298 total properties
Did you mean the neighborhood Winchester?
View 556 Earlymeade Drive Winchester, KY MLS# 26006630
$559,000
4

Beds

4.1

Baths

4,185

Sq.Ft.

556 Earlymeade Drive

Winchester, KY

Bluegrass
View 110 White Conkwright Road Winchester, KY MLS# 26007022
$556,000
5

Beds

3.0

Baths

3,102

Sq.Ft.

110 White Conkwright Road

Winchester, KY

Bluegrass
View 1395 Two Mile Road Winchester, KY MLS# 23018854
$550,500
Studio

Beds

0.0

Baths

1395 Two Mile Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 107 Bella Shae Way Winchester, KY MLS# 24025578
  • New Construction
1 of 10
$550,000
3

Beds

2.1

Baths

2,200

Sq.Ft.

107 Bella Shae Way

Winchester, KY

Bluegrass
View 220 Athens Boonsboro Road Winchester, KY MLS# 25012986
$531,000
5,012

Sq.Ft.

220 Athens Boonsboro Road

Winchester, KY

Bluegrass
View 35-37 Hays Street Winchester, KY MLS# 26002170
$515,000
1,440

Sq.Ft.

35-37 Hays Street

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 595 Earlymeade Drive Winchester, KY MLS# 25506943
$499,000
5

Beds

3.1

Baths

3,823

Sq.Ft.

595 Earlymeade Drive

Winchester, KY

Bluegrass
View 33-41 Winn Avenue Winchester, KY MLS# 25508043
$490,000
Studio

Beds

0.0

Baths

33-41 Winn Avenue

Winchester, KY

Bluegrass
View 265 S Highland Street Winchester, KY MLS# 26004961
$479,000
8

Beds

4.0

Baths

5,058

Sq.Ft.

265 S Highland Street

Winchester, KY

Bluegrass
View 1911 Trapp-Goffs Cor Road Winchester, KY MLS# 26004732
$460,000
3

Beds

2.0

Baths

1,288

Sq.Ft.

1911 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 1911 Trapp-Goffs Cor Road Winchester, KY MLS# 26005750
$460,000
3

Beds

2.0

Baths

1,288

Sq.Ft.

1911 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 42 Mockingbird Valley Road Winchester, KY MLS# 26000113
$452,500
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 222 Ashton Oak Way Winchester, KY MLS# 26008003
$450,000
3

Beds

2.1

Baths

3,444

Sq.Ft.

222 Ashton Oak Way

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26002767
$439,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26004544
$439,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 3886 Jackson Ferry Road Winchester, KY MLS# 26006831
$435,000
4

Beds

2.0

Baths

1,692

Sq.Ft.

3886 Jackson Ferry Road

Winchester, KY

Bluegrass
View 2 Stoney Brook Drive Winchester, KY MLS# 26008275
$435,000
3

Beds

3.1

Baths

3,633

Sq.Ft.

2 Stoney Brook Drive

Winchester, KY

Bluegrass
View 250 Evergreen Drive Winchester, KY MLS# 25009082
  • New Construction
1 of 3
$430,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

250 Evergreen Drive

Winchester, KY

Bluegrass
View 233 Cunningham Lane Winchester, KY MLS# 25507450
$429,900
3

Beds

2.1

Baths

2,258

Sq.Ft.

233 Cunningham Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

298

Estimated median home price

$264,950
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 - 100K36
$100K - 200K72
$200K - 300K66
$300K - 400K38
$400K - 500K20
$500K - 600K13
$600K - 700K12
$700K - 800K15
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse5
Condo0
Commercial14
Rental14
Lots and Land97
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/23/2026)

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 4/23/2026.