320 Woodley Road, Winnetka IL 60093
$4,949,000

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Property Description

Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof, columned portico, and timeless symmetry. Together, these elements create a striking first impression and set the stage for interiors that exude sophistication at every turn. Step inside the grand "bookmatched" marble-floored foyer, where a dramatic staircase sets a refined tone for the home. To one side, the formal living room offers an inviting gathering space anchored by a marble fireplace, while the formal dining room is perfectly scaled for both intimate dinners and large-scale entertaining. A massive, richly paneled home office with dramatic coffered ceilings offers an impressive and inspiring workspace. At the heart of the home, the gourmet kitchen boasts professional-grade appliances, an oversized island, full wall of pantry storage, and a sunlit breakfast area all overlooking the magnificent pool and grounds. A butler's pantry ideally placed between the kitchen and dining room provides effortless entertaining. Just beyond, the kitchen opens to a cozy family room with a fireplace and wet bar, while French doors lead to an expansive covered terrace framed by graceful curved archways and cooled by ceiling fans. This spectacular outdoor living space features a brand-new outdoor kitchen fully equipped for grilling and al fresco dining, leading to the sparkling pool, surrounding patio and yard, creating a seamless setting for summer entertaining and secluded relaxation. A convenient first-floor laundry/mud room right off the 3-car heated garage with epoxy flooring and 2 powder rooms adds everyday ease. Upstairs, the elegantly appointed primary suite offers dual walk-in closets, a dedicated vanity area, and a spa-inspired bath with separate vanities and radiant heated floors. Four well-proportioned additional bedrooms, each with generous closets and either en-suite or adjoining baths, provide comfortable accommodations for family and guests. This level is further enhanced by expansive linen closets, abundant storage, and a dedicated luggage room. The impeccably finished lower-level rivals any private club, featuring a state-of-the-art home theatre, richly paneled billiards and game room, fully outfitted bar, expansive fitness studio, wine cellar, guest suite, and a dedicated woodshop for refined hobbyists or craftsmen. Located in one of Winnetka's most prestigious locations and served by its award-winning schools, this remarkable estate perfectly balances classic sophistication with modern luxury. Combining architectural pedigree, unparalleled amenities, and impeccably landscaped grounds, this is a home to be cherished for generations. Furniture available for sale.

Features & Information

Key Details

  • List Price $4,949,000
  • Property Taxes $29,578
  • Assessments/HOA $2,605
  • Square Feet 13288
  • Year Built 1973
  • Status Active
  • Market Time 7

Rooms

  • Total Rooms 16
  • Number of Bedrooms 5
  • Number of Bathrooms 5.2
  • Primary Bedroom

  • Room Size 16X20
  • Floor Level Second
  • Flooring Carpet
  • Primary Bathroom Full,Double Sink,Whirlpool & Sep Shwr
  • Bedroom 2

  • Room Size 12X16
  • Floor Level Second
  • Flooring Hardwood
  • Bedroom 3

  • Room Size 17X12
  • Floor Level Second
  • Flooring Hardwood
  • Bedroom 4

  • Room Size 13X17
  • Floor Level Second
  • Flooring Hardwood
  • Bedroom 5

  • Room Size 13X12
  • Floor Level Second
  • Flooring Hardwood
  • Bedroom 6

  • Room Size 14X14
  • Floor Level Basement
  • Flooring Carpet
  • Living Room

  • Room Size 17X25
  • Floor Level Main
  • Flooring Hardwood
  • Family Room

  • Room Size 24X17
  • Floor Level Main
  • Flooring Hardwood
  • Dining Room

  • Room Size 19X13
  • Floor Level Main
  • Flooring Marble
  • Kitchen

  • Room Size 21X18
  • Floor Level Main
  • Flooring Stone

Additional Rooms

  • Office

  • Room Size 25X27
  • Floor Level Main
  • Flooring Hardwood
  • Exercise Room

  • Room Size 24X27
  • Floor Level Basement
  • Eating Area

  • Room Size 10X16
  • Floor Level Main
  • Flooring Stone
  • Recreation Room

  • Room Size 26X17
  • Floor Level Basement
  • Flooring Carpet
  • Game Room

  • Room Size 18X21
  • Floor Level Basement
  • Flooring Carpet
  • Foyer

  • Room Size 20X20
  • Floor Level Main
  • Flooring Marble
  • Terrace

  • Room Size 37X12
  • Floor Level Main
  • Flooring Stone
  • Office

  • Room Size 14X13
  • Floor Level Basement
  • Flooring Carpet
  • Laundry

  • Room Size 9X20
  • Floor Level Main
  • Flooring Stone

Interior Features

  • Appliances

  • Appliances Included Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Range Hood
  • Heating & Cooling

  • Heating Type Natural Gas, Forced Air, Zoned
  • Air Conditioning Central Air
  • Fireplace

  • # of Fireplaces 2
  • Type of Fireplace Family Room, Living Room

Exterior Features

  • Building Information

  • Age of Building 51-60 Years
  • Recent Rehab No
  • Parking

  • # of Cars 3

Location

  • County Cook
  • Township New Trier
  • Corporate Limits Unincorporated
  • Directions to Property Locust To North Entrance Of Woodley- 3rd House On The Left.
  • 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 29578.35
  • Tax Year 2023
  • Tax Exemptions Homeowner,Senior
  • Parcel Identification Number 05291030410000
  • Lot Information

  • Lot Size .50-.99 Acre

Listed by Susan Maman 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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