Middlesborough, KY homes for sale & real estate

view of front of house with a garage, a mountain view, and covered porch

view of front of house featuring a porch, a garage, and a front lawn

$1,241 Closing Credit¹

$104,500

2 beds • 1 bath • 1,008 sqft

1813 Winchester Ave, Middlesboro KY 40965

#1288008, Listing Office: Realty Group

$3,741 Closing Credit¹

$315,000

3 beds • 4 baths • 2,349 sqft

915 Lothbury Ave, Middlesboro KY 40965

#1287518, Listing Office: Turn Key Realty

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view of front of home featuring a balcony and a front lawn

$653 Closing Credit¹

$55,000

3 beds • 2 baths

526 Balmoral Rd, Middlesboro KY 40965

#25000454, Listing Office: DIYFlatFee.com

407 Exeter Ave, Middlesboro KY, 40965 land for sale

$29,900

Land • 0.26 Acres

407 Exeter Ave, Middlesboro KY 40965

#1286317

$1,722 Closing Credit¹

$145,000

3 beds • 2 baths

112 Parker Ln, Middlesboro KY 40965

#24026218, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

ranch-style house with a carport and a front lawn

view of front facade with covered porch and a front lawn

$2,672 Closing Credit¹

$225,000

2 beds • 2 baths • 1,144 sqft

505 S S 38th St, Middlesboro KY 40965

#1284881, Listing Office: Turn Key Realty

carpeted spare room featuring a textured ceiling

carpeted spare room with ceiling fan, a large fireplace, and a textured ceiling

Backup offers

$1,424 Closing Credit¹

$119,900

3 beds • 1.5 baths

1200 W Chester Ave, Middlesboro KY 40965

#24024891, Listing Office: Century 21 Virginia Wilder Real Estate

Room to negotiate?

Median Sold Price

$139K

Avg. Sale Time

46 Days

Based on our January 2025 Market Report.

view of front facade featuring a porch and a front lawn

$1,068 Closing Credit¹

$89,900

3 beds • 1 bath • 1,492 sqft

549 S S 43rd St, Middlesboro KY 40965

#1283670, Listing Office: Turn Key Realty

view of front of home with a carport and a front lawn

$2,968 Closing Credit¹

$249,900

3 beds • 1 bath

515 N 25th St, Middlesboro KY 40965

#24024427, Listing Office: WEICHERT REALTORS - Ford Brothers

ranch-style home featuring a garage and a front lawn

view of patio / terrace featuring a porch

ranch-style house featuring a front lawn, a storage unit, and a patio area

$3,669 Closing Credit¹

$309,000

4 beds • 2 baths

123 Twin Acres Rd, Middlesboro KY 40965

#24024070, Listing Office: Action Realty

900 Worchester Ave, Middlesboro KY, 40965 land for sale

Listing photo 2 for 900 Worchester Ave, Middlesboro KY 40965

Listing photo 3 for 900 Worchester Ave, Middlesboro KY 40965

$159,000

Land • 2.75 Acres

900 Worchester Ave, Middlesboro KY 40965

#24024063, Listing Office: Action Realty

rear view of house with a mountain view and a yard

dining room featuring dark wood-type flooring and an inviting chandelier

kitchen featuring white cabinetry, dark hardwood / wood-style floors, and appliances with stainless steel finishes

$3,551 Closing Credit¹

$299,000

4 beds • 2 baths • 2,300 sqft

904 E Cumberland Ave, Middlesboro KY 40965

#1282357

exterior space with a mountain view and a yard

$2,730 Closing Credit¹

$229,900

3 beds • 2 baths • 1,684 sqft

1315 Winchester Ave, Middlesboro KY 40965

#1282005, Listing Office: AAA Realty, Inc.

view of front facade featuring a front yard and a garage

$3,551 Closing Credit¹

$299,000

3 beds • 2.5 baths

109 Hollywood Dr, Middlesboro KY 40965

#24022848, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

ranch-style house featuring a front lawn

$3,551 Closing Credit¹

$299,000

3 beds • 2.5 baths • 3,544 sqft

109 Hollywood Dr, Middlesboro KY 40965

#1280901, Listing Office: Coldwell Banker Bisceglia Real

view of front facade with a wooden deck, a front lawn, and a garage

view of front facade featuring a wooden deck, a front yard, and a garage

view of home's exterior featuring a yard

$1,188 Closing Credit¹

$100,000

3 beds • 1.5 baths • 1,430 sqft

210 Welch Ln, Middlesboro KY 40965

#1280087, Listing Office: REMAX PROFESSIONAL'S

rear view of property with a wooden deck and a lawn

kitchen with sink, stainless steel appliances, a textured ceiling, and hardwood / wood-style flooring

