203 total properties
Did you mean the neighborhood Winchester?
View 16 Virginia Avenue Winchester, KY MLS# 26015227
$40,000
3

Beds

1.0

Baths

1,842

Sq.Ft.

16 Virginia Avenue

Winchester, KY

Bluegrass
View 10 Chickadee Lane Winchester, KY MLS# 26016217
  • Recently Listed
1 of 55
$249,900
3

Beds

1.0

Baths

1,204

Sq.Ft.

10 Chickadee Lane

Winchester, KY

Bluegrass
View 2828 Athens Boonesboro Road Winchester, KY MLS# 26016283
$35,000
Studio

Beds

0.0

Baths

2828 Athens Boonesboro Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 13 Bel Air Drive Winchester, KY MLS# 26016008
$329,000
3

Beds

3.0

Baths

2,068

Sq.Ft.

13 Bel Air Drive

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26015897
$239,000
6

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 411 Boone Avenue Winchester, KY MLS# 26015962
$349,000
4

Beds

2.1

Baths

3,405

Sq.Ft.

411 Boone Avenue

Winchester, KY

Bluegrass
View 209 Connie Lane Winchester, KY MLS# 26015653
$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 136 Sturbridge Lane Winchester, KY MLS# 26015181
$274,900
3

Beds

2.1

Baths

1,604

Sq.Ft.

136 Sturbridge Lane

Winchester, KY

Bluegrass
View 25 Oliver Street Winchester, KY MLS# 26014899
$115,000
3

Beds

1.0

Baths

900

Sq.Ft.

25 Oliver Street

Winchester, KY

Bluegrass
View 608 Colby Road Winchester, KY MLS# 26015128
$369,000
3

Beds

2.1

Baths

1,803

Sq.Ft.

608 Colby Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26014732
$225,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 6888 Bybee Road Winchester, KY MLS# 26014823
$350,000
1

Beds

1.0

Baths

800

Sq.Ft.

6888 Bybee Road

Winchester, KY

Bluegrass
View 119 Gibson Way Winchester, KY MLS# 26014834
$349,900
4

Beds

2.1

Baths

2,325

Sq.Ft.

119 Gibson Way

Winchester, KY

Bluegrass
View 872 Stratton Lane Winchester, KY MLS# 26014681
$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
$139,900
3

Beds

1.0

Baths

1,097

Sq.Ft.

220 E Washington Street

Winchester, KY

Bluegrass
View 18 N Main Street Winchester, KY MLS# 26014568
$199,900
4,300

Sq.Ft.

18 N Main Street

Winchester, KY

Bluegrass
View 122 Spruce Court Winchester, KY MLS# 26014330
$228,500
3

Beds

2.0

Baths

1,210

Sq.Ft.

122 Spruce Court

Winchester, KY

Bluegrass
View 4095 Basin Springs Road Winchester, KY MLS# 26014375
$350,000
Studio

Beds

0.0

Baths

4095 Basin Springs 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

About Winchester

Listings in Winchester, KY

296

Estimated median home price

$275,950
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 - 100K39
$100K - 200K56
$200K - 300K66
$300K - 400K48
$400K - 500K21
$500K - 600K17
$600K - 700K11
$700K - 800K12
$800K - 900K5
$900K - 1M2
$1M - Max19

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse4
Condo0
Commercial14
Rental20
Lots and Land97
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms9

(Data as of 7/25/2026)

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 7/26/2026.