Recently Sold Middlesboro, KY Homes

/9
$85,000 Sold Feb 21, 2025
- Land
- 2.75 Acres
- $30,909 per Acre
- 25 Days On Market
900 Worchester Ave, Middlesboro, KY 40965

Beautiful 2.75 LEVEL ACRES in the heart of the residential section of Middlesboro. Near the Civic Center, Airport, Tennis Courts, Golf Club, National Guard Armory and other amenities. Property runs from Worchester to Ilchester and from 29th St to 28th St. What would you do with this very lovely property? Explore the possibilities and check it out!!

Ann Robinson Action Realty

900 Worchester Ave, Middlesboro, KY 40965
/25
$102,500 Sold Feb 19, 2025
- 2,100 Sq Ft
- $49/SF
- 191 Days On Market
- 3 Beds
- 2 Baths
- Built 1908
512 W Chester Ave, Middlesboro, KY 40965

Three bedroom, 2 bath home located in a quiet neighborhood in Middlesboro, Ky. This home has all of the character of a historic home but with many modern updates. This is a single-family home but has the possibility of being divided into 2 units with one bedroom, bath, and kitchen downstairs and 2 bedrooms, a bathroom and a separate kitchen upstairs. Also included is a large garage with

Michael Hensley REMAX PROFESSIONAL'S

512 W Chester Ave, Middlesboro, KY 40965
/19
$129,000 Sold Feb 17, 2025
- 1,485 Sq Ft
- $87/SF
- 246 Days On Market
- 3 Beds
- 2 Baths
- Built 2015
201 Exeter Ave, Middlesboro, KY 40965

Beautiful home located in Middlesboro. This 3 bedroom, 2 bathroom home is ready for its next owner(s). Convenient to shopping, parks and restaurants. Don't let this home pass you by. Buyer to verify acreage, square footage, manufactured home info and taxes.

Dustin Daniels Mountain Realty

201 Exeter Ave, Middlesboro, KY 40965
/55
$180,000 Sold Feb 12, 2025
- 1,670 Sq Ft
- $108/SF
- 92 Days On Market
- 3 Beds
- 2 Baths
- Built 1946
603 W Chester Ave, Middlesboro, KY 40965

Charming 3-bedroom, 2-bath home with a bonus room and ample storage, conveniently located near downtown Middlesboro! This well-maintained residence features a durable metal roof and vinyl siding, along with a level, easy-to-maintain yard. The detached 1.5-car garage offers additional storage and a workshop area for your hobbies, plus a spacious fenced backyard where kids and pets can play freely.

Beth Combs Turn Key Realty

603 W Chester Ave, Middlesboro, KY 40965
/24
$130,000 Sold Feb 04, 2025
- 1,020 Sq Ft
- $127/SF
- 48 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1947
205 Oakwood Rd, Middlesboro, KY 40965

This is an adorable 2 bedroom, 1 and a half bath home located in a quiet neighborhood in Historic Middlesboro, Ky. Some updates include, new flooring, new metal roof and a new HVAC making this home perfect for a first-time home buyer or someone that is looking to downsize to a low maintenance home. Let your pets run in the fenced in yard. All information is to be verified by the buyer.

Michael Hensley REMAX PROFESSIONAL'S

205 Oakwood Rd, Middlesboro, KY 40965
/19
$235,000 Sold Jan 31, 2025
- 2,100 Sq Ft
- $112/SF
- 318 Days On Market
- 4 Beds
- 1 Bath
- Built 1920
2103 Winchester Ave, Middlesboro, KY 40965

Two for 1! The main house at 2103 Winchester Ave has 2100 sf, one bath and four bedrooms. Home was completely refurbished in 2024. New paint, new HVAC, hardwood floors refinished, new bathroom. Sitting on the back of the lot is 2105 Winchester Ave--a 1040 sf rental house that is currently unoccupied is a one bath two bedroom. New paint in the rental. (Listed as a child listing of this listing).

