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Homes for Sale near Middlesboro Alternative School

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  • /42

    $399,000

    $21K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,350 Sq Ft

    138 Colwyn St, Cumberland Gap, TN 37724

    This beautiful property is located in the Historic Cumberland Gap Tennessee . The main house is a 3 bed 1.5 bath 1 level home with a spacious kitchen and living space. This property also has a newly renovated above garage space with over 2200 square foot heated and cooled space. This space is perfect for a home gym, or home office. This Property is a must see for anyone moving into the area.

    Agent Photo

    Brad Cawood

    Turn Key Realty

    138 Colwyn St, Cumberland Gap, TN 37724
  • /18

    $93,500

    $32K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,426 Sq Ft

    123 Cawood Ln, Middlesboro, KY 40965

    Large Price Reduction!! Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back

    Agent Photo

    Dustin Daniels

    Mountain Realty

    123 Cawood Ln, Middlesboro, KY 40965
  • /13

    $140,000

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    413 S 26th St, Middlesboro, KY 40965

    This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from downtown Middlesboro and the Cumberland Gap National Park. This home has had some great improvements such as a new roof and new windows installed. don't miss your opportunity to call this your own.

    Agent Photo

    Brad Cawood

    Turn Key Realty

    413 S 26th St, Middlesboro, KY 40965
  • /45

    $499,000

    • Land
    • 13.4 Acres
    • $37,239 per Acre

    0 Tower St, Harrogate, TN 37752

    LOCATION - LOCATION- LOCATION! City Farm:13.4 unrestricted level to rolling residential acres of hay fields in the city limits of Harrogate Tennessee. This property is partially fenced, has a silo, barn, paved road frontage, views of Cumberland Mountain, White Rocks of Virginia, Pinnacle of Cumberland Gap Park all located within walking distance to bank, gas, food, grocery, 10 min. to Lincoln

    Agent Photo

    Robin LeFevers

    Stone Realty & Auction

    0 Tower St, Harrogate, TN 37752
  • /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
  • /10

    $339,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,350 Sq Ft

    423 Roslyn Ave, Cumberland Gap, TN 37724

    New Construction in the historic city of Cumberland Gap. Two bedrooms, two full bathrooms, 9 ft ceilings, 2x6 exterior walls, laminate flooring, and a large yard are just some of the qualities that make this new home an amazing option.

    Michael Hensley REMAX PROFESSIONAL'S

    423 Roslyn Ave, Cumberland Gap, TN 37724
  • /14

    $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
  • /28

    $59,900

    • Land
    • 4.24 Acres
    • $14,127 per Acre

    1197 Beans Fork Rd, Middlesboro, KY 40965

    Opportunity awaits on this 4.24-acre tract offering a peaceful setting with endless potential. The property was previously improved with a home that has recently been lost to fire, presenting a unique chance to start fresh and bring your vision to life. With utilities previously in place (buyer to verify), this parcel may offer a head start for rebuilding, whether you're considering a custom

    SARAH RICHARDS RE/MAX Preferred Group

    1197 Beans Fork Rd, Middlesboro, KY 40965
  • /5

    $855,000

    • 2 Beds
    • 2 Baths
    • 15,119 Sq Ft

    725 19th St, Middlesboro, KY 40965

    Prime Multifamily Investment Opportunity Presenting a well-established commercial apartment building in the heart of Middlesboro, Kentucky. Built in 1990, this single-story property offers approximately 15,225 square feet of space ideally suited for residential rental units, providing stable cash flow in a convenient location. Strategically positioned on N 19th Street, the building benefits from

    Beth Combs Turn Key Realty

    725 19th St, Middlesboro, KY 40965
  • /4

    $159,000

    $5K PRICE DROP
    • 700 Sq Ft

    1801 Exeter Ave, Middlesboro, KY 40965

    2 HOMES with one FULLY remodeled home in back 2 bedroom 1 bath Cute as a button! Home on corner lot needs work but would be a very smart investment. With access to ATV friendly roads, close to stores and hospital.1801 Exeter and 1801 1/2 Exeter

