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$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.

$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.

$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

Listing courtesy of Misti McGrath of Realty Group.

$199,000
3 Beds ⋅ 1 Baths ⋅ 26022803 MLS
Just listed 1480 sq ft historical spilt level home at 1102 W Chester Ave Middlesboro Ky. This home is in walking distance from downtown. It has three bedrooms and one bath and 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 dinning area.

1102 W Chester Ave, Middlesboro

Listing courtesy of David Gambrell of Coldwell Banker Bisceglia Realty & Auction Co.

$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

Listing courtesy of Misti McGrath of Realty Group.

$299,900
5 Beds ⋅ 2 Baths ⋅ 26021089 MLS
Looking for a HOME and not just another house? This is it! With 5 bedrooms, 2 baths, a bonus room to use as a den or rec room, and even special features like a light equipped with a built-in blue tooth speaker in the master bathroom. This home was built with 'family living' in mind. The kitchen is equipped with a new island/breakfast bar that seats six and blends seamlessly with the dining area. With lots of room inside plus a pool with nice deck and patio in the back, you have a great blend of inside and outside living. Put this one on your must-see list--it may be the last one you have to look at to find your perfect home.

926 Doncaster Ave, Middlesboro

Listing courtesy of Kevin Bisceglia of Coldwell Banker Bisceglia Realty & Auction Co.

$299,900
5 Beds ⋅ 2 Baths ⋅ 1350786 MLS
Looking for a HOME and not just another house? This is it! With 5 bedrooms, 2 baths, a bonus room to use as a den or rec room, and even special features like a light equipped with a built-in blue tooth speaker in the master bathroom. This home was built with 'family living' in mind. The kitchen is equipped with a new island/breakfast bar that seats six and blends seamlessly with the dining area. With lots of room inside plus a pool with nice deck and patio in the back, you have a great blend of inside and outside living. Put this one on your must-see list--it may be the last one you have to look at to find your perfect home.

926 Doncaster Ave, Middlesboro

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

$279,000
3 Beds ⋅ 3 Baths ⋅ 26020657 MLS
Discover the perfect blend of peaceful living and everyday convenience in this unique, nature-surrounded home located right in town. Set on approximately 0.75 acres, this property offers privacy, scenic surroundings, and abundant natural light through dramatic floor-to-ceiling windows overlooking the wooded landscape and spacious yard. Inside, the home showcases warm character with vaulted wood ceilings, exposed beams, hardwood floors, and a striking custom spiral staircase that creates a true centerpiece. The open kitchen and living area feature custom cabinetry, stainless steel appliances, and seamless flow, ideal for both daily living and entertaining. The main level includes a spacious owner's suite with a luxury bath featuring a jacuzzi tub, walk-in shower, and private balcony access, perfect for enjoying peaceful mountain and nature views. A second bedroom, full guest bath, and access to the rear deck and fenced yard complete the main floor. Upstairs, the loft bedroom provides flexible space for sleeping, office, or retreat. The walk-out finished basement offers additional living space with a full bath, laundry area, and multiple possibilities including recreation, guest quarters, or home office. A heated and cooled converted garage with built-in shelving provides excellent storage or workspace. Recent updates include beautiful hardwood flooring, smart HVAC system, and a lifetime warranty metal roof. Outdoor features include a large storage shed and expansive yard ideal for enjoying wildlife, relaxing, or entertaining. This rare property combines charm, space, and setting—schedule your private showing today to experience it for yourself.

515 Englewood Rd, Middlesboro

Listing courtesy of Kevin Carroll of Backwoods Realty & Development.

$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

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Real.

$279,000
4 Beds ⋅ 2 Baths ⋅ 26020497 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

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

$199,900
4 Beds ⋅ 2 Baths ⋅ 1348714 MLS
Nice 3-bedroom 2 bath home just for the picking. Priced is right with the possibility of a 4th bedroom. The kitchen, dining room, living room, 3 bedrooms and 1 bath are on the main level. The bonus room (optional 4th bedroom), full bath with laundry facilities downstairs. This home has a back deck, patio and storage building. Don't let this one get away!

140 Wellington Drive, Middlesboro

Listing courtesy of Janice Pratt of Fathom Realty TN LLC.

$359,500
3 Beds ⋅ 2 Baths ⋅ 1348099 MLS
This beautiful brick has touches of class to enjoy for a lifetime. With all the beauty of her old style from big rooms, original cherry doors 9 1/2 foot ceilings and original hardwood floors. A fabulous front porch, a 2 car garage with a spacious and playful backyard. On the inside you will enjoy a kitchen that sparkles white with stainless steel appliances and a grand island for cooking and entertaining. The owner's suite hosts a 5-piece bathroom with a double vanity. Move in ready!!!! This house is a once in a lifetime purchase.!!!

2909 W Cumberland Ave, Middlesboro

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

$110,000
3 Beds ⋅ 2 Baths ⋅ 26014433 MLS
Hey Neighbors! If you've been looking for a solid property with room to build some serious sweat equity, you'll want to take a look at this one. Sitting on a spacious corner lot inside the Middlesboro city limits, this 1.5-story brick veneer home offers a massive 1,963 square feet of living space and sits on over half an acre 0.539 acres per (Bell County PVA). With a potential of 4 bedrooms, 2 baths, hardwood floors, and a sturdy metal roof, the foundational pieces are right here waiting for your vision. The home is being sold AS-IS, making it the perfect blank canvas for a dedicated house flipper, an investor looking to grow their rental portfolio, or a handy homeowner wanting to customize their dream space from top to bottom. Several of the rooms are currently unfinished and need to be updated, giving you the unique opportunity to choose your own finishes, layouts, and style without paying for someone else's recent choices. Sit back and sip some sweet tea on the welcoming front porch and plan some landscaping around the spacious yard. Opportunities at this price point with this much square footage don't come around every day in our neck of the woods. So bring your toolbelt, your imagination, and let's go take a peek at this properties potential!

