269 total properties
Did you mean the neighborhood Winchester?
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 148 W Lexington Avenue Winchester, KY MLS# 26008946
$198,900
5

Beds

2.0

Baths

2,444

Sq.Ft.

148 W Lexington Avenue

Winchester, KY

Bluegrass
View 6699 Boonesboro Road Winchester, KY MLS# 25000480
$195,000
Studio

Beds

0.0

Baths

6699 Boonesboro Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1045 Gay Evans Road Winchester, KY MLS# 25002803
$189,900
Studio

Beds

0.0

Baths

1045 Gay Evans Road

Winchester, KY

Bluegrass
View 155 Spring Ridge Way Winchester, KY MLS# 26005457
$188,500
Studio

Beds

0.0

Baths

155 Spring Ridge Way

Winchester, KY

Bluegrass
View 41 Hiawatha Trail Winchester, KY MLS# 26006789
$188,500
3

Beds

1.0

Baths

950

Sq.Ft.

41 Hiawatha Trail

Winchester, KY

Bluegrass
View 3925 Jackson Ferry Road Winchester, KY MLS# 26007287
$180,000
Studio

Beds

0.0

Baths

3925 Jackson Ferry Road

Winchester, KY

Bluegrass
View 229 S Highland Street Winchester, KY MLS# 26008701
$180,000
4

Beds

3.0

Baths

3,462

Sq.Ft.

229 S Highland Street

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 990 Craig Crossing Road Winchester, KY MLS# 22004991
$175,000
Studio

Beds

0.0

Baths

990 Craig Crossing Road

Winchester, KY

Bluegrass
View 2996 Irvine Road Winchester, KY MLS# 26007067
$175,000
Studio

Beds

0.0

Baths

2996 Irvine Road

Winchester, KY

Bluegrass
View 13 Maryland Avenue Winchester, KY MLS# 26008307
$169,000
2

Beds

1.0

Baths

1,472

Sq.Ft.

13 Maryland Avenue

Winchester, KY

Bluegrass
View 175 Magnolia Street Winchester, KY MLS# 26008759
$169,000
3

Beds

1.0

Baths

1,046

Sq.Ft.

175 Magnolia Street

Winchester, KY

Bluegrass
View 12 Apache Trail Winchester, KY MLS# 25500706
$168,500
3

Beds

2.0

Baths

1,026

Sq.Ft.

12 Apache Trail

Winchester, KY

Bluegrass
View 1494 Amster Grove Rd. Road Winchester, KY MLS# 26001738
$165,000
2

Beds

1.1

Baths

1,202

Sq.Ft.

1494 Amster Grove Rd. Road

Winchester, KY

Bluegrass
View 101 Alabama Street Winchester, KY MLS# 26007407
$164,900
1

Beds

2.0

Baths

1,056

Sq.Ft.

101 Alabama Street

Winchester, KY

Bluegrass
View 22 Magnolia Street Winchester, KY MLS# 26009730
$160,900
2

Beds

1.0

Baths

842

Sq.Ft.

22 Magnolia 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 697 Goose Creek Road Winchester, KY MLS# 26008440
$155,000
3

Beds

2.0

Baths

1,848

Sq.Ft.

697 Goose Creek Road

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

About Winchester

Listings in Winchester, KY

298

Estimated median home price

$276,200
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 - 100K31
$100K - 200K66
$200K - 300K71
$300K - 400K49
$400K - 500K17
$500K - 600K17
$600K - 700K10
$700K - 800K9
$800K - 900K2
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family174
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land92
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms7

(Data as of 6/26/2026)

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 6/26/2026.