42 Woodley Road Winnetka, IL ^$ 3,495,000

42 Woodley Road

^$ 3,495,000

Back to search

Recently Listed

42 Woodley Road

Winnetka, IL, 60093

^$ 3,495,000

Bedrooms4 Baths3.3 Sq 4,225

Monthly Estimate*

^$ 21,519

42 Woodley Road, Winnetka, IL 60093 - Image 1

42 Woodley Road, Winnetka, IL 60093 - Image 2

42 Woodley Road, Winnetka, IL 60093 - Image 3

42 Woodley Road, Winnetka, IL 60093 - Image 4

42 Woodley Road, Winnetka, IL 60093 - Image 5

42 Woodley Road, Winnetka, IL 60093 - Image 6

42 Woodley Road, Winnetka, IL 60093 - Image 7

42 Woodley Road, Winnetka, IL 60093 - Image 8

42 Woodley Road, Winnetka, IL 60093 - Image 9

42 Woodley Road, Winnetka, IL 60093 - Image 10

42 Woodley Road, Winnetka, IL 60093 - Image 11

42 Woodley Road, Winnetka, IL 60093 - Image 12

42 Woodley Road, Winnetka, IL 60093 - Image 13

42 Woodley Road, Winnetka, IL 60093 - Image 14

42 Woodley Road, Winnetka, IL 60093 - Image 15

42 Woodley Road, Winnetka, IL 60093 - Image 16

42 Woodley Road, Winnetka, IL 60093 - Image 17

42 Woodley Road, Winnetka, IL 60093 - Image 18

42 Woodley Road, Winnetka, IL 60093 - Image 19

42 Woodley Road, Winnetka, IL 60093 - Image 20

42 Woodley Road, Winnetka, IL 60093 - Image 21

42 Woodley Road, Winnetka, IL 60093 - Image 22

42 Woodley Road, Winnetka, IL 60093 - Image 23

42 Woodley Road, Winnetka, IL 60093 - Image 24

42 Woodley Road, Winnetka, IL 60093 - Image 25

42 Woodley Road, Winnetka, IL 60093 - Image 26

42 Woodley Road, Winnetka, IL 60093 - Image 27

42 Woodley Road, Winnetka, IL 60093 - Image 28

42 Woodley Road, Winnetka, IL 60093 - Image 29

42 Woodley Road, Winnetka, IL 60093 - Image 30

42 Woodley Road, Winnetka, IL 60093 - Image 31

42 Woodley Road, Winnetka, IL 60093 - Image 32

42 Woodley Road, Winnetka, IL 60093 - Image 33

42 Woodley Road, Winnetka, IL 60093 - Image 34

42 Woodley Road, Winnetka, IL 60093 - Image 35

42 Woodley Road, Winnetka, IL 60093 - Image 36

42 Woodley Road, Winnetka, IL 60093 - Image 37

42 Woodley Road, Winnetka, IL 60093 - Image 38

42 Woodley Road, Winnetka, IL 60093 - Image 39

42 Woodley Road, Winnetka, IL 60093 - Image 40

42 Woodley Road, Winnetka, IL 60093 - Image 41

42 Woodley Road, Winnetka, IL 60093 - Image 42

42 Woodley Road, Winnetka, IL 60093 - Image 43

42 Woodley Road, Winnetka, IL 60093 - Image 44

42 Woodley Road, Winnetka, IL 60093 - Image 45

42 Woodley Road, Winnetka, IL 60093 - Image 46

42 Woodley Road, Winnetka, IL 60093 - Image 47

42 Woodley Road, Winnetka, IL 60093 - Image 48

42 Woodley Road, Winnetka, IL 60093 - Image 49

42 Woodley Road, Winnetka, IL 60093 - Image 50

42 Woodley Road, Winnetka, IL 60093 - Image 51

42 Woodley Road, Winnetka, IL 60093 - Image 52

42 Woodley Road, Winnetka, IL 60093 - Image 53

42 Woodley Road, Winnetka, IL 60093 - Image 54

42 Woodley Road, Winnetka, IL 60093 - Image 55

42 Woodley Road, Winnetka, IL 60093 - Image 56

42 Woodley Road, Winnetka, IL 60093 - Image 57

42 Woodley Road, Winnetka, IL 60093 - Image 58

42 Woodley Road, Winnetka, IL 60093 - Image 59

42 Woodley Road, Winnetka, IL 60093 - Image 60

42 Woodley Road, Winnetka, IL 60093 - Image 61

42 Woodley Road, Winnetka, IL 60093 - Image 62

42 Woodley Road, Winnetka, IL 60093 - Image 63

42 Woodley Road, Winnetka, IL 60093 - Image 64

42 Woodley Road, Winnetka, IL 60093 - Image 65

42 Woodley Road, Winnetka, IL 60093 - Image 66

42 Woodley Road, Winnetka, IL 60093 - Image 67

42 Woodley Road, Winnetka, IL 60093 - Image 68

42 Woodley Road, Winnetka, IL 60093 - Image 69

42 Woodley Road, Winnetka, IL 60093 - Image 70

42 Woodley Road, Winnetka, IL 60093 - Image 71

42 Woodley Road, Winnetka, IL 60093 - Image 72

42 Woodley Road, Winnetka, IL 60093 - Image 73

View a Virtual Tour

Single Family Home for sale in Winnetka, IL

for $3,495,000 with 4 bedrooms and 3 full baths, 3 half baths. This 4,225 square foot home was built in 1965.

Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

Single Family Active

Price

^$ 3,495,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 25,026

Style

Contemporary

Year Built

1965

Town/City

Winnetka

County/Region

Cook

MLS | Web ID

12533727

Features

General

Living Area 4225

Sewer Public Sewer

Heating Natural Gas

Cooling Central Air

Possession Negotiable

Roof Shake

Appliances Range Microwave Dishwasher Refrigerator Washer Dryer Disposal

Garage Spaces 2

Association Fee Includes None

Architectural Style Contemporary

Construction Materials Frame Stone

Year Built 1965

Township New Trier

Tax Year 2024

Ownership Fee Simple

Assoc Fee Paid Per Not Applicable

County Cook

New Construction N

Property Type Residential Detached Single

Other Structures Gazebo Guest House

Total Rooms 10

Full Baths 3

Status New

Directions Willow Rd to Hibbard. South on Hibbard to Woodley. North of Illinois. Home is a Woodley address but faces Hibbard.

High School New Trier Twp H.S. Northfield/Wi

City Winnetka

High School District 203

MLS Area Winnetka

Elementary School Avoca West Elementary School

Tax Annual Amount 25026.11

Middle/Junior High School Marie Murphy School

Virtual Tour https://real.vision/42-woodley-road?o=u

Standard Status Active

Middle/Junior School District 37

Elementary School District 37

Interior

Interior Amenities Vaulted Ceiling(s) Dry Bar 1st Floor Bedroom In-Law Floorplan 1st Floor Full Bath Bookcases Granite Counters

Basement Finished Partial

Total Fireplaces 2

Half Baths 3

Laundry Features Main Level

Total Bedrooms 4

Below Grade Finished Area 1372

Room Type Maid Room Family Room

Total Baths 6

Bedrooms Possible 4

Exterior

Parking Features Gravel Garage Door Opener Yes Garage Owned Detached Garage

Lot Features Corner Lot Landscaped

Water Source Public

Total Parking 2

Foundation Details Concrete Perimeter

Lot Dimensions 254 x 155

Waterfront Y/N N

* Excluded Features

List By

@Properties Christie's International Real Estate

Broker

peggylewis@atproperties.com;peggyonlaurel@aol.com

Affordability Calculator

$23,605

Per Month

Monthly Principal & Interest: $21,519
Monthly Property Taxes: $2,086
Monthly Home Insurance: --

Set your offer price

Down Payment

Loan Term

Interest Rate

Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

THE TIME TO SELL IS NOW! What's my home worth?

Nearby

Trends
Schools

Single family listings in Winnetka, IL

Average List Price ^$2,854,645

Percent of Sale Price 18%

About Winnetka, IL

12,298 Population

-2% Since 2002

^$182,976 Median Income

45.24 Median Age

46% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

565834 Elementary School

567821 Middle School

New Trier Twp H.S. Northfield/Wi High School

See complete school information

Pricing History

Date	Price	Price Change	Description
1/16/2026	$3,495,000		Listed Price

Map

More homes like this one

homes for you

See all

42 Woodley Road, Winnetka, IL, 60093 is a Single Family Home for sale at $3,495,000 with 4,225 sqft. 42 Woodley Road has 4 bedrooms, 3.3 baths, and was built in 1965. The property's zip code is 60093 which is in Winnetka, IL

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. 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.

http://www.mredllc.com/comms/resources/DMCA_Notice.pdf

Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Data is updated as of 1/17/2026.

*Full Name

*Email

*Phone

I am interested in financing options

Get more info

By submitting the form, you agree that Weichert^® may contact you via phone or text about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our privacy policy.

Get more info

Looking for an Associate?

Already Working with an Associate?

42 Woodley Road

Single Family Home for sale in Winnetka, IL

Affordability Calculator

Map

More homes like this one

Get more info about this home