221 total properties
Did you mean the neighborhood Winchester?
View 60 Hiawatha Trail Winchester, KY MLS# 26006850
$204,900
3

Beds

1.0

Baths

1,290

Sq.Ft.

60 Hiawatha Trail

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 308 Duclair Drive Winchester, KY MLS# 25018185
$50,000
Studio

Beds

0.0

Baths

308 Duclair Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 228 Holiday Road Winchester, KY MLS# 26006679
$339,900
4

Beds

2.0

Baths

1,843

Sq.Ft.

228 Holiday Road

Winchester, KY

Bluegrass
View 740 Pilot Ridge Lane Winchester, KY MLS# 26006680
$339,900
3

Beds

2.1

Baths

1,608

Sq.Ft.

740 Pilot Ridge Lane

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26006685
  • Recently Listed
1 of 13
$239,900
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 47 Buckner Street Winchester, KY MLS# 26006752
  • Recently Listed
1 of 16
$179,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

47 Buckner Street

Winchester, KY

Bluegrass
View 37 Ashland Avenue Winchester, KY MLS# 26006776
$139,000
2

Beds

1.0

Baths

904

Sq.Ft.

37 Ashland Avenue

Winchester, KY

Bluegrass
View 415 L E Junction Road Winchester, KY MLS# 26006620
  • Recently Listed
1 of 36
OPEN HOUSE: Sunday 4/19 1:00 PM - 3:00 PM
$215,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

415 L E Junction Road

Winchester, KY

Bluegrass
View 117 4th Street Winchester, KY MLS# 25501219
$10,000
Studio

Beds

0.0

Baths

117 4th Street

Winchester, KY

Bluegrass
View 201 Prescott Lane Winchester, KY MLS# 26006371
$259,900
3

Beds

2.0

Baths

1,304

Sq.Ft.

201 Prescott Lane

Winchester, KY

Bluegrass
View 174 Cook Avenue Winchester, KY MLS# 26006389
  • Recently Listed
1 of 15
$139,900
2

Beds

1.0

Baths

986

Sq.Ft.

174 Cook Avenue

Winchester, KY

Bluegrass
View 3610 Stamper Drive Winchester, KY MLS# 26006288
$239,900
3

Beds

2.0

Baths

1,148

Sq.Ft.

3610 Stamper Drive

Winchester, KY

Bluegrass
View 750 Providence Lane Winchester, KY MLS# 26006323
$359,900
Studio

Beds

0.0

Baths

750 Providence Lane

Winchester, KY

Bluegrass
View 4247 Basin Springs Road Winchester, KY MLS# 26006060
$170,000
Studio

Beds

0.0

Baths

4247 Basin Springs Road

Winchester, KY

Bluegrass
View 29 Euclid Avenue Winchester, KY MLS# 26006180
$190,000
3

Beds

2.0

Baths

1,498

Sq.Ft.

29 Euclid Avenue

Winchester, KY

Bluegrass
View 4700 Four Mile Road Winchester, KY MLS# 25501428
$54,900
Studio

Beds

0.0

Baths

4700 Four Mile Road

Winchester, KY

Bluegrass
View 471 Goose Creek Road Winchester, KY MLS# 26006002
$160,000
3

Beds

2.0

Baths

1,248

Sq.Ft.

471 Goose Creek Road

Winchester, KY

Bluegrass
View 104 Jackson Ferry Road Winchester, KY MLS# 26005196
$275,000
4

Beds

2.0

Baths

2,417

Sq.Ft.

104 Jackson Ferry Road

Winchester, KY

Bluegrass
View 168 Buckingham Lane Winchester, KY MLS# 26006049
$339,900
4

Beds

2.1

Baths

2,358

Sq.Ft.

168 Buckingham Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

295

Estimated median home price

$275,000
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 - 100K35
$100K - 200K67
$200K - 300K66
$300K - 400K39
$400K - 500K20
$500K - 600K14
$600K - 700K12
$700K - 800K15
$800K - 900K4
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse5
Condo0
Commercial12
Rental15
Lots and Land96
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/19/2026)

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 4/19/2026.