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$31,250,000 SOLD Aug 2025
Listed at $35,000,000

419 Sheridan Road, Winnetka, IL 60093

Closed
7 beds 9.5 baths 13,894 sqft (assessor) Built 1928 Residential MLS #MRD12134845 146 days on market
Listing courtesy of @properties Christie's International Real Estate · 847-881-0200 · MLS #MRD12134845 · Status: Closed
Defining a league of its own, this is the chance of a lifetime to own the most iconic lakefront estate in IL. The "Windsor House" has been elevated to a new grandeur of living with a best in class collaboration lead by nationally recognized interior design, landscape architects & coastal engineering teams. Gloriously expanded to 2.3 acres with the purchase of 429 Sheridan transformed into a commercial level botanical garden with a Lannon stone custom fountain, manicured hedges & grassy lawn, heated motor court for 10 cars, & meticulously engineered nailess pergola overlooking the infinity pool area with panoramic lake views. The only home on the entire shoreline that is reminiscent of 5-star boutique level European hotel delivering a true vacation living experiences 365 days a year. This French inspired 22 room masterpiece by Mayo & Mayo now sits on 223 feet of private beachfront outfitted with the state-of-the-art double door boathouse & commercial level boardwalk, an edgeless pool /spa set, luxe hotel level changing rooms built into the bluff all on organic award-winning landscaped grounds by Mariani. Get ready to be swept away by the sheer magnificence of the magically revived Windsor House with rooms designed for the finest home entertainment, 7 beds, 9.4 baths, flawless restored details by the finest craftsman including 150 new storm windows, state of the art lighting & security systems and a 2-bedroom separate coachouse for additional living quarters. There is nothing even remotely comparable to this estate and centrally located in premier Winnetka location in the most beautiful neighborhood within walking distance to New Trier, Greeley Elementary, town and train. Let the myself unveil behind the wrought iron gated entrance with layers of purposeful landscaping hiding the beauty of this majestic home. Step inside and prepare to be blown away! A Website will be added shortly with Floor Plans & all Estate Details. House can be purchased furnished. Ask Jena for all details.

Property details

Interior

Appliances
Double Oven, Microwave, Dishwasher, Refrigerator, High End Refrigerator, Stainless Steel Appliance(s), Wine Refrigerator, Cooktop, Oven, Humidifier
Interior features
Vaulted Ceiling(s), Cathedral Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, High Ceilings, Historic/Period Mlwk, Special Millwork
Flooring
Hardwood
Fireplaces
7
Fireplace details
Wood Burning, Gas Starter
Basement
Finished, Full
Laundry
Gas Dryer Hookup, Electric Dryer Hookup, In Unit, Laundry Chute, Multiple Locations, Sink
Additional rooms
Breakfast Room, Foyer, Exercise Room, Library, Play Room, Bedroom 5, Bedroom 6, Bedroom 7
Total rooms
15

Building & exterior

Style
French Provincial
Age
91-100 Years
Exterior
Stone
Exterior features
Hot Tub, Boat Slip, Outdoor Grill
Roof
Slate
Foundation
Concrete Perimeter
Windows
Screens, Drapes
Patio & porch
Patio
Other structures
Gazebo, Pergola, Pool House, RV/Boat Storage, Boat House
Exposure
North,South,East,West,Lake/Water

Parking

Garage spaces
2
Total spaces
2
Parking details
Brick Driveway, Circular Driveway, Side Driveway, Heated Driveway, Garage Door Opener, Heated Garage, On Site, Garage Owned, Attached, Garage

Lot & location

Lot dimensions
273X435X236X441
Lot description
Landscaped, Mature Trees
Township
New Trier
County
Cook
Waterfront
Yes

Utilities

Heating
Natural Gas, Forced Air, Radiant Floor
Cooling
Central Air
Water
Lake Michigan, Public
Sewer
Public Sewer
Electricity
Circuit Breakers, Fuses, 200+ Amp Service
Equipment
Security System, Intercom, Fire Sprinklers, Sump Pump, Sprinkler-Lawn, Backup Sump Pump;, Generator, Multiple Water Heaters, Security Cameras

HOA & community

Assessment includes
None
Community features
Pool, Water Rights, Gated, Street Lights

Schools

Elementary
Greeley Elementary School (36)
Junior high
(36)
High school
New Trier Twp H.S. Northfield/Wi (203)

Taxes & terms

Annual taxes
$392,610 (2023)
Parcel number (PIN)
05212020040000
PIN
05212020040000
Ownership
Fee Simple
Possession
Closing
Special conditions
None
Listed
8/31/2024
Sold
8/29/2025
Sold price
$31,250,000
Want to see this home?

The Dawn Simmons Team (RE/MAX Suburban) can show you any listed property and give you a straight answer on what it's really worth. Call/text Josh at (224) 628-4013.

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