165 total properties
Did you mean the neighborhood Winchester?
View 14 Cook Avenue Winchester, KY MLS# 26011961
  • Recently Listed
1 of 37
$233,000
3

Beds

2.0

Baths

1,261

Sq.Ft.

14 Cook Avenue

Winchester, KY

Bluegrass
View 13 Long Avenue Winchester, KY MLS# 26013004
  • Recently Listed
1 of 31
$240,000
3

Beds

2.0

Baths

1,297

Sq.Ft.

13 Long Avenue

Winchester, KY

Bluegrass
View 310 W Hickman Street Winchester, KY MLS# 26012783
  • Recently Listed
1 of 13
$109,900
4

Beds

2.1

Baths

1,391

Sq.Ft.

310 W Hickman Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 20 Jackson Street Winchester, KY MLS# 26012820
  • Recently Listed
1 of 36
$290,000
3

Beds

2.0

Baths

1,650

Sq.Ft.

20 Jackson Street

Winchester, KY

Bluegrass
View 563 Constitution Drive Winchester, KY MLS# 26012893
$104,900
2

Beds

2.0

Baths

924

Sq.Ft.

563 Constitution Drive

Winchester, KY

Bluegrass
View 162 French Avenue Winchester, KY MLS# 26012319
  • Recently Listed
1 of 40
$299,900
4

Beds

1.0

Baths

2,327

Sq.Ft.

162 French Avenue

Winchester, KY

Bluegrass
View 528 Estes Drive Winchester, KY MLS# 26012351
$234,900
3

Beds

2.0

Baths

1,904

Sq.Ft.

528 Estes Drive

Winchester, KY

Bluegrass
View 104 Bay Hill Drive Winchester, KY MLS# 26012179
  • Recently Listed
1 of 14
$215,000
2

Beds

2.0

Baths

1,200

Sq.Ft.

104 Bay Hill Drive

Winchester, KY

Bluegrass
View 217 Short Street Winchester, KY MLS# 26012199
  • Recently Listed
1 of 50
$229,900
3

Beds

1.0

Baths

1,042

Sq.Ft.

217 Short Street

Winchester, KY

Bluegrass
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
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 125 Kittison Drive Winchester, KY MLS# 26011953
  • Recently Listed
1 of 24
$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 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

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 6/8/2026.