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!
Property Details
Price:
$3,200,000
MLS #:
MRD12555408
Status:
Active
Beds:
6
Baths:
6
Type:
Single Family
Neighborhood:
winnetka
Listed Date:
Feb 16, 2026
Finished Sq Ft:
7,914
Year Built:
1914
WinnetkaWinnetkaHubbard Woods Elementary SchoolCarleton W Washburne SchoolNew Trier Twp H.s. Northfield/wi
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Schools
School District:
203
Elementary School:
Hubbard Woods Elementary School
Middle School:
Carleton W Washburne School
High School:
New Trier Twp H.S. Northfield/Wi
Interior
Bathrooms
4 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Fireplaces Total
4
Heating
Natural Gas, Forced Air
Exterior
Construction Materials
Brick
Garage Spaces
3
Parking Features
Other, Garage Door Opener, Garage, Yes, Garage Owned, Attached
Parking Spots
3
Parking Total
3
Patio And Porch Features
Patio
Roof
Asphalt
Financial
HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2023
Taxes
$38,431
Map
Community
- Address100 Old Green Bay Road Winnetka IL
- CityWinnetka
- CountyCook
- Zip Code60093
Market Summary
Current real estate data for Single Family in Winnetka as of Jun 14, 2026
41
Single Family Listed
73
Avg DOM
546
Avg $ / SqFt
$3,147,146
Avg List Price
Property Summary
- 100 Old Green Bay Road Winnetka IL is a Single Family for sale in Winnetka, IL, 60093. It is listed for $3,200,000 and features 6 beds, 6 baths, and has approximately 7,914 square feet of living space, and was originally constructed in 1914. The current price per square foot is $404. The average price per square foot for Single Family listings in Winnetka is $546. The average listing price for Single Family in Winnetka is $3,147,146.
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100 Old Green Bay Road
Winnetka, IL


