182 total properties
Did you mean the neighborhood Winchester?
View 209 Boone Avenue Winchester, KY MLS# 26011097
  • Virtual Tour
1 of 24
$294,900
3

Beds

2.1

Baths

2,260

Sq.Ft.

209 Boone Avenue

Winchester, KY

Bluegrass
View 162 French Avenue Winchester, KY MLS# 26012319
$294,900
4

Beds

1.0

Baths

2,327

Sq.Ft.

162 French Avenue

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
$289,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 618 Westmeade Drive Winchester, KY MLS# 26009371
$289,900
4

Beds

2.0

Baths

2,116

Sq.Ft.

618 Westmeade Drive

Winchester, KY

Bluegrass
View 54 Locust Drive Winchester, KY MLS# 26007779
$289,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

54 Locust Drive

Winchester, KY

Bluegrass
View 214 S Burns Avenue Winchester, KY MLS# 26014099
  • Recently Listed
1 of 33
$289,000
4

Beds

1.1

Baths

2,170

Sq.Ft.

214 S Burns Avenue

Winchester, KY

Bluegrass
View 110 Buckingham Lane Winchester, KY MLS# 26014133
$289,000
3

Beds

2.0

Baths

1,240

Sq.Ft.

110 Buckingham Lane

Winchester, KY

Bluegrass
View 103 Southern Court Winchester, KY MLS# 26007260
$285,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

103 Southern Court

Winchester, KY

Bluegrass
View 327 Newcastle Lane Winchester, KY MLS# 26004861
$284,900
4

Beds

2.1

Baths

1,693

Sq.Ft.

327 Newcastle Lane

Winchester, KY

Bluegrass
View 133 Bay Hill Drive Winchester, KY MLS# 26012064
$280,000
4

Beds

3.1

Baths

3,276

Sq.Ft.

133 Bay Hill Drive

Winchester, KY

Bluegrass
View 20 Jackson Street Winchester, KY MLS# 26012820
  • Recently Listed
1 of 36
$280,000
3

Beds

2.0

Baths

1,650

Sq.Ft.

20 Jackson Street

Winchester, KY

Bluegrass
View 136 Sturbridge Lane Winchester, KY MLS# 26014151
$279,900
3

Beds

2.1

Baths

1,604

Sq.Ft.

136 Sturbridge Lane

Winchester, KY

Bluegrass
View 116 Sturbridge Lane Winchester, KY MLS# 26011782
  • New Construction
1 of 37
$279,000
3

Beds

2.0

Baths

1,260

Sq.Ft.

116 Sturbridge Lane

Winchester, KY

Bluegrass
View 403 Pueblo Court Winchester, KY MLS# 26010021
$274,900
3

Beds

2.0

Baths

1,311

Sq.Ft.

403 Pueblo Court

Winchester, KY

Bluegrass
View 955 Right Angle Road Winchester, KY MLS# 26013194
  • Recently Listed
1 of 35
$274,900
2

Beds

1.0

Baths

849

Sq.Ft.

955 Right Angle Road

Winchester, KY

Bluegrass
View 137 Eastridge Drive Winchester, KY MLS# 26011465
$274,500
3

Beds

2.0

Baths

1,420

Sq.Ft.

137 Eastridge Drive

Winchester, KY

Bluegrass
View 800 Interstate Drive Winchester, KY MLS# 20111867
$270,000
Studio

Beds

0.0

Baths

800 Interstate Drive

Winchester, KY

Bluegrass
View 720 Terry Drive Winchester, KY MLS# 26009068
$270,000
3

Beds

2.0

Baths

1,779

Sq.Ft.

720 Terry Drive

Winchester, KY

Bluegrass
View 205 Providence Lane Winchester, KY MLS# 26010776
$269,900
3

Beds

1.0

Baths

1,644

Sq.Ft.

205 Providence Lane

Winchester, KY

Bluegrass
View 104 Jackson Ferry Road Winchester, KY MLS# 26005196
$269,000
4

Beds

2.0

Baths

2,417

Sq.Ft.

104 Jackson Ferry Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

295

Estimated median home price

$274,500
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 - 100K30
$100K - 200K65
$200K - 300K73
$300K - 400K47
$400K - 500K17
$500K - 600K16
$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
Farms4

(Data as of 6/21/2026)

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 6/22/2026.