Newest Homes for Sale in Middlesboro, KY

• 

  

  

  /31

  $185,000

  $23K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  23 Castleford Way, Middlesboro, KY 40965

  Back on the market at no fault of the seller! Located in the desirable Ambleside subdivision, this beautifully maintained and tastefully decorated two-story home features soft, calming paint colors, gorgeous luxury vinyl flooring, and a warm, welcoming feel throughout. This charming home offers 3 spacious bedrooms and 1.5 bathrooms. The main level includes a comfortable living room, formal dining

  Beth Combs Turn Key Realty

  23 Castleford Way, Middlesboro, KY 40965
• 

  

  

  /41

  $135,000

  • 5 Beds
  • 4 Baths
  • 2,844 Sq Ft

  215 S 21st St, Middlesboro, KY 40965

  Megan Stanaford Black Diamond Realty

  215 S 21st St, Middlesboro, KY 40965
• 

  

  

  /11

  $219,999

  $5K 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
• 

  

  

  /20

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,652 Sq Ft

  116 N Petersborough Ave, Middlesboro, KY 40965

  Exceptional 3 bedrooms, 1 bath home in the heart of Middlesboro. Located just off Cumberland Ave on 30th St, this home's location is what you have been looking for--within walking distance of downtown, schools, and the hospital. Just down the street from the T-ball field and the city pool. With hardwood floors throughout and beautiful wood trim, this house is waiting for a family to make it a

  Kevin Bisceglia Coldwell Banker Bisceglia Real

  116 N Petersborough Ave, Middlesboro, KY 40965
• 

  

  

  /12

  $225,000

  • 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 great for the mother-in-law. The apartment is open space with 1 bdrm and a full bath. 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. Great student home and rental!!

  Steve Mason REMAX PROFESSIONAL'S

  908 W Chester Ave, Middlesboro, KY 40965
• 

  

  /18

  $125,000

  • 2 Beds
  • 1.5 Baths
  • 1,426 Sq Ft

  123 Cawood Ln, Middlesboro, KY 40965

  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 mudroom/workshop provides

  

  Dustin Daniels

  Mountain Realty

  (606) 717-1149

  123 Cawood Ln, Middlesboro, KY 40965
• 

  

  /40

  $239,000

  $10K 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
• 

  

  /29

  $299,000

  • 5 Beds
  • 2.5 Baths
  • 3,068 Sq Ft

  207 Arthur Heights, Middlesboro, KY 40965

  CHARMING VICTORIA HOME. Experience the timeless allure of this late-1800s Victorian masterpiece, where historic character meets expansive modern living. Boasting over 2,404 finished square feet—plus a versatile 600-square-foot finished attic space—this impressive residence offers a total of five spacious bedrooms, providing ample room for family, guests, or a dedicated home office. The primary

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  207 Arthur Heights, Middlesboro, KY 40965
• 

  

  /13

  $75,000

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  918 E Cumberland Ave, Middlesboro, KY 40965

  Old home needs work with an attached older home that needs to be torn down. Great Location on Cumberland Ave behind Food City

  Steve Mason REMAX PROFESSIONAL'S

  918 E Cumberland Ave, Middlesboro, KY 40965
• 

  

  /4

  $164,000

  • 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
• 

  

  /19

  $44,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  406 W Rochester Ave, Middlesboro, KY 40965

  Cottage style, 3 bedroom 2 bathroom home with chain link fencing in the city limits of Middlesboro KY. PVA records show 0.18 of an acre, city water, city sewer. Home needs some work but would make a great permanent home or use as a rental. Close to LMU and all the beauty Southeastern KY offers! 5 minutes to the Cumberland Gap National Park, shopping and more! Buyer to verify all property

  Megan Stanaford Black Diamond Realty

  406 W Rochester Ave, Middlesboro, KY 40965
• 

  

  /18

  $135,000

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  2002 Winchester Ave, Middlesboro, KY 40965

  CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  2002 Winchester Ave, 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
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  /4

  $25,000

  • Land
  • 7,492 Sq Ft
  • $145,349 per Acre

  109 Bloomsbury Ave, Middlesboro, KY 40965

  50x150 lot; used to have a home on premises but that has been removed. City utilities available, buyer to verify all aspects of the property.

  Megan Stanaford Black Diamond Realty

  109 Bloomsbury Ave, Middlesboro, KY 40965
• 

  

  /3

  $35,000

  • Land
  • 14,853 Sq Ft
  • $102,639 per Acre

  2107 Winchester Ave, Middlesboro, KY 40965

  PRIME LOCATION, NO FLOOD ZONE! Discover the ultimate blank canvas within the city limits. This fully cleared, level, and build ready lot offers an exceptional opportunity to build your dream home, or next investment project. Situated entirely outside the FEMA flood zone, this lot offers peace of mind and reduced insurance costs. All city utilities are ready for connection. This lot would always

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  2107 Winchester Ave, Middlesboro, KY 40965
• 

  

  /11

  $49,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  6, Middlesboro, KY 40965

  Don't miss out on your chance to own this slightly used 2025 3 bedroom 2 bath home in the heart of Middlesboro. Located in a family friendly community that values affordability with space rent at $175. Available for showings now!

