$4,949,000

320 Woodley Road, Winnetka, IL 60093

Active
5 beds (6 possible) 5.5 baths 13,000 sqft (estimated) Built 1973 Residential MLS #MRD12698685 7 days on market
Listing courtesy of @properties Christie's International Real Estate · 847-881-0200 · MLS #MRD12698685 · Status: Active
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.

Property details

Interior

Appliances
Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Range Hood
Interior features
Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, Special Millwork, Separate Dining Room, Workshop
Flooring
Hardwood
Fireplaces
2
Fireplace details
Gas Log, Gas Starter
Basement
Finished, Full
Laundry
Main Level, Gas Dryer Hookup, Sink
Additional rooms
Office, Bedroom 5, Bedroom 6, Exercise Room, Eating Area, Recreation Room, Game Room, Foyer, Terrace
Total rooms
16

Building & exterior

Style
Georgian
Age
51-60 Years
Exterior
Brick
Exterior features
Outdoor Grill
Roof
Slate
Foundation
Concrete Perimeter
Windows
Screens, Drapes
Patio & porch
Patio, Porch

Parking

Garage spaces
3
Total spaces
3
Parking details
Asphalt, Circular Driveway, Garage Door Opener, Heated Garage, Yes, Garage Owned, Attached, Garage

Lot & location

Lot dimensions
394x193x275
Lot description
Landscaped, Mature Trees
Township
New Trier
County
Cook

Utilities

Heating
Natural Gas, Forced Air, Zoned
Cooling
Central Air
Water
Lake Michigan, Public
Sewer
Public Sewer

HOA & community

Assessment
$2,605 / annually
Assessment includes
None

Schools

Elementary
(37)
Junior high
(37)
High school
New Trier Twp H.S. Northfield/Wi (203)

Taxes & terms

Annual taxes
$29,578 (2023)
Parcel number (PIN)
05291030410000
PIN
05291030410000
Ownership
Fee Simple
Possession
Closing
Special conditions
List Broker Must Accompany
Listed
7/8/2026

Rooms

RoomSizeLevelFlooring
Office25X27MainHardwood
Bedroom 513X12SecondHardwood
Bedroom 614X14BasementCarpet
Exercise Room24X27Basement
Eating Area10X16MainStone
Recreation Room26X17BasementCarpet
Game Room18X21BasementCarpet
Foyer20X20MainMarble
Terrace37X12MainStone
Office14X13BasementCarpet
Bedroom 212X16SecondHardwood
Bedroom 317X12SecondHardwood
Bedroom 413X17SecondHardwood
Dining Room19X13MainMarble
Family Room24X17MainHardwood
Kitchen21X18MainStone
Laundry9X20MainStone
Living Room17X25MainHardwood
Master Bedroom16X20SecondCarpet

What would this home cost per month?

Using this listing's actual tax bill (2023) and actual HOA assessment — adjust anything.

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

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