    Misti McGrath Realty Group

    1801 Exeter Ave, Middlesboro, KY 40965
  • /5

    $30,000

    • Land
    • 1.26 Acres
    • $23,810 per Acre

    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
  • /2

    $50,000

    • Land
    • 16,639 Sq Ft
    • $130,890 per Acre

    0000 Edgewood Rd, Middlesboro, KY 40965

    Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

    Megan Stanaford Black Diamond Realty

    0000 Edgewood Rd, Middlesboro, KY 40965
  • /9

    $220,000

    $30K PRICE DROP
    • Land
    • 21.5 Acres
    • $10,233 per Acre

    0 Cumberland Estates Rd, Cumberland Gap, TN 37724

    Welcome to Cumberland Gap, TN where you can feel like you are in the country but have a town nearby. Whether you come to farm or enjoy the views, this is the place to do it all! This 21.5 acre property includes a barn, fencing, an intermittent spring along with electric. Buyer to verify all information. Don't miss out!!!!

    Shanda Violet Realty Group

    0 Cumberland Estates Rd, Cumberland Gap, TN 37724
  • /4

    $49,900

    • Land
    • 30,492 Sq Ft
    • $71,286 per Acre

    Lot 30 Robbins Ln, Harrogate, TN 37752

    Perfect lot to build your dream home!. Located in a desriable neighborhood in Harrogate, TN. Beutiful mountain views and convenient to Lincoln Memorial University main campus and the Kentucky State Line.

    Michael Hensley REMAX PROFESSIONAL'S

    Lot 30 Robbins Ln, Harrogate, TN 37752
  • /2

    $145,000

    • Land
    • 32,670 Sq Ft
    • $193,333 per Acre

    TBD Londonderry Rd, Harrogate, TN 37752

    Direct access to Londonderry Rd. this 0.75ac building lot is perfect for a duplex, new homes or your new office building. This property is just steps away to access the Harrogate/Cumberland Gap Greenway walking/biking trail or minutes to Lincoln Memorial University, Cumberland Gap Tunnel, the national park or within a short drive you can enjoy a day on Norris Lake or Powell River. Londonderry

    Beth Combs Backwoods Realty & Development

    TBD Londonderry Rd, Harrogate, TN 37752
  • /39

    $369,000

    • 3 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    139 Gracyn Ln, Harrogate, TN 37752

    Spacious 3-bedroom, 3.5-bath condo located in the desirable Cedar Creek community in Harrogate, TN. This well-maintained home offers over-sized living spaces and a versatile flex room with a private full bath that has previously been used as a fourth bedroom, home office, workout room, and guest suite. The main-level primary suite features a large walk-in closet and private bath, while the second

    Amanda Hoskins Backwoods Realty & Development

    139 Gracyn Ln, Harrogate, TN 37752
  • /2

    $389,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    116 Bristol Rd, Harrogate, TN 37752

    New Construction!!! Just in time for the new school year. Welcome to this beautifully crafted new construction offering 1,800 square feet of modern living with thoughtful design throughout. This home features three spacious bedrooms, two luxury baths. The open-concept floor plan seamlessly connects the living, and kitchen areas perfect for entertaining. The kitchen is finished with granite

    Lisa Stacy-Gibbs Turn Key Realty

    116 Bristol Rd, Harrogate, TN 37752
  • /18

    $135,000

    Pre-Foreclosure
    • 3 Beds
    • 1.5 Baths
    • 1,963 Sq Ft

    901 Exeter Ave, Middlesboro, KY 40965

    Hey Neighbors! If you've been looking for a solid property with room to build some serious sweat equity, you'll want to take a look at this one. Sitting on a spacious corner lot inside the Middlesboro city limits, this 1.5-story brick veneer home offers a massive 1,963 square feet of living space and sits on over half an acre 0.539 acres per (Bell County PVA). With a potential of 4 bedrooms, 2

    Russell Tribell Fathom Realty KY LLC

    901 Exeter Ave, Middlesboro, KY 40965
  • /2

    $485,000

    513 Forge Ridge Rd, Harrogate, TN 37752

    Income-Producing Multi-Family Opportunity in Harrogate, TN! Excellent investment opportunity featuring four single-family homes situated on approximately 2.5 acres just minutes from the center of Harrogate. All homes are currently tenant-occupied and producing income, making this a turnkey option for investors seeking immediate cash flow. The spacious acreage allows for privacy between units

    Beth Combs Backwoods Realty & Development

    513 Forge Ridge Rd, Harrogate, TN 37752
  • /10

    $399,900

    • Land
    • 20.33 Acres
    • $19,670 per Acre

    000 Forge Ridge Rd, Harrogate, TN 37752

    ROLLING LAND, FENCED, BARN, PUBLIC WATER AT THE BARN, Several nice building lots with a mountain view. Great place to build a home.

