Middlesboro KY Real Estate & Homes for Sale

39 Properties Found

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Beds:
4
Baths:
2.00
Sq.Ft.:
995
Status:
NEW LISTING
MLS#:
26001939
Type:
Single Family
Subdivision:
Rural
Lot size:
0.21 Acres
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

Beds:
3
Baths:
2.00
Sq.Ft.:
1,238
Status:
NEW LISTING
MLS#:
1327952
Type:
Single Family
Lot size:
0.24 Acres
Year built:
1958
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Real 606-248-4932
View additional info

ADDITIONAL INFORMATION

Have you been looking for a cozy home on a quiet, family-friendly street to raise your family? You need to put this one on your ''must see'' list. Newly remodeled with new floors, new lights, new windows, new doors, and new fencing! With 3 bedrooms and 1 and 1/2 baths, this home is the perfect starter home. The fenced in yard is flat with lots of room for kids--don't miss out on this one. Schedule an appointment today!

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
639539
Type:
Single Family
Year built:
2009
A broker reciprocity listing Courtesy: RE/MAX Preferred Group Sarah Richards
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ADDITIONAL INFORMATION

3-bedroom, 2-bath home situated on a spacious 0.66-acre lot, offering the perfect blend of privacy and convenience. Located just minutes from all the amenities Middlesboro has to offer, this property provides easy access to shopping, dining, schools, and highways. Enjoy the generous outdoor space with plenty of room for gardening, entertaining, or future improvements. A great opportunity for comfortable living with the feel of country space right in town. Schedule your showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,832
Status:
NEW LISTING
MLS#:
1327623
Type:
Single Family
Lot size:
0.23 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

Beautiful move-in ready renovated Property. Home features four bedrooms 2 1/2 baths. kitchen features soft closed custom cabinets, kitchen island and stainless steel appliances. Laminated floors throughout the home. Enjoy your coffee on screened in back porch. Storage building for your tools, lawnmower etc..Property is located within minutes from Lmu main campus, Shopping, restaurants, and hospital. No flood insurance needed!!

Beds:
2
Baths:
1.00
Sq.Ft.:
952
Status:
Active
MLS#:
1327412
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
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ADDITIONAL INFORMATION

I love a good sunroom, don't you? Recently updated 2-bedroom 1 bath home is move in ready! Extra-large fenced in level yard with a garage perfect for tinkering! Electric and plumbing included in the updates. You won't find a home like this in this price range! Come see for yourself!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,240
Status:
Active
MLS#:
26001413
Type:
Single Family
Subdivision:
Downtown
Lot size:
0.38 Acres
Year built:
1950
A broker reciprocity listing Courtesy: Century 21 Pinnacle 859-623-1900
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ADDITIONAL INFORMATION

Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

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
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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.:
1,230
Status:
Active
MLS#:
26000523
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.18 Acres
Year built:
1965
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
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ADDITIONAL INFORMATION

Cottage style, 3 bedroom 2 bathroom home with chain link fencing in the city limits of Middlesboro KY. PVA records show 0.18 of an acre, city water, city sewer. Home needs some work but would make a great permanent home or use as a rental. Close to LMU and all the beauty Southeastern KY offers! 5 minutes to the Cumberland Gap National Park, shopping and more! Buyer to verify all property information.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
1325838
Type:
Single Family
Lot size:
0.24 Acres
Year built:
1955
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
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ADDITIONAL INFORMATION

This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment behind the house. The apartment is open space with 1 bdrm and a full bath. Apartment is rented. Metal roof, vinyl siding and windows, hardwood, laminate & tile floors. Privacy and a chain link fenced in back yard, 2 storage buildings, level back yard.

Beds:
1
Baths:
1.00
Sq.Ft.:
800
Status:
Active
MLS#:
1324643
Type:
Single Family
Lot size:
0.19 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,100
Status:
Active
MLS#:
25508059
Type:
Single Family
Subdivision:
Rural
Lot size:
0.4 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Kentucky Land and Home 859-619-9970
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ADDITIONAL INFORMATION

Renovated and truly move in ready! Proudly owned by just one owner, this home shows exceptional care from the moment you step inside. Fresh paint, new luxury vinyl and laminate flooring, and thoughtful updates throughout create a clean, modern feel. The kitchen shines with new granite countertops, an updated sink and faucet, and finishes that pair beautifully with the existing cabinetry. Down the hall, the bathroom has been tastefully updated as well. Concerned about major components? You can relax here. The HVAC is only 5 years old (5 yr warranty left), the water heater is new, and the roof was replaced in 2013. Gutter guards have been added for easy maintenance, and even the backyard shed features brand new interior wood. With the washer and dryer included all that's left to do is move in and start living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,612
Status:
Active
MLS#:
1323746
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
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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:
5
Baths:
3.00
Sq.Ft.:
2,542
Status:
Active
MLS#:
1323538
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, central heat and 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, country setting. This home is in the county but is minutes to hospital and shopping.

