Middlesboro, KY Homes for Sale

/4
$200,000
- 3 Beds
- 1.5 Baths
- 1,800 Sq Ft
3008 State Highway 441, Middlesboro, KY 40965

This Newly Remodeled home is located just minutes away from downtown Middlesboro and the Historic Cumberland Gap National Park, It features new floors, kitchen, bathrooms and a newly designed up stairs. Don't miss your chance to own this beautiful home. (inside Pictures coming soon)

Brad Cawood Turn Key Realty

3008 State Highway 441, Middlesboro, KY 40965
/24
$199,900
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
63 Old Pineville Pike, Middlesboro, KY 40965

Remodeled and gorgeous! This home has completely remodeled throughout with gorgeous kitchen and new bathrooms! This home was stripped down to the studs! Laminate floors are waterproof. The master bathroom has a double bowl sink, nice walk-in shower. There are 3 bedrooms and 2 full bathroom, large living room, kitchen with new farmhouse sink. The kitchen extends to dining room, range,

Virginia Wilder Century 21 Virginia Wilder Real Estate

63 Old Pineville Pike, Middlesboro, KY 40965
/15
$299,000
- 3 Beds
- 4 Baths
- 2,349 Sq Ft
915 E Lothbury Ave, Middlesboro, KY 40965

Charming & Spacious Home with Poolside Living in Historic Middlesboro! This 3-bedroom, 4-bath home offers an abundance of space, comfort, and entertainment features for the whole family. Step outside to your own private retreat featuring a inground pool, a dedicated pool room with its own shower, and a convenient outdoor bathroom—ideal for summer gatherings. Unwind on the screened-in porch with

Beth Combs Turn Key Realty

915 E Lothbury Ave, Middlesboro, KY 40965
/17
$249,900
- 3 Beds
- 2 Baths
- 1,221 Sq Ft
5 Abbey Ln, Middlesboro, KY 40965

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

Kevin Bisceglia Coldwell Banker Bisceglia Real

5 Abbey Ln, Middlesboro, KY 40965
/21
$289,900
- 3 Beds
- 3 Baths
- 2,210 Sq Ft
515 Englewood Rd, Middlesboro, KY 40965

Explore this charming home offering a blend of tranquility and convenience! Nestled in town yet surrounded by nature, this rare gem features a spacious walk-out finished basement and an open kitchen/living room with stainless steel appliances. Loft bedroom.Enjoy panoramic views from the expansive glass windows overlooking the .75-acre yard, perfect for daily wildlife sightings from your

Beth Combs Turn Key Realty

515 Englewood Rd, Middlesboro, KY 40965
/57
$315,000
- 3 Beds
- 2.5 Baths
- 2,512 Sq Ft
440 Sams Mountain, Middlesboro, KY 40965

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!!

Steve Mason REMAX PROFESSIONAL'S

440 Sams Mountain, Middlesboro, KY 40965
/24
$284,900
- 3 Beds
- 2 Baths
- 2,096 Sq Ft
10 Thaxted Ln, Middlesboro, KY 40965

HIDDEN GEM! This beautiful one level home is located in Middlesboro, just outside the city limits in a private area in Ambleside subdivision. This home has 2096 sf of living space, all on one level, with 3 bedrooms and 2 full baths. There is a spacious kitchen with custom cabinets and steel appliances which stay with the house. The stove has a convection oven and the refrigerator has French

Kevin Bisceglia Coldwell Banker Bisceglia Real

10 Thaxted Ln, Middlesboro, KY 40965
/15
$205,000
- 3 Beds
- 2 Baths
- 1,312 Sq Ft
708 Ilchester Ave, Middlesboro, KY 40965

Newly renovated 3 bedroom, 2 bath house located in a great neighborhood in Middlesboro, Ky. Within minutes of Lincoln Memorial university.

Michael Hensley REMAX PROFESSIONAL'S

708 Ilchester Ave, Middlesboro, KY 40965
/43
$209,900
- 3 Beds
- 2 Baths
- 1,684 Sq Ft
1315 Winchester Ave, Middlesboro, KY 40965

MIDDLESBORO KENTUCKYThis home is perfect for entertaining. It sits on a corner lot with plenty of accessible parking. There is a disability ramp if one is needed. Large living room with a gas fireplace. This home has a large dinning room with the kitchen having plenty of cabinets for storage. There is a walk-in pantry and a separate laundry room. Three (3) bedrooms and two (2) full

Janice Pratt AAA Realty, Inc.

