Middlesborough, KY homes for sale & real estate

Middlesborough, KY Homes for Sale

Two properties for 1 price! This 1,040,sf house is included with the sale of 2103 Winchester Ave. This 2nd house has 2 bedrooms, 1 bath, a kitchen and living room. Totally cleaned up and painted in 2024. You can't beat the convenience of living in 1 house and renting the other, or you can have rental property with homes that look brand new.

Middlesborough, KY Homes for Sale

This 3,544 sf home built approximately in 1965 was completely remodeled and updated in 2022. The list of upgrades is extensive! In addition to all updated electrical wiring with new switches, new receptacles (including GFI outlets), and new LED lighting, a new roof, TWO new HVAC units, new crown molding, new baseboards, and new paint, the kitchen cabinets were refinished with all new hardware, new countertops were installed, a new sink and faucet were installed, and a new tile floor was installed. The library has recessed lighting an French doors. Both the entertainment room and the den had new recessed lighting, new carpet and new paint. The dining room and formal living room both got new

Middlesborough, KY Homes for Sale

Charming fully renovated 2-bedroom, 1-bathroom home featuring ample storage and a detached garage. Enjoy a spacious, fully fenced backyard. Recent upgrades include new plumbing and electrical systems, mini-split heating and cooling units, a tankless water heater, brand-new flooring, windows, and fresh paint throughout.

Middlesborough, KY Homes for Sale

This beautiful home conveniently located close to all amenities of downtown Middlesboro is a must see! A 3 bedroom 2 bath, spacious 1900 sqft is perfect for your family. Featuring gorgeous hardwood throughout and lots of storage space. Within walking distance of Yellow Creek School and a short drive to the hospital, this location offers spectacular views of the mountains while maintaining the convenience of close access to all things Middlesboro.

Middlesborough, KY Homes for Sale

This adorable 2 story home located in Ambleside Subdivision, has 3 bedrooms, (all bedrooms and one full bathroom is upstairs) the main floor has a living room, formal dining room, kitchen with range and refrigerator, the large laundry room has a washer and dryer that will stay with home, one-half bathroom on main floor, this home comes with an attached garage and a nice storage shed. The back patio offers great space for outdoor entertaining and relaxing. Home has central heat and air, double pane windows that tilt, city water and city sewer, yet in the county (no city taxes). Possession on day of closing, nice yard, concrete driveway; Buyer gets possession at closing. Home is located in th

Middlesborough, KY Homes for Sale

Enjoy the mountain and country setting from your front porch in this 3 bedroom 2 bath charming ranch style home with a concrete driveway situated on . 66 acres. Perfect for enjoying the serene country setting while rocking your cares and troubles away. Inside, the well maintained kitchen comes equipped with modern appliances, ensuring convenience for all your culinary needs, The large living room, provides adequate room for entertaining guest and passing through kitchen that exits to the side deck, . A large formal dining area for social gatherings and laundry area. Also, a primary bedroom complete with its own ensuite bath. This spacious home is perfect for a growing family. Conveniently l

Middlesborough, KY Homes for Sale

Home has had a recent fire in one bedroom. Excellent location with an awesome, oversized, level lot. Very pretty built ins with an option to expand the kitchen or create a fantastic mud room. Needs a little work, but would be a great investment! Buyer/Buyers agent to verify all information.

Middlesborough, KY Homes for Sale

Ranch style with a 2-car garage on a large level lot. metal roof, vinyl siding, vinyl windows. Home needs some TLC. Needs flooring, paint update bathrooms and kitchen.

Middlesborough, KY Homes for Sale

Do you hear the mountains calling you? This cute little chalet nestled in mother nature's canopy offers low maintenance yard. The location offers hiking, exploring, kayaking, fishing and the arrival of the 2025 Elk Lodge and Nature Preserve with restaurants, gift shops, state of the art playground and observatory. If your looking as an investment property, there are several Airbnb currently.

Middlesborough, KY Homes for Sale

135 HIGHPOINT RD MIDDLESBORO KY Nice three (3) bedroom one (1) bath brick home located in a country setting. Cherry kitchen cupboard. Minutes away from downtown Middlesboro, Walmart, and LMU.

Middlesborough, KY Homes for Sale

Newly Remodeled 3 bedroom 2 bath with fenced yard located seconds away from downtown Middlesboro. and minutes away from LMU. Don't miss your chance to get this beautiful move in ready home.