Beds:
3
Baths:
2.00
Sq.Ft.:
960
Status:
Active
MLS#:
1323130
Type:
Single Family
Lot size:
0.32 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Turn Key Realty 423-869-5111
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ADDITIONAL INFORMATION

This property is now under auction terms. All Bids must be submitted during the auction via the property service listing page at https://www.servicelinkauction.com/property-details/13-duncan-ln-middlesboro-40965-ky-united-states-trd. This sale is subject to a 5% or $2,500 minimum buyer s premium pursuant to the auction Terms & Conditions. All bids will be subject to seller approval (minimums may apply). This property is now under auction terms. All Bids must be submitted during the auction via the property's listing page at www.servicelinkauction.com. This sale is subject to a 5% or $2,500 minimum buyer's premium pursuant to the auction Terms & Conditions. All bids will be subject to seller approval (minimums may apply)

Beds:
3
Baths:
2.00
Sq.Ft.:
934
Status:
Active
MLS#:
25506029
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.49 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
View additional info

ADDITIONAL INFORMATION

Newly Remodeled, move-in ready home. This home is nestled in the heart of Middlesboro on a .489 acre lot. This home has 3 bedrooms and 2 newly renovated bathrooms. The washer and dryer will stay with home. This quiet cozy home has a log cabin look with a large covered front porch. I also has a carport or breezeway to get to the garage. This home also has a fenced in chicken coop. All the amenities are easily accessible.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
1319805
Type:
Single Family
Lot size:
0.36 Acres
Year built:
1996
A broker reciprocity listing Courtesy: Mountain Realty 865-345-5050
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ADDITIONAL INFORMATION

Charming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beautifully maintained 3-bedroom, 2-bathroom home located close to shopping, restaurants, schools, and parks — everything you need is just minutes away! Inside, you'll find a warm and inviting layout featuring hardwood and vinyl flooring, offering both style and durability. The spacious living areas are perfect for relaxing or entertaining family and friends. Step outside to enjoy a generous yard with two outdoor storage sheds, providing plenty of room for tools, hobbies, or extra storage. Whether you're a first-time buyer, growing family, or possibly downsizing, this home has something for everyone. Don't miss this great opportunity—schedule your showing today! Buyer to verify taxes, square feet, and acreage.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,375
Status:
Active
MLS#:
1319571
Type:
Single Family
Lot size:
0.4 Acres
Year built:
2022
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Beautiful and practically brand new! This 3 bedroom 2 bath home is perfect for a sweet family! From the ground up, this home is only 3 years old. All appliances included, very well taken care of. You HAVE to see this one!!

Beds:
3
Baths:
1.00
Sq.Ft.:
792
Status:
Active
MLS#:
25504336
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.09 Acres
Year built:
1991
A broker reciprocity listing Courtesy: Coldwell Banker Bisceglia Realty & Auction Co 606-248-4932
View additional info

ADDITIONAL INFORMATION

This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and one bath with a large kitchen and large living room. This home needs some attention but has a lot of potential. The downstairs could be used as apartment or extra living space. There is another home on the property and might be possible to repair.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,088
Status:
Active
MLS#:
25502716
Type:
Single Family
Subdivision:
City Limits
Lot size:
1 Acres
Year built:
1945
A broker reciprocity listing Courtesy: Black Diamond Realty 606-552-0879
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ADDITIONAL INFORMATION

Cozy 3 bedroom, 1 bathroom home sitting on a surveyed acre with detached 1 car garage that has room for a workshop, storage, crafting etc. The yard is level with a gentle slope on the front edge of the property. There is right of way access to the creek as well. Inside the home, you'll find a large living room and 3 nice sized bedrooms. The kitchen is adequate as well as the dining area. Front and back covered porches, perfect for relaxing. Walking distance to Yellowcreek Elementary, Middlesboro High School and the Middle School. About a mile and half to Middlesboro ARH hospital. Call for a showing!

