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200 Colonial Hts, Middlesboro
$2,750,000
99 Beds ⋅ 58 Baths ⋅ 26012553 MLS

200 Colonial Hts, Middlesboro

Listing courtesy of Chris McHargue of Huddleston Real Estate.

Selling Office: .

850 Big Buck Lane, Middlesboro
$555,000
5 Beds ⋅ 4 Baths ⋅ 1312141 MLS
First Time on The Market this gorgeous contemporary home was custom built in 2022 with approximately 4,331 SF including the 2 car attached garage. This home has 3 'En Suites' plus 2 more bedrooms for a total of 5 bedrooms and 4 full bathrooms. The unique ceilings were designed just for this home! You will find the large living room to be relaxing with a built-in electric fireplace. The custom kitchen has lots of cabinets and countertops and an island plus a walk-in pantry making this kitchen a dream! The dining room extends from the kitchen with lots of windows! The laundry room has a large sink and leads to the attached 2 car garage. The main 'En Suite' is on the main floor and extends to the large bathroom with two sinks and a lady slipper soaking tub in addition to the large walk-in custom tile shower with 2 shower heads. The walk-in closet leaves nothing to be desired with clothing rods and shelving big enough to dress a Queen. Upstairs are 4 more bedrooms (2 of them are ''en suites'') for a total of 2 full bathrooms upstairs, and a family room. The owners of this home left nothing to be desired, it has it all!! There is a covered front porch for relaxing and listening to the birds and the back covered deck offers privacy. This home comes with 2 Trane heat pumps, Pella Windows that double tilt, high speed internet, the security system allows you to see inside the homes and outside of the home from your phone, public water, nice yard, storage shed with shelving. This home comes with a state-of-the-art chicken coop, The location is wonderful with lots of privacy yet close to shopping and hospital, located in the county yet close to downtown.

850 Big Buck Lane, Middlesboro

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

Selling Office: .

1308 Gloucester Ave, Middlesboro
$539,000
5 Beds ⋅ 4 Baths ⋅ 1322541 MLS
This beautiful 5 bedroom 3.5 bath home located in Middlesboro, Kentucky comes complete with a large 3 car garage with an unfinished second story over the garage. With 1.3 acres, a fenced back yard, swimming pool and much more this house is an amazing gem hidden right in the middle of the city . Don't miss your chance to own this stunning home.

1308 Gloucester Ave, Middlesboro

Listing courtesy of Brad Cawood of Turn Key Realty. 423-869-5111

Selling Office: .

3306 W Cumberland Ave, Middlesboro
$340,000
3 Beds ⋅ 2 Baths ⋅ 1335347 MLS
Newly remodeled home on Cumberland Ave, right next to Middlesboro Elementary School. Sitting on a half acre lot, this spacious home has been updated in every way in the past year. The plumbing and electrical have both been updated. The fireplace has been inspected for safety and a new damper installed. The HVAC system and the water heater are both new. In addition, this home has all new appliances, new flooring, new ceiling fans, and a brand new roof installed in March of 2026. Don't wait on this one--it won't last long!

3306 W Cumberland Ave, Middlesboro

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

Selling Office: .

805 Worchester Ave, Middlesboro
$324,900
5 Beds ⋅ 3 Baths ⋅ 1315952 MLS
This home has been brought back beyond its Glory!! Completely remodeled from the sub flooring to the roof. This 5 bds, 3 full baths, new kitchen w/Quartz counter tops, marble back splash, stainless appliances, new LVP flooring, Breath taking bathrooms, master on the main, 3 bdrms upstairs with a full bath 2 HVAC units. 2 car garage w new garage doors. Also, a fenced in back yard!! NOT IN THE FLOOD ZONE! IT'S A MUST SEE!!

805 Worchester Ave, Middlesboro

Listing courtesy of Steve Mason of REMAX PROFESSIONAL'S.

Selling Office: .

409 Fairview Rd, Middlesboro
$310,000
4 Beds ⋅ 4 Baths ⋅ 25508417 MLS
This 4 bedroom 3 1/2 bath ranch is siting on 2.17 acres minutes from downtown. With a view of the mountains this brick ranch has a in ground pool, a sunroom that has a view of the mountains, a long paved driveway and plenty of garage space. The detached garage could be used for a work shop or for more storage. The property has been recently surveyed. The house is move in ready, just needs a little TLC.

409 Fairview Rd, Middlesboro

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

Selling Office: .