Middlesborough, KY Homes for Sale

This charming home in a residential area downtown Middlesboro. Relax on the perfect porch or enjoy the level backyard with patio and pergola to offer shade and enjoy the beautiful sunsets. This exquisite 2-bedroom 1 bath home has original hardwood floors and amazing character with its wide trim all while having new modern double pane lifetime windows. After a long day you can relax in your new modern soaker tub. New HVAC installed 3/2024 New 2024 electric water heater. 200-amp power service with complete rewiring. NO OLD WIRES IN THIS HOME!!!!! Stainless steel appliances, separate laundry room/pantry. All new paint inside and outside!!! Beautiful wide driveway leads into a 2-car garage with

Middlesborough, KY Homes for Sale

4 Bedroom 1 bath brick, one and a half story home on a large level lot. 4 year old roof, 2 year old HVAC, new appliances, HARDWOOD FLOORS, formal dining room with additional laundry room. Ready for new owners! First time home buyers, investors, upsizers, and downsizers are all welcome! Buyer/agent to verify all information.

Middlesborough, KY Homes for Sale

Charming 3-bedroom, 2-bath home with a bonus room and ample storage, conveniently located near downtown Middlesboro! This well-maintained residence features a durable metal roof and vinyl siding, along with a level, easy-to-maintain yard. The detached 1.5-car garage offers additional storage and a workshop area for your hobbies, plus a spacious fenced backyard where kids and pets can play freely. Inside, you'll find new flooring throughout, fresh paint, and updated lighting, electrical switches, and outlets. The garage roof is less than five years old, and the kitchen boasts stainless steel appliances replaced in 2019. The HVAC system has been serviced and includes a newly replaced blower/f

Middlesborough, KY Homes for Sale

Wonderfully maintained home sitting on approximately 4+/- acres, beautiful flat, and cleared at the dead end of 22nd St. VERY private and perfectly seated home makes you feel like you're away from everything while being close to town. Lots of landscaping providing extra privacy. Room to build more homes, investment properties, or keep it all to yourself for gardening in the fertile soil or have a mini orchard! Buyer/Buyers agent to verify all information

Middlesborough, KY Homes for Sale

Beautiful Traditional Brick Ranch with Basement! This home has 1698sq/ft on the main floor with an additional 1476sq/ft in the basement. Nestled in the center of Middlesboro with a curved driveway and a 2 car carport with a storage unit between them. The home has two entrances from the carport for easy entry. There are two bonus rooms with a formal living room and formal dining area. The main suite has a beautiful walk-in shower with overhead sky-lights for natural lighting. Also in the main suit has a walk-in closet. There is a galley kitchen with built-in appliances. The basement can be an in-law suite with a studio apartment set-up and full kitchen. This is a charming home! Schedule an

Middlesborough, KY Homes for Sale

How cute is this?! Newly renovated with gorgeous views of Middlesboro and within walking distance to shopping and Churches. Redesigned interior with brand new plumbing, electric, and hvac. buyer/agent to verify all information

Middlesborough, KY Homes for Sale

If you love a home with great craftmanship and structural authenticity, then you need only look at this beautifully crafted home. As you come up the driveway, you will find this home nestled and surround by nature's canvas for privacy. This home's exterior is built with Crab Orchard stone. The stone is a rare sandstone quarried from the Crab Orchard Mountain of the Cumberland Plateau. With an expansive living room and family room combination you will find the living room walls lined with milled stained wood panels. A stone fire place is the focal point as you enter the home. The fireplace has an installed ventilator heater that keeps the living room cozy on those cool Fall nights. Main l

Middlesborough, KY Homes for Sale

Spacious 4 Bedroom 2 Bathroom home conveniently located in Middlesboro just minutes from local schools, shopping, restaurants and hospital. Home also features a large bonus room, vinyl windows, back deck, storage shed along with a fenced back yard and a two-car carport. Home is in need of some TLC.

Middlesborough, KY Homes for Sale

This Brick home is located on 0.5 acres with a beautiful mountain view. It was built in the 1950s. It has three bedrooms with one full bathroom. It has approximately 1200 sq ft of living space. Within minutes of downtown Middlesboro and Walmart. 10 minutes from LMU

Middlesborough, KY Homes for Sale

Nestled in the highly sought-after Ambleside community, this stunning 6,000-square-foot estate offers unparalleled luxury and comfort. Situated on a sprawling 2.29-acre lot, this residence boasts 4 generously-sized bedrooms, each with its own en-suite bathroom, ensuring privacy and convenience for every family member. Step inside and be greeted by updated flooring that flows seamlessly throughout the home as well as many more upgrades. The main level features a formal dining room perfect for hosting elegant dinners and a spacious living area ideal for relaxation and entertainment. The lower level is a true standout, featuring a separate kitchen, a cozy living room, and two versatile offices

Middlesborough, KY Homes for Sale

You'll have it all in this beautiful ranch style home on Twin Acres Rd. Living room, dining, kitchen, breakfast, den with fireplace, 4 bedrooms, 2 full baths, bonus room, and large sunroom overlooking the backyard. Level yard, partially fenced, easy care brick construction, 2 car attached garage, patio, covered front porch, storage room. Great location. .. convenient to shopping, schools, and hospital!

