219 total properties
Did you mean the neighborhood Winchester?
View 412 Pueblo Court Winchester, KY MLS# 26008794
  • Virtual Tour
1 of 30
$312,000
3

Beds

2.1

Baths

2,648

Sq.Ft.

412 Pueblo Court

Winchester, KY

Bluegrass
View 28 Churchill Drive Winchester, KY MLS# 26008797
$310,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
View 872 Stratton Lane Winchester, KY MLS# 26014681
  • Recently Listed
1 of 30
$310,000
4

Beds

2.0

Baths

2,285

Sq.Ft.

872 Stratton Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1045 Early Drive Winchester, KY MLS# 20111875
$300,000
1,675

Sq.Ft.

1045 Early Drive

Winchester, KY

Bluegrass
View 322 S Burns Avenue Winchester, KY MLS# 26004053
$299,999
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 26012206
$299,900
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$299,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass
View 147 Sunset Heights Winchester, KY MLS# 26011009
$294,900
3

Beds

2.0

Baths

2,128

Sq.Ft.

147 Sunset Heights

Winchester, KY

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

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

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 618 Westmeade Drive Winchester, KY MLS# 26009371
$284,900
4

Beds

2.0

Baths

2,116

Sq.Ft.

618 Westmeade Drive

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 136 Sturbridge Lane Winchester, KY MLS# 26015181
  • Recently Listed
1 of 26
$279,900
3

Beds

2.1

Baths

1,604

Sq.Ft.

136 Sturbridge Lane

Winchester, KY

Bluegrass
View 20 Jackson Street Winchester, KY MLS# 26012820
$275,000
3

Beds

2.0

Baths

1,650

Sq.Ft.

20 Jackson Street

Winchester, KY

Bluegrass
View 304 Newcastle Lane Winchester, KY MLS# 26015267
  • Recently Listed
1 of 25
$275,000
3

Beds

2.1

Baths

1,787

Sq.Ft.

304 Newcastle Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

287

Estimated median home price

$280,000
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 - 100K29
$100K - 200K62
$200K - 300K66
$300K - 400K49
$400K - 500K19
$500K - 600K15
$600K - 700K10
$700K - 800K9
$800K - 900K4
$900K - 1M2
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family172
Townhouse4
Condo0
Commercial11
Rental19
Lots and Land85
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms7

(Data as of 7/2/2026)

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 7/3/2026.