worthy of all the days and all the naps. Located a stone's throw away from Middlesboro Schools, restaurants, hospital and the best 4-wheeling in our area, with LMU being only 6 miles away, Talk about convenient!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,386
Status:
NEW LISTING
MLS#:
1356828
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1992
A broker reciprocity listing Courtesy: Heartland Real Estate, LLC 423-869-0075
View additional info

ADDITIONAL INFORMATION

You just gotta see how cute this place is in person for yourself! Completely furnished and move-in ready, you will find this 3 bdrm 2 bath home with covered front porch and carport. You will LOVE this huge back deck, big enough for a ping pong table, bring your hot tub, add a big screen TV for the ultimate entertaining and game watching pad!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,200
Status:
NEW LISTING
MLS#:
1356645
Type:
Single Family
Lot size:
2 Acres
Year built:
1939
A broker reciprocity listing Courtesy: Backwoods Realty & Development 423-419-5742
View additional info

ADDITIONAL INFORMATION

Enjoy a peaceful country setting just minutes from downtown Middlesboro! Situated on approximately 2 acres, this rustic 3-bedroom, 1-bath cabin combines charm, usable outdoor space, and convenient access to shopping, dining, and medical facilities. Inside, hardwood floors complement the home's warm character, while the updated kitchen features stainless steel appliances. A pellet stove provides supplemental heat, and the washer and dryer are included. Additional features include a metal roof, covered front porch, mature trees, and a spacious, level backyard with room for gardening or outdoor enjoyment. A 1-car garage, covered carport, workshop, and storage building provide ample space for parking, tools, and hobbies. The unfinished basement offers additional storage. Bring your personal touches and make this country retreat your own!

Beds:
2
Baths:
1.00
Sq.Ft.:
700
Status:
NEW LISTING
MLS#:
26026368
Type:
Single Family
Lot size:
0.27 Acres
Year built:
1942
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

TWO HOMES FOR THE PRICE OF ONE!!! live in the recently remodeled 2 bed /1 bath homes while you renovate the other home on this parcel that has already been gutted for the new owner to start working on it! This is a great opportunity for real estate investors or those looking to get into rental properties! LMU (Main Campus) being just 15 minutes brings a huge demand for rental properties just like this! Less than 5 minutes to a hospital and downtown Middlesboro, also minutes away from National & State Parks! Don't miss out on this opportunity! Schedule your showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,968
Status:
NEW LISTING
MLS#:
1356392
Type:
Single Family
Lot size:
1.02 Acres
Year built:
1937
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

Beautiful historic home in the heart of Middlesboro. Within walking distance of Fords Wood Park and downtown Middlesboro, this home is an undiscovered gem. With 4 bedrooms and 2 1/2 bathrooms, this exceptional home has lots of room for a growing family. The large unfinished basement has lots of room for storage and has the washer and dryer (which stays with the home). Every inch of this home was built for comfort and sophisticated living. Lovingly cared for over the years, you don't want to miss your personal tour of this beauty. Come let us show you your new home!

Beds:
2
Baths:
1.00
Sq.Ft.:
876
Status:
NEW LISTING
MLS#:
1356312
Type:
Single Family
Lot size:
0.3 Acres
Year built:
1952
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

Completely remodeled and move-in ready! This charming 2-bedroom, 1-bath home offers a fresh, updated interior with new laminate flooring and carpet throughout, along with a beautifully remodeled kitchen. Recent improvements include a new roof, siding, and fresh paint, providing peace of mind and modern appeal. Situated on a level lot in a great location, the property also features a detached one-car garage for convenient parking and additional storage. A wonderful opportunity for anyone looking for a low maintenance home.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,542
Status:
Active
MLS#:
1355491
Type:
Single Family
Lot size:
4.4 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

This gorgeous cape cod home sits on 4.4 acres with deer visiting often. This home has 5 bedrooms, 2.5 bathrooms, formal living room with fireplace, family room (could be used as formal dining room) a second fireplace in the sunroom, amazing kitchen with island, the kitchen counter tops are granite, the stainless-steel appliances stay, which include double wall ovens, gas range with gas oven (natural gas), side by side refrigerator and dishwasher. Island has a breakfast bar. The kitchen extends into the dining area. The master suite is on the main level with tray ceiling. There is a half bathroom on the main floor for guests. The beautiful staircase leads to 4 bedrooms and one full bathroom upstairs. The laundry room also has a mop sink and is off from the 2-car heated garage. There is a laundry chute in this home, main floor heating is natural gas/heat pump/air, the upstairs has electric heat pump/air, high quality bamboo flooring, crown molding, double pane windows, natural gas, public water, internet available, lots of storage, 2-50 gallon water heaters, new shingle roof installed October 2025, home comes with extra-large storage shed, awesome views from this property. The 12 X 32 detached garage/storage shed has a roll up door for easy access. This home is conveniently located in Middlesboro in the beautiful Vista Venado Subdivision, one mile to shopping and dining, and to hospital.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,168
Status:
Active
MLS#:
26025315
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1984
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

