190 total properties
Did you mean the neighborhood Winchester?
View 28 Churchill Drive Winchester, KY MLS# 26008797
  • Recently Listed with Virtual Tour
1 of 31
$330,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
  • Recently Listed
1 of 32
$329,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
View 374 N Middletown Road Winchester, KY MLS# 25005575
$329,500
3

Beds

2.0

Baths

1,719

Sq.Ft.

374 N Middletown Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 360 N Middletown Road Winchester, KY MLS# 25005577
$329,500
3

Beds

2.0

Baths

1,792

Sq.Ft.

360 N Middletown Road

Winchester, KY

Bluegrass
View 322 S Burns Avenue Winchester, KY MLS# 26004053
$327,500
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 215 Old Log Lick Road Winchester, KY MLS# 26003717
$325,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

215 Old Log Lick Road

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 26003842
$325,000
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
View 225 Plantations Drive Winchester, KY MLS# 25506523
$324,900
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

Winchester, KY

Bluegrass
View 412 Pueblo Court Winchester, KY MLS# 26008794
  • Recently Listed with Virtual Tour
1 of 30
OPEN HOUSE: Sunday 5/3 2:00 PM - 4:00 PM
$322,500
3

Beds

2.1

Baths

2,648

Sq.Ft.

412 Pueblo Court

Winchester, KY

Bluegrass
View 128 Cherokee Drive Winchester, KY MLS# 26003806
$319,900
5

Beds

2.0

Baths

2,082

Sq.Ft.

128 Cherokee Drive

Winchester, KY

Bluegrass
View 113 Strawberry Lane Winchester, KY MLS# 26006879
$316,900
3

Beds

2.0

Baths

1,780

Sq.Ft.

113 Strawberry Lane

Winchester, KY

Bluegrass
View 200 Dubuy Drive Winchester, KY MLS# 26008021
  • Recently Listed
1 of 20
$312,000
3

Beds

2.1

Baths

1,858

Sq.Ft.

200 Dubuy Drive

Winchester, KY

Bluegrass
View 219 Bartram Court Winchester, KY MLS# 26009207
  • Recently Listed
1 of 35
$310,000
3

Beds

2.1

Baths

1,696

Sq.Ft.

219 Bartram Court

Winchester, KY

Bluegrass
View 144 Holly Avenue Winchester, KY MLS# 26002633
$308,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
View 118 Windridge Drive Winchester, KY MLS# 26006695
$307,900
3

Beds

2.0

Baths

1,617

Sq.Ft.

118 Windridge Drive

Winchester, KY

Bluegrass
View 1045 Early Drive Winchester, KY MLS# 20111875
$300,000
1,675

Sq.Ft.

1045 Early Drive

Winchester, KY

Bluegrass
View 1508 Ford Hampton Road Winchester, KY MLS# 25503339
$300,000
2

Beds

1.0

Baths

1,531

Sq.Ft.

1508 Ford Hampton Road

Winchester, KY

Bluegrass
View 103 Southern Court Winchester, KY MLS# 26007260
$300,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

103 Southern Court

Winchester, KY

Bluegrass
View 4025 Jackson Ferry Road Winchester, KY MLS# 26007284
$300,000
Studio

Beds

0.0

Baths

4025 Jackson Ferry Road

Winchester, KY

Bluegrass
View 306 Trapp-Goffs Cor Road Winchester, KY MLS# 26008462
$299,900
4

Beds

2.0

Baths

1,840

Sq.Ft.

306 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

302

Estimated median home price

$269,000
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 - 100K36
$100K - 200K70
$200K - 300K71
$300K - 400K39
$400K - 500K23
$500K - 600K12
$600K - 700K10
$700K - 800K15
$800K - 900K3
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family171
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land96
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 4/28/2026)

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 4/28/2026.