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Winnetka, IL, 60093 • 60093 • Cook County
$306/sqft
7Beds
10Baths
8,754Sqft
0.93 acLot
1939Built
Character Home
Built 1939 · 87 years of history
Outdoor Living
Patio
4 Fireplaces
Family Room · Master Bedroom · Basement · Den/Library
3-Car Garage
Gravel · Garage Door Opener · Heated Garage · On Site · Garage Owned · Attached · Garage
Premium Finishes
Walk-In Closet(s)
Hardwood Floors
Quality flooring throughout
This home is getting attention
Listed 587 days ago · 26 views
Demand and pricing signals for this listing
26 views
People checking out this listing
587 days on market
Established listing
$306/sqft
Price per square foot
This home ranks in the top 47% of listings most likely to go under contract soon, based on market activity and demand signals.
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Single Family · Built 1939 · Historic
Welcome to 58 Woodley Road; a singular combination of space, land, and privacy, in one of Winnetka's most esteemed neighborhoods. A park-like setting punctuated by stone walkways and gardens creates a magical backdrop for the stately brick manse of over 8,000 (above grade) square feet. This residence is a testament to classic design. Beautiful, newly installed white-oak floors, wainscoting, dentil moulding, tray ceilings, custom built-ins and arched doorways lend an air of timeless elegance throughout. Stepping through the grand foyer, the home unfolds with a sense of expansiveness with stunning site-lines to the backyard. Formal and informal entertaining spaces, including a spacious living room and dining room, as well as an enormous family room with French doors opening to the backyard offer a great first floor flow. A beautiful sunroom, adorned with vaulted ceilings, abundant windows and six French doors, invites you to linger over morning coffee or spend a leisurely afternoon amidst the surrounding greenery. A handsome office boasts rich paneling, a fireplace and built-in bookshelves. The traditional-style kitchen, which opens to the family room, is a culinary haven, appointed with an 8-burner Wolf range, a large pantry and spacious center island. An adjoining breakfast room equally captivates with views of the backyard. A large mudroom is every bit a luxury as it offers a sink, a command center, and a second Sub-Zero refrigerator for extra food storage. A thoughtfully redesigned staircase leads upstairs to more private spaces. Expansive and sun-kissed with a dramatic vaulted ceiling, the primary bedroom doubles as a sanctuary with dual walk-in closets, dual baths, and separate water closets. A generously sized shower "room" connects them. Completing this level are three well-appointed ensuite bedrooms, and a separate au pair or in-law "wing" with two rooms, a full bath, and its own staircase and veranda. Two rooms and a full bath reside on the third level, providing the ideal space for a second office, teen hangout, kids playroom, or private guest quarters. The finished basement offers a world of possibilities. Marble flooring sets the stage for an expansive entertainment area, while a dedicated craft room, rec room, and a well-stocked bar with an ice maker cater to every leisure pursuit. A gym and wine cellar ensure there's a space for everyone to enjoy. This finely crafted estate delivers an unparalleled living experience on sought after Woodley Road in Winnetka.
Standout features identified
Our analysis highlights stately brick manse, finished basement, and well-appointed ensuite bedrooms as key attractions of this home.
Based on current rates
Est. 6.75% rate · 30yr fixed · $2,144,000 loan
Full calculator →Key facts and listing details
14 categories of property features
19 rooms detailed
Master Bedroom
SecondBedroom2
SecondBedroom3
SecondBedroom4
SecondBedroom5
SecondBedroom6
SecondMarket data and value estimates
3 schools rated nearby
Winnetka, IL, 60093
27 events
25 years of records
Local context around this listing
Winnetka, IL • Cook County
Nearby cities
Nearby zip codes
Based on information submitted to the MLS GRID as of 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. [Click here for more information](/mls-disclaimers/#17)
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