409 Fairview Rd, Middlesboro
$310,000
4 Beds ⋅ 4 Baths ⋅ 1324858 MLS
This 4 bedroom, 3 1/2 bath ranch is sitting on 2.17 acres just minutes from downtown Middlesboro, but is considered outside the city limits. With a view of the mountains, this brick ranch has an in-ground pool, a sunroom that has a view of the mountains, a long paved driveway and plenty of garage space. The detached garage could be used for a workshop or for more storage. The property has been recently surveyed. This home is move-in ready and waiting for your personal touch. Don't wait on this one!

409 Fairview Rd, Middlesboro

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

Selling Office: .

832 N 25th St, Middlesboro
$305,000
6 Beds ⋅ 4 Baths ⋅ 25011376 MLS
beautiful and spacious home located within the city limits of Middlesboro. this property consists of a main home and a separate apartment. The main home has four beds and 3 baths (2 full and 1 half). It has potential for a home office, home library, etc. The apartment that sits above the garage provides a unique income producing opportunity. It has 2 bedrooms and 1 full bath. Great location, minutes from downtown, short drive to Cumberland Gap National Park.

832 N 25th St, Middlesboro

Listing courtesy of Blake Ramey of Century 21 Virginia Wilder Real Estate.

Selling Office: .

314 Picadilly Court, Middlesboro
$293,000
4 Beds ⋅ 3 Baths ⋅ 1324603 MLS
Spacious home located in Ambleside subdivision. This home has 4 bedrooms and 2 1/2 bathrooms. The home was completely remodeled approximately 2 years ago, with a new roof, new flooring throughout, and a completely updated kitchen. HVAC system replaced in January 2025. Don't let this one get past you, make it a must see!

314 Picadilly Court, Middlesboro

Listing courtesy of Patsy Barnett of Coldwell Banker Bisceglia Real.

Selling Office: .

440 Sams Mountain, Middlesboro
$279,000
3 Beds ⋅ 3 Baths ⋅ 1307361 MLS
This is a very nice private home. Comes with lot 10-11. Open concept with a lot of windows to let the sun light in, master on the main level, 2 car garage, wood deck, large kitchen with a long island with a flat gas range, with bar stools. This is a must see!! Close to town but in a quiet area. Don't wait call today for your showing! BUYER TO VERIFY SQUARE FOOTAGE!!

440 Sams Mountain, Middlesboro

Listing courtesy of Steve Mason of REMAX PROFESSIONAL'S.

Selling Office: .

913 Doncaster St, Middlesboro
$249,900
3 Beds ⋅ 2 Baths ⋅ 1336350 MLS
This home is located in the city of Middlesboro minutes away from the hospital, close to downtown. Walmart, LMU are minutes away. It's located in a very safe neighborhood. The home includes a 364' single care garage.

913 Doncaster St, Middlesboro

Listing courtesy of Janice Pratt of Fathom Realty TN LLC.

Selling Office: .

2802 W Cumberland Ave, Middlesboro
$245,000
3 Beds ⋅ 2 Baths ⋅ 1347176 MLS
Exceptional and holy smokes what style! 3-bedroom 1.5 bath home on a Cumberland Avenue corner lot. The rebirth of this home and the current owners have turned this home into an absolute DREAM! Very light yard maintenance so you can spend all your time on the front porch watching the world go by or in front of the gorgeous fireplace, let's go see!

2802 W Cumberland Ave, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

Selling Office: .

907 Doncaster Ave, Middlesboro
$240,000
3 Beds ⋅ 2 Baths ⋅ 1336322 MLS
907 DONCASTER MIDDLESBORO KY 40965 This home is located in the city of Middlesboro minutes away from the hospital, close to downtown. Walmart, LMU are minutes away. It's located in a very safe neighborhood. The home includes a 280' single car garage; 240' back deck; and a 154' covered front porch.

907 Doncaster Ave, Middlesboro

Listing courtesy of Janice Pratt of Fathom Realty TN LLC.

Selling Office: .

206 Summit Drive, Middlesboro
$240,000
4 Beds ⋅ 3 Baths ⋅ 1327623 MLS
Beautiful move-in ready renovated Property. Home features four bedrooms 2 1/2 baths. kitchen features soft closed custom cabinets, kitchen island and stainless steel appliances. Laminated floors throughout the home. Enjoy your coffee on screened in back porch. Storage building for your tools, lawnmower etc..Property is located within minutes from Lmu main campus, Shopping, restaurants, and hospital. No flood insurance needed!!

206 Summit Drive, Middlesboro

Listing courtesy of Sharon K Teaney of Century 21 Virginia Wilder Real Estate.