$1,614 Closing Credit¹

$135,900

3 beds • 2 baths • 1,120 sqft

100 Ellenwood Rd, Middlesboro KY 40965

#1279180

view of front of home with a porch and a front lawn

kitchen with dark hardwood / wood-style floors, stainless steel appliances, and sink

entryway with a textured ceiling, a wealth of natural light, and dark hardwood / wood-style floors

$2,019 Closing Credit¹

$170,000

4 beds • 1 bath • 2,073 sqft

1002 Chester Ave, Middlesboro KY 40965

#1278129, Listing Office: Realty Group

view of front of house featuring covered porch, an outdoor structure, and a garage

$2,791 Closing Credit¹

$235,000

2 beds • 1 bath • 2,031 sqft

512 N 25th St, Middlesboro KY 40965

#1278575

113 Hollywood Dr, Middlesboro KY, 40965, 3 bedrooms, 2.5 baths house for sale

Listing photo 2 for 113 Hollywood Dr, Middlesboro KY 40965

Listing photo 3 for 113 Hollywood Dr, Middlesboro KY 40965

$3,551 Closing Credit¹

$299,000

3 beds • 2.5 baths • 3,174 sqft

113 Hollywood Dr, Middlesboro KY 40965

#1277166, Listing Office: Coldwell Banker Bisceglia Real

$2,837 Closing Credit¹

$238,900

3 beds • 1 bath

164 Lake Hill Rd, Middlesboro KY 40965

#24019529, Listing Office: Turn Key Realty

kitchen with appliances with stainless steel finishes, exhaust hood, sink, and hanging light fixtures

living room featuring a fireplace, light carpet, and an inviting chandelier

$2,837 Closing Credit¹

$238,900

3 beds • 1 bath • 3,136 sqft

164 Lake Hill Rd, Middlesboro KY 40965

#1276491, Listing Office: Turn Key Realty

single story home with a garage and a front yard

$3,680 Closing Credit¹

$309,900

4 beds • 2 baths • 3,338 sqft

123 Twin Acres Rd, Middlesboro KY 40965

#1275549, Listing Office: Action Realty

0 Home Run Rd, Middlesboro KY, 40965 land for sale

$19,500

Land • 1.14 Acres

0 Home Run Rd, Middlesboro KY 40965

#24018475, Listing Office: Century 21 Virginia Wilder Real Estate

view of front facade with a front lawn and covered porch

view of front of house featuring central air condition unit, a porch, and a front yard

view of front of home with a front yard and a porch

$3,681 Closing Credit¹

$310,000

5 beds • 3.5 baths

2410 Cumberland Ave, Middlesboro KY 40965

#24018171, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

view of front of house featuring covered porch, cooling unit, and a front yard

view of front facade featuring a front yard and a porch

view of front of property with a porch and a front yard

$3,681 Closing Credit¹

$310,000

5 beds • 3.5 baths • 3,000 sqft

2410 Cumberland Ave, Middlesboro KY 40965

#1274726, Listing Office: Coldwell Banker Bisceglia Real

view of front of home with a front lawn and covered porch

$938 Closing Credit¹

$79,000

3 beds • 1.5 baths • 1,364 sqft

1619 Winchester Ave, Middlesboro KY 40965

#1273937, Listing Office: Realty Group

view of front facade featuring a porch, a garage, and a front yard

view of front facade featuring a porch and a garage

$4,511 Closing Credit¹

$379,900

5 beds • 4 baths • 2,943 sqft

717 S 27th St, Middlesboro KY 40965

#1271628, Listing Office: REMAX PROFESSIONAL'S

living room with hardwood / wood-style flooring, ceiling fan, a fireplace, and a textured ceiling