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:
3
Baths:
2.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
1316511
Type:
Single Family
Lot size:
0.14 Acres
Year built:
2024
A broker reciprocity listing Courtesy: Fathom Realty TN LLC 888-455-6040
View additional info

ADDITIONAL INFORMATION

New custom built home in the heart of Middlesboro. This home features three (3) bedrooms and two (2) bathrooms. Walking up to the home you are immediately greeted with a covered front porch constructed using composite decking and adorned with large columns. As you enter this home you are met with a spacious living room/kitchen/dinning room designed in an open concept style. Kitchen is complete with custom cabinets and granite countertops. As you continue down the hall way you will find two (2) bedrooms and a full bathroom along with a utility room with washer/dryer hook up. The Master Suite is at he end of the hallway and is complete with a large walk-in closet and a walk-in shower. Bathrooms complete with built-in blue tooth speakers. LED lighting throughout the home. In the fenced-in back yard there is a 16' x 20' storage shed on a concrete slab. This home is minutes from downtown Middlesboro, hospital, Walmart and LMU.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,856
Status:
Active
MLS#:
1316259
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1987
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

🏡 The Château on the Creek - Home for Sale in Middlesboro, KY (Bell County) Welcome to The Château on the Creek, a beautifully updated 3-bedroom, 2.5-bathroom home in Middlesboro, KY (Bell County). Offering 1,856 sq. ft. of living space, a detached garage, and a backyard oasis, this move-in ready property combines timeless charm with modern updates. The exterior has been completely redone within the last 2 years, featuring stone accents, new vinyl siding, and custom cedar shutters for a true craftsman-style look and stunning curb appeal. Inside, you'll enjoy soaring cathedral ceilings, a cozy stone fireplace, and gleaming hardwood and tile flooring. The kitchen is a showpiece with floor-to-ceiling custom cabinetry, brand-new appliances, and a designer backsplash. The primary suite (over 300 sq. ft.) includes custom cabinetry, granite counters, and an updated en-suite bath. Step outside to your private retreat: a custom pool deck with above-ground pool, perfect for entertaining or relaxing. The large backyard includes multiple storage buildings with electricity—one ideal for a home office or workshop. A 672 sq. ft. detached garage provides ample storage and parking. Covered front and back porches complete this craftsman-inspired home. 🔑 Key Features: 3 bedrooms, 2.5 bathrooms 1,856 sq. ft. living space 672 sq. ft. detached garage Exterior fully redone in last 2 years with stone accents, new siding, cedar shutters, and craftsman details Cathedral ceilings & stone fireplace New kitchen appliances, backsplash & faucet Primary suite with custom cabinetry & granite counters Hardwood & tile flooring throughout Above-ground pool with new custom deck Multiple storage buildings (home office potential) Covered front & back porches ✨ Don't miss your chance to own The Château on the Creek — an updated, move-in ready Bell County home with character, curb appeal, and plenty of space to enjoy

Beds:
5
Baths:
3.00
Sq.Ft.:
2,250
Status:
Active
MLS#:
1315952
Type:
Single Family
Lot size:
0.3 Acres
Year built:
1942
A broker reciprocity listing Courtesy: REMAX PROFESSIONAL'S 423-869-3000
View additional info

ADDITIONAL INFORMATION

This home has been brought back beyond its Glory!! Completely remodeled from the sub flooring to the roof. This 5 bds, 3 full baths, new kitchen w/Quartz counter tops, marble back splash, stainless appliances, new LVP flooring, Breath taking bathrooms, master on the main, 3 bdrms upstairs with a full bath 2 HVAC units. 2 car garage w new garage doors. Also, a fenced in back yard!! NOT IN THE FLOOD ZONE! IT'S A MUST SEE!!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,056
Status:
Active
MLS#:
25503302
Type:
Single Family
Subdivision:
City Limits
Lot size:
0.2 Acres
A broker reciprocity listing Courtesy: Century 21 Virginia Wilder Real Estate 276-861-2023
View additional info

ADDITIONAL INFORMATION

Great potential for a starter home or investment. Does need some work. Close to LMU, Cumberland National Park, Middlesboro Country Club, and local restaurants.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,456
Status:
Active
MLS#:
1315173
Type:
Single Family
Lot size:
0.4 Acres
Year built:
1922
A broker reciprocity listing Courtesy: Realty Group 423-626-6353
View additional info

ADDITIONAL INFORMATION

Super cute house with a great lay out! Fenced in corner lot, excellent outdoor space with oversized garage, a little tlc and this home will shine!

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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.

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 Broker ReciprocitySM Program of the Northern Kentucky Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than the owner of this site are marked with the Broker ReciprocitySM logo or the Broker ReciprocitySM thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers. The broker providing the data believes the data to be correct, but advises interested parties to confirm the data before relying on it in a purchase decision. Copyright 2026 Northern Kentucky Multiple Listing Service, Inc. All rights reserved.



Middlesboro Real Estate

Middlesboro is located in Kentucky.

Middlesboro Weather

Middlesboro Map

Middlesboro Real Estate Market Conditions

  • Median sales price

    $175,000
    -3276800%
    change since last quarter
  • # Active listings

    50
    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