View 228 Holiday Road Winchester, KY MLS# 26006679
$334,900
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 750 Providence Lane Winchester, KY MLS# 26006323
$359,900
Studio

Beds

0.0

Baths

750 Providence Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 133 Shala-Mar Rue Winchester, KY MLS# 26005511
$359,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

133 Shala-Mar Rue

Winchester, KY

Bluegrass
View 1291-1299 Muddy Creek Road Winchester, KY MLS# 26005152
$329,900
3

Beds

2.0

Baths

1,222

Sq.Ft.

1291-1299 Muddy Creek Road

Winchester, KY

Bluegrass
View 221 Moundale Avenue Winchester, KY MLS# 26004551
$345,000
3

Beds

2.1

Baths

2,628

Sq.Ft.

221 Moundale Avenue

Winchester, KY

Bluegrass
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$405,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

Winchester, KY

Bluegrass
View 23 Windridge Drive Winchester, KY MLS# 26004120
$344,900
3

Beds

2.0

Baths

1,858

Sq.Ft.

23 Windridge Drive

Winchester, KY

Bluegrass
View 322 S Burns Avenue Winchester, KY MLS# 26004053
$315,000
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 225 Plantations Drive Winchester, KY MLS# 25506523
$324,900
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

Winchester, KY

Bluegrass
View 128 Cherokee Drive Winchester, KY MLS# 26003806
$319,900
5

Beds

2.0

Baths

2,082

Sq.Ft.

128 Cherokee Drive

Winchester, KY

Bluegrass
View 215 Old Log Lick Road Winchester, KY MLS# 26003717
$325,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

215 Old Log Lick Road

Winchester, KY

Bluegrass
View 144 Holly Avenue Winchester, KY MLS# 26002633
$308,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
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 137 East Broadway Street Winchester, KY MLS# 25508602
$374,000
1,536

Sq.Ft.

137 East Broadway Street

Winchester, KY

Bluegrass
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 5
$365,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$399,900
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 206 Jett Drive Winchester, KY MLS# 24018286
  • New Construction
1 of 24
$365,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

206 Jett Drive

Winchester, KY

Bluegrass
View 39 S Main Street Winchester, KY MLS# 25014867
$415,000
3,538

Sq.Ft.

39 S Main Street

Winchester, KY

Bluegrass
View 205 Evergreen Drive Winchester, KY MLS# 25009077
  • New Construction
1 of 3
$395,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

205 Evergreen Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

296

Estimated median home price

$281,950
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 - 100K30
$100K - 200K64
$200K - 300K68
$300K - 400K43
$400K - 500K24
$500K - 600K17
$600K - 700K11
$700K - 800K13
$800K - 900K3
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family174
Townhouse2
Condo0
Commercial14
Rental18
Lots and Land89
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms6

(Data as of 5/20/2026)

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 5/20/2026.