View 35 Cherokee Court Winchester, KY MLS# 25508113
$255,000
4

Beds

2.0

Baths

2,332

Sq.Ft.

35 Cherokee Court

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 217 S Highland Street Winchester, KY MLS# 25507680
$209,000
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 590 Craig Crossing Winchester, KY MLS# 25506729
$154,900
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 102 Augusta Drive Winchester, KY MLS# 24022901
$29,000
Studio

Beds

0.0

Baths

102 Augusta Drive

Winchester, KY

Bluegrass
View 3208 Ford Hampton Road Winchester, KY MLS# 25506476
$139,000
2

Beds

1.0

Baths

807

Sq.Ft.

3208 Ford Hampton Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 368 Flanagan Station Road Winchester, KY MLS# 25009200
$199,500
Studio

Beds

0.0

Baths

368 Flanagan Station Road

Winchester, KY

Bluegrass
View 12541 Ironworks Road Winchester, KY MLS# 25506465
$70,000
Studio

Beds

0.0

Baths

12541 Ironworks Road

Winchester, KY

Bluegrass
View 605 College Street Winchester, KY MLS# 25506124
$199,900
2

Beds

1.0

Baths

1,484

Sq.Ft.

605 College Street

Winchester, KY

Bluegrass
View 204 Wigeon Court Winchester, KY MLS# 25005098
$49,500
Studio

Beds

0.0

Baths

204 Wigeon Court

Winchester, KY

Bluegrass
View 7950 Four Mile Road Winchester, KY MLS# 25503896
$123,000
Studio

Beds

0.0

Baths

7950 Four Mile Road

Winchester, KY

Bluegrass
View 75 4th Street Winchester, KY MLS# 25501915
$10,000
Studio

Beds

0.0

Baths

75 4th Street

Winchester, KY

Bluegrass
View 101 Royal Oak Drive Winchester, KY MLS# 25501641
$64,900
Studio

Beds

0.0

Baths

101 Royal Oak Drive

Winchester, KY

Bluegrass
View 102 Royal Oak Drive Winchester, KY MLS# 25501642
$64,900
Studio

Beds

0.0

Baths

102 Royal Oak Drive

Winchester, KY

Bluegrass
View 12 Apache Trail Winchester, KY MLS# 25500706
$168,500
3

Beds

2.0

Baths

1,026

Sq.Ft.

12 Apache Trail

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 2110 Athens Boonesboro Road Winchester, KY MLS# 25500014
$225,000
Studio

Beds

0.0

Baths

2110 Athens Boonesboro Road

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$299,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass
View 271 April Way Winchester, KY MLS# 25016184
$215,000
2

Beds

1.1

Baths

1,120

Sq.Ft.

271 April Way

Winchester, KY

Bluegrass
View 1940 Athens Boonesboro Road Winchester, KY MLS# 25012636
$125,000
Studio

Beds

0.0

Baths

1940 Athens Boonesboro Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

311

Estimated median home price

$275,000
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 - 100K35
$100K - 200K67
$200K - 300K72
$300K - 400K44
$400K - 500K24
$500K - 600K17
$600K - 700K11
$700K - 800K13
$800K - 900K4
$900K - 1M2
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family180
Townhouse2
Condo0
Commercial16
Rental17
Lots and Land96
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms6

(Data as of 5/17/2026)

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 5/18/2026.