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Newest Homes for Sale in Middlesboro, KY

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  • /13

    $455,000

    • 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
  • /23

    $225,000

    • 2 Beds
    • 2.5 Baths
    • 960 Sq Ft

    615 S 22nd St, Middlesboro, KY 40965

    Come check out this beautifully renovated 2 bedroom, 2.5 bath home, metal roof, open concept, privacy fence, new concrete driveway, large back deck for entertaining, outbuilding for storage, great location, new kitchen appliances, new water heater and more! 10 minute drive Lincoln Memorial University's main campus and approx 20 minutes LMU's Vet school. Schedule today to see this pretty home.

    Megan Stanaford Black Diamond Realty

    615 S 22nd St, Middlesboro, KY 40965
  • /18

    $170,000

    • 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. This home features open kitchen/ dinning area , plenty of space and a great back yard area. Don't miss your chance to own this wonderful home.

    Agent Photo

    Brad Cawood

    Turn Key Realty

    (606) 755-9266

    409 Meadow Ln, Middlesboro, KY 40965
  • /20

    $279,000

    • 3 Beds
    • 3 Baths
    • 2,210 Sq Ft

    515 Englewood Rd, Middlesboro, KY 40965

    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

    Beth Combs Turn Key Realty

    515 Englewood Rd, Middlesboro, KY 40965
  • /15

    $142,000

    • 3 Beds
    • 1 Bath
    • 1,404 Sq Ft

    708 W Chester Ave, Middlesboro, KY 40965

    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.

    Michael Hensley REMAX PROFESSIONAL'S

    708 W Chester Ave, Middlesboro, KY 40965
  • /5

    $30,000

    0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965

    LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

    Sharon Teaney Century 21 Virginia Wilder Real Estate

    0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965
  • /40

    $249,000

    • 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 a

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    301 Doe's Crossing, Middlesboro, KY 40965
  • /20

    $197,000

    • 3 Beds
    • 1.5 Baths
    • 1,238 Sq Ft

    1200 W Chester Ave, Middlesboro, KY 40965

    Have you been looking for a cozy home on a quiet, family-friendly street to raise your family? You need to put this one on your ''must see'' list. Newly remodeled with new floors, new lights, new windows, new doors, and new fencing! With 3 bedrooms and 1 and 1/2 baths, this home is the perfect starter home. The fenced in yard is flat with lots of room for kids--don't miss out on this one.

    Patsy Barnett Coldwell Banker Bisceglia Real

    1200 W Chester Ave, Middlesboro, KY 40965
  • /36

    $259,000

    • 4 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    206 Summit Dr, Middlesboro, KY 40965

    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

    Sharon Teaney Century 21 Virginia Wilder Real Estate

    206 Summit Dr, Middlesboro, KY 40965
  • /23

    $150,000

    • 2 Beds
    • 1 Bath
    • 952 Sq Ft

    359 Beans Fork Rd, Middlesboro, KY 40965

    I love a good sunroom, don't you? Recently updated 2-bedroom 1 bath home is move in ready! Extra-large fenced in level yard with a garage perfect for tinkering!Electric and plumbing included in the updates. You won't find a home like this in this price range! Come see for yourself!

    Misti McGrath Realty Group

    359 Beans Fork Rd, Middlesboro, KY 40965
  • /51

    $250,000

    • 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 make 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 town.

    Megan Stanaford Black Diamond Realty

    119 Wagon Hollow Rd, Middlesboro, KY 40965
  • /9

    $139,000

    • Land
    • 5.33 Acres
    • $26,079 per Acre

    312 Blakely Ln, Middlesboro, KY 40965

    Rare find! 5.33 undeveloped acres in Middlesboro on Blakely Lane, off Cumberland Ave. Zoned R-1. Land is mostly level with a drop to the creek behind. Portion near the creek is in the floor plain. Several building sites on the land above the flood plain. Easy access to Cumberland Ave yet away from the noise and traffic.

    Ann Robinson Action Realty

    312 Blakely Ln, Middlesboro, KY 40965
  • /27

    $119,900

    • 2 Beds
    • 2 Baths
    • 1,240 Sq Ft

    816 W Chester Ave, Middlesboro, KY 40965

    Ranch-style home built in 1950 offering over 1,200 square feet with 2 bedrooms and 2 full bathrooms. Features include a covered patio, a fireplace in the living room, and additional space suitable for a den or workspace. The home sits on an approximate 0.38-acre lot.

    James Martin Century 21 Pinnacle

    816 W Chester Ave, Middlesboro, KY 40965
  • /2

    $40,000

    0 Windermere, Middlesboro, KY 40965

    Here is your chance to own land in AMBLESIDE!! I heard a rumor they aren't making any more! 2 lots listed together for $40k or seller is willing to separate the property for qualified, serious buyers.Seller is willing to have property cleared for buyer. In county with city sewer and water!

    Misti McGrath Realty Group

    0 Windermere, Middlesboro, KY 40965
  • /17

    $159,900

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    405 S 37th St, Middlesboro, KY 40965

    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.

