32 Woodley Road, Winnetka IL 60093
$4,950,000

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Property Description

Nestled down a winding, private road on 1.9 meticulous park-like acres, this grand, almost 10,000 square foot residence exudes luxury and timeless elegance. The front entrance is set apart from the road by a sweeping circular drive bordered by private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal powder room and two coat closets, you are greeted by the sophistication that defines this home. The main level features a spacious, step down living room with inlaid floors, a marble, gas and wood fireplace, and two picture windows that fill the room with natural light. Pass through the living room to an adjoining, architecturally beautiful solarium with a slate floor, that offers panoramic views of the lush grounds surrounding the residence. The formal dining room also features inlaid floors, and picture window. The handsome family room with custom cabinetry, lighting, millwork, and a marble, gas and wood fireplace, provides the perfect space for entertaining and relaxation while overlooking a yard large enough for a pool. The family room seamlessly flows into a large kitchen area that includes not only a custom kitchen but also a breakfast room, butler's pantry, back staircase, and mud room. The butler's pantry has an ice maker, second dishwasher, and beverage refrigerator. Upstairs the luxurious primary bedroom suite boasts a marble, gas and wood fireplace, walk-in closet, and an adjoining sun room with stunning views of the grounds. It is perfect for family gatherings, office space or nursery. Adjacent to the dual sink primary bath with a vanity table, there is a winding staircase that leads upstairs to the third floor where you will find a beautifully crafted wardrobe/dressing room with many custom built-ins, lighting and mirrors. This lovely area conveniently leads to an exercise room, powder room and an oversized cedar closet, and this completes the third floor. There are four additional family bedrooms on the second floor, two share a Jack and Jill bathroom, one has its own en-suite, and the fifth bedroom suite offers versatile living space. The fifth bedroom and sitting room, located near the back stairs, welcomes an in-law arrangement, live in nanny, or out of town guests. The full basement offers at least another 2444 square feet of living space and includes a large recreation room with fireplace, billiard room, wet bar, spacious laundry room, large cedar closet, another storage room with built-in shelving, and a powder room. The yard is professionally landscaped, private, and nearly two acres is quite hard to come by in Winnetka. Additional features of this remarkable residence include: a three car, heated, attached garage, magnificent craftsmanship, glorious room sizes, four fireplaces, a slate roof, copper gutters, circular driveway and uncommon privacy. This residence is a true gem in the heart of Winnetka. Live a life of luxury and sophistication in this exceptional home. Woodley Road, with its canopy of mature trees, is a coveted private oasis, and yet is conveniently located near town, train, restaurants, schools and a public golf course. This property is not located in the flood plane. NO SIGN

Features & Information

Key Details

  • List Price $4,950,000
  • Property Taxes $40,361
  • Assessments/HOA $3,500
  • Square Feet 8039
  • Year Built 1943
  • Status Active
  • Market Time 455

Rooms

  • Total Rooms 15
  • Number of Bedrooms 5
  • Number of Bathrooms 4.3
  • Primary Bedroom

  • Room Size 21X23
  • Floor Level Second
  • Flooring Carpet
  • Primary Bathroom Full,Double Sink,Whirlpool
  • Bedroom 2

  • Room Size 17X13
  • Floor Level Second
  • Flooring Carpet
  • Bedroom 3

  • Room Size 17X15
  • Floor Level Second
  • Flooring Carpet
  • Bedroom 4

  • Room Size 21X14
  • Floor Level Second
  • Flooring Carpet
  • Bedroom 5

  • Room Size 15X13
  • Floor Level Second
  • Flooring Carpet
  • Living Room

  • Room Size 33X21
  • Floor Level Main
  • Flooring Carpet
  • Family Room

  • Room Size 19X14
  • Floor Level Main
  • Flooring Carpet
  • Dining Room

  • Room Size 20X15
  • Floor Level Main
  • Flooring Carpet
  • Kitchen

  • Room Size 12X15
  • Floor Level Main
  • Flooring Hardwood

Additional Rooms

  • Breakfast Room

  • Room Size 12X9
  • Floor Level Main
  • Flooring Hardwood
  • Recreation Room

  • Room Size 36X33
  • Floor Level Basement
  • Flooring Carpet
  • Sitting Room

  • Room Size 14X22
  • Floor Level Second
  • Flooring Carpet
  • Exercise Room

  • Room Size 20X28
  • Floor Level Third
  • Flooring Carpet
  • Heated Sun Room

  • Room Size 22X14
  • Floor Level Main
  • Flooring Slate
  • Den

  • Room Size 18X12
  • Floor Level Second
  • Flooring Carpet
  • Foyer

  • Room Size 21X16
  • Floor Level Main
  • Flooring Marble
  • Pantry

  • Room Size 11X11
  • Floor Level Main
  • Flooring Hardwood
  • Storage

  • Room Size 18X13
  • Floor Level Third
  • Flooring Carpet
  • Laundry

  • Room Size 22X16
  • Floor Level Basement
  • Flooring Vinyl

Interior Features

  • Appliances

  • Appliances Included Double Oven, Dishwasher, Refrigerator, Bar Fridge, Washer, Dryer, Disposal, Trash Compactor, Cooktop, Oven, Range Hood, Gas Cooktop, Electric Oven
  • Heating & Cooling

  • Heating Type Natural Gas, Forced Air, Steam, Sep Heating Systems - 2+
  • Air Conditioning Central Air, Zoned
  • Fireplace

  • # of Fireplaces 4
  • Type of Fireplace Family Room, Living Room, Master Bedroom, Basement

Exterior Features

  • Building Information

  • Age of Building 81-90 Years
  • Exposure South
  • Recent Rehab No
  • Parking

  • # of Cars 3

Location

  • County Cook
  • Township New Trier
  • Corporate Limits Unincorporated
  • Directions to Property Hill Road West Of Locust To Woodley. Turn South On Woodley To 32. At The Fork Follow The Road To Your Right
  • Schools

  • Elementary School District 37
  • Junior High District 37
  • High School District: 203
  • School Name New Trier Twp H.S. Northfield/Wi
  • Property Taxes

  • Tax 40361
  • Tax Year 2023
  • Tax Exemptions Homeowner
  • Parcel Identification Number 05291001010000
  • Lot Information

  • Lot Size 1.0-1.99 Acres

Listed by Katharine Hackett for @properties Christie's International Real Estate | Source: MRED as distributed by MLS GRID

Based on information submitted to the MLS GRID as of 8/21/2026 12:02 AM. 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.

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