Auction! $2,300,000 is the suggested opening bid for the online auction. It is not an asking price. There is an unpublished reserve price that is higher. 15 Woodley Road is a rare opportunity to acquire a very special property on one of Winnetka's most highly sought-after streets. This estate has a timeless, quiet elegance you feel from the moment you approach the pillared entrance and pull into the circular driveway. Its idyllic setting includes two plus acres of well-manicured lawns and lush landscaping including English gardens, a myriad of terraces and fountains, and a recently refinished tennis court. Built to last with only the finest craftsmanship, this home has been impeccably maintained by the same family for over four decades. Traditional and yet updated in design, the home's exquisite architectural detail, hand carved millwork and moldings just cannot be found in new construction. A grand two-story foyer sets the scene for the rest of the home which features oak hardwood floors throughout. The flow and expanse of this 6 bedroom, 6.5 bath home is perfect for today's lifestyle with large, gracious rooms for entertaining plus plenty of cozy spaces for smaller gatherings. From the well-appointed living room with impressive crown moldings and gas fireplace to the handsome paneled library/office with adjacent wet bar, this home is ideal for both grand entertaining and comfortable family life. The newer Chef's kitchen has marble countertops, top-of-the-line appliances, and a butler's pantry that leads to a family room with custom, built-in media center and French doors that open onto the main entertaining patio. The spacious second floor boasts wide hallways and two, separate wings. The east wing has an oversized master suite plus two other large ensuite bedrooms, an office (or 7th bedroom) with an ensuite bath, and a laundry room. In the west wing, there are three more bedrooms and two full baths conveniently accessed from the back staircase that leads to the mudroom and kitchen. The finished lower level is ready for fun for the whole family with a recreation room, a billiards room, and a game room with full bar. This timeless classic set on over two acres of private gorgeous grounds is ready for the next lucky owners to make their memories here. Pre-auction offers highly encouraged! This property is expected to sell prior to the online auction.
Single-familyProperty Type
1937Year Built
2.2 acresLot Size
3 car garageParking
Listed by Diana Peterson• AW Properties Global/Auction Works
Listed by Erica Goldman• Jameson Sotheby's International Realty
Bought with Diana Peterson• AW Properties Global/Auction Works
Bought with Erica Goldman• Jameson Sotheby's International Realty
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
7
Baths
6
Stories
2
Lot width
—
Lot depth
—
Lot size
2.2 Acres
Year renovated
—
Sq. Ft.
6,057
Year built
1937
Style
Single Family Residential
County
Cook County
APN
05291010150000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 16, 2026.
R3
Single-Family Residence District
The R-3 Single-Family Residence District is intended to provide a semi-urban environment of single-family homes on relatively large lots. This district creates for lot sizes adequate to accommodate individual wells and sewage disposal systems. Schools, recreation and social facilities, religious facilities and public facilities which serve the residents living in the district are allowed. All commercial activities are prohibited, except for selected recreation and sanitary uses.
Permitted uses
Include but are not limited to:
Greenhouse / nursery
Religious facility
Housing-Group
Housing-Single unit
Educational/school
Library
Museum / gallery
Golf related
Cemetery
Park & open space
Property details
Parking
Parking Information
# Of Cars: 3
# of Garage Spaces: 3
Parking: Garage
Garage Ownership: Owned
Garage On-Site: Yes
Garage Type: Attached
Garage Details: Garage Door Opener(s),Transmitter(s),Heated,7 Foot or more high garage door
Driveway: Asphalt,Circular,Side Drive
Interior
Virtual Tour
Additional Media Type 1: Video
Bathroom Information
# of Baths (Full): 6
# of Baths (1/2): 2
Bath Amenities: Separate Shower,Double Sink,Bidet,Soaking Tub