289 total properties
Did you mean the neighborhood Winchester?
View 11 Shelley Drive Winchester, KY MLS# 26007607
$224,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

11 Shelley Drive

Winchester, KY

Bluegrass
View 34 Hays Street Winchester, KY MLS# 26007612
  • Recently Listed
1 of 32
$222,500
4

Beds

1.1

Baths

2,450

Sq.Ft.

34 Hays Street

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 26007617
  • Recently Listed
1 of 27
$388,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 220 Hibiscus Lane Winchester, KY MLS# 26007618
  • Recently Listed
1 of 57
$350,000
3

Beds

2.0

Baths

1,640

Sq.Ft.

220 Hibiscus Lane

Winchester, KY

Bluegrass
View 465 Morris Road Winchester, KY MLS# 26007545
  • Recently Listed
1 of 73
$775,000
5

Beds

3.0

Baths

4,437

Sq.Ft.

465 Morris Road

Winchester, KY

Bluegrass
View 402 Harney Drive Winchester, KY MLS# 26007559
  • Recently Listed
1 of 33
$275,000
3

Beds

1.1

Baths

1,634

Sq.Ft.

402 Harney Drive

Winchester, KY

Bluegrass
View 101 Alabama Street Winchester, KY MLS# 26007407
  • Recently Listed
1 of 41
$169,900
1

Beds

2.0

Baths

1,056

Sq.Ft.

101 Alabama Street

Winchester, KY

Bluegrass
View 118 Windridge Drive Winchester, KY MLS# 26006695
  • Recently Listed
1 of 67
$307,900
3

Beds

2.0

Baths

1,617

Sq.Ft.

118 Windridge Drive

Winchester, KY

Bluegrass
View 3760 Old Boonesboro Road Winchester, KY MLS# 26006697
$1,290,000
5

Beds

5.0

Baths

5,666

Sq.Ft.

3760 Old Boonesboro Road

Winchester, KY

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

Sq.Ft.

101 Jefferson Street

Winchester, KY

Bluegrass
View 1480 Irvine Road Winchester, KY MLS# 26007244
  • Recently Listed
1 of 54
OPEN HOUSE: Sunday 4/12 2:00 PM - 4:00 PM
$749,900
3

Beds

3.1

Baths

3,388

Sq.Ft.

1480 Irvine Road

Winchester, KY

Bluegrass
View 103 Southern Court Winchester, KY MLS# 26007260
  • Recently Listed
1 of 24
$300,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

103 Southern Court

Winchester, KY

Bluegrass
View 21 Kentucky Street Winchester, KY MLS# 26007124
$219,900
3

Beds

2.0

Baths

1,340

Sq.Ft.

21 Kentucky Street

Winchester, KY

Bluegrass
View 4025 Jackson Ferry Road Winchester, KY MLS# 26007284
$300,000
Studio

Beds

0.0

Baths

4025 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3991 Jackson Ferry Road Winchester, KY MLS# 26007285
$97,500
Studio

Beds

0.0

Baths

3991 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3961 Jackson Ferry Road Winchester, KY MLS# 26007286
$97,500
Studio

Beds

0.0

Baths

3961 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3925 Jackson Ferry Road Winchester, KY MLS# 26007287
$180,000
Studio

Beds

0.0

Baths

3925 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3821 Jackson Ferry Road Winchester, KY MLS# 26007288
$150,000
Studio

Beds

0.0

Baths

3821 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3759 Jackson Ferry Road Winchester, KY MLS# 26007289
$105,000
Studio

Beds

0.0

Baths

3759 Jackson Ferry Road

Winchester, KY

Bluegrass
View 318 Buffalo Trace Winchester, KY MLS# 26007299
  • New Construction
1 of 15
$234,900
3

Beds

2.0

Baths

1,200

Sq.Ft.

318 Buffalo Trace

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

288

Estimated median home price

$267,000
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 - 100K36
$100K - 200K66
$200K - 300K68
$300K - 400K35
$400K - 500K17
$500K - 600K14
$600K - 700K11
$700K - 800K14
$800K - 900K5
$900K - 1M3
$1M - Max19

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family158
Townhouse6
Condo0
Commercial12
Rental15
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms7

(Data as of 4/11/2026)

Information deemed reliable but not guaranteed.

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 4/12/2026.