Kevin Bisceglia Coldwell Banker Bisceglia Real

2103 Winchester Ave, Middlesboro, KY 40965
/20
$106,000 Sold Jan 30, 2025
- 676 Sq Ft
- $157/SF
- 71 Days On Market
- 1 Bed
- 1 Bath
- Built 1996
409 Shillilah Village, Middlesboro, KY 40965

Do you hear the mountains calling you? This cute little chalet nestled in mother nature's canopy offers low maintenance yard. The location offers hiking, exploring, kayaking, fishing and the arrival of the 2025 Elk Lodge and Nature Preserve with restaurants, gift shops, state of the art playground and observatory. If your looking as an investment property, there are several Airbnb currently.

Dawn Risner Turn Key Realty

409 Shillilah Village, Middlesboro, KY 40965
/18
$58,000 Sold Jan 27, 2025
- 920 Sq Ft
- $63/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1996
401 S 20th St, Middlesboro, KY 40965

Conveniently located within walking distance of downtown Middlesboro, this home is minutes from local shopping, restaurants, schools, and hospital. This manufactured home was built in 1996 and has 920 square feet. It has 3 bedrooms and 2 bathrooms. This property could also be great as an investment property.

Kevin Bisceglia Coldwell Banker Bisceglia Real

401 S 20th St, Middlesboro, KY 40965
/28
$185,000 Sold Jan 23, 2025
- 1,400 Sq Ft
- $132/SF
- 131 Days On Market
- 3 Beds
- 2 Baths
- Built 1955
908 W Chester Ave, Middlesboro, KY 40965

Very well maintained 3 bedroom, 2 bath home located on Chester Avenue in Middlesboro. Main part of the home is 2 bedrooms with an attached one bedroom suite that can also be used as an apartment. New bathroom remodeled recently and new flooring throughout. Large fenced in backyard for privacy. Make an appointment to see this wonderful home today.

Michael Hensley REMAX PROFESSIONAL'S

908 W Chester Ave, Middlesboro, KY 40965
/9
$24,501 Sold Jan 02, 2025
- 1,548 Sq Ft
- $16/SF
- 10 Days On Market
- 3 Beds
- 1 Bath
- Built 1909
311 S 22nd St, Middlesboro, KY 40965

Great opportunity to buy this fixer upper located in Middlesboro, KY. and sitting on a +/- .17 acre lot. The interior has 1548 sq. ft. with 3 bedrooms and 1 bathroom.

Aaron Brailer RealHome Services and Solutions, Inc.

311 S 22nd St, Middlesboro, KY 40965
/35
$185,700 Sold Dec 13, 2024
- 1,552 Sq Ft
- $120/SF
- 78 Days On Market
- 3 Beds
- 1 Bath
- Built 1969
204 Summit Dr, Middlesboro, KY 40965

This is a beauty, ready to move into, recently remodeled, with 3 bedrooms, one full modern bathroom with amazing shower heads, new stainless steel kitchen appliances, nice modern kitchen with new cabinets and counter tops. Large family room, living room that leads into formal dining area, laundry room (washer stays), insulated windows, new roof, new laminate floors and hardwood floors have been

Virginia Wilder Century 21 Virginia Wilder Real Estate

204 Summit Dr, Middlesboro, KY 40965
/23
$210,000 Sold Dec 13, 2024
- 2,206 Sq Ft
- $95/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1992
1009 W Rochester Ave, Middlesboro, KY 40965

Need space? I got you! 3 oversized bedrooms with BONUS ROOMS (more than one) Formal dining room, impressive sized kitchen with eat in space. Private main suite area with separate entrance and a detached 2 car garage, all on a level corner lot (fenced in back yard!) in the heart of Middlesboro. Let's go look asap!

