94 total properties
Did you mean the neighborhood Winchester?
View 16 Virginia Avenue Winchester, KY MLS# 26015227
  • Recently Listed
1 of 40
$40,000
3

Beds

1.0

Baths

1,842

Sq.Ft.

16 Virginia Avenue

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 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 18 N Main Street Winchester, KY MLS# 26014568
$199,900
4,300

Sq.Ft.

18 N Main Street

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 65 Fitch Avenue Winchester, KY MLS# 26013935
  • Recently Listed
1 of 27
$152,500
3

Beds

1.1

Baths

1,680

Sq.Ft.

65 Fitch Avenue

Winchester, KY

Bluegrass
View 371 E Washington Street Winchester, KY MLS# 26013772
$180,000
3

Beds

1.0

Baths

1,198

Sq.Ft.

371 E Washington Street

Winchester, KY

Bluegrass
View 750 Craig Crossing # Lot #7 Winchester, KY MLS# 26013322
$154,900
Studio

Beds

0.0

Baths

750 Craig Crossing # Lot #7

Winchester, KY

Bluegrass
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$124,500
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

Winchester, KY

Bluegrass
View 107 Patio Street Winchester, KY MLS# 26013181
$160,000
2

Beds

1.0

Baths

864

Sq.Ft.

107 Patio Street

Winchester, KY

Bluegrass
View 310 W Hickman Street Winchester, KY MLS# 26012783
$109,900
4

Beds

2.1

Baths

1,391

Sq.Ft.

310 W Hickman Street

Winchester, KY

Bluegrass
View 563 Constitution Drive Winchester, KY MLS# 26012893
$99,500
2

Beds

2.0

Baths

924

Sq.Ft.

563 Constitution Drive

Winchester, KY

Bluegrass
View 104 Bay Hill Drive Winchester, KY MLS# 26012179
$199,000
2

Beds

2.0

Baths

1,200

Sq.Ft.

104 Bay Hill Drive

Winchester, KY

Bluegrass
View 590 Craig Crossing Winchester, KY MLS# 25506729
$152,500
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 225 Buffalo Trace Winchester, KY MLS# 26011564
$199,900
3

Beds

2.0

Baths

915

Sq.Ft.

225 Buffalo Trace

Winchester, KY

Bluegrass
View 2799 Pine Ridge Road Winchester, KY MLS# 26011430
$99,900
3

Beds

2.0

Baths

675

Sq.Ft.

2799 Pine Ridge Road

Winchester, KY

Bluegrass
View 128 Bay Hill Drive Winchester, KY MLS# 26011449
$200,000
3

Beds

2.0

Baths

1,289

Sq.Ft.

128 Bay Hill Drive

Winchester, KY

Bluegrass
View Lot 3 Plantations Drive Winchester, KY MLS# 26011487
$78,500
Studio

Beds

0.0

Baths

Lot 3 Plantations Drive

Winchester, KY

Bluegrass
View Lot 4 Plantations Drive Winchester, KY MLS# 26011488
$78,500
Studio

Beds

0.0

Baths

Lot 4 Plantations Drive

Winchester, KY

Bluegrass
View 265 Cunningham Lane Winchester, KY MLS# 26010094
$199,900
3

Beds

2.0

Baths

1,140

Sq.Ft.

265 Cunningham Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

293

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 - 200K63
$200K - 300K70
$300K - 400K49
$400K - 500K18
$500K - 600K17
$600K - 700K10
$700K - 800K9
$800K - 900K3
$900K - 1M2
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family175
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land86
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms7

(Data as of 6/28/2026)

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 6/29/2026.