224 total properties
Did you mean the neighborhood Winchester?
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 443 Jameson Way Winchester, KY MLS# 26000614
$221,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson Way

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
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 10 Upper Street Winchester, KY MLS# 25004895
$205,000
3

Beds

2.1

Baths

2,380

Sq.Ft.

10 Upper Street

Winchester, KY

Bluegrass
View 104 Bella Shae Way Winchester, KY MLS# 26000264
  • New Construction
1 of 10
$591,650
3

Beds

2.1

Baths

2,200

Sq.Ft.

104 Bella Shae Way

Winchester, KY

Bluegrass
View 113 Mimosa Drive Winchester, KY MLS# 26000273
$80,000
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
View 149 Winn Ave Winchester, KY MLS# 26000197
$286,000
12

Beds

4.0

Baths

4,010

Sq.Ft.

149 Winn Ave

Winchester, KY

Bluegrass
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$129,900
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

Winchester, KY

Bluegrass
View 100 Duclair Drive Winchester, KY MLS# 22024061
$100,000
Studio

Beds

0.0

Baths

100 Duclair Drive

Winchester, KY

Bluegrass
View 120 Knox Court Winchester, KY MLS# 22024088
$150,000
Studio

Beds

0.0

Baths

120 Knox Court

Winchester, KY

Bluegrass
View 125 Knox Court Winchester, KY MLS# 22024090
$150,000
Studio

Beds

0.0

Baths

125 Knox Court

Winchester, KY

Bluegrass
View 250 Duclair Drive Winchester, KY MLS# 22024097
$110,000
Studio

Beds

0.0

Baths

250 Duclair Drive

Winchester, KY

Bluegrass
View 260 Duclair Drive Winchester, KY MLS# 22024098
$110,000
Studio

Beds

0.0

Baths

260 Duclair Drive

Winchester, KY

Bluegrass
View 139 Jacob Court Winchester, KY MLS# 22024111
$110,000
Studio

Beds

0.0

Baths

139 Jacob Court

Winchester, KY

Bluegrass
View 125 Jacob Court Winchester, KY MLS# 22024114
$110,000
Studio

Beds

0.0

Baths

125 Jacob Court

Winchester, KY

Bluegrass
View 115 Jacob Court Winchester, KY MLS# 22024116
$110,000
Studio

Beds

0.0

Baths

115 Jacob Court

Winchester, KY

Bluegrass
View 42 Mockingbird Valley Road Winchester, KY MLS# 26000113
$452,500
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 213 Orchid Court Winchester, KY MLS# 25502706
$325,000
4

Beds

3.0

Baths

1,776

Sq.Ft.

213 Orchid Court

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

270

Estimated median home price

$277,350
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 - 100K31
$100K - 200K57
$200K - 300K63
$300K - 400K36
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family147
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land80
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/16/2026)

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 3/18/2026.