Misti McGrath Realty Group

1009 W Rochester Ave, Middlesboro, KY 40965
/20
$135,000 Sold Dec 11, 2024
- 1,456 Sq Ft
- $93/SF
- 55 Days On Market
- 3 Beds
- 1 Bath
- Built 1997
316 Avondale Ave, Middlesboro, KY 40965

Check out this cute ranch home!! The property features 3 bedrooms, 1 bath, eat-in kitchen with ample cabinets and countertops space. Kitchen appliances, washer and dryer convey with home. 2024 renovations; new laminated flooring throughout, new gutters being installed, new shutters, furnace 1 year old. Your Kids and pets will love the level fenced in back yard. Property is located less than

Sharon Teaney Century 21 Virginia Wilder Real Estate

316 Avondale Ave, Middlesboro, KY 40965
/12
$45,000 Sold Dec 04, 2024
- 1,100 Sq Ft
- $41/SF
- 26 Days On Market
- 3 Beds
- 1 Bath
- Built 1965
712 Balmoral Rd, Middlesboro, KY 40965

Home has had a recent fire in one bedroom. Excellent location with an awesome, oversized, level lot. Very pretty built ins with an option to expand the kitchen or create a fantastic mud room.Needs a little work, but would be a great investment!Buyer/Buyers agent to verify all information.

Misti McGrath Realty Group

712 Balmoral Rd, Middlesboro, KY 40965
/19
$280,000 Sold Nov 21, 2024
- 1,796 Sq Ft
- $156/SF
- 50 Days On Market
- 4 Beds
- 2 Baths
- Built 1966
114 George Ann Dr, Middlesboro, KY 40965

3 bedroom 2 bath in an excellent neighborhood! PRIME location right next door to the hospital, restaurants and schools. Numerous updates to this home, including, kitchen, new laundry room, massive second living area that could easily be turned into a main suite, expansive deck for entertaining your guests. Full unfinished basement ready for your imagination. Call today for your private tour!

Misti McGrath Realty Group

114 George Ann Dr, Middlesboro, KY 40965
/48
$447,750 Sold Nov 21, 2024
- 4,300 Sq Ft
- $104/SF
- 42 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1992
515 Worchester Ave, Middlesboro, KY 40965

Charming and Spacious Family Home in Historical MiddlesboroWelcome to this beautifully maintained 4-bedroom, 3.5-bathroom home located in the picturesque and historic town of Middlesboro, KY. This residence offers a blend of classic charm and modern convenience, making it an ideal choice for families or those who like to have guests.Upon entering, you'll find a welcoming formal

Michael Hensley REMAX PROFESSIONAL'S

515 Worchester Ave, Middlesboro, KY 40965
/28
$143,000 Sold Nov 20, 2024
- 960 Sq Ft
- $149/SF
- 41 Days On Market
- 3 Beds
- 1.5 Baths
- Built 2000
211 Gum Springs Rd, Middlesboro, KY 40965

Located in Middlesboro, KY, this charming 3-bedroom, 2-bathroom home is waiting for you to add your personal touch. Enjoy unwinding on the expansive deck that wraps nearly around the house. The large walk-out basement provides ample storage space. The home features freshly painted walls, new carpeting, and updated bathrooms.

Beth Combs Turn Key Realty

211 Gum Springs Rd, Middlesboro, KY 40965
/15
$137,694 Sold Nov 18, 2024
- 1,066 Sq Ft
- $129/SF
- 205 Days On Market
- 3 Beds
- 1 Bath
- Built 1972
114 E Rochester Ave, Middlesboro, KY 40965

BACK ON THE MARKET. No fault of the home. Charming three bedroom one bath home that is nestled in the heart of downtown Middlesboro on a semi-private street. This home sits on a 50'X150' level lot with a new deck to the kitchen entry. The front porch has been recently painted and wood railings have been added which enhances the charm. This home has all new laminate flooring and fresh paint

Sheila Durham Coldwell Banker Bisceglia Real

114 E Rochester Ave, Middlesboro, KY 40965
/7
$35,000 Sold Nov 14, 2024
- Land
- 0.35 Acre
- $100,000 per Acre
- 55 Days On Market
403 Winchester Ave, Middlesboro, KY 40965

Beautiful flat, fenced lot in Middlesboro, KY located near down town. A Must see for anyone thinking of moving to Middlesboro.

