Kentucky

Homes for Sale in Middlesboro

“47 active listings in Middlesboro, Kentucky · Average list price $274,615”

47 listings

Avg $274,615

141 days avg

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Market Overview

Middlesboro Real Estate at a Glance

Current market statistics for Middlesboro, KY

Active Listings

$275K

Avg Price

$115

Price/Sqft

141

Avg Days

Price Range

From

$15,000

$1,790,000

Property Types

Nearby Cities

Explore homes for sale in cities near Middlesboro, Kentucky

Listing selection

Homes to Explore

Active listings from the middlesboro collection

$120K

215 S 21st Street

Middlesboro, KY

$106K

412 N 24th Street

Middlesboro, KY

$200K

116 Edgewood Road

Middlesboro, KY

$200K

140 Wellington Drive

$227K

717 S 27th Street

More listings

Homes for Sale in Middlesboro

Every active listing in Middlesboro, browsable page by page.

Single Family

$274K

230 Windermere Drive

Middlesboro, KY

3 bd2 ba2,099

Single Family

$470K

225 Sherwood Road

Middlesboro, KY

3 bd3 ba3,258

Single Family

$235K

508 Worchester Avenue

Middlesboro, KY

3 bd2 ba2,191

Land

$25K

Bowling Rd

Middlesboro, KY

0 bd0 ba0

Single Family

$285K

406 N 25th St

Middlesboro, KY

3 bd2 ba2,400

Single Family

$625K

2247 State Highway 188

Middlesboro, KY

4 bd5 ba5,426

Single Family

$176K

114 E Rochester Avenue

Middlesboro, KY

3 bd1 ba1,066

Single Family

$320K

103 Sherwood Rd

Middlesboro, KY

5 bd3 ba3,000

Single Family

$235K

88 Tracy Ridge Rd

Middlesboro, KY

3 bd2 ba1,600

Single Family

$315K

1015 Old Wilson Lane

Middlesboro, KY

4 bd3 ba2,488

Single Family

$146K

810 W Rochester Ave

Middlesboro, KY

3 bd2 ba1,386

Land

$1.8M

113 N 18th St

Middlesboro, KY

0 bd0 ba0

Single Family

$150K

305 N 15th St

Middlesboro, KY

2 bd1 ba876

Single Family

$175K

1801 & 1801 1/2 Exeter Avenue

Middlesboro, KY

2 bd1 ba700

Land

$139K

312 Blakely Lane

Middlesboro, KY

0 bd0 ba0

Single Family

$106K

412 N 24th Street

Middlesboro, KY

3 bd2 ba1,966

Single Family

$160K

8 Castleford Way

Middlesboro, KY

3 bd2 ba1,168

Single Family

$129K

708 W Chester Ave

Middlesboro, KY

3 bd1 ba1,404

Single Family

$215K

209 S 19th Street

Middlesboro, KY

3 bd2 ba1,352

Single Family

$219K

812 Worchester Ave

Middlesboro, KY

4 bd2 ba1,544

Single Family

$199K

1102 W Chester Avenue

Middlesboro, KY

3 bd1 ba1,480

Multi-Family

$299K

312 W Chester Avenue

Middlesboro, KY

6 bd4 ba3,594

Single Family

$279K

515 Englewood Road

Middlesboro, KY

3 bd3 ba2,210

Single Family

$200K

140 Wellington Drive

Middlesboro, KY

4 bd2 ba1,612

Single Family

$135K

125 Cawood Lane

Middlesboro, KY

2 bd2 ba1,400

Single Family

$51K

518 S 43rd St

Middlesboro, KY

2 bd1 ba920

Single Family

$200K

116 Edgewood Road

Middlesboro, KY

3 bd2 ba2,154

Multi-Family

$230K

623 N 20th Street

Middlesboro, KY

6 bd6 ba2,700

Single Family

$227K

717 S 27th Street

Middlesboro, KY

5 bd4 ba3,195

Commercial

$325K

1803 W Cumberland Avenue

Middlesboro, KY

0 bd0 ba12,210

Single Family

$279K

400 Gloucester Avenue

Middlesboro, KY

4 bd2 ba2,032

Commercial

$375K

601 N 15th Street

Middlesboro, KY

0 bd0 ba3,200

Single Family

$120K

215 S 21st Street

Middlesboro, KY

5 bd4 ba2,844

Single Family

$265K

207 Arthur Heights

Middlesboro, KY

5 bd3 ba3,068

Single Family

$135K

2002 Winchester Avenue

Middlesboro, KY

2 bd1 ba1,120

Land

$21K

109 Bloomsbury Avenue

Middlesboro, KY

0 bd0 ba0

Land

$29K

2107 Winchester Avenue

Middlesboro, KY

0 bd0 ba0

Single Family

$295K

717 Highway 441

Middlesboro, KY

5 bd3 ba2,100

Land

$50K

Edgewood Road

Middlesboro, KY

0 bd0 ba0

Land

$15K

205 Exeter Avenue

Middlesboro, KY

0 bd0 ba0

Single Family

$230K

156 Wellington Drive

Middlesboro, KY

3 bd2 ba1,320

Single Family

$100K

405 S 37th Street

Middlesboro, KY

4 bd2 ba1,908

Land

$15K

118 Polly Hollow Right Fork Rd

Middlesboro, KY

0 bd0 ba0

Land

$275K