Selling Office: .

5 Abbey Ln, Middlesboro
$239,500
3 Beds ⋅ 2 Baths ⋅ 25013090 MLS
Tired of living in a house where you don't know your neighbors and feel like you can't enjoy your neighborhood? You can change all that with this 3 bedroom, 2 bath HOME in Ambleside subdivision. Have a problem with stairs? Not anymore. Two of the bedrooms and one bath are on the 2nd floor, but one bedroom and bath are on the first level. Nice open concept living room/dining room. You can enjoy your neighborhood sitting on your covered front porch or sitting on your covered patio in your fenced-in back yard. Make an appointment today. We'll be glad to welcome you home.

5 Abbey Ln, Middlesboro

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

Selling Office: .

5 Abbey Lane, Middlesboro
$239,500
3 Beds ⋅ 2 Baths ⋅ 1309187 MLS
Tired of living in a house where you don't know your neighbors and feel like you can't enjoy your neighborhood? You can change all that with this 3 bedroom, 2 bath HOME in Ambleside subdivision. Have a problem with stairs? Not anymore. Two of the bedrooms and one bath are on the 2nd floor, but one bedroom and bath are on the first level. Nice open concept living room/dining room. You can enjoy your neighborhood sitting on your covered front porch or sitting on your covered patio in your fenced-in back yard. Make an appointment today. We'll be glad to welcome you home.

5 Abbey Lane, Middlesboro

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

Selling Office: .

1203 Winchester Ave, Middlesboro
$225,000
4 Beds ⋅ 3 Baths ⋅ 26004238 MLS
Beautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal living room with hardwood floors. There is a gas fireplace that could be a dining room or an extension of the living room. The dining area is right off the galley kitchen with a door leading onto the carpeted porch easy for entertaining or cooking outside. There is easy access from the carport right into the large open den/family room. Also on the main level there is an office with a half bath, 2 bedrooms and one full bath. The upstairs has 2 bedrooms and a full bath. The home sits on a nice level lot, combining with the lot next door for a total of 1/2 acre.

1203 Winchester Ave, Middlesboro

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

Selling Office: .

1203 Winchester Ave, Middlesboro
$225,000
4 Beds ⋅ 3 Baths ⋅ 1331672 MLS
Beautiful home in the heart of Middlesboro. Make a grand entrance to the spacious formal living room with hardwood floors and a gas fireplace. The dining area is right off the galley kitchen, which has a door leading onto the carpeted porch-perfect for entertaining or cooking outside. There is easy access from the carport right into the large open den/family room. Also on the main level there is a bonus room with a 1/2 bath that could be used as a home office, 2 bedrooms, and 1 full bath. The upstairs has 2 bedrooms and a full bath. The home sits on a nice level lot, combining with the lot next door for a total of 1/2 acre

1203 Winchester Ave, Middlesboro

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

Selling Office: .

4921 W CUMBERLAND Ave, Middlesboro
$223,000
3 Beds ⋅ 2 Baths ⋅ 1319805 MLS
Charming 3-Bedroom Home in a Prime Location! Discover comfort and convenience in this beautifully maintained 3-bedroom, 2-bathroom home located close to shopping, restaurants, schools, and parks — everything you need is just minutes away! Inside, you'll find a warm and inviting layout featuring hardwood and vinyl flooring, offering both style and durability. The spacious living areas are perfect for relaxing or entertaining family and friends. Step outside to enjoy a generous yard with two outdoor storage sheds, providing plenty of room for tools, hobbies, or extra storage. Whether you're a first-time buyer, growing family, or possibly downsizing, this home has something for everyone. Don't miss this great opportunity—schedule your showing today! Buyer to verify taxes, square feet, and acreage.

4921 W CUMBERLAND Ave, Middlesboro

Listing courtesy of Dustin Clay Daniels of Mountain Realty.

Selling Office: .

810 Worchester Ave, Middlesboro
$222,500
3 Beds ⋅ 3 Baths ⋅ 1333149 MLS
This stunning older home is in pristine condition! This home has 3 bedrooms (primary bedroom on main level) and 3 full bathrooms, large extended living room, family room with gas log fireplace (natural gas), dining area that extends into the kitchen. The kitchen has a breakfast bar. All appliances stay with home including washer and dryer. The laundry room has a sink that is convenient for prewash items. There is an attached 2 car garage with pull down ladder to attic for extra storage. There is a ramp in the garage to go into the house. The driveway is concrete. The yard is level and has a nice firepit area in back yard. You can enjoy the covered front porch to relax or the concrete patio in the back of house. This home is estimated to have been built in 1950, but looks much newer! You can see that has been well maintained inside and outside. Home has central heat and air. High speed internet available. It is less than 5 minutes from the hospital, shopping is close by also, yet you have a country setting with a mountain view.