Brad Cawood Turn Key Realty

403 Winchester Ave, Middlesboro, KY 40965
/46
$302,000 Sold Oct 24, 2024
- 1,920 Sq Ft
- $157/SF
- 23 Days On Market
- 4 Beds
- 3 Baths
- Built 2006
164 Brush Mountain Cir, Miracle, KY 40856

Have you been looking for your very own getaway in the mountains of Kentucky? This is what you have been looking for! Located in a gated community in the beautiful mountains, only minutes away from downtown Middlesboro. This expansive home has 3,000 sf of living space with 4 bedrooms and 3 bathrooms, with a built-in garage on the lower level. It has 2 heat pumps to keep you comfortable and a

Kevin Bisceglia Coldwell Banker Bisceglia Real

164 Brush Mountain Cir, Miracle, KY 40856
/20
$220,000 Sold Oct 18, 2024
- 1,480 Sq Ft
- $149/SF
- 67 Days On Market
- 3 Beds
- 2 Baths
- Built 1996
1013 Doncaster Ave, Middlesboro, KY 40965

Fantastic 3 bed 2 bath home that is immaculate! Newer Roof and water heater, brand new fridge and even the washer and dryer stay!! You MUST make plans to see this beautiful home, the lawn is perfect! Flat and big enough to house the POOL that stays with the home and much more! This back deck is calling your name! Come sit for a spell.

Misti McGrath Realty Group

1013 Doncaster Ave, Middlesboro, KY 40965
/28
$170,000 Sold Sep 27, 2024
- 1,800 Sq Ft
- $94/SF
- 163 Days On Market
- 3 Beds
- 2 Baths
- Built 1969
815 Exeter Ave, Middlesboro, KY 40965

Situated on just over half an acre, this newly renovated home has a walkout basement, three bedrooms, and two baths. Step inside to discover a spacious living room, perfect for entertaining guests or relaxing with loved ones. The kitchen features stainless steel appliances and tongue-and-groove ceilings, adding character and charm. Hardwood floors grace the living spaces, while ample windows

Beth Combs Turn Key Realty

815 Exeter Ave, Middlesboro, KY 40965
/15
$96,500 Sold Sep 25, 2024
- 810 Sq Ft
- $119/SF
- 30 Days On Market
- 2 Beds
- 1 Bath
- Built 1970
106 Ellenwood Rd, Middlesboro, KY 40965

The two bedroom, one-bath home is a charming urban bungalow, perfect for those who like to embrace city living. Leave the car at home and enjoy walking or bicycling. The house offers a porch providing the welcoming entrance to the home. Upon entering the home will enjoy the neutral tones and living room offers a cozy and inviting ambiance. The kitchen is compact but efficient, equipped with

Dawn Risner Turn Key Realty

106 Ellenwood Rd, Middlesboro, KY 40965
/31
$283,250 Sold Sep 23, 2024
- 2,000 Sq Ft
- $142/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1918
2909 W Cumberland Ave, Middlesboro, KY 40965

This beautiful brick has touches of class to enjoy for a lifetime. With all the beauty of her old style from big rooms, original cherry doors 9 1/2 foot ceilings and original hardwood floors. A fabulous front porch, a 2 car garage with a spacious and playful backyard. On the inside you will enjoy a kitchen that sparkles white with stainless steel appliances and a grand island for cooking and

Lisa Stacy-Gibbs Turn Key Realty

2909 W Cumberland Ave, Middlesboro, KY 40965
/28
$139,000 Sold Sep 19, 2024
- 1,237 Sq Ft
- $112/SF
- 31 Days On Market
- 2 Beds
- 2 Baths
- Built 1946
808 Manchester Ave, Middlesboro, KY 40965

Charming 3 bedroom, 2 bath house for sale in Middleboro with 150x50 chain link fenced yard on a quiet street. Owners have recently installed central heat and air and a new water heater, and have remodeled the bedrooms and bathrooms. There are hardwood floors in the living room and bedrooms, with vinyl plank in the kitchen, bathrooms, and laundry room. It has a metal roof, a screened back porch, a

Kevin Bisceglia Coldwell Banker Bisceglia Real

808 Manchester Ave, Middlesboro, KY 40965
/2
$18,000 Sold Sep 17, 2024
- Land
- 0.35 Acre
- $51,429 per Acre
- 72 Days On Market
0 S 29th St, Middlesboro, KY 40965

Level building lot in a great neighborhood. Very convenient to downtown and shopping.