    Steve Mason REMAX PROFESSIONAL'S

    000 Forge Ridge Rd, Harrogate, TN 37752
  • /17

    $129,900

    $30K PRICE DROP
    • 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
  • /46

    $325,000

    • 4 Beds
    • 2.5 Baths
    • 2,488 Sq Ft

    1015 Old Wilson Ln, Middlesboro, KY 40965

    Super nice four bedroom, two and 1/2 bath, 2488 sq ft with hardwood floors on a level lot in Middlesboro. Welcome to a home designed for the way you live. This stunning split level residence offers the perfect architectural solution for those seeking distinct spaces without sacrificing an open feel. This home offers privacy and distinct zones for living, working and relaxing.

    David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

    1015 Old Wilson Ln, Middlesboro, KY 40965
  • /3

    $34,999

    • Land
    • 16,988 Sq Ft
    • $89,741 per Acre

    Lot 29 Zachary Ct, Harrogate, TN 37752

    Excellent building lot in a very desirable location. Located in beautiful Harrogate, TN. Just minutes to Lincoln Memorial University main campus and to the Kentucky state line.

    Michael Hensley REMAX PROFESSIONAL'S

    Lot 29 Zachary Ct, Harrogate, TN 37752
  • /34

    $279,900

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft

    635 Washington Ave, Harrogate, TN 37752

    Move-in ready! 3 bedroom, 2 bath home in great shape and ready for a new family. You can't beat the location--less than 1 mile to the main campus of Lincoln Memorial University. Would be the perfect location for rental property or for your forever home. Don't let this one get away!

    Kevin Bisceglia Coldwell Banker Bisceglia Real

    635 Washington Ave, Harrogate, TN 37752
  • /38

    $342,500

    $13K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,042 Sq Ft

    327 Colwyn Ave, Cumberland Gap, TN 37724

    Nestled in the historic town of Cumberland Gap, this beautifully updated 4-bedroom, 2-bath home offers stunning mountain views and the charm of small-town living near the famous Cumberland Gap. With extensive recent upgrades throughout, this move-in ready property combines modern updates with scenic surroundings. Inside, you'll find updated flooring on the main level (2021), new flooring in the

    Michael Hensley REMAX PROFESSIONAL'S

    327 Colwyn Ave, Cumberland Gap, TN 37724
  • /37

    $350,000

    • 5 Beds
    • 4 Baths
    • 3,195 Sq Ft

    717 S 27th St, Middlesboro, KY 40965

    This open floor plan home is waiting for your large family. This home features 5 bedrooms and 4 full baths, cathedral ceilings, a rock fireplace in the living room, and a full, unfinished basement just waiting for you to make more living space. Located in downtown with an out-of-town feel, get in to see this home now. *Buyer to verify acreage and septic.

    Barry Turner RE/MAX LakeTime Realty London

    717 S 27th St, Middlesboro, KY 40965
  • /11

    $214,999

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 3,948 Sq Ft

    2621 W Cumberland Ave, Middlesboro, KY 40965

    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!

    Kelsey Kelley Keller Williams Legacy Group

    2621 W Cumberland Ave, Middlesboro, KY 40965
  • /17

    $315,900

    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft

    171 Stonefield Dr, Harrogate, TN 37752

    Beautiful stone and brick condo featuring 2 bedrooms, 2 baths, and a 2 car garage.. Desirable community and close to amenities and Lincoln Memorial University.This well-maintained home offers upgraded laminated wood flooring in the hall, kitchen, laundry, dining and living room. Kitchen offers upgraded stainless steel appliances. All bedrooms are conveniently located on the main floor. The

    Dawn Risner Turn Key Realty

    171 Stonefield Dr, Harrogate, TN 37752
  • /46

    $125,000

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

    1720 Exeter Ave, Middlesboro, KY 40965

    Welcome to 1720 Exeter Avenue, this adorable fixer has tons of potential with 2 living areas, a detached garage, brand new metal roof, and a fully fenced yard! Less than 5 minutes to schools and hospital, and only 15 minutes from LMU Harrogate main campus. Offered at a great price! Call or text today to schedule a showing!

