187 total properties
Did you mean the neighborhood Winchester?
View 175 Overlooking Drive Winchester, KY MLS# 26003583
$359,000
3

Beds

2.0

Baths

2,080

Sq.Ft.

175 Overlooking Drive

Winchester, KY

Bluegrass
View 538 S Maple Street Winchester, KY MLS# 26000925
  • New Construction
1 of 32
$354,900
3

Beds

2.1

Baths

1,628

Sq.Ft.

538 S Maple Street

Winchester, KY

Bluegrass
View 1128-1130 Dale Drive Winchester, KY MLS# 26000922
$345,000
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 215 Old Log Lick Road Winchester, KY MLS# 26003717
  • Recently Listed
1 of 84
$343,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

215 Old Log Lick Road

Winchester, KY

Bluegrass
View 322 S Burns Avenue Winchester, KY MLS# 26004053
  • Recently Listed
1 of 97
$339,900
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 297 S Main Street Winchester, KY MLS# 25501793
$335,000
6

Beds

4.0

Baths

3,544

Sq.Ft.

297 S Main Street

Winchester, KY

Bluegrass
View 120 Pilot View Road Winchester, KY MLS# 26003979
$334,000
3

Beds

2.1

Baths

1,900

Sq.Ft.

120 Pilot View Road

Winchester, KY

Bluegrass
View 225 Plantations Drive Winchester, KY MLS# 25506523
$332,700
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

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
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 213 Orchid Court Winchester, KY MLS# 25502706
$325,000
4

Beds

3.0

Baths

1,776

Sq.Ft.

213 Orchid Court

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 26003842
  • Recently Listed
1 of 67
$325,000
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
View 128 Cherokee Drive Winchester, KY MLS# 26003806
  • Recently Listed
1 of 36
$319,900
5

Beds

2.0

Baths

2,082

Sq.Ft.

128 Cherokee Drive

Winchester, KY

Bluegrass
View 144 Holly Avenue Winchester, KY MLS# 26002633
$319,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
View 219 Woodbine Court Winchester, KY MLS# 26002508
$315,000
4

Beds

2.0

Baths

1,751

Sq.Ft.

219 Woodbine Court

Winchester, KY

Bluegrass
View 55 Hillcrest Drive Winchester, KY MLS# 26004166
  • Recently Listed
1 of 12
$305,000
5

Beds

2.0

Baths

2,214

Sq.Ft.

55 Hillcrest 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 3811 Combs Ferry Road Winchester, KY MLS# 26004722
$300,000
Studio

Beds

0.0

Baths

3811 Combs Ferry Road

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

About Winchester

Listings in Winchester, KY

271

Estimated median home price

$275,700
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 - 100K31
$100K - 200K57
$200K - 300K64
$300K - 400K36
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family147
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land81
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/15/2026)

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 3/16/2026.