View 1410 Dry Fork Creek Road Winchester, KY MLS# 25503598
$435,000
3

Beds

2.0

Baths

1,064

Sq.Ft.

1410 Dry Fork Creek Road

Winchester, KY

Bluegrass
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$439,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

Winchester, KY

Bluegrass
View 1125 W Lexington Avenue Winchester, KY MLS# 24015897
$439,900
2,269

Sq.Ft.

1125 W Lexington Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 870 Pilot View Road Winchester, KY MLS# 26000270
  • Recently Listed
1 of 21
$440,000
3

Beds

2.0

Baths

1,568

Sq.Ft.

870 Pilot View Road

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$450,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$450,000
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 233 Cunningham Lane Winchester, KY MLS# 25507450
$450,000
3

Beds

2.1

Baths

2,258

Sq.Ft.

233 Cunningham Lane

Winchester, KY

Bluegrass
View 42 Mockingbird Valley Road Winchester, KY MLS# 26000113
$452,500
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25017324
$498,900
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25500168
$498,900
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 5199 Schollsville Road Winchester, KY MLS# 25502093
$499,000
4

Beds

3.0

Baths

2,647

Sq.Ft.

5199 Schollsville Road

Winchester, KY

Bluegrass
View 595 Earlymeade Drive Winchester, KY MLS# 25506943
$499,000
5

Beds

3.1

Baths

3,823

Sq.Ft.

595 Earlymeade Drive

Winchester, KY

Bluegrass
View 414 Fairholme Way Winchester, KY MLS# 25505996
  • New Construction
1 of 18
$499,900
4

Beds

3.0

Baths

2,300

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass
View 1005 Early Drive Winchester, KY MLS# 20111871
$500,000
Studio

Beds

0.0

Baths

1005 Early Drive

Winchester, KY

Bluegrass
View 5515 Van Meter Road Winchester, KY MLS# 25012984
$524,900
4

Beds

2.0

Baths

2,940

Sq.Ft.

5515 Van Meter Road

Winchester, KY

Bluegrass
View 808 Bypass Road Winchester, KY MLS# 25011326
$525,000
5,094

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 808 Bypass Road Winchester, KY MLS# 25015851
$525,000
2

Beds

1.1

Baths

5,054

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 107 Bella Shae Way Winchester, KY MLS# 24025578
  • New Construction
1 of 10
$550,000
3

Beds

2.1

Baths

2,200

Sq.Ft.

107 Bella Shae Way

Winchester, KY

Bluegrass
View 33-41 Winn Avenue Winchester, KY MLS# 25508043
  • Recently Listed
1 of 2
$550,000
Studio

Beds

0.0

Baths

33-41 Winn Avenue

Winchester, KY

Bluegrass
View 125 Casa Landa Way Winchester, KY MLS# 25508316
  • Recently Listed
1 of 86
$550,000
4

Beds

3.1

Baths

3,848

Sq.Ft.

125 Casa Landa Way

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

252

Estimated median home price

$299,000
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 - 100K27
$100K - 200K47
$200K - 300K56
$300K - 400K38
$400K - 500K25
$500K - 600K10
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family144
Townhouse3
Condo0
Commercial12
Rental18
Lots and Land72
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms13

(Data as of 1/8/2026)

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 1/8/2026.