901 Exeter Ave, Middlesboro

Listing courtesy of Russell Tribell of Fathom Realty KY LLC.

$120,000
5 Beds ⋅ 4 Baths ⋅ 26011288 MLS
Investment Opportunity - Fire-Damaged Home at 215 S. 21st Street, Middlesboro, KY Investor Special! This property at 215 S. 21st Street, Middlesboro, KY has sustained significant fire damage and is being offered as-is. This is an excellent opportunity for experienced investors, contractors, or buyers looking for a major renovation or potential rebuild project. Situated in an established neighborhood, the property offers convenient access to schools, shopping, restaurants, and other local amenities. Property Highlights: * Heavily damaged by fire * Sold as-is * Ideal for investors, contractors, or rehab specialists * Potential renovation or redevelopment opportunity * Convenient Middlesboro location Buyers are encouraged to conduct their own inspections and due diligence to determine the best use of the property. If you're looking for your next project, this could be the opportunity you've been waiting for.

215 S 21st St, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$200,000
3 Beds ⋅ 2 Baths ⋅ 26013326 MLS
Mountain Views, Privacy & Endless Possibilities! Discover the perfect blend of privacy, space, and convenience at 116 Edgewood Road in Middlesboro. This spacious 2,154-square-foot home offers 3 bedrooms and 2 full bathrooms, nestled on approximately 0.75 acres while remaining within walking distance of downtown amenities. Step inside to find a versatile floor plan with multiple living areas and flexible spaces that can easily accommodate additional bedrooms, home offices, recreation rooms, or multi-generational living. The home's unique layout even presents the potential for conversion into separate living quarters, making it an attractive opportunity for homeowners and investors alike. Enjoy beautiful mountain, city, and park views from your property while experiencing the peace and privacy of a wooded setting where local wildlife is often seen. The home features central heating and cooling, a detached garage, ample parking, durable metal roofing, and city utilities. Recent improvements have already been completed, providing a solid foundation for the next owner to personalize and make their own. Whether you're searching for a spacious family home, an investment opportunity, or a property with room to grow, this unique Middlesboro residence offers exceptional value. Property Highlights 3 Bedrooms | 2 Bathrooms 2,154 Sq. Ft. of Living Space Approximately 0.75 Acres Detached Garage & Additional Parking Mountain, City & Park Views Central Heating & Air Conditioning Flexible Layout with Multi-Use Spaces Potential for Multi-Family or Income-Producing Use Convenient Access to Downtown Middlesboro Don't miss this rare opportunity to own a spacious home with privacy, views, and unlimited potential in the heart of Middlesboro. Schedule your private showing today!

116 Edgewood Rd, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$264,900
5 Beds ⋅ 3 Baths ⋅ 26010558 MLS
CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary bedroom is currently under renovation, offering the rare opportunity to add your final personal touch to the suite. While the primary bedroom bath has been completely remodeled with a walk in shower, bluetooth speakers, Step into your personal sanctuary with this top-of-the-line intelligent toilet. A seamless one-piece, skirted design, this smart fixture features a motion-activated lid that opens upon approach and an automatic, high-efficiency flush for ultimate sanitation. The integrated bidet offers customizable warm water cleaning, heated seating for year-round comfort, and an automatic air purifier to keep the atmosphere fresh and serene. The heart of the home flows through classic spaces designed for both grand entertaining and quiet retreats. Enjoy the traditional elegance of the parlor, a formal dining room for holiday gatherings, and a comfortable living room. Outside, the large wrap-around porch serves as the perfect vantage point for beautiful neighborhood views, while the screened-in porch and fenced in courtyard beautiful elegance to the home.

207 Arthur Hts, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

$230,000
3 Beds ⋅ 2 Baths ⋅ 26005639 MLS
Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is highlighted by a charming fireplace—perfect for gathering on cooler evenings. The eat-in kitchen offers a warm and functional space for everyday meals. Step outside to enjoy a large backyard complete with a swimming pool, an expansive deck, and a screened-in area attached to the deck—perfect for relaxing without worrying about pests while still enjoying the outdoors. Whether you're hosting guests or unwinding after a long day, this outdoor space has it all. With its flexible layout, multiple living spaces, and great indoor and outdoor amenities, this home has something for everyone. Don't miss your chance to make it yours!

156 Wellington Dr, Middlesboro

Listing courtesy of Megan Stanaford of Black Diamond Realty.

$135,000
2 Beds ⋅ 1 Baths ⋅ 26010030 MLS
CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car carport, providing ample shaded parking and storage. Don't miss this gem, conveniently located close to all the local amenities. Plus only a 10 minutes drive to LMU main campus.

2002 Winchester Ave, Middlesboro

Listing courtesy of Sheila Durham of Coldwell Banker Bisceglia Realty & Auction Co.

$129,900
4 Beds ⋅ 2 Baths ⋅ 26000834 MLS
Looking for a home to raise your family? Don't let this one go by! Spacious 4 bedrooms, 2 bath home with a fenced in yard, this one is just the right size for a growing family. Just minutes from the hospital and schools, yet tucked away on a side street with little traffic. Let us show you your new home today! Schedule a showing before it's gone.

405 S 37th St, Middlesboro

Listing courtesy of Kevin Bisceglia of Coldwell Banker Bisceglia Realty & Auction Co.

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.