$2,374 Closing Credit¹

$199,900

3 beds • 1 bath • 1,661 sqft

811 Gloucester Ave, Middlesboro KY 40965

#1270976, Listing Office: REMAX PROFESSIONAL'S

ranch-style house featuring a front yard

view of front of property featuring a front lawn

ranch-style home featuring covered porch and a front lawn

$2,250 Closing Credit¹

$189,500

3 beds • 2 baths • 1,500 sqft

104 Hollywood Dr, Middlesboro KY 40965

#1263727, Listing Office: REMAX PROFESSIONAL'S

view of side of property with a wooden deck

kitchen featuring lofted ceiling with beams, sink, dishwasher, light wood-type flooring, and wooden ceiling

kitchen featuring sink, appliances with stainless steel finishes, and light hardwood / wood-style flooring

$3,443 Closing Credit¹

$289,900

3 beds • 3 baths • 2,210 sqft

515 Englewood Rd, Middlesboro KY 40965

#1262597, Listing Office: Turn Key Realty

new england style home with central AC and a front yard

cape cod-style house featuring a front lawn and a porch

view of property exterior featuring a lawn

$5,225 Closing Credit¹

$440,000

5 beds • 4 baths

101 Kim Ln, Middlesboro KY 40965

#24008758, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

new england style home with central AC unit and a front yard

cape cod home featuring covered porch and a front yard

$5,225 Closing Credit¹

$440,000

5 beds • 4 baths • 3,874 sqft

101 Kim Ln, Middlesboro KY 40965

#1261697, Listing Office: Coldwell Banker Bisceglia Real

living room with a textured ceiling, ceiling fan, and dark wood-type flooring

living room with dark hardwood / wood-style floors, a textured ceiling, and ceiling fan

$6,531 Closing Credit¹

$550,000

4 beds • 2.5 baths

1015 Old Wilson Ln, Middlesboro KY 40965

#24005120, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

114 Dalewood Rd, Middlesboro KY, 40965 land for sale

Listing photo 2 for 114 Dalewood Rd, Middlesboro KY 40965

Listing photo 3 for 114 Dalewood Rd, Middlesboro KY 40965

$22,000

Land • 0.01 Acres

114 Dalewood Rd, Middlesboro KY 40965

#1254837, Listing Office: Mountain Realty

423 N 10th St, Middlesboro KY, 40965 land for sale

Listing photo 2 for 423 N 10th St, Middlesboro KY 40965

Listing photo 3 for 423 N 10th St, Middlesboro KY 40965

$1,250,000

Land • 64.84 Acres

423 N 10th St, Middlesboro KY 40965

#1247661, Listing Office: Coldwell Banker Bisceglia Real

$1,247 Closing Credit¹

$105,000

3 beds • 2 baths • 1,296 sqft

252 Chasteen Dr, Middlesboro KY 40965

#1241257, Listing Office: Century 21 Virginia Wilder Real Estate

back of house featuring a lawn and central AC unit

rear view of property featuring central air condition unit and a lawn

$2,018 Closing Credit¹

$169,900

4 beds • 2 baths

501 N 25th St, Middlesboro KY 40965

#23018246, Listing Office: Coldwell Banker Bisceglia Realty & Auction Co

Middlesborough, KY Real Estate Market Overview

Browse 38 homes for sale in Middlesborough, KY. View properties, photos, nearby real estate with school and housing market information. In January 2025 in Middlesborough, KY there were 19.2% less homes for sale than in December 2024. While the average time on the market in January 2025 was 46 days, the median list price was $139,000. Over 0 listings were sold over their listed price in January 2025 in Middlesborough, KY. In the same period over 3 listings were sold below the listed price and 0 listings were sold for the listed price.

From Rocket Homes Real Estate and based on county public records data

Schools near Middlesborough, KY

Elementary Schools

Middlesboro Elementary School
3400 Cumberland Ave
Public District PK-4

Middle Schools

Yellow Creek School Center
4840 W Cumberland Ave
Public District PK-8
Middlesboro Middle School
4400 W Cumberland Ave
Public District 5-8

High Schools

Middlesboro High School
4404 W Cumberland Ave
Public District 9-12

Data provided by Great Schools

Homes for sale in Middlesborough, KY

Middlesborough, KY Real Estate Market Overview

What is it like to live in Middlesborough, KY

Overview

Housing types

Advantages

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Schools near Middlesborough, KY

Housing market reports in Bell County

Homes for sale near Middlesborough, KY

Top real estate cities in Kentucky