  Neely Gray VMF Homes

  6, Middlesboro, KY 40965
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  /35

  $179,900

  $7K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,028 Sq Ft

  1200 W Chester Ave, Middlesboro, KY 40965

  Charming Home for Sale in Middlesboro, KY - 1200 W Chester Ave Welcome to this inviting home located in the heart of Middlesboro! Situated on a spacious corner lot at 1200 W Chester Avenue, this property offers comfort, convenience, and small-town charm—all in one. Comfortable living spaces with plenty of natural light. Functional kitchen with ample cabinet storage Generous yard—perfect for

  Megan Stanaford Black Diamond Realty

  1200 W Chester Ave, Middlesboro, KY 40965
• 

  

  /30

  $279,900

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  127 Alpine Rd, Middlesboro, KY 40965

  This charming property offers the perfect blend of cozy indoor living and expansive outdoor space. Nestled in the heart of Middlesboro this home is situated on 1.5 acres. This brick ranch home with a basement has 1344 square feet, and features 3 bedrooms and 2 baths on the main floor along with the washer and dryer. The home provides plenty of room for family and guests. The heart of the home is

  Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  127 Alpine Rd, Middlesboro, KY 40965
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  /67

  $180,000

  $5K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 2,430 Sq Ft

  713 Exeter Ave, Middlesboro, KY 40965

  Welcome to the stunning 713 Exeter Ave located in the lovely town of Middlesboro KY, less than 5 minutes to downtown Middlesboro, 15 minutes from LMU, & super close to Norris Lake. This home makes a perfect residence for anyone looking in the area and would make a great rental property as well! This home offers ample space with 4 bedrooms on the main level and tons of potential for a loft or 2

  Victoria Allen Century 21 Virginia Wilder Real Estate

  713 Exeter Ave, 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
• 

  /2

  $960,000

  • 2 Beds
  • 2 Baths
  • 6,696 Sq Ft

  508 & 512 Winchester Ave, Middlesboro, KY 40965

  Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to

  Beth Combs Turn Key Realty

  508 & 512 Winchester Ave, Middlesboro, KY 40965
• 

  /2

  $182,000

  • 2 Beds
  • 2 Baths
  • 1,608 Sq Ft

  414 S 24th St, Middlesboro, KY 40965

  Prime commercial opportunity at 414 S 24th Street in Middlesboro, KY! This versatile property offers excellent visibility and accessibility in a well-established area, just minutes from historic downtown Middlesboro and major routes. Ideal for office space, retail, professional services, or an investment property with strong potential in Bell County. Spacious layout, solid construction, and

  Beth Combs Turn Key Realty

  414 S 24th St, Middlesboro, KY 40965
• 

  

  /16

  $295,000

  $15K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,100 Sq Ft

  717 Highway 441, Middlesboro, KY 40965

  Beautiful 5-Bedroom Home on 1.165 Acres - Middlesboro, KY Welcome to 717 Highway 441, a stunning custom manufactured home offering space, comfort, and modern charm—all set on a generous 1.165-acre lot. This gorgeous home features 5 spacious bedrooms and 3 full bathrooms, perfect for families of all sizes. Step inside to find large, open rooms, ample closet space, and beautifully designed

  Megan Stanaford Black Diamond Realty

  717 Highway 441, 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
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  /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
• 

  /2

  $15,000

  $5K PRICE DROP

  • Land
  • 5,488 Sq Ft
  • $119,048 per Acre

  205 Exeter Ave, Middlesboro, KY 40965

  Great lot, city utilities available.

  Megan Stanaford Black Diamond Realty

  205 Exeter Ave, Middlesboro, KY 40965
• 

  

  /27

  $104,900

  $15K 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
• 

  

  /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
• 

  

  /3

  $125,000

  $50K PRICE DROP

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

  120 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

  120 Redwood Rd Unit A & B, Middlesboro, KY 40965
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  /17

  $245,000

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  156 Wellington Dr, Middlesboro, KY 40965

  Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is

  Megan Stanaford Black Diamond Realty

  156 Wellington Dr, Middlesboro, KY 40965
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  /24

  $159,000

  $41K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /5

  $22,500

  $8K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $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

  $20,000

  $5K PRICE DROP

  • Land
  • 13,068 Sq Ft
  • $66,667 per Acre

  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
• 

  

  /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
• 

  

  /15

  $135,000

  $7K PRICE DROP

  • 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

  • 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
• 

  

  /29

  $259,000

  $20K PRICE DROP

  • 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
• 

  

  /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

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