27

Homes for Sale near Middlesboro High School

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  • /20

    $399,000

    • 3 Beds
    • 3 Baths
    • 3,397 Sq Ft

    103 Kingsbury Woods Rd, Middlesboro, KY 40965

    Rare opportunity to own a premier golf course property on Hole #2 at the Middlesboro Golf Course—one of only four homes situated directly on the course. Perfectly positioned on a generous 0.67-acre lot, this spacious residence offers a grand total living space, including a finished basement, providing plenty of room to live, entertain, and relax. With three bedrooms and three full baths, the home

    Anthony Gigilo ListWithFreedom.com

    103 Kingsbury Woods Rd, Middlesboro, KY 40965
  • /3

    $50,000

    • 3 Beds
    • 1 Bath
    • 728 Sq Ft

    105 Nutwood Rd, Middlesboro, KY 40965

    3 bed, 1 bath fixer-upper in Middlesboro, KY! Great investment opportunity—flip, rent, or make it your own. City water/sewer (per public record). Priced for potential—bring your ideas!

    Megan Stanaford Black Diamond Realty

    105 Nutwood Rd, 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
  • /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
  • /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
  • /2

    $25,000

    2503 Exeter Ave, Middlesboro, KY 40965

    Level, city, corner Lot available for building or doublewide placement!Buyer/agent to verify all information

    Misti McGrath Realty Group

    2503 Exeter Ave, 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
  • /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
  • /13

    $299,000

    • Land
    • 1.69 Acres
    • $176,923 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
  • /2

    $30,000

    • 2 Beds
    • 1 Bath
    • 1,244 Sq Ft

    103 Nutwood Rd, Middlesboro, KY 40965

    Great investment opportunity. 2 bedroom 1 bathroom home, city utilities. Call for showings.

    Megan Stanaford Black Diamond Realty

    103 Nutwood Rd, Middlesboro, KY 40965
  • /27

    $115,000

    • 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
  • /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
  • /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
  • /48

    $575,000

    • 4 Beds
    • 3.5 Baths
    • 3,480 Sq Ft

    2794 US Hwy 25 E, Middlesboro, KY 40965

    This property presents an exceptional opportunity for investment. Situated in Bell County, it is conveniently located within a short distance of Middlesboro city limits, approximately two miles away. The property boasts over 550 feet of road frontage on a highly visible traffic area, specifically on Highway 25E. This prime location offers a unique chance for investors to establish a new business

    Sharon Teaney Century 21 Virginia Wilder Real Estate

    2794 US Hwy 25 E, 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
  • /3

    $175,000

    • 4 Beds
    • 2 Baths
    • 1,664 Sq Ft

    102 Redwood Rd Unit A & B, Middlesboro, KY 40965

    Great investment opportunity with this one. Built in 2000 per appraisal, this property offers a total of 1,664 square feet and is currently occupied by reliable, long-term tenants. Each unit features 2 bedrooms and 1 bathroom, providing comfortable living space for residents. The address, listed as 102 A&B Redwood Road, originates from a previous appraisal. The property is confirmed per the

    Megan Stanaford Black Diamond Realty

    102 Redwood Rd Unit A & B, 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
  • /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
  • /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
  • /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
  • /2

    $20,000

    • Land
    • 0.13 Acre
    • $158,730 per Acre

    205 Exeter Ave, Middlesboro, KY 40965

    Great lot, city utilities available.

    Megan Stanaford Black Diamond Realty

    205 Exeter Ave, Middlesboro, KY 40965
  • /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
  • /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
  • /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
  • /32

    $239,900

    • 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
  • /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
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