Middlesboro Real Estate

Welcome to Middlesboro, Kentucky – a charming city nestled in the heart of Bell County, where the beauty of the Appalachian Mountains meets a rich tapestry of history and community spirit. Founded in 1888, Middlesboro is uniquely situated within a meteorite crater, giving it a distinctive topography that adds to its allure. This vibrant city boasts a friendly atmosphere, making it an ideal place for families, retirees, and outdoor enthusiasts alike.

Middlesboro is known for its lush landscapes and outdoor recreational opportunities. With the nearby Cumberland Gap National Historical Park, residents and visitors can immerse themselves in nature, exploring miles of scenic trails, picturesque views, and diverse wildlife. The city also offers a wealth of local parks, perfect for picnics, sports, and family gatherings.

The downtown area is a delightful blend of historic architecture and modern amenities. Here, you’ll find unique shops, cozy cafes, and local restaurants serving up delicious Southern cuisine. The community is tight-knit, with numerous events and festivals throughout the year that celebrate the city's heritage and foster a sense of belonging.

Education is a priority in Middlesboro, with access to quality schools and higher education institutions, ensuring that residents have ample opportunities for growth and learning.

Whether you’re seeking a peaceful retreat or an active lifestyle, Middlesboro welcomes you with open arms. Come discover the charm and warmth of this hidden gem in Kentucky – where every day feels like home.

Newest Listings in Middlesboro

$139,000

26025959 MLS

Rare find! 5.33 ac of undeveloped land in Middlesboro! Land is zoned R-1 and is mostly level with a drop to the creek behind. Portion near the creek is in the flood plain. Several buildable sites above the flood plain. Easy access to Cumberland Ave but very private. Survey with flood plain distinction available on request.

312 Blakely Ln, Middlesboro

Listing courtesy of Ann Robinson of Mountain Realty Group LLC.

$99,900

3 Beds ⋅ 3 Baths ⋅ 26025732 MLS

Incredible Opportunity to Own a Unique 3 Level A-Frame Retreat Situated on 1.70 Acres! This One-Of-A-Kind Property Features Spacious Bedrooms, Soaring Ceilings Throughout the Main Level and a Dramatic Floor-To-Ceiling Rock Fireplace Creating a Stunning Focal Point. A Separate Stone Fireplace in the Walk-Out Lower Level Adds Additional Character and Warmth. Enjoy Outdoor Living From the Expansive Wrap Around Deck, Perfect for Entertaining, Relaxing, or Taking in the Peaceful Surroundings. Large Detached Carport Provides Convenient Covered Parking. Property Needs Updating and Renovations, Offering Excellent Potential for Investors, Renovation Enthusiasts or Buyers Looking To Create Their Own Private Retreat. Bring Your Vision and Unlock the Full Potential of This Exceptional Property! Sold As-Is. Virtual staging has been used in some photos to illustrate potential furniture placement/design.

141 Lick Fork Rd, Middlesboro

Listing courtesy of Derek Eisenberg of Continental Real Estate Group.

$199,000

3 Beds ⋅ 1 Baths ⋅ 1355810 MLS

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!

1102 W Chester Ave, Middlesboro

Listing courtesy of Kevin J Bisceglia of Coldwell Banker Bisceglia Real.

$1,790,000

25008431 MLS

Opportunity Alert! Whatever your business idea, this property has the potential to make it a reality. From location to actual usable space and even more property to expand, there is no shortage of boxes that this commercial property will check mark. Offering three separate buildings with large open spaces, office area, worship space plus a large apartment that could be rented or used by the new owner. These buildings are red steel buildings and have stood strong over the years with many years of life ahead of them. With all of the items mentioned above, this property could be used for a storage facility, boat and RV storage, turn it into a medical or health clinic, auto repair, even a possible church! Let your mind dream a little and then set up a showing to see how this listing can make it happen.

3133 Us Highway 25e, Middlesboro

Listing courtesy of G Daniel Carmack of Sallie Davidson, Realtors.

$598,000

25008609 MLS

Prime property with prime opportunity. This vacant land sits right on a main highway, just minutes from the upcoming Boones Ridge Wildlife project. Over 3 acres of land to build your dream business with thousands of eyes each day passing by, theres no better place than this property in Bell County.

Us Highway 25, Middlesboro

Listing courtesy of G Daniel Carmack of Sallie Davidson, Realtors.

$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.

$175,000

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.

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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.