36

Middlesboro, KY Houses for Sale

Section Image Section Image
  • /18

    $184,900

    • 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.

    Agent Photo

    Brad Cawood

    Turn Key Realty

    (606) 729-0510

    409 Meadow Ln, Middlesboro, KY 40965
  • /50

    $235,000

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    4921 W Cumberland Ave, Middlesboro, KY 40965

    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

    Agent Photo

    Dustin Daniels

    Mountain Realty

    (606) 713-0736

    4921 W Cumberland Ave, Middlesboro, KY 40965
  • /2

    $165,000

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    4605 W Cumberland Ave, Middlesboro, KY 40965

    One level ranch style home with 3 bedrooms, 2 bathrooms, living room, eat in kitchen, laundry room, central heat and air, nice level yard, paved driveway covered front porch, high speed internet available, double pane windows, public water and public sewer, hardwood floors, storage shed, range, refrigerator, washer and dryers stay with home, This home is less than half a mile from hospital.

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    4605 W Cumberland Ave, 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
  • /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
  • /16

    $180,000

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    918 E Cumberland Ave, Middlesboro, KY 40965

    This home rest on a lot that goes from city street to ally. This home has 3 bedrooms and one bath with a large kitchen and large living room. This home needs some attention but has a lot of potential. The downstairs could be used as apartment or extra living space. There is another home on the property and might be possible to repair.

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    918 E Cumberland Ave, Middlesboro, KY 40965
  • /5

    $70,000

    • 2 Beds
    • 1 Bath
    • 1,456 Sq Ft

    1720 Exeter Ave, Middlesboro, KY 40965

    Super cute house with a great lay out! Fenced in corner lot, excellent outdoor space with oversized garage, a little tlc and this home will shine!

    Misti McGrath Realty Group

    1720 Exeter Ave, Middlesboro, KY 40965
  • /20

    $269,500

    • 3 Beds
    • 2.5 Baths
    • 1,692 Sq Ft

    220 Windermere Dr, Middlesboro, KY 40965

    BEAUTIFUL MOVE IN READY HOME IN AMBLESIDE. Discover your next home in Ambleside, a tranquil subdivision in the heart of Middlesboro outside the city limits. With the beautiful landscaped yard that offers a warm, inviting atmosphere. Enjoy the peaceful suburban setting with the convenience of nearby amenities including shopping, dining, parks and entertainment. This home has 3 bedrooms with the

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    220 Windermere Dr, Middlesboro, KY 40965
  • /2

    $99,000

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    923 Winchester Ave, Middlesboro, KY 40965

    This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    923 Winchester Ave, 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
  • /11

    $112,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    903 Ilchester Ave, Middlesboro, KY 40965

    Great potential for a starter home or investment. Does need some work. Close to LMU, Cumberland National Park, Middlesboro Country Club, and local restaurants.

    Blake Ramey Century 21 Virginia Wilder Real Estate

    903 Ilchester Ave, Middlesboro, KY 40965
  • /34

    $165,000

    • 3 Beds
    • 2 Baths
    • 1,088 Sq Ft

    123 Upper Gibson Ln, Middlesboro, KY 40965

    Cozy 3 bedroom, 1 bathroom home sitting on a surveyed acre with detached 1 car garage that has room for a workshop, storage, crafting etc. The yard is level with a gentle slope on the front edge of the property. There is right of way access to the creek as well. Inside the home, you'll find a large living room and 3 nice sized bedrooms. The kitchen is adequate as well as the dining area. Front

    Megan Stanaford Black Diamond Realty

    123 Upper Gibson Ln, Middlesboro, KY 40965
  • /53

    $245,000

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft

    129 Lower Gibson Ln, Middlesboro, KY 40965

    🏡 The Chateau on the Creek - Home for Sale in Middlesboro, KY (Bell County)Welcome to The Chateau on the Creek, a beautifully updated 3-bedroom, 2.5-bathroom home in Middlesboro, KY (Bell County). Offering 1,856 sq. ft. of living space, a detached garage, and a backyard oasis, this move-in ready property combines timeless charm with modern updates.The exterior has been

    Michael Hensley REMAX PROFESSIONAL'S

    129 Lower Gibson Ln, 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
  • /27

    $24,900

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    13 Duncan Ln, Middlesboro, KY 40965

    This property is now under auctionterms. All Bids must be submitted during the auction via the property service listing page at www.servicelinkauction.com. This sale is subject to a 5% or $2,500 minimum buyer s premium pursuant to the auction Terms & Conditions. All bids will be subject toseller approval (minimums may apply). This property is now under auction terms. All Bids must be

    Beth Combs Turn Key Realty

    13 Duncan Ln, Middlesboro, KY 40965
  • /28

    $229,900

    • 4 Beds
    • 2.5 Baths
    • 2,456 Sq Ft

    1203 Winchester Ave, Middlesboro, KY 40965

    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

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    1203 Winchester Ave, Middlesboro, KY 40965
  • /24

    $185,000

    • 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
  • /35

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    807 Exeter Ave, Middlesboro, KY 40965

    New custom built home in the heart of Middlesboro. This home features three (3) bedrooms and two (2) bathrooms. Walking up to the home you are immediately greeted with a covered front porch constructed using composite decking and adorned with large columns. As you enter this home you are met with a spacious living room/kitchen/dinning room designed in an open concept style. Kitchen is

    Janice Pratt AAA Realty, Inc.

