292 total properties
Did you mean the neighborhood Winchester?
View 240 Athens Boonesboro Road Winchester, KY MLS# 26004512
$429,900
4

Beds

2.1

Baths

1,500

Sq.Ft.

240 Athens Boonesboro Road

Winchester, KY

Bluegrass
View 20 Edgewood Drive Winchester, KY MLS# 26009517
  • Virtual Tour
1 of 47
OPEN HOUSE: Sunday 6/14 12:00 PM - 2:00 PM
$427,000
3

Beds

2.1

Baths

2,288

Sq.Ft.

20 Edgewood Drive

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 26007128
$425,000
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 23 Wheeler Avenue Winchester, KY MLS# 26011905
  • Recently Listed
1 of 51
$400,000
8

Beds

5.0

Baths

4,687

Sq.Ft.

23 Wheeler Avenue

Winchester, KY

Bluegrass
View 233 Schollsville Road Winchester, KY MLS# 26012231
$400,000
3

Beds

2.0

Baths

1,347

Sq.Ft.

233 Schollsville Road

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$399,900
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 0 Fairholme Way Winchester, KY MLS# 26011689
$399,000
Studio

Beds

0.0

Baths

0 Fairholme Way

Winchester, KY

Bluegrass
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$398,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

Winchester, KY

Bluegrass
View 205 Evergreen Drive Winchester, KY MLS# 25009077
  • New Construction
1 of 3
$395,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

205 Evergreen Drive

Winchester, KY

Bluegrass
View 18 Casa Landa Way Winchester, KY MLS# 26011118
$395,000
3

Beds

2.0

Baths

1,883

Sq.Ft.

18 Casa Landa Way

Winchester, KY

Bluegrass
View 178 Hawthorne Drive Winchester, KY MLS# 26012931
  • Recently Listed
1 of 26
$390,000
3

Beds

2.1

Baths

2,156

Sq.Ft.

178 Hawthorne Drive

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 26007617
$388,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
View 382 S Main Street Winchester, KY MLS# 26008931
$385,000
4

Beds

3.0

Baths

3,310

Sq.Ft.

382 S Main Street

Winchester, KY

Bluegrass
View 270 Evergreen Drive Winchester, KY MLS# 25009085
  • New Construction
1 of 3
$380,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

270 Evergreen Drive

Winchester, KY

Bluegrass
View 137 East Broadway Street Winchester, KY MLS# 25508602
$374,000
1,536

Sq.Ft.

137 East Broadway Street

Winchester, KY

Bluegrass
View 107 Gibson Way Winchester, KY MLS# 26013361
  • Recently Listed
1 of 20
$369,000
3

Beds

2.1

Baths

2,266

Sq.Ft.

107 Gibson Way

Winchester, KY

Bluegrass
View 206 Jett Drive Winchester, KY MLS# 24018286
  • New Construction
1 of 24
$365,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

206 Jett Drive

Winchester, KY

Bluegrass
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 7
$365,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 502 W Lexington Avenue Winchester, KY MLS# 26010324
$360,000
4

Beds

2.3

Baths

4,798

Sq.Ft.

502 W Lexington Avenue

Winchester, KY

Bluegrass
View 3359 Trapp-Goffs Corner Road Winchester, KY MLS# 26012322
$360,000
1

Beds

2.0

Baths

2,179

Sq.Ft.

3359 Trapp-Goffs Corner Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

292

Estimated median home price

$274,700
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 - 200K64
$200K - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K16
$600K - 700K11
$700K - 800K11
$800K - 900K2
$900K - 1M4
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family175
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land88
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/14/2026)

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 6/14/2026.