263 total properties
Did you mean the neighborhood Winchester?
View 187 Hawthorne Drive Winchester, KY MLS# 26015824
$420,000
3

Beds

2.0

Baths

2,027

Sq.Ft.

187 Hawthorne Drive

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26015897
  • Recently Listed
1 of 39
$239,000
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 411 Boone Avenue Winchester, KY MLS# 26015962
  • Recently Listed
1 of 64
$349,000
4

Beds

2.1

Baths

3,405

Sq.Ft.

411 Boone Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 107 Hibiscus Lane Winchester, KY MLS# 26015608
  • Recently Listed
1 of 64
$419,500
4

Beds

2.1

Baths

1,978

Sq.Ft.

107 Hibiscus Lane

Winchester, KY

Bluegrass
View 209 Connie Lane Winchester, KY MLS# 26015653
  • Recently Listed
1 of 30
$315,000
4

Beds

3.0

Baths

1,840

Sq.Ft.

209 Connie Lane

Winchester, KY

Bluegrass
View 800 Interstate Drive Winchester, KY MLS# 20111867
$270,000
Studio

Beds

0.0

Baths

800 Interstate Drive

Winchester, KY

Bluegrass
View 1005 Early Drive Winchester, KY MLS# 20111871
$500,000
Studio

Beds

0.0

Baths

1005 Early Drive

Winchester, KY

Bluegrass
View 308 W Lexington Avenue Winchester, KY MLS# 26015570
$825,000
3,570

Sq.Ft.

308 W Lexington Avenue

Winchester, KY

Bluegrass
View 304 Newcastle Lane Winchester, KY MLS# 26015267
  • Recently Listed
1 of 25
$275,000
3

Beds

2.1

Baths

1,787

Sq.Ft.

304 Newcastle Lane

Winchester, KY

Bluegrass
View 2509 Mount Sterling Road Winchester, KY MLS# 26015372
$749,900
4

Beds

3.1

Baths

4,346

Sq.Ft.

2509 Mount Sterling Road

Winchester, KY

Bluegrass
View 136 Sturbridge Lane Winchester, KY MLS# 26015181
  • Recently Listed
1 of 26
$279,900
3

Beds

2.1

Baths

1,604

Sq.Ft.

136 Sturbridge Lane

Winchester, KY

Bluegrass
View 25 Oliver Street Winchester, KY MLS# 26014899
  • Recently Listed
1 of 36
$125,000
3

Beds

1.0

Baths

900

Sq.Ft.

25 Oliver Street

Winchester, KY

Bluegrass
View 608 Colby Road Winchester, KY MLS# 26015128
  • Recently Listed
1 of 29
$414,800
3

Beds

2.1

Baths

1,803

Sq.Ft.

608 Colby Road

Winchester, KY

Bluegrass
View 1661 Waterworks Road Winchester, KY MLS# 26015130
$429,000
4

Beds

2.1

Baths

2,793

Sq.Ft.

1661 Waterworks Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26014732
$235,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 6888 Bybee Road Winchester, KY MLS# 26014823
  • Recently Listed
1 of 62
$350,000
1

Beds

1.0

Baths

800

Sq.Ft.

6888 Bybee Road

Winchester, KY

Bluegrass
View 119 Gibson Way Winchester, KY MLS# 26014834
  • Recently Listed
1 of 28
$355,000
4

Beds

2.1

Baths

2,325

Sq.Ft.

119 Gibson Way

Winchester, KY

Bluegrass
View 665 Lillies Ferry Road Winchester, KY MLS# 26014623
$545,000
Studio

Beds

0.0

Baths

665 Lillies Ferry Road

Winchester, KY

Bluegrass
View 872 Stratton Lane Winchester, KY MLS# 26014681
  • Recently Listed
1 of 30
$310,000
4

Beds

2.0

Baths

2,285

Sq.Ft.

872 Stratton Lane

Winchester, KY

Bluegrass
View 220 E Washington Street Winchester, KY MLS# 26014553
$155,000
3

Beds

1.0

Baths

1,097

Sq.Ft.

220 E Washington Street

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

285

Estimated median home price

$280,000
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 - 100K29
$100K - 200K61
$200K - 300K66
$300K - 400K49
$400K - 500K20
$500K - 600K15
$600K - 700K11
$700K - 800K8
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family170
Townhouse4
Condo0
Commercial11
Rental18
Lots and Land85
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms7

(Data as of 7/3/2026)

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 7/3/2026.