Welcome to 8 Castleford Way located in the beautiful subdivision Ambleside. This home is also conveniently located near National & state parks. This home includes a screened back porch and fenced backyard. Master Bed / Bath on main level of the home including the living room, kitchen, and laundry! Call or text today to schedule your showing!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,966
Status:
Active
MLS#:
26025309
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.12 Acres
Year built:
1898
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
View additional info

ADDITIONAL INFORMATION

Beds:
3
Baths:
1.00
Sq.Ft.:
1,404
Status:
Active
MLS#:
1354572
Type:
Single Family
Lot size:
0.16 Acres
Year built:
1950
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

Great little 3 bedroom house in a wonderful neighborhood in historic Middlesboro, Ky. Very convenient to downtown and Lincoln Memorial university. Fenced in back yard and large eat in kitchen make this a good option for just about anyone. Would also make a great opportunity for someone wanting to purchase a rental property.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,016
Status:
Active
MLS#:
1355383
Type:
Single Family
Subdivision:
VISTA VENADO PHASE III
Lot size:
2.74 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Backwoods Realty & Development 423-419-5742
View additional info

ADDITIONAL INFORMATION

Welcome to 2010 Twin Fawn Trail in the beautiful mountains of the New phase III of Vista Venado!!! This barndominium style NEW BUILT home sits on 2.74 A of beautiful land with breathtaking views for as far as you can see. This beauty offers 2016 sq ft of open-concept living space, perfect for every day living or entertaining. With touches of class in every room, this 3 bedroom 2 bathroom has a detached 2 car oversized garage with a bonus room over top!!This house has water provided by VV SO NO water bill comes with this house. With LMU minutes away and shopping just outside your front door this front porch is one you wont want to miss. Truly the opportunity of a lifetime!!! Call Today

Beds:
3
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
1354108
Type:
Single Family
Subdivision:
Hickman
Lot size:
0.4 Acres
Year built:
2002
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

3 bed, 2 bath ranch style home located in a great neighborhood in the historic town of Middlesboro, Ky. Nice level lot with a fenced in back yard for your pets and privacy where you can enjoy the mountain views. Just minutes from the hospital and shopping as well as Lincoln Memorial University.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,480
Status:
Active
MLS#:
1355810
Type:
Single Family
Lot size:
0.43 Acres
Year built:
1964
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

1480 sf spilt level home at 1102 W Chester Ave. This home is within walking distance to downtown, schools and hospital. It has three bedrooms and one bath, with a large den with a beautiful fireplace. The eat-in kitchen is right off the den area. There is a covered, screened-in porch just off the dining area. Lots of room for a growing family--don't let someone else take advantage of this opportunity!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,260
Status:
Active
MLS#:
1353618
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1956
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

This brick ranch style home has 3 bedrooms, 2 bathrooms, living room has a fireplace which adds beauty but is inoperable. The kitchen is spacious with lots of kitchen cabinets, pantry and a nice spacious laundry room. This property is nice and level and includes a paved driveway, storage shed in back yard. Home has a heat pump, internet available, nice double pane windows, city water and city sewer, home is conveniently located, close to hospital, shopping and LMU in Harrogate.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,352
Status:
Active
MLS#:
26022968
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.5 Acres
Year built:
2022
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
View additional info

ADDITIONAL INFORMATION

209 S. 19th Street, Middlesboro, KY 40965 Beautiful 2022 manufactured home offering approximately 1,352 sq. ft. of comfortable living space with 3 bedrooms and 2 bathrooms. The home is situated in a private setting while still conveniently located within town. Features include city utilities and a concrete block foundation. The PVA reflects approximately 0.50 acre; buyer to verify acreage and all property information. A great opportunity for buyers looking for a newer home with convenient in-town access and a private feel. Schedule your showing today

Beds:
4
Baths:
2.00
Sq.Ft.:
1,544
Status:
Active
MLS#:
1352799
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Isn't she lovely?! Located right in the middle of Middlesboro Ky. 4 bedroom 2 bath home with a beautiful kitchen! Yard space for all the things on a quiet street. Excellent home to check out today!

