View 19 Cherokee Court Winchester, KY MLS# 25507379
$230,000
3

Beds

1.0

Baths

1,134

Sq.Ft.

19 Cherokee Court

Winchester, KY

Bluegrass
View 2721 Pretty Run Road Winchester, KY MLS# 24025198
$215,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

2721 Pretty Run Road

Winchester, KY

Bluegrass
View 208 Watercrest Way Winchester, KY MLS# 25507056
$255,000
3

Beds

2.1

Baths

1,416

Sq.Ft.

208 Watercrest Way

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 214 S Burns Avenue Winchester, KY MLS# 25506625
$312,000
4

Beds

1.1

Baths

2,170

Sq.Ft.

214 S Burns Avenue

Winchester, KY

Bluegrass
View 720 Estes Drive Winchester, KY MLS# 25506836
$249,900
3

Beds

1.0

Baths

1,494

Sq.Ft.

720 Estes Drive

Winchester, KY

Bluegrass
View 202 Dubuy Drive Winchester, KY MLS# 25506536
$305,000
3

Beds

2.1

Baths

1,800

Sq.Ft.

202 Dubuy Drive

Winchester, KY

Bluegrass
View 21 Virginia Avenue Winchester, KY MLS# 25506127
$255,000
3

Beds

2.0

Baths

1,749

Sq.Ft.

21 Virginia Avenue

Winchester, KY

Bluegrass
View 590 Craig Crossing Winchester, KY MLS# 25506729
$159,900
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 8 Village Drive Winchester, KY MLS# 25506553
$295,000
3

Beds

2.0

Baths

1,979

Sq.Ft.

8 Village Drive

Winchester, KY

Bluegrass
View 6504 Combs Ferry Road Winchester, KY MLS# 25506634
$425,000
5

Beds

3.1

Baths

2,564

Sq.Ft.

6504 Combs Ferry Road

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
$147,000
2

Beds

1.0

Baths

807

Sq.Ft.

3208 Ford Hampton Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 125 Summerhill Way Winchester, KY MLS# 25506492
$259,900
3

Beds

2.0

Baths

1,333

Sq.Ft.

125 Summerhill Way

Winchester, KY

Bluegrass
View 114 Magnolia Street Winchester, KY MLS# 25506511
$115,000
2

Beds

1.0

Baths

910

Sq.Ft.

114 Magnolia Street

Winchester, KY

Bluegrass
View 225 Plantations Drive Winchester, KY MLS# 25506523
$349,900
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

Winchester, KY

Bluegrass
View 368 Flanagan Station Road Winchester, KY MLS# 25009200
$206,000
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 12 Linden Avenue Winchester, KY MLS# 25506319
$240,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

12 Linden Avenue

Winchester, KY

Bluegrass
View 4530 Ironworks Road Winchester, KY MLS# 25506282
$399,000
4

Beds

3.0

Baths

2,518

Sq.Ft.

4530 Ironworks Road

Winchester, KY

Bluegrass
View Lot 3 Plantations Drive Winchester, KY MLS# 25506247
$78,500
Studio

Beds

0.0

Baths

Lot 3 Plantations Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

248

Estimated median home price

$299,000
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 - 100K26
$100K - 200K47
$200K - 300K55
$300K - 400K40
$400K - 500K22
$500K - 600K9
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family138
Townhouse3
Condo0
Commercial12
Rental17
Lots and Land72
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms14

(Data as of 1/5/2026)

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 1/5/2026.