View 265 Cunningham Lane Winchester, KY MLS# 26010094
$200,000
3

Beds

2.0

Baths

1,140

Sq.Ft.

265 Cunningham Lane

Winchester, KY

Bluegrass
View 605 College Street Winchester, KY MLS# 25506124
$199,900
2

Beds

1.0

Baths

1,484

Sq.Ft.

605 College Street

Winchester, KY

Bluegrass
View 148 W Lexington Avenue Winchester, KY MLS# 26008946
$199,900
5

Beds

2.0

Baths

2,444

Sq.Ft.

148 W Lexington Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 368 Flanagan Station Road Winchester, KY MLS# 25009200
$199,500
Studio

Beds

0.0

Baths

368 Flanagan Station Road

Winchester, KY

Bluegrass
View 58 hughes Avenue Winchester, KY MLS# 26002214
$199,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

58 hughes 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
View 41 Hiawatha Trail Winchester, KY MLS# 26006789
$189,999
3

Beds

1.0

Baths

950

Sq.Ft.

41 Hiawatha Trail

Winchester, KY

Bluegrass
View 1045 Gay Evans Road Winchester, KY MLS# 25002803
$189,900
Studio

Beds

0.0

Baths

1045 Gay Evans Road

Winchester, KY

Bluegrass
View 5105 Combs Ferry Road Winchester, KY MLS# 26002767
$189,000
Studio

Beds

0.0

Baths

5105 Combs Ferry Road

Winchester, KY

Bluegrass
View 5434 Pine Ridge Road Winchester, KY MLS# 26010230
  • Recently Listed
1 of 31
$189,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

5434 Pine Ridge 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 7th Street Winchester, KY MLS# 25506758
$185,900
3

Beds

2.0

Baths

1,116

Sq.Ft.

41 7th Street

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 697 Goose Creek Road Winchester, KY MLS# 26008440
$180,000
3

Beds

2.0

Baths

1,848

Sq.Ft.

697 Goose Creek 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 334 S Burns Avenue Winchester, KY MLS# 26003334
$179,000
3

Beds

1.1

Baths

1,636

Sq.Ft.

334 S Burns Avenue

Winchester, KY

Bluegrass
View 175 Magnolia Street Winchester, KY MLS# 26008759
$179,000
3

Beds

1.0

Baths

1,046

Sq.Ft.

175 Magnolia 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 1494 Amster Grove Rd. Road Winchester, KY MLS# 26001738
$175,000
2

Beds

1.1

Baths

1,202

Sq.Ft.

1494 Amster Grove Rd. 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

About Winchester

Listings in Winchester, KY

309

Estimated median home price

$275,000
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 - 100K35
$100K - 200K65
$200K - 300K72
$300K - 400K44
$400K - 500K24
$500K - 600K17
$600K - 700K11
$700K - 800K13
$800K - 900K4
$900K - 1M2
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family179
Townhouse2
Condo0
Commercial16
Rental17
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms6

(Data as of 5/18/2026)

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 5/19/2026.