1315 Winchester Ave, Middlesboro, KY 40965
/66
$329,900
- 6 Beds
- 3.5 Baths
- 4,033 Sq Ft
832 N 25th St, Middlesboro, KY 40965

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,

Blake Ramey Century 21 Virginia Wilder Real Estate

832 N 25th St, Middlesboro, KY 40965
/36
$249,900
- 3 Beds
- 2 Baths
- 1,900 Sq Ft
4921 W Cumberland Ave, Middlesboro, KY 40965

Nice Ranch style home with an oversized 1 car garage with a 2-car carport attached, 3 bd, 2 full baths, large dining / kitchen area, laundry room, comes with 2 storage buildings This is a very nice home. Ready to move in and no work to be done. Close to main town or hit the woods with your side by side.

Steve Mason REMAX PROFESSIONAL'S

4921 W Cumberland Ave, Middlesboro, KY 40965
/29
$249,900
- 4 Beds
- 2.5 Baths
- 2,020 Sq Ft
825 S 28th St, Middlesboro, KY 40965

Beautiful, split foyer home with 4 bedrooms and 2 1⁄2 bathrooms. The upstairs features a kitchen with plenty of space for storage, updated appliances, and tile floors. This home allows the natural light to shine through in all the rooms. The dining room and living room are open for entertainment or a growing family. The primary bedroom and bath are on the main floor. The guest bath is

Kevin Bisceglia Coldwell Banker Bisceglia Real

825 S 28th St, Middlesboro, KY 40965
/41
$259,900
- 3 Beds
- 2.5 Baths
- 2,016 Sq Ft
301 Doe's Crossing, Middlesboro, KY 40965

This 2-story gorgeous home sits in the mountains of Kentucky and is located in the desired subdivision of Vista Venado! This home sits on 0.944 acre. The main floor offers an open floor plan with a large living room with gas log fireplace. The living room extends to the formal dining area. The spacious kitchen has room for a breakfast table. The kitchen appliances stay with home and includes

Virginia Wilder Century 21 Virginia Wilder Real Estate

301 Doe's Crossing, Middlesboro, KY 40965
/25
$225,000
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
505 S South 38th St, Middlesboro, KY 40965

Located in Middlesboro, KY, this property is conveniently close to the hospital, schools, banks, shopping, and downtown historic Middlesboro, where you'll find charming boutiques and excellent dining options. This 2-bedroom, 2-bathroom brick home features an unfinished basement and sits on nearly an acre of land. Currently generating rental income, it also makes a great option for a first-time

Beth Combs Turn Key Realty

505 S South 38th St, Middlesboro, KY 40965
/3
$110,000
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
413 S 26th St, Middlesboro, KY 40965

Cute little 2-bedroom 1 bath house with great size backyard for family gathering. This house is in a great location convenient to schools, shopping, and walking the town.

Lisa Stacy-Gibbs Turn Key Realty

413 S 26th St, Middlesboro, KY 40965
/15
$115,000
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
921 Winchester Ave, Middlesboro, KY 40965

This country style home has 2 bedrooms with optional 3rd bedroom, 2 bathrooms, living room, dining room, kitchen, and large laundry room, central heat and air is about 6 years old, insulated windows are about 10 years old, seller is installing new cook stove and refrigerator, home has city water and city sewer, high speed internet available, concrete driveway, storage shed stays with home. Level

Virginia Wilder Century 21 Virginia Wilder Real Estate

921 Winchester Ave, Middlesboro, KY 40965
/5
$55,000
- 3 Beds
- 1 Bath
- 1,344 Sq Ft
510 W Chester Ave, Middlesboro, KY 40965

Excellent location on this fixer upper in Middlesboro. 3 bed 1 bath, oversized kitchen with a nice level yard.Buyer/buyers agent to verify all information

Misti McGrath Realty Group

510 W Chester Ave, Middlesboro, KY 40965
/28
$179,900
- 3 Beds
- 1.5 Baths
- 1,040 Sq Ft
164 Walker Ln, Middlesboro, KY 40965

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.