Michael Hensley REMAX PROFESSIONAL'S

0 S 29th St, Middlesboro, KY 40965
/12
$300,000 Sold Sep 10, 2024
- 1,792 Sq Ft
- $167/SF
- 29 Days On Market
- 3 Beds
- 2 Baths
500 Englewood Rd, Middlesboro, KY 40965

Beautiful home with spectacular location; close to Walmart, the hospital, city schools and 5 minutes to LMU's main campus. This home has cathedral ceilings in the great room and dining room. The floor to ceiling rock fireplace with gas logs is the focal point of these rooms. You will love the beautiful windows which allow an abundance of natural light into the home. The 3 bedrooms are large and

Megan Stanaford Century 21 Virginia Wilder Real Estate

500 Englewood Rd, Middlesboro, KY 40965
/16
$55,000 Sold Sep 09, 2024
- 1,870 Sq Ft
- $29/SF
- 19 Days On Market
- 3 Beds
- 2 Baths
- Built 1930
312 S 23rd St, Middlesboro, KY 40965

Affordable older home located in town, close to downtown amenities. Living room, formal dining room, kitchen, 3 bedrooms, 2 full baths, 2 bonus rooms. Level lot, mostly fenced in the back. New central heat and air. Needs some TLC.

Ann Robinson Action Realty

312 S 23rd St, Middlesboro, KY 40965
/11
$142,500 Sold Aug 26, 2024
- 3,360 Sq Ft
- $42/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
403 E Lothbury Ave, Middlesboro, KY 40965

Ranch style home within the city limits of downtown Middlesboro. Plenty of square footage in this home with fireplace in family room. Spacious eat-in-kitchen. Complete with three bedrooms and two full baths. Deck, storage building and partially fenced yard. Call or text Listing Broker for additional information and to schedule to view.

Linda Pope Renaissance Realty Group

403 E Lothbury Ave, Middlesboro, KY 40965
/39
$202,500 Sold Aug 23, 2024
- 1,200 Sq Ft
- $169/SF
- 95 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
807 Exeter Ave, Middlesboro, KY 40965

New Custom-Built Home in the heart of Middlesboro, featuring three bedrooms and two bathrooms, just minutes to town, hospital, shopping, grocery stores and a short drive to LMU Main Campus. Walking up to the home, you are immediately greeted with a covered front porch constructed using composite decking and adorned with large columns. Entering the home, you are met with a spacious living

Steve Mason REMAX PROFESSIONAL'S

807 Exeter Ave, Middlesboro, KY 40965
/6
$55,000 Sold Aug 21, 2024
- 2,064 Sq Ft
- $27/SF
- 7 Days On Market
- 3 Beds
- 3 Baths
- Built 1925
307 W Chester Ave, Middlesboro, KY 40965

Step into a piece of history with this charming 1925 Sears, Roebuck and Co. house, waiting eagerly for your personal touch and complete remodeling. Nestled on a generous 0.17-acre lot, this potential 3-bedroom, 3-full bath home offers ample space and endless possibilities! Located less than 10 minutes from LMU and within walking distance to downtown Middlesboro's vibrant restaurants and

Cookie Russell Realty Network, Inc

307 W Chester Ave, Middlesboro, KY 40965
/2
$35,000 Sold Jan 21, 2025
- Land
- 0.01 Acre
- $3,500,000 per Acre
- 26 Days On Market
117 Winchester Ave, Middlesboro, KY 40965

READY TO BUILD OR BUY YOUR OWN MANUFACTURED HOME.

Lisa Stacy-Gibbs Turn Key Realty

117 Winchester Ave, Middlesboro, KY 40965
/18
$60,000 Sold Jul 25, 2025
- 1,204 Sq Ft
- $50/SF
- 171 Days On Market
- 2 Beds
- 1 Bath
- Built 1930
3575 Highway 441, Middlesboro, KY 40965

Sheila Durham Coldwell Banker Bisceglia Real

3575 Highway 441, Middlesboro, KY 40965

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