294 total properties
Did you mean the neighborhood Winchester?
View 316 Maryland Avenue Winchester, KY MLS# 26011496
$255,000
3

Beds

2.0

Baths

1,809

Sq.Ft.

316 Maryland Avenue

Winchester, KY

Bluegrass
View 377 Crescent Avenue Winchester, KY MLS# 26013350
  • Recently Listed
1 of 49
$254,500
3

Beds

1.1

Baths

1,533

Sq.Ft.

377 Crescent Avenue

Winchester, KY

Bluegrass
View 18 N Main Street Winchester, KY MLS# 25004978
$250,000
4,300

Sq.Ft.

18 N Main Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 130 E Broadway Street Winchester, KY MLS# 26004331
$250,000
4

Beds

3.0

Baths

2,445

Sq.Ft.

130 E Broadway Street

Winchester, KY

Bluegrass
View 3056 Irvine Road Winchester, KY MLS# 26007074
$250,000
Studio

Beds

0.0

Baths

3056 Irvine Road

Winchester, KY

Bluegrass
View 115 Watercrest Circle Winchester, KY MLS# 26002338
$249,990
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 1128-1130 Dale Drive Winchester, KY MLS# 26000922
$249,900
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass
View 1128-1130 Dale Drive Winchester, KY MLS# 26005390
$249,900
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass
View 123 Sunset Heights Winchester, KY MLS# 26009360
$249,900
3

Beds

2.0

Baths

1,446

Sq.Ft.

123 Sunset Heights

Winchester, KY

Bluegrass
View 12 Pocahontas Trail Winchester, KY MLS# 26012275
  • New Construction
1 of 21
$249,900
3

Beds

2.0

Baths

1,064

Sq.Ft.

12 Pocahontas Trail

Winchester, KY

Bluegrass
View 17 Holiday Road Winchester, KY MLS# 26013480
$249,900
3

Beds

1.1

Baths

1,161

Sq.Ft.

17 Holiday Road

Winchester, KY

Bluegrass
View 30 Virginia Avenue Winchester, KY MLS# 26013434
  • Recently Listed
1 of 46
$247,000
3

Beds

1.0

Baths

1,050

Sq.Ft.

30 Virginia Avenue

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 190 Privacy Lane Winchester, KY MLS# 25501332
$240,000
Studio

Beds

0.0

Baths

190 Privacy Lane

Winchester, KY

Bluegrass
View 407 Pueblo Court Winchester, KY MLS# 26010046
$240,000
3

Beds

2.0

Baths

1,244

Sq.Ft.

407 Pueblo Court

Winchester, KY

Bluegrass
View 13 Long Avenue Winchester, KY MLS# 26013004
  • Recently Listed
1 of 31
$240,000
3

Beds

2.0

Baths

1,297

Sq.Ft.

13 Long Avenue

Winchester, KY

Bluegrass
View 125 Kittison Drive Winchester, KY MLS# 26011953
  • Recently Listed
1 of 25
$237,500
3

Beds

1.0

Baths

1,100

Sq.Ft.

125 Kittison Drive

Winchester, KY

Bluegrass
View 357 Silverton Way Winchester, KY MLS# 26003487
$235,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

357 Silverton Way

Winchester, KY

Bluegrass
View 13 Arlington Road Winchester, KY MLS# 26005875
$235,000
4

Beds

2.0

Baths

1,431

Sq.Ft.

13 Arlington Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26011064
$235,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26013563
  • Recently Listed
1 of 41
$235,000
4

Beds

1.0

Baths

1,609

Sq.Ft.

120 Windsor Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

293

Estimated median home price

$274,900
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 - 100K29
$100K - 200K64
$200K - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K16
$600K - 700K11
$700K - 800K11
$800K - 900K2
$900K - 1M4
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family176
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land88
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/15/2026)

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 6/15/2026.