Beth Combs Turn Key Realty

164 Walker Ln, Middlesboro, KY 40965
/54
$425,000
- 1,500 Sq Ft
119 Wagon Hollow Rd, Middlesboro, KY 40965

Welcome to the best of all worlds! One home and an operational store that fronts Highway 217. Several outbuildings and just over 20 acres makes this the perfect property for homesteading as seller had livestock on the property at one time. The land is gently rolling to level, Pineville city water in place, spectrum internet and you're off the beaten path but just a 15 minute drive back into

Megan Stanaford Black Diamond Realty

119 Wagon Hollow Rd, Middlesboro, KY 40965
/16
$159,000
- 3 Beds
- 1 Bath
- 1,320 Sq Ft
428 Wilderness Rd, Middlesboro, KY 40965

Beautiful house located in Middlesboro Kentucky minutes away from Lincoln Memorial University and Cumberland Gap National Park. This home features beautiful hardwood floors, a great yard and even a garage. Don't miss the chance to own this wonderful home.

Brad Cawood Turn Key Realty

428 Wilderness Rd, Middlesboro, KY 40965
/5
$22,500
- Land
- 0.36 Acre
- $62,500 per Acre
526 Balmoral Rd, Middlesboro, KY 40965

Lot available within the city limits of Middlesboro KY; The Bell County Ky online PVA site shows approximately 0.355 of an acre more or less. City utilities are available. There was a home on the property but was demoed April 2025. Buyer to verify all pertinent information; sold as is where is.

Megan Stanaford Black Diamond Realty

526 Balmoral Rd, Middlesboro, KY 40965
/2
$10,500
- Land
- 0.40 Acre
- $26,250 per Acre
4163 441, Middlesboro, KY 40965

This is a rare vacant lot on the beltline in Middlesboro. Electric and sewer on site.

David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

4163 441, Middlesboro, KY 40965
/45
$100,000
- 6 Beds
- 4 Baths
- 2,520 Sq Ft
416 Winchester Ave, Middlesboro, KY 40965

Come check out 416 Winchester Ave Middlesboro KY. This property could be utilized as apartments or as one large unit. Parking allows for 4 vehicles out front and the driveway allows for a couple more. Level lot, tons of space. Public records show the building being built in 1891, there is a metal roof that's approximately a year old, hardwood flooring throughout with a mix of some vinyl flooring.

Megan Stanaford Black Diamond Realty

416 Winchester Ave, Middlesboro, KY 40965
/2
$17,000
- Land
- 1.14 Acres
- $14,912 per Acre
0 Home Run Rd, Middlesboro, KY 40965

Take a look at this beautiful land with 1.14 acres located in city limits of Middlesboro, KY. Doublewide homes welcome, it is unrestricted and has city water, city sewer and electric available! Sits fronting a paved street and is close to downtown Middlesboro.

Virginia Wilder Century 21 Virginia Wilder Real Estate

0 Home Run Rd, Middlesboro, KY 40965
/48
$2,500,000
- 3 Beds
- 1.5 Baths
- 1,976 Sq Ft
259 Watson Ln, Middlesboro, KY 40965

Offering for the first time on the market, this beautiful 92 acre property with 82 acres within city limits and 10 acres in the county. There is a beautiful hayfield and from that hayfield downtown Middlesboro can be seen as well as a view of the Pinnacle. This property comes with 2 homes. The main house has 3 bedrooms, 1 full bathroom and a half bathroom, foyer with staircase leading

Virginia Wilder Century 21 Virginia Wilder Real Estate

259 Watson Ln, Middlesboro, KY 40965
/7
$27,500
- 3 Beds
- 1 Bath
- 2,470 Sq Ft
524 Avondale Ave, Middlesboro, KY 40965

Attention investors and DIY enthusiasts! Multiple exit strategies: finish this remodel then either flip, rent or move in! Home being sold as is. Cash offers preferred but will consider financed all offers.

Dustin Hepburn

524 Avondale Ave, Middlesboro, KY 40965
/18
$189,000
- 4 Beds
- 1.5 Baths
- 1,120 Sq Ft
409 Meadow Ln, Middlesboro, KY 40965

This 4 bedroom home is located just minutes away from Downtown Middlesboro KY. With upgraded kitchen and new floors this house is a hidden gem.

