219 total properties
Did you mean the neighborhood Winchester?
View 3622 Stamper Drive Winchester, KY MLS# 26012206
  • Recently Listed
1 of 43
$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
  • Recently Listed
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
  • Recently Listed
1 of 24
$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
  • Recently Listed
1 of 51
$400,000
8

Beds

5.0

Baths

4,687

Sq.Ft.

23 Wheeler Avenue

Winchester, KY

Bluegrass
View 125 Kittison Drive Winchester, KY MLS# 26011953
  • Recently Listed
1 of 22
$239,000
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 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 207 Abbeywood Drive Winchester, KY MLS# 26011852
$285,000
3

Beds

2.1

Baths

1,894

Sq.Ft.

207 Abbeywood Drive

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
  • Recently Listed
1 of 3
$399,000
Studio

Beds

0.0

Baths

0 Fairholme Way

Winchester, KY

Bluegrass
View 116 Sturbridge Lane Winchester, KY MLS# 26011782
  • Recently Listed
1 of 37
$290,000
3

Beds

2.0

Baths

1,260

Sq.Ft.

116 Sturbridge Lane

Winchester, KY

Bluegrass
View 516 Hidden Hills Way Winchester, KY MLS# 26011540
$225,000
3

Beds

2.0

Baths

1,134

Sq.Ft.

516 Hidden Hills Way

Winchester, KY

Bluegrass
View 225 Buffalo Trace Winchester, KY MLS# 26011564
  • Recently Listed
1 of 24
$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
  • Recently Listed
1 of 23
$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
  • Recently Listed
1 of 30
$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
  • Recently Listed
1 of 38
$289,900
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

About Winchester

Listings in Winchester, KY

280

Estimated median home price

$269,950
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 - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K14
$600K - 700K5
$700K - 800K10
$800K - 900K1
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family160
Townhouse4
Condo0
Commercial13
Rental18
Lots and Land89
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms4

(Data as of 6/7/2026)

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 6/9/2026.