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

Sq.Ft.

39 S Main Street

Winchester, KY

Bluegrass
View 6504 Combs Ferry Road Winchester, KY MLS# 25506634
$425,000
5

Beds

3.1

Baths

2,564

Sq.Ft.

6504 Combs Ferry Road

Winchester, KY

Bluegrass
View 1857 Ironworks Road Winchester, KY MLS# 25505808
$420,000
5

Beds

2.1

Baths

2,924

Sq.Ft.

1857 Ironworks Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 188 Big Stoner Road Winchester, KY MLS# 25017409
$419,000
4

Beds

2.1

Baths

2,388

Sq.Ft.

188 Big Stoner Road

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 25504953
$405,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
View 145 Codella Drive Winchester, KY MLS# 22007107
$400,000
Studio

Beds

0.0

Baths

145 Codella Drive

Winchester, KY

Bluegrass
View 397 Calmes Boulevard Winchester, KY MLS# 25500875
$399,550
4

Beds

3.1

Baths

2,637

Sq.Ft.

397 Calmes Boulevard

Winchester, KY

Bluegrass
View 4530 Ironworks Road Winchester, KY MLS# 25506282
$399,000
4

Beds

3.0

Baths

2,518

Sq.Ft.

4530 Ironworks Road

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 408 Corinne Court Winchester, KY MLS# 25501469
$394,999
3

Beds

2.0

Baths

1,604

Sq.Ft.

408 Corinne Court

Winchester, KY

Bluegrass
View 6239 Old Boonesboro Road Winchester, KY MLS# 25505595
$389,900
4

Beds

2.0

Baths

2,659

Sq.Ft.

6239 Old Boonesboro Road

Winchester, KY

Bluegrass
View 101 E Lexington Avenue Winchester, KY MLS# 25015191
$388,000
5

Beds

3.0

Baths

2,762

Sq.Ft.

101 E Lexington Avenue

Winchester, KY

Bluegrass
View 3600 Crowe Ridge Road Winchester, KY MLS# 25507522
  • Recently Listed
1 of 39
$384,900
4

Beds

4.1

Baths

3600 Crowe Ridge Road

Winchester, KY

Bluegrass
View 200 Evergreen Drive Winchester, KY MLS# 25009076
  • New Construction
1 of 3
$380,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

200 Evergreen Drive

Winchester, KY

Bluegrass
View 230 Evergreen Drive Winchester, KY MLS# 25009081
  • New Construction
1 of 3
$380,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

230 Evergreen Drive

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 300 Calmes Boulevard Winchester, KY MLS# 25504889
$379,717
3

Beds

2.1

Baths

2,636

Sq.Ft.

300 Calmes Boulevard

Winchester, KY

Bluegrass
View 133 Shala-Mar Rue Winchester, KY MLS# 25507513
  • Recently Listed
1 of 36
$379,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

133 Shala-Mar Rue

Winchester, KY

Bluegrass
View 23 1/2 Wheeler Avenue Winchester, KY MLS# 25500496
$375,000
8

Beds

4.0

Baths

3,706

Sq.Ft.

23 1/2 Wheeler Avenue

Winchester, KY

Bluegrass
View 395 Croxton Way Winchester, KY MLS# 23015432
$374,900
Studio

Beds

0.0

Baths

395 Croxton Way

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

276

Estimated median home price

$274,900
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 - 200K55
$200K - 300K57
$300K - 400K41
$400K - 500K24
$500K - 600K11
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family142
Townhouse4
Condo0
Commercial12
Rental19
Lots and Land94
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms14

(Data as of 12/24/2025)

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 12/25/2025.