$3,200,000
6
beds
4
baths
2
half baths
7,914
square ft

100 Old Green Bay Road
Winnetka, Illinois 60093

New / MLS #12555408 / Single Family / Winnetka
Listing information updated 2/20/2026 at 10:23am
Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside the impressive front hall and discover a flowing first floor anchored by a gracious living room, elegant dining room with butler's pantry and a stunning custom kitchen. Here, custom cabinetry, a large island with seating for four, double dishwashers, dual SubZero refrigerators with freezer drawers, and double ovens (and a steam oven) create a true chef's haven. A sun-filled breakfast room with bay window frames serene views of the west terrace and lush lawn, while the adjacent family room with fireplace and grand scale opens to the grilling and dining terrace, making entertaining seamless. Additional first-floor highlights include a music room with fireplace, versatile sunporch/office with French doors to the terrace, two powder rooms, and a generous mudroom connecting to the three-car attached garage with a huge walk-up attic above. The second floor offers a luxurious primary suite, complete with a private sitting room with fireplace, large bath, and generous walk-in closet. Three additional bedrooms, an updated hall bath, and a convenient laundry room complete the second level. On the third floor, a light-filled getaway offers two more bedrooms, a hall bath, and a spacious bonus room perfect for play, work, or retreat. The fully renovated (and excavated) lower level is designed for fun and relaxation, featuring a media/recreation room, large playroom, entertaining bar, sauna, and full bath. With abundant storage across all four floors-including oversized attic and basement storage rooms - this home blends charm with true functionality. Outdoors, the expansive property lives like a private park, with terraces which are ideal for alfresco dining, summer gatherings, and quiet evenings surrounded by nature. All of this in an ideal 10+ location!

See it in person

Open House

12:00pm - 2:00pm 2/22/26

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Listing Office: Compass

Listing Office Phone: 847.446.9600

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 2/20/2026 at 10:23am. 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. Some listings have been excluded from this website.


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100 Old Green Bay Road, Winnetka, IL 60093 is a single family home currently listed at $3,200,000. 100 Old Green Bay Road features 6 Beds, 4 Baths, 2 Half Baths. This single family home has been listed on @properties Christie's International Real Estate since February 16th, 2026 and was built in 1914. Nearby schools include Hubbard Woods Elementary School, Carleton W Washburne School, and New Trier Twp H.s. Northfield/Wi. The nearest transit stops include Hubbard Woods Metra Metra Union Pacific North line.