View 402 McDowell Drive Winchester, KY MLS# 26000341
  • Recently Listed with Virtual Tour
1 of 36
$299,500
4

Beds

2.1

Baths

2,136

Sq.Ft.

402 McDowell Drive

Winchester, KY

Bluegrass
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$439,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

Winchester, KY

Bluegrass
View 870 Pilot View Road Winchester, KY MLS# 26000270
  • Recently Listed
1 of 7
$440,000
3

Beds

2.0

Baths

1,568

Sq.Ft.

870 Pilot View Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 113 Mimosa Drive Winchester, KY MLS# 26000273
  • Recently Listed
1 of 5
$95,000
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
$425,000
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
  • Recently Listed
1 of 24
$290,000
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 120 Sunset Heights Winchester, KY MLS# 26000061
  • Recently Listed
1 of 24
$275,000
3

Beds

2.0

Baths

1,440

Sq.Ft.

120 Sunset Heights

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
View 41 7th Street Winchester, KY MLS# 25506758
$190,000
3

Beds

2.0

Baths

1,116

Sq.Ft.

41 7th Street

Winchester, KY

Bluegrass
View 446 Tremont Lane Winchester, KY MLS# 25508633
  • Recently Listed
1 of 33
$367,000
4

Beds

2.1

Baths

2,811

Sq.Ft.

446 Tremont Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

252

Estimated median home price

$297,000
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 - 100K27
$100K - 200K48
$200K - 300K56
$300K - 400K38
$400K - 500K24
$500K - 600K10
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family142
Townhouse3
Condo0
Commercial12
Rental17
Lots and Land72
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms14

(Data as of 1/6/2026)

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 1/7/2026.