Middlesboro Homes for Sale

Welcome to Middlesboro, Kentucky – a hidden gem nestled in the heart of Bell County! This charming city, rich in history and surrounded by the breathtaking beauty of the Appalachian Mountains, offers a unique blend of small-town charm and modern conveniences. Known for its friendly community and vibrant local culture, Middlesboro is the perfect place for families, retirees, and anyone looking to embrace a peaceful lifestyle.

Middlesboro boasts a variety of recreational opportunities, with nearby parks and outdoor activities that invite residents to explore the stunning natural landscapes. From hiking trails that lead to panoramic views to serene lakes perfect for fishing, the area is a haven for nature lovers. The city's historic downtown area features quaint shops, delightful eateries, and local events that foster a strong sense of community.

For those considering making Middlesboro their home, you'll be pleased to discover a diverse selection of homes for sale. Whether you’re searching for a cozy cottage, a spacious family home, or a charming bungalow, Middlesboro has something to suit every taste and budget. The real estate market here is both accessible and inviting, making it an ideal time to invest in your dream home.

With its rich heritage, welcoming atmosphere, and an array of housing options, Middlesboro is not just a place to live – it’s a place to thrive. Come and experience the warmth of this community for yourself, and find out why so many are choosing to call Middlesboro home!

Newest Middlesboro Homes for Sale

$175,000

4 Beds ⋅ 2 Baths ⋅ 1355737 MLS

EXCELLENT home in an EXCELLENT location! 4 bedrooms 2 full baths with a huge bonus room, this home packs a big punch. Great primary suite with walk in shower, and a jetted tub to soak all your cares away. Beautiful low maintenance landscaping. Great starter home!

808 N 28th St, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

$475,000

5 Beds ⋅ 3 Baths ⋅ 1355491 MLS

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.

2004 Twin Fawn Tr, Middlesboro

Listing courtesy of Virginia Wilder of Century 21 Virginia Wilder Real Estate.

$180,000

3 Beds ⋅ 2 Baths ⋅ 26025315 MLS

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!

8 Castleford Way, Middlesboro

Listing courtesy of Victoria Allen of Century 21 Virginia Wilder Real Estate.

$105,900

3 Beds ⋅ 2 Baths ⋅ 26025309 MLS

412 N 24th St, Middlesboro

Listing courtesy of Dawn Risner of Turn Key Realty.

$575,000

3 Beds ⋅ 2 Baths ⋅ 1355383 MLS

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

2010 Twin Fawn Trail, Middlesboro

Listing courtesy of Lisa Stacy-Gibbs of Backwoods Realty & Development.

$169,000

3 Beds ⋅ 2 Baths ⋅ 1355373 MLS

Don't miss your chance to own this beautifully updated 3-bedroom, 2-bathroom residence situated in the heart of Middlesboro, KY. Seamlessly blending modern convenience with classic charm. Step inside to an open and light-filled floor plan featuring brand-new flooring, fresh paint, and updated lighting fixtures throughout. The spacious living area flows effortlessly into a modernized kitchen complete with new cabinetry, updated countertops, and sleek appliances--perfect for daily living and easy entertaining

810 1/2 Rochester Ave, Middlesboro

Listing courtesy of Brad Cawood of Backwoods Realty & Development.

$60,000

3 Beds ⋅ 2 Baths ⋅ 26024908 MLS

Investors alert! This lovely bi-level home is in need of repairs but has great potential. Home features three bedrooms, kitchen, dining, and bath on the main level with a spacious family room and bath on the lower level. A generous 2 car attached garage is an added bonus. All this located in the city of Middlesboro and priced to sell! Call today before it's gone!

834 S 31st St, Middlesboro

Listing courtesy of Joann Baker of Joann Baker & Associates.

$129,000

3 Beds ⋅ 1 Baths ⋅ 1354572 MLS

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.

708 W Chester Ave, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$235,000

3 Beds ⋅ 2 Baths ⋅ 1354108 MLS

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.

800 S 28th St, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$119,900

3 Beds ⋅ 2 Baths ⋅ 1353618 MLS

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.

706 Ilchester Ave, Middlesboro

Listing courtesy of Virginia Wilder of Century 21 Virginia Wilder Real Estate.

$215,000

3 Beds ⋅ 2 Baths ⋅ 26022968 MLS

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

209 S 19th St, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$229,000

4 Beds ⋅ 2 Baths ⋅ 1352799 MLS

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!

812 Worchester Ave, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

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Listings courtesy of Spartanburg Association of Realtors as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.