View 724 Terry Drive Winchester, KY MLS# 25503172
$279,500
3

Beds

2.0

Baths

2,250

Sq.Ft.

724 Terry Drive

Winchester, KY

Bluegrass
View 528 Estes Drive Winchester, KY MLS# 25503055
$249,900
3

Beds

2.0

Baths

1,904

Sq.Ft.

528 Estes Drive

Winchester, KY

Bluegrass
View 101 Jefferson Street Winchester, KY MLS# 25502866
$1,200,000
7,744

Sq.Ft.

101 Jefferson Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 6 Monroe Avenue Winchester, KY MLS# 25502677
  • Virtual Tour
1 of 27
$182,000
3

Beds

2.0

Baths

1,305

Sq.Ft.

6 Monroe Avenue

Winchester, KY

Bluegrass
View 114 Mallard Lane Winchester, KY MLS# 25502189
$372,900
4

Beds

3.0

Baths

2,105

Sq.Ft.

114 Mallard Lane

Winchester, KY

Bluegrass
View 134 Fontaine Boulevard Winchester, KY MLS# 25502273
$429,500
4

Beds

2.1

Baths

2,747

Sq.Ft.

134 Fontaine Boulevard

Winchester, KY

Bluegrass
View 128 Cherokee Drive Winchester, KY MLS# 25502349
$319,900
5

Beds

2.0

Baths

2,082

Sq.Ft.

128 Cherokee Drive

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 25502064
$265,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 5105 Combs Ferry Road Winchester, KY MLS# 25502066
$200,000
Studio

Beds

0.0

Baths

5105 Combs Ferry Road

Winchester, KY

Bluegrass
View 1015 Old Stone Church Road Winchester, KY MLS# 25502084
$1,500,000
Studio

Beds

0.0

Baths

1015 Old Stone Church Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 25502233
$265,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 5105 Combs Ferry Road Winchester, KY MLS# 25502234
$200,000
Studio

Beds

0.0

Baths

5105 Combs Ferry Road

Winchester, KY

Bluegrass
View 1600 Ironworks Road Winchester, KY MLS# 25002637
$799,900
Studio

Beds

0.0

Baths

1600 Ironworks Road

Winchester, KY

Bluegrass
View 1600 Ironworks Road Winchester, KY MLS# 25002638
$799,900
Studio

Beds

0.0

Baths

1600 Ironworks Road

Winchester, KY

Bluegrass
View 75 4th Street Winchester, KY MLS# 25501915
$10,000
Studio

Beds

0.0

Baths

75 4th Street

Winchester, KY

Bluegrass
View 150 Spencer Lane Winchester, KY MLS# 25005016
$70,000
Studio

Beds

0.0

Baths

150 Spencer Lane

Winchester, KY

Bluegrass
View 12569-B Ironworks Road Winchester, KY MLS# 25005019
$67,500
Studio

Beds

0.0

Baths

12569-B Ironworks Road

Winchester, KY

Bluegrass
View 297 S Main Street Winchester, KY MLS# 25501793
$335,000
6

Beds

4.0

Baths

3,544

Sq.Ft.

297 S Main Street

Winchester, KY

Bluegrass
View 7300 Old Boonesboro Road Winchester, KY MLS# 25501816
$824,900
4

Beds

3.0

Baths

3,311

Sq.Ft.

7300 Old Boonesboro Road

Winchester, KY

Bluegrass
View 211 Ashton Oak Way Winchester, KY MLS# 25501640
  • New Construction
1 of 10
$215,000
Studio

Beds

0.0

Baths

211 Ashton Oak Way

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

256

Estimated median home price

$299,000
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 - 100K22
$100K - 200K48
$200K - 300K63
$300K - 400K39
$400K - 500K23
$500K - 600K10
$600K - 700K11
$700K - 800K10
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family152
Townhouse3
Condo0
Commercial11
Rental17
Lots and Land67
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms14

(Data as of 1/16/2026)

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 1/19/2026.

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 1/19/2026.