219 total properties
Did you mean the neighborhood Winchester?
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 12 Pocahontas Trail Winchester, KY MLS# 26012275
  • New Construction
1 of 21
$249,900
3

Beds

2.0

Baths

1,064

Sq.Ft.

12 Pocahontas Trail

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
The time to sell is now! THE TIME TO SELL IS NOW!
View 86 Brink Avenue Winchester, KY MLS# 26011897
$225,000
3

Beds

2.0

Baths

1,136

Sq.Ft.

86 Brink Avenue

Winchester, KY

Bluegrass
View 23 Wheeler Avenue Winchester, KY MLS# 26011905
$389,900
8

Beds

5.0

Baths

4,687

Sq.Ft.

23 Wheeler Avenue

Winchester, KY

Bluegrass
View 125 Kittison Drive Winchester, KY MLS# 26011953
$235,500
3

Beds

1.0

Baths

1,100

Sq.Ft.

125 Kittison Drive

Winchester, KY

Bluegrass
View 525 Colby Ridge Boulevard Winchester, KY MLS# 26011873
$219,500
3

Beds

2.0

Baths

1,197

Sq.Ft.

525 Colby Ridge Boulevard

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 590 Craig Crossing Winchester, KY MLS# 25506729
$152,500
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 0 Fairholme Way Winchester, KY MLS# 26011689
$399,000
Studio

Beds

0.0

Baths

0 Fairholme Way

Winchester, KY

Bluegrass
View 116 Sturbridge Lane Winchester, KY MLS# 26011782
  • New Construction
1 of 37
$277,500
3

Beds

2.0

Baths

1,260

Sq.Ft.

116 Sturbridge Lane

Winchester, KY

Bluegrass
View 225 Buffalo Trace Winchester, KY MLS# 26011564
$199,900
3

Beds

2.0

Baths

915

Sq.Ft.

225 Buffalo Trace

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 128 Bay Hill Drive Winchester, KY MLS# 26011449
$200,000
3

Beds

2.0

Baths

1,289

Sq.Ft.

128 Bay Hill Drive

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 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 13 Lakeview Drive Winchester, KY MLS# 26011497
$315,000
3

Beds

2.0

Baths

1,932

Sq.Ft.

13 Lakeview Drive

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26011064
$235,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 339 S Main Street Winchester, KY MLS# 26010684
$219,900
4

Beds

1.1

Baths

1,848

Sq.Ft.

339 S Main Street

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 7/2/2026.