321 Chester Avenue

Middlesboro, KY

0 bd0 ba0

Land

$598K

US Highway 25

Middlesboro, KY

0 bd0 ba0

Land

$23K

526 Balmoral Road

Middlesboro, KY

0 bd0 ba0

Commercial

$1.8M

3133 US Highway 25E

Middlesboro, KY

0 bd0 ba0

Showing 1–47 of 47 · Page 1 of 1

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Turn the listings into a short list with a clearer read on the Middlesboro market, its neighborhoods, and the home features that matter to you.

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Local market guide

Middlesboro Housing Market

Browse 47 active listings in Middlesboro, Kentucky. The average list price for this active inventory is $274,615. Compare the price and property details reported in each listing.

Average list price $274,615 · Range $15,000–$1,790,000 · 47 active listings

Buyer questions

Frequently Asked Questions

How many active listings are available in Middlesboro, Kentucky?

The current inventory contains 47 active listings in Middlesboro, KY.

What is the average list price in Middlesboro, Kentucky?

The average list price among current active listings in Middlesboro, KY is $274,615. Current list prices range from $15,000 to $1,790,000.

What is the average days on market for active listings in Middlesboro?

Current active listings in Middlesboro, KY report an average of 141 days on market.

What is the average list price per square foot in Middlesboro?

The average list price per square foot among current active listings in Middlesboro, KY is $115.

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Browse Middlesboro by home feature

Homes with Solar Features Homes with EV Chargers Homes with Pools Waterfront Homes Homes with Views Homes with Recorded Price Reductions Listings Added to PropertySimple in the Past 7 Days Homes Built Since 2024

Nationwide collections

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Waterfront ListingsListings Marked Waterfront Listings in Mountain StatesSix-State Collection Multi-Family & Commercial ListingsListings by Property Type Listings with 3+ BedroomsThree or More Bedrooms Listings Priced at $1.5M+Listings by Asking Price Listings Built Since 2015Listings by Year Built

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Homes for Sale in Middlesboro

Middlesboro Real Estate at a Glance

Price Range

Property Types

Nearby Cities

Homes to Explore

More from Middlesboro

215 S 21st Street

412 N 24th Street

116 Edgewood Road

140 Wellington Drive

717 S 27th Street

207 Arthur Heights

103 Sherwood Rd

1015 Old Wilson Lane

Homes for Sale in Middlesboro

230 Windermere Drive

225 Sherwood Road

508 Worchester Avenue

Bowling Rd

406 N 25th St

2247 State Highway 188

114 E Rochester Avenue

103 Sherwood Rd

88 Tracy Ridge Rd

1015 Old Wilson Lane

810 W Rochester Ave

113 N 18th St

305 N 15th St

1801 & 1801 1/2 Exeter Avenue

312 Blakely Lane

412 N 24th Street

8 Castleford Way

708 W Chester Ave

209 S 19th Street

812 Worchester Ave

1102 W Chester Avenue

312 W Chester Avenue

515 Englewood Road

140 Wellington Drive

125 Cawood Lane

518 S 43rd St

116 Edgewood Road

623 N 20th Street

717 S 27th Street

1803 W Cumberland Avenue

400 Gloucester Avenue

601 N 15th Street

215 S 21st Street

207 Arthur Heights

2002 Winchester Avenue

109 Bloomsbury Avenue

2107 Winchester Avenue

717 Highway 441

Edgewood Road

205 Exeter Avenue

156 Wellington Drive

405 S 37th Street

118 Polly Hollow Right Fork Rd

321 Chester Avenue

US Highway 25

526 Balmoral Road

3133 US Highway 25E

Middlesboro Housing Market

Frequently Asked Questions

How many active listings are available in Middlesboro, Kentucky?

What is the average list price in Middlesboro, Kentucky?

What is the average days on market for active listings in Middlesboro?

What is the average list price per square foot in Middlesboro?

Browse Middlesboro by home feature

Explore by listing details

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