Beds:
2
Baths:
1.00
Sq.Ft.:
936
Status:
Active
MLS#:
1352038
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

If you've been looking for a project here it is! Handyman special, would make a super cute flip! Or at this price you can buy it for just the land! Please do not go without an agent. Buyer/Buyers agent to confirm all information

Beds:
5
Baths:
2.00
Sq.Ft.:
2,664
Status:
Active
MLS#:
1350786
Type:
Single Family
Subdivision:
Southwood Estates
Lot size:
0.43 Acres
Year built:
1996
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

Looking for a HOME and not just another house? This is it! With 5 bedrooms, 2 baths, a bonus room to use as a den or rec room, and even special features like a light equipped with a built-in blue tooth speaker in the master bathroom. This home was built with 'family living' in mind. The kitchen is equipped with a new island/breakfast bar that seats six and blends seamlessly with the dining area. With lots of room inside plus a pool with nice deck and patio in the back, you have a great blend of inside and outside living. Put this one on your must-see list--it may be the last one you have to look at to find your perfect home.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,032
Status:
Active
MLS#:
1350232
Type:
Single Family
Lot size:
0.48 Acres
Year built:
1930
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also has a fill-pot feature next to the stove. The kitchen's backdown is where you will , find a covered deck--perfect for entertaining family and friends. Situated on a quiet dead-end street, this property combines the convenience of downtown living with the privacy and tranquility you've been looking for. The home offers a flexible floor plan with two bedrooms on the main level with cedar lined closets and two bedrooms upstairs. The foyer entryway offers a closet and space for coats and shoes to conveniently stored. A spacious living room with a fireplace creates a warm gathering space, while the formal dining room and vented sunroom provide additional areas for relaxation and entertaining. The basement includes a two-car garage, workshop, and ample storage space, offering plenty of room for hobbies and organization. Schedule an appointment TODAY!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,612
Status:
Active
MLS#:
1348714
Type:
Single Family
Subdivision:
Ambleside
Lot size:
0.29 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Fathom Realty TN LLC 888-455-6040
View additional info

ADDITIONAL INFORMATION

Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
1348099
Type:
Single Family
Lot size:
0.24 Acres
Year built:
1918
A broker reciprocity listing Courtesy: Backwoods Realty & Development 423-419-5742
View additional info

ADDITIONAL INFORMATION

This beautiful brick has touches of class to enjoy for a lifetime. With all the beauty of her old style from big rooms, original cherry doors 9 1/2 foot ceilings and original hardwood floors. A fabulous front porch, a 2 car garage with a spacious and playful backyard. On the inside you will enjoy a kitchen that sparkles white with stainless steel appliances and a grand island for cooking and entertaining. The owner's suite hosts a 5-piece bathroom with a double vanity. Move in ready!!!! This house is a once in a lifetime purchase.!!!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
1346436
Type:
Single Family
Lot size:
0.4 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Cute as a button! This adorable cottage style home would make an excellent choice for a first home! Come see today!

Beds:
2
Baths:
1.00
Sq.Ft.:
920
Status:
Active
MLS#:
1345724
Type:
Single Family
Lot size:
0.3 Acres
Year built:
1928
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

Two bedroom, 1 bath home located in a great neighborhood. Large bedrooms, living room, and kitchen. Don't miss the opportunity to make this home your own.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,154
Status:
Active
MLS#:
26013326
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.76 Acres
Year built:
1995
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
View additional info

ADDITIONAL INFORMATION

Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, space, and convenience at 116 Edgewood Road in Middlesboro. This spacious 2,154-square-foot home offers 3 bedrooms and 2 full bathrooms, nestled on approximately 0.75 acres while remaining within walking distance of downtown amenities. Step inside to find a versatile floor plan with multiple living areas and flexible spaces that can easily accommodate additional bedrooms, home offices, recreation rooms, or multi-generational living. The home's unique layout even presents the potential for conversion into separate living quarters, making it an attractive opportunity for homeowners and investors alike. Enjoy beautiful mountain, city, and park views from your property while experiencing the peace and privacy of a wooded setting where local wildlife is often seen. The home features central heating and cooling, a detached garage, ample parking, durable metal roofing, and city utilities. Recent improvements have already been completed, providing a solid foundation for the next owner to personalize and make their own. Whether you're searching for a spacious family home, an investment opportunity, or a property with room to grow, this unique Middlesboro residence offers exceptional value. Property Highlights 3 Bedrooms 2 Bathrooms 2,154 Sq. Ft. of Living Space Approximately 0.75 Acres Detached Garage & Additional Parking Mountain, City & Park Views Central Heating & Air Conditioning Flexible Layout with Multi-Use Spaces Potential for Multi-Family or Income-Producing Use Convenient Access to Downtown Middlesboro Don't miss this rare opportunity to own a spacious home with privacy, views, and unlimited potential in the heart of Middlesboro. Schedule your private showing today!

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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 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

    $164,800
    -3276800%
    change since last quarter
  • # Active listings

    60
    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