810 Worchester Ave, Middlesboro

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

Selling Office: .

2621 Cumberland Ave, Middlesboro
$221,500
3 Beds ⋅ 2 Baths ⋅ 26011050 MLS
Opportunities are built on the right properties and this could be the one! The potential of this home is limitless. a home with instant equity to put your finishing touches on!

2621 Cumberland Ave, Middlesboro

Listing courtesy of Kelsey Kelley of Keller Williams Legacy Group.

Selling Office: .

127 Alpine Rd, Middlesboro
$214,000
3 Beds ⋅ 2 Baths ⋅ 26007901 MLS
This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is designed for comfort and gatherings highlighting the fireplace in the dining area to create a warm inviting atmosphere. This home has built in shelving and natural wood cabinets in the kitchen along with an island. The potential is endless with an additional 634 square feet of living finished living space in the basement with a fireplace. The basement has a finished bathroom and additional 624 square feet unfinished that can be used as a workshop or other workspace. Walk out of the basement onto a large patio area. There is a short walk to the fenced in area and barn that can house many animal options. This home is near all the amenities including groceries, entertainment, shopping and restaurants. This is a rare gem in the heart of Middlesboro. Call for an appointment today!

127 Alpine Rd, Middlesboro

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

Selling Office: .

140 Chasteen Drive, Middlesboro
$202,000
3 Beds ⋅ 2 Baths ⋅ 1319433 MLS
If you have been looking for a home to call your own, don't miss out on this lovely home with a white picket fence. A spacious 1,800 sf home with 3 bedrooms and 2 bathrooms on a large lot with a fenced-in back yard. You will love the kitchen with granite countertops and the laminate and tile flooring throughout. Don't let this one get away. We'll be happy to show you how this home can be your home.

140 Chasteen Drive, Middlesboro

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

Selling Office: .

515 N 25th St, Middlesboro
$196,000
3 Beds ⋅ 1 Baths ⋅ 1297570 MLS
Cute as I'll get out! And no, I don't mean cute as in little either. This one packs a big punch so don't just do a drive-by, you MUST see inside! 3 bedrooms with multiple bonus rooms and extra, extra storage space. Charming character and the quality of yesteryear, you'll feel the comfort just walking through the door. Let's go! Buyer/Agent to verify all information

515 N 25th St, Middlesboro

Listing courtesy of Misti McGrath of Realty Group.

Selling Office: .

11 Castleford Way, Middlesboro
$189,500
3 Beds ⋅ 1 Baths ⋅ 25508059 MLS
Price Improvement + Seller offering $5,000 toward buyer's closing cost with an acceptable offer! This one checks the boxes and close to Major Regional Colleges! Recent repairs completed, including crawlspace improvements this home is Renovated and move in ready, county taxed (not city!), and not in a flood zone, this home is an ideal match for first time buyers, downsizers, or anyone wanting low maintenance living. It also sits in a prime location just minutes from major regional colleges like Southeast Kentucky Community & Technical College (5-10 minutes) and Lincoln Memorial University in Harrogate, TN (about 15 minutes) including the LMU Vet School and LMU DCOM. Union College and the University of the Cumberlands are also within an easy commute. Proudly owned by just one owner, the care shows the moment you step inside. Fresh paint, new luxury vinyl and laminate flooring, and thoughtful updates throughout create that clean feeling. The kitchen shines with new granite countertops, an updated sink and faucet, and finishes that pair beautifully with the existing cabinetry. Down the hall, the bathroom has been tastefully updated as well. Major components offer peace of mind: the HVAC is only 5 years old with 5 years of warranty remaining, the water heater is new, and the roof was replaced in 2013. Gutter guards add easy maintenance, and even the backyard shed features brand new interior wood. With the washer and dryer included, you can move right in and get to living.

11 Castleford Way, Middlesboro

Listing courtesy of Jennifer Ware of Kentucky Land and Home.

Selling Office: .

