100 Old Green Bay Road
Winnetka, IL, 60093 $ 3,200,000
Bedrooms6 Baths4.2 Sq 7,914 Monthly Estimate*
$ 19,703
for $3,200,000 with 6 bedrooms and 4 full baths, 2 half baths. This 7,914 square foot home was built in 1914 on a lot size of 0.57.
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!
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FeaturesGeneralLiving Area 7914
Sewer Public Sewer
Heating Natural Gas Forced Air
Cooling Central Air
Possession Negotiable
Roof Asphalt
Garage Spaces 3
Association Fee Includes None
Construction Materials Brick
Year Built 1914
Electric 200+ Amp Service
Township New Trier
Tax Year 2023
Ownership Fee Simple
Assoc Fee Paid Per Not Applicable
County Cook
New Construction N
Property Type Residential Detached Single
Total Rooms 15
Full Baths 4
Status Active
Directions Sheridan Road to Scott Street; west to Old Green Bay then north to 100 Old Green Bay.
High School New Trier Twp H.S. Northfield/Wi
City Winnetka
High School District 203
MLS Area Winnetka
Elementary School Hubbard Woods Elementary School
Tax Annual Amount 38431
Middle/Junior High School Carleton W Washburne School
Additional Parcels Y/N N
Standard Status Active
Middle/Junior School District 36
Elementary School District 36
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InteriorBasement Partially Finished Full
Total Fireplaces 4
Fireplace Features Wood Burning Gas Log Gas Starter
Half Baths 2
Total Bedrooms 6
Room Type Bonus Room Bedroom 5 Bedroom 6 Eating Area Family Room Foyer Mud Room Office Recreation Room Storage Terrace
Total Baths 6
Bedrooms Possible 6
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ExteriorParking Features Other Garage Door Opener Garage Yes Garage Owned Attached
Water Source Lake Michigan
Total Parking 3
Foundation Details Brick/Mortar Concrete Perimeter
Lot Dimensions 24668
Lot Size Acres 0.57
Waterfront Y/N N
Other Equipment Ceiling Fan(s) Sump Pump Sprinkler-Lawn Air Purifier Backup Sump Pump;
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* Excluded FeaturesList Byjoanne.hudson@compass.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $19,703
- Monthly Property Taxes
- $3,203
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Winnetka, IL
Average List Price $2,657,364
Percent of Sale Price 17%
About Winnetka, IL 12,298 Population
-2% Since 2002
$ 182,976 Median Income
45.24 Median Age
46% Households with Children
Trends Information provided by ATTOM Data Solutions.
566463 Elementary School
566222 Middle School
New Trier Twp H.S. Northfield/Wi High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 2/16/2026 | $3,200,000 | | Listed Price |