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

Beds

0.0

Baths

1005 Early Drive

Winchester, KY

Bluegrass
View 414 Fairholme Way Winchester, KY MLS# 25505996
  • New Construction
1 of 18
$499,900
4

Beds

3.0

Baths

2,300

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass
View 5199 Schollsville Road Winchester, KY MLS# 25502093
$499,000
4

Beds

3.0

Baths

2,647

Sq.Ft.

5199 Schollsville Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 595 Earlymeade Drive Winchester, KY MLS# 25506943
  • Recently Listed
1 of 47
$499,000
5

Beds

3.1

Baths

3,823

Sq.Ft.

595 Earlymeade Drive

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25017324
$498,900
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25500168
$498,900
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 670 Lillies Ferry Road Winchester, KY MLS# 25506481
$489,000
3

Beds

2.0

Baths

2,053

Sq.Ft.

670 Lillies Ferry Road

Winchester, KY

Bluegrass
View 1410 Dry Fork Creek Road Winchester, KY MLS# 25503299
$485,000
3

Beds

2.0

Baths

1,064

Sq.Ft.

1410 Dry Fork Creek Road

Winchester, KY

Bluegrass
View 1410 Dry Fork Creek Road Winchester, KY MLS# 25503598
$485,000
3

Beds

2.0

Baths

1,064

Sq.Ft.

1410 Dry Fork Creek Road

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$475,000
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 42 Mockingbird Valley Road Winchester, KY MLS# 25501297
$457,900
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$450,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass
View 233 Cunningham Lane Winchester, KY MLS# 25507450
  • Recently Listed
1 of 34
$450,000
3

Beds

2.1

Baths

2,258

Sq.Ft.

233 Cunningham Lane

Winchester, KY

Bluegrass
View 129 Lana Lane Winchester, KY MLS# 25019329
$449,000
4

Beds

3.0

Baths

2,844

Sq.Ft.

129 Lana Lane

Winchester, KY

Bluegrass
View 1125 W Lexington Avenue Winchester, KY MLS# 24015897
$439,900
2,269

Sq.Ft.

1125 W Lexington Avenue

Winchester, KY

Bluegrass
View 134 Fontaine Boulevard Winchester, KY MLS# 25502273
$434,500
4

Beds

2.1

Baths

2,747

Sq.Ft.

134 Fontaine Boulevard

Winchester, KY

Bluegrass
View 220 Evergreen Drive Winchester, KY MLS# 25009079
  • New Construction
1 of 3
$430,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

220 Evergreen 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 265 Evergreen Drive Winchester, KY MLS# 25009083
  • New Construction
1 of 3
$430,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

265 Evergreen Drive

Winchester, KY

Bluegrass
View 39 S Main Street Winchester, KY MLS# 25014867
$429,000
3,538

Sq.Ft.

39 S Main Street

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

278

Estimated median home price

$272,450
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 - 100K38
$100K - 200K56
$200K - 300K56
$300K - 400K44
$400K - 500K24
$500K - 600K10
$600K - 700K10
$700K - 800K8
$800K - 900K7
$900K - 1M3
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family143
Townhouse5
Condo0
Commercial13
Rental19
Lots and Land93
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms15

(Data as of 12/12/2025)

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 12/13/2025.