Middlesboro Homes with Restrictions

Middlesboro Homes with Restrictions

Welcome to Middlesboro, a charming city nestled in the heart of Kentucky. With its rich history and picturesque surroundings, Middlesboro offers a unique blend of small-town charm and modern conveniences.

Located in the state of Kentucky, Middlesboro is known for its friendly community, vibrant culture, and stunning natural beauty. Whether you're exploring the historic downtown area, hiking in the nearby mountains, or enjoying a round of golf at one of the local courses, there's something for everyone to enjoy in Middlesboro.

If you're looking for a home in Middlesboro with restrictions, you're in luck. From gated communities to neighborhoods with specific architectural guidelines, there are plenty of options to choose from. Whether you're looking for a quiet retreat or a bustling community, Middlesboro has something to offer for every lifestyle.

Don't miss the opportunity to make Middlesboro your new home. With its welcoming atmosphere, diverse real estate options, and convenient location, Middlesboro is the perfect place to put down roots and start your next chapter. Experience the best of Kentucky living in Middlesboro – where small-town charm meets modern living.

Newest Middlesboro Homes with Restrictions

103 Sherwood Rd, Middlesboro
$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
1015 Old Wilson Lane, Middlesboro
$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
810 W Rochester Ave, Middlesboro
$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
113 N 18th St, Middlesboro
$1,750,000
1356342 MLS
Established turnkey towing and auto repair business ready for you to take on. Building has 2 offices, waiting room, 2 half baths, with a 10k sq foot garage featuring 4 lifts, 8 bays, tire machine, air compressor, new roof and mini split system, new gas heat (one unit not installed). Paint booth included in the back of the building with new separate electric ready to go. Paint booth comes with everything you need to get started brand new never used Vinyl wrap, cutter and laminator. Everything goes with the exception of personal tools and one air compressor. Including but not limited to, 8 trucks different sizes and ages 3 rollbacks, one medium duty wrecker, 2 smaller wreckers and the only rotator tow truck within a 60 mile radius. Please call for more information.

113 N 18th St, Middlesboro
1102 W Chester Ave, Middlesboro
$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
2004 Twin Fawn Tr, Middlesboro
$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
2010 Twin Fawn Trail, Middlesboro
$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
810 1/2 Rochester Ave, Middlesboro
$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
800 S 28th St, Middlesboro
$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
812 Worchester Ave, Middlesboro
$219,000
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
110 Danbury Ave, Middlesboro
$17,000
2 Beds ⋅ 1 Baths ⋅ 1352038 MLS
If you've been looking for a project here it is! Handyman special, would make a super cute flip! Or at this price you can buy it for just the land! Please do not go without an agent. Buyer/Buyers agent to confirm all information

110 Danbury Ave, Middlesboro
400 Gloucester Ave, Middlesboro
$279,000
4 Beds ⋅ 2 Baths ⋅ 1350232 MLS
Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also has a fill-pot feature next to the stove. The kitchen's backdown is where you will , find a covered deck--perfect for entertaining family and friends. Situated on a quiet dead-end street, this property combines the convenience of downtown living with the privacy and tranquility you've been looking for. The home offers a flexible floor plan with two bedrooms on the main level with cedar lined closets and two bedrooms upstairs. The foyer entryway offers a closet and space for coats and shoes to conveniently stored. A spacious living room with a fireplace creates a warm gathering space, while the formal dining room and vented sunroom provide additional areas for relaxation and entertaining. The basement includes a two-car garage, workshop, and ample storage space, offering plenty of room for hobbies and organization. Schedule an appointment TODAY!

400 Gloucester Ave, Middlesboro
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