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Detached Single · Winnetka, IL
$2,785,000
6 beds · 5.5 baths
82 Woodley Road, Winnetka, IL, 60093
A brick-and-mortar place to make your own — room to make it home.
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What’s special

Central air2-car garage1.50-acre lotIn-unit laundry
Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush, manicured grounds set the stage. Inside, the craftsmanship is unmistakable. You'll find expansive living spaces defined by rich architectural details and massive windows that frame the private, park-like backyard. The chef's kitchen is a masterpiece of function and style, flowing effortlessly into inviting family spaces that feel warm despite their scale. A first floor bedroom includes a private full bath and access to the patio. The primary suite serves as a genuine retreat, complete with a spa bath and enough closet space to satisfy any wardrobe. A sitting area surrounded by windows and a walkout overlooks the exquisite property. Each additional bedroom is en-suite and generously sized, ensuring everyone has their own corner of comfort. The third level includes flexible space with 3 lovely rooms and a full bath. There is an extra bonus space above the attached garage-perfect for a studio! Outside, the property truly shines. The expansive patio and rolling lawns create an incredible backdrop for summer garden parties or a quiet evening under the stars. Living here means more than just enjoying a beautiful residence; it's about the Winnetka lifestyle. You're minutes away from world-class schools, boutique shopping in the village, the shores of Lake Michigan, and the Metra for an easy commute to the city. It's sophisticated, it's private, and it's ready for its next chapter.
— the listing agent’s description

The home

6 beds
5.5 baths
Built in 1937
1.50-acre lot
2-car garage
Detached Single
Colonial

What it’ll cost

$22,421 taxes / yr
$3,000/mo HOA
7 days on dwello

Estimated monthly payment

$20,488/mo
Principal & interest$14,808
Property taxes$1,868
Homeowners insurance$812
HOA dues$3,000
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WED
Jun 3
THU
Jun 4
FRI
Jun 5
SAT
Jun 6
11:00 am
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7 days on dwello
Price history
Listed for sale
Jun 24, 2026
$2,785,000
Property taxes
2025
Annual tax bill (MLS)
$22,421/yr
Assessed value
2026
County assessor
$201,000~$2,010,000 mkt
2025
$201,000~$2,010,000 mkt
2024
$121,938~$1,219,380 mkt
2023
$121,938~$1,219,380 mkt
2022
$121,938~$1,219,380 mkt
2021
$133,974~$1,339,740 mkt
2020
$133,973~$1,339,730 mkt
2019
$182,470~$1,824,700 mkt
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 GasBrickPublic 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
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Nearby places via OpenStreetMap — approximate; verify what matters to you. Map © Mapbox © OpenStreetMap.
MLS listing dataMRED
Listed by Michael Mitchell · @properties Christie's International Real Estate
Listing last updated Jun 30, 2026 · data refreshed from the MLS Jun 30, 2026, 6:38 PM CT
Based on information submitted to the MLS GRID as of Jun 30, 2026, 6:38 PM 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.
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