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320 Woodley Road, Winnetka, IL 60093 (Sold on )

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 $4,949,000

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  • 5 BedBeds
  • 7 BathBaths
  • 13,000 SqftSqft
  • TypeSingle Family
  • Active
  • MLS# 12698685

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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.


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Property Details 320 Woodley Road, Winnetka, IL, 60093

General

  • MLS#: 12698685
  • Property Type: Single Family
  • List Date: 07/08/2026
  • Year Built: 1973
  • Area: Winnetka
  • Township: New Trier
  • County: Cook
  • Beds: 5
  • Full Bath: 5
  • Half Bath: 2
  • Total Baths: 7

Interior Features

  • Interior Features: Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Workshop
  • Fireplace Features: 2
  • Flooring: Hardwood

Exterior Features

  • Exterior Features: Outdoor Grill

Schools

  • School District: 37
  • High School: New Trier Twp H.S. Northfield/Wi

Structure

  • Style: Georgian
  • Roof: Slate

Size & Lot

  • Sq.Ft.: 13,000

Utilities

  • Cooling: Central Air
  • Sewer: Public Sewer
  • Water: Lake Michigan, Public

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