261 total properties
Did you mean the neighborhood Winchester?
View 6699 Boonesboro Road Winchester, KY MLS# 25000480
$195,000
Studio

Beds

0.0

Baths

6699 Boonesboro Road

Winchester, KY

Bluegrass
View 175 Magnolia Street Winchester, KY MLS# 25503492
$194,900
3

Beds

1.0

Baths

1,046

Sq.Ft.

175 Magnolia Street

Winchester, KY

Bluegrass
View 1045 Gay Evans Road Winchester, KY MLS# 25002803
$189,900
Studio

Beds

0.0

Baths

1045 Gay Evans Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 357 E Washington Street Winchester, KY MLS# 26000958
$189,900
3

Beds

2.0

Baths

1,328

Sq.Ft.

357 E Washington Street

Winchester, KY

Bluegrass
View 109 Quail Ridge Road Winchester, KY MLS# 26000647
$189,500
2

Beds

2.1

Baths

1,197

Sq.Ft.

109 Quail Ridge Road

Winchester, KY

Bluegrass
View 41 7th Street Winchester, KY MLS# 25506758
$188,900
3

Beds

2.0

Baths

1,116

Sq.Ft.

41 7th Street

Winchester, KY

Bluegrass
View 356 Colby Ridge Boulevard Winchester, KY MLS# 26002026
$184,000
2

Beds

1.1

Baths

1,102

Sq.Ft.

356 Colby Ridge Boulevard

Winchester, KY

Bluegrass
View 990 Craig Crossing Road Winchester, KY MLS# 22004991
$175,000
Studio

Beds

0.0

Baths

990 Craig Crossing Road

Winchester, KY

Bluegrass
View 6 Monroe Avenue Winchester, KY MLS# 25502677
  • Virtual Tour
1 of 27
$175,000
3

Beds

2.0

Baths

1,305

Sq.Ft.

6 Monroe Avenue

Winchester, KY

Bluegrass
View 1494 Amster Grove Rd. Road Winchester, KY MLS# 26001738
$175,000
2

Beds

1.1

Baths

1,202

Sq.Ft.

1494 Amster Grove Rd. Road

Winchester, KY

Bluegrass
View 10 Pocahontas Winchester, KY MLS# 26002018
$175,000
2

Beds

1.1

Baths

924

Sq.Ft.

10 Pocahontas

Winchester, KY

Bluegrass
View 102 W Hickman Street Winchester, KY MLS# 25017468
$171,000
2

Beds

1.0

Baths

870

Sq.Ft.

102 W Hickman Street

Winchester, KY

Bluegrass
View 220 E Washington Street Winchester, KY MLS# 26002506
$169,900
3

Beds

1.0

Baths

1,097

Sq.Ft.

220 E Washington Street

Winchester, KY

Bluegrass
View 12 Apache Trail Winchester, KY MLS# 25500706
$168,500
3

Beds

2.0

Baths

1,026

Sq.Ft.

12 Apache Trail

Winchester, KY

Bluegrass
View 233 E Washington Street Winchester, KY MLS# 26002299
$160,000
2

Beds

1.0

Baths

1,088

Sq.Ft.

233 E Washington Street

Winchester, KY

Bluegrass
View 590 Craig Crossing Winchester, KY MLS# 25506729
$159,900
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 730 Byrd Avenue Winchester, KY MLS# 26004038
  • Recently Listed
1 of 31
$155,000
3

Beds

1.0

Baths

1,160

Sq.Ft.

730 Byrd Avenue

Winchester, KY

Bluegrass
View 1030 Craig Crossing Road Winchester, KY MLS# 22004993
$150,000
Studio

Beds

0.0

Baths

1030 Craig Crossing Road

Winchester, KY

Bluegrass
View 120 Knox Court Winchester, KY MLS# 22024088
$150,000
Studio

Beds

0.0

Baths

120 Knox Court

Winchester, KY

Bluegrass
View 125 Knox Court Winchester, KY MLS# 22024090
$150,000
Studio

Beds

0.0

Baths

125 Knox Court

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

255

Estimated median home price

$270,000
Winchester KY Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Kentucky real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, KY.

Homes for Sale by Price in Winchester, KY

PriceCount
$0 - 100K30
$100K - 200K54
$200K - 300K58
$300K - 400K35
$400K - 500K17
$500K - 600K12
$600K - 700K9
$700K - 800K10
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family135
Townhouse5
Condo0
Commercial13
Rental18
Lots and Land81
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms10

(Data as of 3/4/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Metro Search Multiple Listing Service. Real Estate listings held by IDX brokers (licensees) other than Weichert Realtors are marked with the IDX logo and detailed information about them includes the name of the IDX brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

© 2026 Metro Search Multiple Listing Service, Inc. All rights reserved.

Data is updated as of 3/5/2026.

Listing data provided courtesy of the Internet Data Exchange Program of Bluegrass REALTORS.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Bluegrass REALTORS. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 3/5/2026.