Brad Cawood Turn Key Realty

409 Meadow Ln, Middlesboro, KY 40965
/21
$190,000
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
626 S 22nd St, Middlesboro, KY 40965

Wonderfully maintained home sitting on 12 beautiful flat, and cleared lots 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

Misti McGrath Realty Group

626 S 22nd St, Middlesboro, KY 40965
/13
$349,900
- Land
- 1.69 Acres
- $207,041 per Acre
321 W Chester Ave, Middlesboro, KY 40965

1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Pharmacy, Banks, Theater, Auto Repair, Hotel-Motel, Bed & Breakfast, and Multi Family Copy of Middlesboro Zoning attached. All city utilities available.

Kevin Bisceglia Coldwell Banker Bisceglia Real

321 W Chester Ave, Middlesboro, KY 40965
/11
$190,000
- 3 Beds
- 1 Bath
- 996 Sq Ft
105 Mudlick Rd, Middlesboro, KY 40965

Charming 3-Bedroom Ranch on 3.89 Scenic Acres!Welcome to this delightful 3-bedroom, 1-bath ranch-style home nestled on 3.89 picturesque acres with stunning mountain views. This inviting property offers the perfect blend of peaceful country living and convenient access to town, schools, shopping, and outdoor recreation.Step inside to find a cozy yet spacious layout, ideal for family

Aaron Rose Realty Network, Inc

105 Mudlick Rd, Middlesboro, KY 40965
/16
$29,900
- Land
- 2.32 Acres
- $12,888 per Acre
LOT 9 Brush Mountain Cir, Miracle, KY 40856

Discover tranquility at Brush Mountain Farms in Bell County, KY—a 2.32-acre wooded retreat in a gated community. Enjoy peace, privacy, and wildlife, with hiking trails and a developing wildlife preserve (Boone's Ridge) visible from the property. Located just 15 minutes from Boones Ridge Wildlife Park and 20 minutes from Pineville and Middlesboro, offering easy access to town amenities. Ideal for

Tabitha House CENTURY 21 Advantage Realty

LOT 9 Brush Mountain Cir, Miracle, KY 40856
/31
$179,900
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
180 Stevenson Bridge Rd, Middlesboro, KY 40965

Charming Rustic Cabin with Modern Comforts on 2 Acres Welcome to 180 Stevenson Branch Rd in Middlesboro, KY—where country charm meets convenience. Just minutes from historic downtown Middlesboro, you'll enjoy easy access to quaint shops, local restaurants, major retailers, medical offices, banks, and hospitals—all while savoring the serenity of rural living. Nestled on a hillside and surrounded

Beth Combs Turn Key Realty

180 Stevenson Bridge Rd, Middlesboro, KY 40965
/16
$145,000
- 3 Beds
- 2 Baths
- 648 Sq Ft
138 Robinson Ln, Middlesboro, KY 40965

Check out this charming 3-bedroom, 2-bath home featuring a spacious covered porch, updated master bathroom, fenced backyard, and beautiful tile and hardwood flooring throughout. Conveniently located just minutes from historic downtown Middlesboro, KY.

Beth Combs Turn Key Realty

138 Robinson Ln, Middlesboro, KY 40965
/27
$314,900
- 3 Beds
- 2 Baths
- 2,270 Sq Ft
900 Twin Fawn Trail, Middlesboro, KY 40965

In the beautiful hills of Vista Venado lies the gorgeous 3 bedroom and 2 bath 900 Twin Fawn Trail.From the trey ceilings to the marble flooring, to the jetted tub this home is breathtaking! Your HOA fee of $20/month gives you unlimited water with very light restrictions. Massive patio for all your entertaining. Brand new french drain system.Quiet neighborhood perfect for evening

Misti McGrath Realty Group

900 Twin Fawn Trail, Middlesboro, KY 40965
/31
$458,000
- 5 Beds
- 4 Baths
- 3,146 Sq Ft
523 N 30th St, Middlesboro, KY 40965

Spacious All-Brick Home with Attached Guest Quarters - Prime Location! This beautifully maintained, all-brick home offers exceptional flexibility and space, featuring a main residence with 3 bedrooms, 2 bathrooms, a bonus room perfect for a home office, rec room, or additional sleeping area, and two laundry rooms for added convenience.In addition, the property includes a fully separate,

Beth Combs Turn Key Realty

523 N 30th St, Middlesboro, KY 40965
/24
$185,000
- 3 Beds
- 1 Bath
- 2,000 Sq Ft
515 N 25th St, Middlesboro, KY 40965

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

Misti McGrath Realty Group

515 N 25th St, Middlesboro, KY 40965
/32
$299,000
- 3 Beds
- 2.5 Baths
- 3,174 Sq Ft
113 Hollywood Dr, Middlesboro, KY 40965

