View all 63 photos
Detached Single · Winnetka, IL
$2,250,000
4 beds · 4.5 baths · 4,225 sqft
42 Woodley Road, Winnetka, IL, 60093
A brick-and-mortar place to make your own — room to make it home.
Active
What’s special
Central air2-car garageIn-unit laundry
Rarely available first floor primary! 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. Owner extremely motivated!!!
— the listing agent’s description
The home
4 beds
4.5 baths
4,225 sqft
Built in 1965
Lot 254 x 155
2-car garage
Detached Single
Contemporary
What it’ll cost
$533 / sqft
$25,026 taxes / yr
No HOA
55 days on dwello
Estimated monthly payment
$14,705/mo
Principal & interest$11,963
Property taxes$2,086
Homeowners insurance$656
Get pre-qualified →Connect with a licensed lender in the dwello network.
Estimate only — not a loan offer. Example rate; taxes and insurance estimated; your actual rate, payment, taxes, and insurance will vary. dwello is not a lender. Equal Housing Opportunity.
Tour it with a real dwello agent
The agent who meets you here is an actual dwello Home Group team member who knows these streets — not a stranger who bought your name from a portal. You get straight answers on the spot, and the same person stays with you through closing.
On our team, vettedYour info is never soldWith you through closing
Tour this home
In person, on your schedule — a dwello agent meets you there.
WED
Jun 3
THU
Jun 4
FRI
Jun 5
SAT
Jun 6
11:00 am
Schedule a tour
55 days on dwello
Price history
Listed for sale
Jun 9, 2026
$2,250,000
Earlier records
Listed
Jan 15, 2026
$2,250,000
From MLS records — independently verify.
Property taxes
2025
Annual tax bill (MLS)
Assessed value
2026
County assessor
2025
2024
2023
2022
2021
2020
2019
Assessed value from the Cook County Assessor (open records). Estimated market ≈ assessed × 10 for residential; not an appraisal — verify with the assessor.
Features
Central AirNatural GasFrameStonePublic SewerGravelGarage Door Opener
Schools
Elementary — Avoca West Elementary School
Middle — Marie Murphy School
High — New Trier Twp H.S. Northfield/Wi
Assigned schools per the listing — always verify enrollment + boundaries with the district.
Neighborhood
Loading map…
Nearby places via OpenStreetMap — approximate; verify what matters to you. Map © Mapbox © OpenStreetMap.
MLS listing data
Listed by Peggy Lewis · @properties Christie's International Real Estate
Listing last updated Aug 2, 2026 · data refreshed from the MLS Aug 2, 2026, 8:03 AM CT
Based on information submitted to the MLS GRID as of Aug 2, 2026, 8:03 AM CT. Listing data © MRED LLC, distributed by MLS GRID — deemed reliable but not guaranteed; independently verify. Anything shown below this point is not MLS listing data.
See it in personA real dwello agent on our team — never a sold lead.
Schedule a tour
Message
No pressure — reach out whenever you’re ready.
Similar homes nearby
$2,499,000Active
3 bd · 4.5 ba · 3,610 sqft
1192 Chatfield Road
Winnetka, IL
$2,695,000Active
4 bd · 4.5 ba · 4,509 sqft
1140 Oakley Avenue
Winnetka, IL
$1,725,000Active
5 bd · 4.5 ba · 6,580 sqft
555 Cherry Street
Winnetka, IL
$2,795,000Active
5 bd · 5.5 ba · 4,089 sqft
73 Locust Road
Winnetka, IL
