302 total properties
Did you mean the neighborhood Winchester?
View 110 White Conkwright Road Winchester, KY MLS# 26007022
$556,000
5

Beds

3.0

Baths

3,102

Sq.Ft.

110 White Conkwright Road

Winchester, KY

Bluegrass
View 300 Rolling Hills Lane Winchester, KY MLS# 1805484
$925,000
Studio

Beds

0.0

Baths

300 Rolling Hills Lane

Winchester, KY

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

Beds

0.0

Baths

1600 Ironworks Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1600 Ironworks Road Winchester, KY MLS# 25002638
$799,900
Studio

Beds

0.0

Baths

1600 Ironworks Road

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 41 Hiawatha Trail Winchester, KY MLS# 26006789
$189,999
3

Beds

1.0

Baths

950

Sq.Ft.

41 Hiawatha Trail

Winchester, KY

Bluegrass
View 3886 Jackson Ferry Road Winchester, KY MLS# 26006831
$435,000
4

Beds

2.0

Baths

1,692

Sq.Ft.

3886 Jackson Ferry Road

Winchester, KY

Bluegrass
View 150 Spencer Lane Winchester, KY MLS# 26006848
$137,500
Studio

Beds

0.0

Baths

150 Spencer Lane

Winchester, KY

Bluegrass
View 60 Hiawatha Trail Winchester, KY MLS# 26006850
$204,900
3

Beds

1.0

Baths

1,290

Sq.Ft.

60 Hiawatha Trail

Winchester, KY

Bluegrass
View 186 Chardonnay Court Winchester, KY MLS# 26006869
  • Recently Listed
1 of 71
$799,000
4

Beds

2.1

Baths

7,058

Sq.Ft.

186 Chardonnay Court

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 113 Strawberry Lane Winchester, KY MLS# 26006879
$316,900
3

Beds

2.0

Baths

1,780

Sq.Ft.

113 Strawberry Lane

Winchester, KY

Bluegrass
View 308 Duclair Drive Winchester, KY MLS# 25018185
$50,000
Studio

Beds

0.0

Baths

308 Duclair Drive

Winchester, KY

Bluegrass
View 2509 Mount Sterling Road Winchester, KY MLS# 26005374
$799,900
4

Beds

3.1

Baths

4,922

Sq.Ft.

2509 Mount Sterling Road

Winchester, KY

Bluegrass
View 228 Holiday Road Winchester, KY MLS# 26006679
$339,900
4

Beds

2.0

Baths

1,843

Sq.Ft.

228 Holiday Road

Winchester, KY

Bluegrass
View 740 Pilot Ridge Lane Winchester, KY MLS# 26006680
$339,900
3

Beds

2.1

Baths

1,608

Sq.Ft.

740 Pilot Ridge Lane

Winchester, KY

Bluegrass
View 1775 Irvine Road Winchester, KY MLS# 26006681
$695,000
3

Beds

4.0

Baths

4,008

Sq.Ft.

1775 Irvine Road

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26006685
$239,900
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 47 Buckner Street Winchester, KY MLS# 26006752
$174,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

47 Buckner Street

Winchester, KY

Bluegrass
View 37 Ashland Avenue Winchester, KY MLS# 26006776
$139,000
2

Beds

1.0

Baths

904

Sq.Ft.

37 Ashland Avenue

Winchester, KY

Bluegrass
View 415 L E Junction Road Winchester, KY MLS# 26006620
$205,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

415 L E Junction Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

298

Estimated median home price

$264,950
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 - 200K72
$200K - 300K66
$300K - 400K38
$400K - 500K20
$500K - 600K13
$600K - 700K12
$700K - 800K15
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse5
Condo0
Commercial14
Rental14
Lots and Land97
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/23/2026)

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 4/23/2026.