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

Kevin Bisceglia Coldwell Banker Bisceglia Real

113 Hollywood Dr, Middlesboro, KY 40965
/33
$297,500
- 5 Beds
- 3.5 Baths
- 3,000 Sq Ft
2410 Cumberland Ave, Middlesboro, KY 40965

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

Kevin Bisceglia Coldwell Banker Bisceglia Real

2410 Cumberland Ave, Middlesboro, KY 40965
/5
$29,900
- Land
- 18 Acres
- $1,656 per Acre
0 Highway 217 Unit 25005121, Middlesboro, KY 40965

18.005 acre lot at Brush Mountain Farms. This is a great property for a cabin. Great views with a walking trail nearby. This property is located in a gated community and has an HOA with restrictions. Call for a showing.

David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

0 Highway 217 Unit 25005121, Middlesboro, KY 40965
/22
$119,000
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
252 Chasteen Dr, Middlesboro, KY 40965

This home has 3 bedrooms and 2 full bathrooms, living room, family room, 2 eat-in kitchens, 2 laundry hookups, attached storage shed, level lot with chain link fence, seller said it could be made into two apartments. Central heat and air, gas cook stove, natural gas, city water, city sewer. It is close to hospital. NEW ROOF It won't last long at this price!

Virginia Wilder Century 21 Virginia Wilder Real Estate

252 Chasteen Dr, Middlesboro, KY 40965

Showing Results 1 - 40, Page 1 of 2

Kentucky Bell County Middlesboro

Why Live in Middlesboro

Middlesboro, Kentucky, is a small city located in a meteor crater just west of the historic Cumberland Gap. This unique location provides residents with access to a variety of recreational and historic sites, including the Cumberland Gap National Historical Park. The park offers miles of trails leading to caves, creeks, scenic viewpoints, and Civil War landmarks, making it a prime spot for those seeking things to do outdoors. Middlesboro also features several city parks and the historic Middlesboro Country Club, the oldest continuously operating golf course in America. The city is home to a mix of Craftsman-style and midcentury ranch homes, with some properties dating back to the 1910s. While new construction has been limited since the 1990s, there are communities for manufactured homes available. Community events like the Cumberland Mountain Fall Festival and activities at Binghamtown Baptist Church and the Middlesboro-Bell County Public Library foster a strong sense of community. The main street area along Cumberland Avenue hosts local coffee shops, pizza parlors, and other eateries, while 12th Street offers chain restaurants and big box retailers. However, residents should be aware of potential flooding due to the city's topography and heavy traffic around the Cumberland Gap Tunnel during peak hours. Middlesboro Independent Schools have average ratings, and the city is also home to the Middlesboro Campus for Southeast Kentucky Community & Technical College.

Learn more about living in Middlesboro

Frequently Asked Questions

What is the average home price in Middlesboro, KY?

Homes for sale in Middlesboro, KY have an average home price of $347,363.

How many homes have sold over the last 12 months in Middlesboro, KY?

43 homes have sold in Middlesboro, KY over the last 12 months.

What are the most popular zip codes in Middlesboro, KY?

The most popular zip codes in Middlesboro, KY include 40965, 37724, 37752, 37870 and 40977.

How much do you need to make to afford a house in Middlesboro?

The median home price in Middlesboro is $249,000. If you put a 20% down payment of $49,800 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $1,290 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $55K a year to afford the median home price in Middlesboro.

How are the schools in Middlesboro, KY?

Middlesboro, KY has highly rated public and private schools. Some of the best schools in Middlesboro based on Niche Grades are Gateway Christian School, Yellow Creek School Center and Bell County High School. Browse all the schools in Middlesboro, KY to learn more.

Home Trends in Middlesboro, KY

On average, homes in Middlesboro, KY sell after 31 days on the market compared to the national average of 70 days. The median sale price for homes in Middlesboro, KY over the last 12 months is $300,000, up 97% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$300,000

Median Single Family Sale Price

$260,000

Average Price Per Sq Ft

$201

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.70

Median List Price

$249,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

97%

How to Buy a Home How to Finance a Home How to Sell a Home

More About Living in Middlesboro

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.