Middlesboro Homes under $500,000

Welcome to Middlesboro, Kentucky – a hidden gem nestled in the heart of Bell County, where the charm of small-town living meets the breathtaking beauty of the Appalachian Mountains. This vibrant city, known for its rich history and strong sense of community, offers an inviting atmosphere that is perfect for families, retirees, and everyone in between.

Middlesboro is uniquely positioned, surrounded by stunning natural landscapes, including the majestic Pine Mountain and the serene waters of local lakes and rivers. Outdoor enthusiasts will revel in the abundance of recreational opportunities, from hiking and fishing to biking and birdwatching. The city's historic downtown area boasts delightful shops and eateries, fostering a sense of connection among residents and visitors alike.

For those considering a move to this picturesque area, Middlesboro offers an impressive selection of homes under $500,000, making it an ideal destination for first-time homebuyers, growing families, or anyone seeking a peaceful retreat without breaking the bank. From charming bungalows to spacious family homes, the real estate market here caters to a variety of tastes and budgets, ensuring that you can find the perfect place to call home.

With its affordable housing options, vibrant community spirit, and stunning natural surroundings, Middlesboro is more than just a place to live – it’s a place to thrive. Come explore the possibilities and discover why so many are choosing to make this enchanting city their new home. Your dream home in Middlesboro awaits!

Newest Middlesboro Homes under $500,000

$375,000

5 Beds ⋅ 3 Baths ⋅ 1357377 MLS

Here is your chance to meet 103 Sherwood Rd, the home with a huge personality. New construction and cookie cutter style lovers, I need you to look away. This home is unlike any other. The love this home has been shown truly shines, Updated to suit todays needs, but at the same time holding on to that mid century modern style. In addition to having 5 bedrooms and 3 baths you have a massive bonus room perfect for use as a den, family room, game room or theatre room, depending on your needs, Sitting on approximately half an acre right across from Fords Woods Park. Outside lighting, several brick flower beds, and a patio worth sharing with friends. This home packs a punch I can't even fully explain. You're going to have to see this one yourself, the pictures do not do justice. Buyer/Buyers Agent to verify all information.

103 Sherwood Rd, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

$235,000

3 Beds ⋅ 2 Baths ⋅ 1357060 MLS

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.

88 Tracy Ridge Rd, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$315,000

4 Beds ⋅ 3 Baths ⋅ 1356915 MLS

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!

1015 Old Wilson Lane, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

$145,900

3 Beds ⋅ 2 Baths ⋅ 1356828 MLS

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!

810 W Rochester Ave, Middlesboro

Listing courtesy of Nichole Goins of Heartland Real Estate, LLC.

$158,000

3 Beds ⋅ 1 Baths ⋅ 1356645 MLS

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!

180 Stevenson Branch Rd, Middlesboro

Listing courtesy of Melanie Mullins of Backwoods Realty & Development.

$175,000

2 Beds ⋅ 1 Baths ⋅ 26026368 MLS

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!

1801 & 1801 1/2 Exeter Ave, Middlesboro

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

$158,000

2 Beds ⋅ 1 Baths ⋅ 1356312 MLS

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.

305 N 15th St, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

$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.

$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.

$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.

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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.