116 N Petersborough Ave, Middlesboro
$187,000
3 Beds ⋅ 1 Baths ⋅ 26018934 MLS
Exceptional 3 bedrooms, 1 bath home in the heart of Middlesboro. Located just off Cumberland Ave on 30th St, this home's location is what you have been looking for--within walking distance of downtown, schools, and the hospital. Just down the street from the T-ball field and the city pool. With hardwood floors throughout and beautiful wood trim, this house is waiting for a family to make it a home! Don't wait---make an appointment to tour this home-it is a must-see!

116 N Petersborough Ave, Middlesboro

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

Selling Office: .

116 N Petersborough Ave, Middlesboro
$187,000
3 Beds ⋅ 1 Baths ⋅ 1341032 MLS
Exceptional 3 bedrooms, 1 bath home in the heart of Middlesboro. Located just off Cumberland Ave on 30th St, this home's location is what you have been looking for--within walking distance of downtown, schools, and the hospital. Just down the street from the T-ball field and the city pool. With hardwood floors throughout and beautiful wood trim, this house is waiting for a family to make it a home! Don't wait---make an appointment to tour this home-it is a must-see!

116 N Petersborough Ave, Middlesboro

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

Selling Office: .

23 Castleford Way, Middlesboro
$183,500
3 Beds ⋅ 2 Baths ⋅ 1331558 MLS
Come see this move in ready home, located in the desirable Ambleside subdivision, this beautifully maintained and tastefully decorated two-story home features soft, calming paint colors, gorgeous luxury vinyl flooring, and a warm, welcoming feel throughout. This charming home offers 3 spacious bedrooms and 1.5 bathrooms. The main level includes a comfortable living room, formal dining room, kitchen, large laundry room, and an attached garage for added convenience. A storage shed also provides extra room for storage, tools, or outdoor equipment. Step outside to enjoy the back patio, perfect for relaxing evenings or entertaining family and friends in a peaceful outdoor setting. Conveniently located just minutes from Downtown Middlesboro, you'll enjoy easy access to local dining, shopping, and small-town charm, along with community events, live music, and seasonal entertainment at the Levitt AMP Middlesboro Music Series Pavilion. Outdoor enthusiasts will appreciate being near Cumberland Gap National Historical Park, offering hiking trails, scenic beauty, rich history, and endless outdoor adventure. Situated in Bell County near the borders of Kentucky, Tennessee, and Virginia, this location provides convenient access to all three states while allowing you to enjoy the beauty and history of the Cumberland Gap region. Thoughtfully maintained and full of character, this super cute home offers the perfect blend of comfort, charm, and functionality -- making it easy to settle in and feel right at home. Seller will pay up to $2500.00 in Buyer's closing cost.

23 Castleford Way, Middlesboro

Listing courtesy of Beth Combs of Backwoods Realty & Development.

Selling Office: .

164 Walker Lane, Middlesboro
$176,500
3 Beds ⋅ 2 Baths ⋅ 1325032 MLS
Charming 3 Bedroom, 2 Bath Home - Fully Updated and Move-In Ready! Renovations and upgrades installed in 2023, this beautifully maintained home offers numerous upgrades throughout. Enjoy brand-new 12 ml vinyl plank flooring, solid wood soft-close kitchen cabinets, new countertops, a modern kitchen sink and fixtures, and a full suite of new stainless steel appliances—including washer and dryer. This year the crawlspace was professionally encapsulated with a transferable lifetime warranty and includes a commercial-grade dehumidifier for optimal moisture control. Updated PEX waterlines add peace of mind and efficiency. Outside, you'll find a 10x16 storage shed with an added loft, perfect for additional storage. The private yard creates a peaceful retreat, and the large picture window in the dining room offers the ideal spot for bird watching. This home is in excellent condition—stylish, updated, and completely move-in ready. Located just minutes from town, Lincoln Memorial University, Southeast College, the hospital, shops, and restaurants. Don't miss this one—it's truly a must-see!

164 Walker Lane, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

Selling Office: .

114 Rochester Ave, Middlesboro
$175,000
3 Beds ⋅ 2 Baths ⋅ 1320839 MLS
Charming Fully Remodeled Brick Ranch - Move-In Ready! Welcome home to this beautifully updated 3-bedroom, 2-bath brick ranch situated on a large lot just minutes from downtown Middlesboro. Step inside to discover a completely remodeled interior featuring brand-new laminate flooring throughout, a stunning new kitchen with modern cabinetry and appliances, and two fully updated bathrooms. This home also boasts a new roof, updated plumbing, stylish new light fixtures, and fresh finishes from top to bottom.

114 Rochester Ave, Middlesboro

Listing courtesy of Mike Hensley of REMAX PROFESSIONAL'S.

Selling Office: .

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.

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