    Victoria Allen Century 21 Virginia Wilder Real Estate

    1720 Exeter Ave, Middlesboro, KY 40965
  • /15

    $59,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    518 S 43rd St, Middlesboro, KY 40965

    Two bedroom, 1 bath home located in a great neighborhood. Large bedrooms, living room, and kitchen. Don't miss the opportunity to make this home your own.

    Michael Hensley REMAX PROFESSIONAL'S

    518 S 43rd St, Middlesboro, KY 40965
  • /40

    $232,500

    $17K PRICE DROP
    • 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
  • /14

    $325,000

    • 3 Beds
    • 2 Baths
    • 2,579 Sq Ft

    516 Cumberland Estates Rd, Cumberland Gap, TN 37724

    Horse-Friendly 3BR / 2BA Brick Home with Stable - Cumberland Gap / HarrogateThis three-bedroom, two-bath brick home offers room to spread out, with hardwood floors on both levels, a deck off the master bedroom, and a concrete patio just outside the kitchen. An attached garage adds convenience, while high-speed fiber internet keeps you connected.Set on about three acres, the property

    Brad Croisdale Realty Executives Associates

    516 Cumberland Estates Rd, Cumberland Gap, TN 37724
  • /13

    $275,000

    $75K PRICE DROP
    • Land
    • 1.69 Acres
    • $162,722 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
  • /21

    $219,900

    $30K PRICE DROP
    • 4 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
  • /15

    $315,000

    • 4 Beds
    • 2 Baths
    • 1,823 Sq Ft

    135 Granby Ln, Harrogate, TN 37752

    Welcome home to this charming 4-bedroom, 2-bath ranch-style property offering comfortable one-level living in a convenient location near Lincoln Memorial University. This well-maintained home features a spacious layout with plenty of room for family and guests. Enjoy year-round relaxation in the bright and inviting sunroom, perfect for morning coffee or entertaining. Outside, the fully fenced and

    Dylan Lee Ball Realty & Auction, Inc.

    135 Granby Ln, Harrogate, TN 37752
  • /41

    $134,000

    $1K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,844 Sq Ft

    215 S 21st St, Middlesboro, KY 40965

    Investment Opportunity - Fire-Damaged Home at 215 S. 21st Street, Middlesboro, KY Investor Special! This property at 215 S. 21st Street, Middlesboro, KY has sustained significant fire damage and is being offered as-is. This is an excellent opportunity for experienced investors, contractors, or buyers looking for a major renovation or potential rebuild project. Situated in an established

    Megan Stanaford Black Diamond Realty

    215 S 21st St, Middlesboro, KY 40965
  • /27

    $94,900

    $25K PRICE DROP
    • 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
  • /5

    $29,000

    • Land
    • 39,204 Sq Ft
    • $32,222 per Acre

    0 Bowling Rd Unit 1344123, Middlesboro, KY 40965

    0.9 Acres Partially cleared with wooded area in back for privacy. City limits. All utilities available. Perfect location for a home or two right next to the mountains!

    Misti McGrath Realty Group

    0 Bowling Rd Unit 1344123, Middlesboro, KY 40965
  • /14

    $150,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    422 Wilderness Rd, Middlesboro, KY 40965

    Super cute starter home with 2 beds and 1 full bath. Recently remodeled with excellent updates.The backyard is an oasis with additional building with electricity. Starter home, income producing property, downsizing or whatever fits your needs, this home has it!

    Misti McGrath Realty Group

    422 Wilderness Rd, Middlesboro, KY 40965
  • /22

    $400,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    935 Shawanee Rd, Harrogate, TN 37752

    Brand New Construction with Mountain ViewsWelcome to this beautifully crafted new construction offering 1,500 square feet of modern living with thoughtful design throughout. This home features three spacious bedrooms, 2 Full bathrooms, providing comfort and privacy for family or guests.The open-concept floor plan seamlessly connects the living, dining, and kitchen areas--perfect for

    Steve Mason REMAX PROFESSIONAL'S

    935 Shawanee Rd, Harrogate, TN 37752

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