186 total properties
Did you mean the neighborhood Winchester?
View 618 Westmeade Drive Winchester, KY MLS# 26009371
  • Recently Listed
1 of 38
$296,900
4

Beds

2.0

Baths

2,116

Sq.Ft.

618 Westmeade 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 103 Southern Court Winchester, KY MLS# 26007260
$295,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

103 Southern Court

Winchester, KY

Bluegrass
View 327 Newcastle Lane Winchester, KY MLS# 26004861
$294,900
4

Beds

2.1

Baths

1,693

Sq.Ft.

327 Newcastle Lane

Winchester, KY

Bluegrass
View 2225 Old Boonesboro Road Winchester, KY MLS# 26004523
$289,900
3

Beds

2.0

Baths

1,995

Sq.Ft.

2225 Old Boonesboro Road

Winchester, KY

Bluegrass
View 55 Hillcrest Drive Winchester, KY MLS# 26004166
$289,000
5

Beds

2.0

Baths

2,214

Sq.Ft.

55 Hillcrest Drive

Winchester, KY

Bluegrass
View 426 E Broadway Street Winchester, KY MLS# 26007906
$289,000
5

Beds

2.0

Baths

1,838

Sq.Ft.

426 E Broadway Street

Winchester, KY

Bluegrass
View 211 Lindsey Court Winchester, KY MLS# 26003170
$285,000
3

Beds

2.0

Baths

1,790

Sq.Ft.

211 Lindsey Court

Winchester, KY

Bluegrass
View 404 Wellington Way Winchester, KY MLS# 25505330
$275,700
3

Beds

2.0

Baths

1,682

Sq.Ft.

404 Wellington Way

Winchester, KY

Bluegrass
View 104 Jackson Ferry Road Winchester, KY MLS# 26005196
$275,000
4

Beds

2.0

Baths

2,417

Sq.Ft.

104 Jackson Ferry Road

Winchester, KY

Bluegrass
View 192 Prescott Lane Winchester, KY MLS# 26005798
$275,000
3

Beds

2.1

Baths

1,550

Sq.Ft.

192 Prescott Lane

Winchester, KY

Bluegrass
View 402 Harney Drive Winchester, KY MLS# 26007559
$275,000
3

Beds

1.1

Baths

1,634

Sq.Ft.

402 Harney Drive

Winchester, KY

Bluegrass
View 110 Buckingham Lane Winchester, KY MLS# 26008814
$275,000
3

Beds

2.0

Baths

1,240

Sq.Ft.

110 Buckingham Lane

Winchester, KY

Bluegrass
View 720 Terry Drive Winchester, KY MLS# 26009068
  • Recently Listed
1 of 57
$275,000
3

Beds

2.0

Baths

1,779

Sq.Ft.

720 Terry Drive

Winchester, KY

Bluegrass
View 115 Watercrest Circle Winchester, KY MLS# 26002338
$274,950
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 800 Interstate Drive Winchester, KY MLS# 20111867
$270,000
Studio

Beds

0.0

Baths

800 Interstate Drive

Winchester, KY

Bluegrass
View 164 Buckingham Lane Winchester, KY MLS# 26009383
  • Recently Listed
1 of 25
$270,000
3

Beds

2.0

Baths

1,190

Sq.Ft.

164 Buckingham Lane

Winchester, KY

Bluegrass
View 1128-1130 Dale Drive Winchester, KY MLS# 26000922
$269,500
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
$269,500
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

301

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 - 300K70
$300K - 400K38
$400K - 500K23
$500K - 600K13
$600K - 700K10
$700K - 800K16
$800K - 900K3
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family171
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 5/1/2026)

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 5/2/2026.