Middlesborough, KY Homes for Sale

Charming country home in the city limits of Middlesboro. This home has 1204sq/ft with 2 bedrooms and an office space. The laundry room is off from the kitchen for easy access. There is a spacious living room with laminate flooring. The large bathroom has a single bowl vanity and tub/shower combination. This home has a nice feeling of home and won't last long.

Middlesborough, KY Homes for Sale

Need space? I got you! 3 oversized bedrooms with BONUS ROOMS (more than one) Formal dining room, impressive sized kitchen with eat in space. Private main suite area with separate entrance and a detached 2 car garage, all on a level corner lot (fenced in back yard!) in the heart of Middlesboro. Let's go look asap!

Middlesborough, KY Homes for Sale

Remarkable Folk Victorian Historical Home. This home was built in 1908, redesigned for today's modern living, yet still encompassing the original charm. This home is nestled in the residential district of Cumberland Ave in Middlesboro. The inviting covered porch takes you back to the time that ''porch sitting'' in the evening was the thing to do and leads you into the entryway with tall ceilings and natural wood trim. With 3,000 sf of living space, this home with 5 bedrooms and 3 1/2 baths has enough space to raise a family in comfort and style. On the main floor there is a spacious living room, formal dining room, kitchen, half bath and the primary bedroom with a full bath. There is a laun

Middlesborough, KY Homes for Sale

Freshy fresh! This home has had a major facelift and reconfiguration. 2 bedroom one bath on an excellent, level Winchester Ave lot. Brand new flooring throughout and fresh paint makes this one move in ready! Bring your atvs, and all your tools cause there's plenty of room in the 2 car garage with additional work space! Close to trail heads, schools, Churches, stores and hospital!

Middlesborough, KY Homes for Sale

this home has already been gutted and ready for your imagination! Great corner lot, with a little work this one will shine like a diamond

Middlesborough, KY Homes for Sale

Very well maintained 3 bedroom, 2 bath home located on Chester Avenue in Middlesboro. Main part of the home is 2 bedrooms with an attached one bedroom suite that can also be used as an apartment. New bathroom remodeled recently and new flooring throughout. Large fenced in backyard for privacy. Make an appointment to see this wonderful home today.

Middlesborough, KY Homes for Sale

Tri level home with 4 bedrooms 2 baths, one upstairs and one downstairs. , lots of storage buildings, living room and family room downstairs both have fireplaces, covered back patio, paved/concreted driveway. Within 10 minutes to schools, shopping and 2 colleges, brick and siding, upper covered porch, back wooden covered porch, concrete sidewalks, front bay window, 2 storage sheds and 1 large tool-house with storage, nice fixtures and very clean. The kitchen has custom wood cabinets, Sun room and formal dining room.

Middlesborough, KY Homes for Sale

Custom built home new in 2016 with beautiful mountain views. Main level has a large open concept den with stone fireplace and cathedral ceiling, kitchen, utility room, four bedrooms and three full bathrooms. Spacious Master Suite is upstairs and complete with two walk-in closets, full bathroom with walk-in shower and a garden tub. Large bonus room above the single car garage. Spacious back deck. Full walk-out unfinished basement. New Roof in July 2023.

Middlesborough, KY Homes for Sale

Three bedroom, two bath well maintained home in beautiful Ambleside Subdivision. Living room and kitchen/dining room combo. Hardwood floors, covered porch and attached 2 car garage. All three bedrooms and the bathrooms are on the main level with a bonus room upstairs that could be used as a fourth bedroom or office. Don't wait on this one, they never last long .

Middlesborough, KY Homes for Sale

This 3 bedroom, 1 bath brick home is located on a quiet dead-end street in the heart of historic Middlesboro, Ky. With a large level fenced in back yard and a wooded area to your right, you will have plenty of privacy. The interior includes large bedrooms, a dining room, and a large living room area.

Middlesborough, KY Homes for Sale

Three bedroom, 2 bath home located in a quiet neighborhood in Middlesboro, Ky. This home has all of the character of a historic home but with many modern updates. This is a single-family home but has the possibility of being divided into 2 units with one bedroom, bath, and kitchen downstairs and 2 bedrooms, a bathroom and a separate kitchen upstairs. Also included is a large garage with electric and water. This one has lots of potential.

Middlesborough, KY Homes for Sale

If you need extra space, this could be just what you are looking for!! This home has 4 bedrooms and one full bathroom, large living room, kitchen that extends to dining room, range, refrigerator, washer and dryer stay with home, laundry area, covered front and back porch, central gas heat and central air, double pane tilt windows, metal roof approximately 2 years old, home has vinyl siding that is less than a year old, high crawl space large enough to stand with dirt floor, great place for storage; internet available, natural gas, located in the county yet approximately a mile from Walmart. City water, septic system, fenced yard,