177 total properties
Did you mean the neighborhood Winchester?
View 111 Jacob Court Winchester, KY MLS# 22024120
$100,000
Studio

Beds

0.0

Baths

111 Jacob Court

Winchester, KY

Bluegrass
View 225 Jacob Court Winchester, KY MLS# 22024121
$100,000
Studio

Beds

0.0

Baths

225 Jacob Court

Winchester, KY

Bluegrass
View 215 Duclair Drive Winchester, KY MLS# 22024123
$100,000
Studio

Beds

0.0

Baths

215 Duclair Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 169 Duclair Drive Winchester, KY MLS# 22024124
$100,000
Studio

Beds

0.0

Baths

169 Duclair Drive

Winchester, KY

Bluegrass
View 165 Duclair Drive Winchester, KY MLS# 22024126
$100,000
Studio

Beds

0.0

Baths

165 Duclair Drive

Winchester, KY

Bluegrass
View 155 Duclair Drive Winchester, KY MLS# 22024128
$100,000
Studio

Beds

0.0

Baths

155 Duclair Drive

Winchester, KY

Bluegrass
View 141 Duclair Drive Winchester, KY MLS# 22024130
$100,000
Studio

Beds

0.0

Baths

141 Duclair Drive

Winchester, KY

Bluegrass
View 129 Duclair Drive Winchester, KY MLS# 22024133
$100,000
Studio

Beds

0.0

Baths

129 Duclair Drive

Winchester, KY

Bluegrass
View 115 Duclair Drive Winchester, KY MLS# 22024134
$100,000
Studio

Beds

0.0

Baths

115 Duclair Drive

Winchester, KY

Bluegrass
View 2799 Pine Ridge Road Winchester, KY MLS# 26011430
$99,900
3

Beds

2.0

Baths

675

Sq.Ft.

2799 Pine Ridge Road

Winchester, KY

Bluegrass
View 563 Constitution Drive Winchester, KY MLS# 26012893
$99,500
2

Beds

2.0

Baths

924

Sq.Ft.

563 Constitution Drive

Winchester, KY

Bluegrass
View 160 Rector Lane Winchester, KY MLS# 26005903
$84,900
Studio

Beds

0.0

Baths

160 Rector Lane

Winchester, KY

Bluegrass
View Lot 3 Plantations Drive Winchester, KY MLS# 26011487
$78,500
Studio

Beds

0.0

Baths

Lot 3 Plantations Drive

Winchester, KY

Bluegrass
View Lot 4 Plantations Drive Winchester, KY MLS# 26011488
$78,500
Studio

Beds

0.0

Baths

Lot 4 Plantations Drive

Winchester, KY

Bluegrass
View 235 Plantations Drive # LOT 4 Winchester, KY MLS# 26018695
$78,500
Studio

Beds

0.0

Baths

235 Plantations Drive # LOT 4

Winchester, KY

Bluegrass
View 229 Plantations Drive # LOT 1 Winchester, KY MLS# 26018697
$78,500
Studio

Beds

0.0

Baths

229 Plantations Drive # LOT 1

Winchester, KY

Bluegrass
View 231 Plantations Drive # LOT 2 Winchester, KY MLS# 26018705
$78,500
Studio

Beds

0.0

Baths

231 Plantations Drive # LOT 2

Winchester, KY

Bluegrass
View 233 Plantations Drive # LOT 3 Winchester, KY MLS# 26018706
$78,500
Studio

Beds

0.0

Baths

233 Plantations Drive # LOT 3

Winchester, KY

Bluegrass
View 237 Plantations Drive # LOT 5 Winchester, KY MLS# 26018710
$78,500
Studio

Beds

0.0

Baths

237 Plantations Drive # LOT 5

Winchester, KY

Bluegrass
View 239 Plantations Drive # LOT 6 Winchester, KY MLS# 26018711
$78,500
Studio

Beds

0.0

Baths

239 Plantations Drive # LOT 6

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

297

Estimated median home price

$277,000
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 - 100K39
$100K - 200K56
$200K - 300K67
$300K - 400K48
$400K - 500K21
$500K - 600K17
$600K - 700K11
$700K - 800K12
$800K - 900K5
$900K - 1M2
$1M - Max19

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse4
Condo0
Commercial15
Rental20
Lots and Land97
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms9

(Data as of 7/28/2026)

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 7/29/2026.