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    405 S 37th St, Middlesboro, KY 40965
  • /21

    $199,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    908 W Chester Ave, Middlesboro, KY 40965

    This home is older home well maintained, 2 bd 1 full bath with an efficiency apartment behind the house. The apartment is open space with 1 bdrm and a full bath. Apartment is rented. Metal roof, vinyl siding and windows, hardwood, laminate & tile floors. Privacy and a chain link fenced in back yard, 2 storage buildings, level back yard.

    Steve Mason REMAX PROFESSIONAL'S

    908 W Chester Ave, Middlesboro, KY 40965
  • /16

    $79,900

    • 2,256 Sq Ft

    417-A&B Avondale Ave, Middlesboro, KY 40965

    Has the up stairs new flooring some new windows roof 7 years old hot water 7 years old new gutters with gutter guards. Bring your vision and bring this fixer upper back to life.

    Nancy Maiden Mountain Realty

    417-A&B Avondale Ave, 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
  • /32

    $217,000

    • 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
  • /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
  • /2

    $189,000

    4607 W Cumberland Ave, Middlesboro, KY 40965

    This is a great opportunity to own investment property or live in one unit and rent the other unit to make mortgage payment, each unit has 1 bedroom, 1 full bathroom, living room, eat-in kitchen and laundry area; each unit comes with range, refrigerator, washer and dryer. Apartments sit on level lot, paved driveway, public water and public sewer, each unit has a heat pump, decks have been stained

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    4607 W Cumberland Ave, Middlesboro, KY 40965
  • /21

    $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 Fathom Realty TN LLC

    140 Wellington Dr, 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
  • /36

    $159,900

    • 3 Beds
    • 2 Baths
    • 934 Sq Ft

    45 Fourmile Run Rd, Middlesboro, KY 40965

    Newly Remodeled, move-in ready home. This home is nestled in the heart of Middlesboro on a .489 acre lot. This home has 3 bedrooms and 2 newly renovated bathrooms. The washer and dryer will stay with home. This quiet cozy home has a log cabin look with a large covered front porch. I also has a carport or breezeway to get to the garage. This home also has a fenced in chicken coop. All the

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    45 Fourmile Run Rd, Middlesboro, KY 40965
  • /50

    $232,500

    • 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
  • /16

    $130,000

    • 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
  • /8

    $194,500

    • 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
  • /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
  • /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
  • /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 complete

    Janice Pratt Fathom Realty TN LLC

    807 Exeter Ave, Middlesboro, KY 40965
  • /53

    $240,000

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

    129 Lower Gibson Ln, Middlesboro, KY 40965

    🏡 The Château on the Creek - Home for Sale in Middlesboro, KY (Bell County) Welcome to The Château 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 completely redone

    Michael Hensley REMAX PROFESSIONAL'S

    129 Lower Gibson Ln, Middlesboro, KY 40965
  • /48

    $334,900

    • 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. Also, a fenced in back yard!! NOT IN THE

    Steve Mason REMAX PROFESSIONAL'S

    805 Worchester Ave, Middlesboro, KY 40965
  • /5

    $15,000

    118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965

    Unrestricted lot in a good location in Middlesboro. Has old home on the property that does not hold any value and would need to be disposed of.

    Michael Hensley REMAX PROFESSIONAL'S

    118 Polly Hollow Right Fork Rd, Middlesboro, KY 40965
  • /38

    $359,000

    • 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
  • /36

    $285,000

    00 Highway 217 & 1344, Middlesboro, KY 40965

    UNIQUE OPPORTUNITY PROPERTY. This property offers plenty of potential. Formerly Shillelagh garage and swimming hole, this property has above the ground fuel tanks that could provide ATV's, Side-by-side, farm equipment fuel for work or entertainment. There are Off-road trails for ATV enthusiasts to enjoy the endless trails. These 9.613 surveyed acres can be used for residential, commercial

    Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

    00 Highway 217 & 1344, Middlesboro, KY 40965
  • /4

    $49,900

    • Land
    • 0.34 Acre
    • $146,765 per Acre

    1107 Winchester Ave, Middlesboro, KY 40965

    Large building lot in Middlesboro. Zoned R-2 Residential, the lot has plenty of room to build a home. It's rare to find a lot in Middlesboro that is level and ready for building.

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    1107 Winchester Ave, 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
  • /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
  • /24

    $175,000

    • 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, refrigerator

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    63 Old Pineville Pike, Middlesboro, KY 40965
  • /52

    $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 upstairs,

    Virginia Wilder Century 21 Virginia Wilder Real Estate

    259 Watson Ln, Middlesboro, KY 40965

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What is the average home price in Middlesboro, KY?
Homes for sale in Middlesboro, KY have an average home price of $358,542.
How many homes have sold over the last 12 months in Middlesboro, KY?
42 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 $269,900. If you put a 20% down payment of $54,000 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $1,300 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $56K a year to afford the median home price in Middlesboro. Learn how much home you can afford with our Home Affordability Calculator.
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

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%
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