152 total properties
Did you mean the neighborhood Winchester?
View 133 Bay Hill Drive Winchester, KY MLS# 26012064
  • Recently Listed
1 of 24
$280,000
4

Beds

3.1

Baths

3,276

Sq.Ft.

133 Bay Hill Drive

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 720 Terry Drive Winchester, KY MLS# 26009068
$275,000
3

Beds

2.0

Baths

1,779

Sq.Ft.

720 Terry Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
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 164 Buckingham Lane Winchester, KY MLS# 26009383
$270,000
3

Beds

2.0

Baths

1,190

Sq.Ft.

164 Buckingham Lane

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
View 86 Bon-Haven Avenue Winchester, KY MLS# 26009398
$269,000
4

Beds

2.0

Baths

2,295

Sq.Ft.

86 Bon-Haven Avenue

Winchester, KY

Bluegrass
View 20 Bon Haven Avenue Winchester, KY MLS# 26011883
$269,000
4

Beds

3.0

Baths

1,850

Sq.Ft.

20 Bon Haven Avenue

Winchester, KY

Bluegrass
View 311 Geronimo Court Winchester, KY MLS# 26011798
$268,900
4

Beds

2.1

Baths

1,510

Sq.Ft.

311 Geronimo Court

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 119 Sunset Heights Winchester, KY MLS# 26012905
  • Recently Listed
1 of 21
OPEN HOUSE: Saturday 6/20 12:00 PM - 2:00 PM
$265,000
3

Beds

1.0

Baths

1,324

Sq.Ft.

119 Sunset Heights

Winchester, KY

Bluegrass
View 55 Hillcrest Drive Winchester, KY MLS# 26004166
$264,900
5

Beds

2.0

Baths

2,214

Sq.Ft.

55 Hillcrest Drive

Winchester, KY

Bluegrass
View 280 Pine Ridge Road Winchester, KY MLS# 26004070
$260,000
3

Beds

1.0

Baths

1,296

Sq.Ft.

280 Pine Ridge Road

Winchester, KY

Bluegrass
View 3614 Stamper Drive Winchester, KY MLS# 25017189
$259,500
3

Beds

2.0

Baths

1,247

Sq.Ft.

3614 Stamper Drive

Winchester, KY

Bluegrass
View 564 Trapp-Goffs Cor Road Winchester, KY MLS# 26000897
$259,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

564 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 316 Maryland Avenue Winchester, KY MLS# 26011496
$255,000
3

Beds

2.0

Baths

1,809

Sq.Ft.

316 Maryland Avenue

Winchester, KY

Bluegrass
View 377 Crescent Avenue Winchester, KY MLS# 26013350
  • Recently Listed
1 of 49
$254,500
3

Beds

1.1

Baths

1,533

Sq.Ft.

377 Crescent Avenue

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

293

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 - 100K29
$100K - 200K64
$200K - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K16
$600K - 700K11
$700K - 800K11
$800K - 900K2
$900K - 1M4
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family176
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land88
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/15/2026)

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 6/15/2026.