$2,785,000

82 Woodley Road, Winnetka, IL 60093

Active
6 beds 5.5 baths Built 1937 Residential MLS #MRD12680099 7 days on market
Listing courtesy of @properties Christie's International Real Estate · 847-892-4800 · MLS #MRD12680099 · Status: Active
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.

Property details

Interior

Appliances
Range, Dishwasher, High End Refrigerator, Disposal, Stainless Steel Appliance(s), Range Hood, Humidifier
Interior features
1st Floor Bedroom, 1st Floor Full Bath, Walk-In Closet(s), Bookcases, Separate Dining Room
Flooring
Hardwood
Fireplaces
2
Fireplace details
Gas Log, Gas Starter
Basement
Crawl Space
Laundry
Main Level, Upper Level, Multiple Locations
Additional rooms
Bedroom 5, Bedroom 6, Play Room, Breakfast Room, Exercise Room, Sitting Room, Other Room, Walk In Closet
Total rooms
14

Building & exterior

Style
Colonial
Age
81-90 Years
Exterior
Brick
Exterior features
Balcony, Outdoor Grill
Roof
Shake
Patio & porch
Patio

Parking

Garage spaces
2
Total spaces
2
Parking details
Gravel, Garage Door Opener, Yes, Garage Owned, Attached, Garage

Lot & location

Lot dimensions
164.9X407X164.9X397
Lot description
Dimensions to Center of Road, Landscaped
Township
New Trier
County
Cook

Utilities

Heating
Natural Gas
Cooling
Central Air
Water
Lake Michigan
Sewer
Public Sewer
Equipment
Intercom, CO Detectors, Ceiling Fan(s), Sump Pump, Sprinkler-Lawn

HOA & community

Assessment
$3,000 / annually
Assessment includes
Other

Schools

Elementary
Avoca West Elementary School (37)
Junior high
Marie Murphy School (37)
High school
New Trier Twp H.S. Northfield/Wi (203)

Taxes & terms

Annual taxes
$22,421 (2024)
Parcel number (PIN)
05291020960000
PIN
05291020960000
Ownership
Fee Simple
Possession
Closing
Special conditions
List Broker Must Accompany
Listed
6/24/2026

Rooms

RoomSizeLevelFlooring
Bedroom 514X15ThirdHardwood
Bedroom 614X13ThirdHardwood
Play Room15X29ThirdHardwood
Breakfast Room11X9Main
Exercise Room20X19SecondHardwood
Sitting Room19X14SecondHardwood
Other Room19X13MainHardwood
Walk In Closet18X12SecondHardwood
Bedroom 215X14SecondHardwood
Bedroom 315X14SecondHardwood
Bedroom 413X10MainHardwood
Dining Room19X15MainOther
Family Room20X14MainHardwood
Kitchen19X16MainHardwood
LaundryN/A
Living Room21X29MainHardwood
Master Bedroom17X16SecondHardwood

What would this home cost per month?

Using this listing's actual tax bill (2024) and actual HOA assessment — adjust anything.

Rates move daily — edit to today's quote. Under 20% down adds PMI automatically.

Estimated monthly payment
$0
Principal & interest
Property taxes
Insurance
PMI (under 20% down)
HOA / assessments

Estimates only — not a loan offer or quote; your rate, insurance and PMI depend on your credit and lender. Run other scenarios on the full mortgage calculator, or ask us to connect you with lenders our clients actually close with.

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