    807 Exeter Ave, Middlesboro, KY 40965
  • /16

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,612 Sq Ft

    140 Wellington Dr, Middlesboro, KY 40965

    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!

    Janice Pratt AAA Realty, Inc.

    140 Wellington Dr, Middlesboro, KY 40965
  • /37

    $249,000

    • 4 Beds
    • 3 Baths
    • 1,966 Sq Ft

    6 Hampton Ct, Middlesboro, KY 40965

    Beautiful split foyer home in Ambleside. The view from the front window is amazing. This well-maintained home has a primary bedroom and bath on both the floors. The kitchen is spacious with all custom built cabinets, a built-in pantry, and a breakfast bar. There are 3 bedrooms on the main floor with 2 baths. The large living room overlooks the community and a beautiful view of the mountains.

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    6 Hampton Ct, Middlesboro, KY 40965
  • /52

    $198,500

    • 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
  • /21

    $279,900

    • 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
  • /32

    $240,000

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft

    11 Castleford Way, Middlesboro, KY 40965

    Renovated and truly move in ready! Proudly owned by just one owner, this home shows exceptional care from the moment you step inside. Fresh paint, new luxury vinyl and laminate flooring, and thoughtful updates throughout create a clean, modern feel. The kitchen shines with new granite countertops, an updated sink and faucet, and finishes that pair beautifully with the existing cabinetry. Down the

    Jennifer Ware Kentucky Land and Home

    11 Castleford Way, Middlesboro, KY 40965
  • /40

    $525,000

    • 5 Beds
    • 2.5 Baths
    • 2,542 Sq Ft

    2004 Twin Fawn Trail, Middlesboro, KY 40965

    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

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    2004 Twin Fawn Trail, Middlesboro, KY 40965
  • /10

    $293,000

    • 4 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    314 Picadilly Ct, Middlesboro, KY 40965

    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!

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    314 Picadilly Ct, Middlesboro, KY 40965
  • /22

    $109,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    252 Chasteen Dr, Middlesboro, KY 40965

    Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily

    Aaron Rose Realty Network, Inc

    252 Chasteen Dr, Middlesboro, KY 40965
  • /12

    $100,000

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    310 Barkley Dr, Middlesboro, KY 40965

    2 bed, 1 bath, manufactured home sitting on a large level lot. Conveniently located to shopping and Harrogate, TN.

    Michael Hensley REMAX PROFESSIONAL'S

    310 Barkley Dr, Middlesboro, KY 40965
  • /2

    $17,000

    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

    $349,900

    • 5 Beds
    • 3 Baths
    • 2,250 Sq Ft

    805 Worchester Ave, Middlesboro, KY 40965

    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. IT'S A MUST SEE!!

    Steve Mason REMAX PROFESSIONAL'S

    805 Worchester Ave, 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
  • /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
  • /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
  • /5

    $229,000

    • 3 Beds
    • 2 Baths
    • 1,375 Sq Ft

    280 Parker Ln, Middlesboro, KY 40965

    Beautiful and practically brand new! This 3 bedroom 2 bath home is perfect for a sweet family! From the ground up, this home is only 3 years old. All appliances included, very well taken care of. You HAVE to see this one!!

    Misti McGrath Realty Group

    280 Parker Ln, 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
  • /38

    $369,900

    • 4 Beds
    • 2.5 Baths
    • 3,885 Sq Ft

    2702 Cumberland Ave, Middlesboro, KY 40965

    Don't miss this opportunity to own a historic home on Cumberland Avenue with a rare corner lot. This 3,800 sq ft turn of the century home, that has been completely updated, boasts 4 bedrooms, 2 full baths and 1 half bath. On the primary level you'll find a covered front porch, sun room, large living room, and oversized dedicated dining area. Off of the dining room, you'll find a massive kitchen

    Darrell Lewis DIY Flat Fee.com

    2702 Cumberland Ave, 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

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.

Home Trends in Middlesboro, KY

Housing Trends

Median Sale Price
$300,000
Median Single Family Sale Price
$300,000
Average Price Per Sq Ft
$207
Number of Homes for Sale
5
Last 12 months Home Sales
42
Months of Supply
1.40
Median List Price
$269,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
100%
How to Buy a Home How to Finance a Home How to Sell a Home