225 total properties
Did you mean the neighborhood Winchester?
View 115 Watercrest Circle Winchester, KY MLS# 26002338
$279,950
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 58 hughes Avenue Winchester, KY MLS# 26002214
$199,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

58 hughes Avenue

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
The time to sell is now! THE TIME TO SELL IS NOW!
View 414 Wellington Way Winchester, KY MLS# 26002092
$254,900
3

Beds

2.0

Baths

1,251

Sq.Ft.

414 Wellington Way

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 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 107 Woodduck Court Winchester, KY MLS# 26001532
$429,900
3

Beds

2.1

Baths

2,652

Sq.Ft.

107 Woodduck Court

Winchester, KY

Bluegrass
View 5434 Pine Ridge Road Winchester, KY MLS# 26001199
$195,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

5434 Pine Ridge Road

Winchester, KY

Bluegrass
View 564 Trapp-Goffs Cor Road Winchester, KY MLS# 26000897
$269,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

564 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 1270 Sewell Shop Road Winchester, KY MLS# 26000914
$354,900
5

Beds

2.0

Baths

1,952

Sq.Ft.

1270 Sewell Shop Road

Winchester, KY

Bluegrass
View 17 Euclid Avenue Winchester, KY MLS# 26000917
$249,900
3

Beds

2.0

Baths

1,656

Sq.Ft.

17 Euclid Avenue

Winchester, KY

Bluegrass
View 1128-1130 Dale Drive Winchester, KY MLS# 26000922
$299,900
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass
View 538 S Maple Street Winchester, KY MLS# 26000925
  • New Construction
1 of 32
$349,900
3

Beds

2.1

Baths

1,628

Sq.Ft.

538 S Maple Street

Winchester, KY

Bluegrass
View 6699 Boonesboro Road Winchester, KY MLS# 25000480
$195,000
Studio

Beds

0.0

Baths

6699 Boonesboro Road

Winchester, KY

Bluegrass
View 400 Wexford Drive Winchester, KY MLS# 26000557
$110,000
3

Beds

1.1

Baths

1,260

Sq.Ft.

400 Wexford Drive

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000601
$295,000
2

Beds

1.0

Baths

1,170

Sq.Ft.

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000610
$295,000
Studio

Beds

0.0

Baths

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 646 Laura Dr E Laura Drive Winchester, KY MLS# 26000619
$249,000
3

Beds

2.0

Baths

1,534

Sq.Ft.

646 Laura Dr E Laura Drive

Winchester, KY

Bluegrass
View 113 Mimosa Drive Winchester, KY MLS# 26000273
$70,000
3

Beds

2.0

Baths

750

Sq.Ft.

113 Mimosa Drive

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 4305 Old Boonesboro Road Winchester, KY MLS# 26000275
$375,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

4305 Old Boonesboro Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG

About Winchester

Listings in Winchester, KY

296

Estimated median home price

$269,500
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 - 200K69
$200K - 300K66
$300K - 400K39
$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 Land95
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/21/2026)

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 4/21/2026.