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  • $31,250,000

    419 Sheridan Rd, Winnetka, IL 60093

    7beds
    13,894sqft
    Single Family Residence
    Built in 1928
    2.3 Acres Lot
    $-- Zestimate®
    $2,249/sqft
    $10,014 Estimated rent

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    $216,764/mo

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    What's special

    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.

    Zillow last checked: 7 hours ago

    Listing updated: September 15, 2025 at 09:20am

    Listing courtesy of:

    Jena Radnay 312-925-9899,

    @properties Christie's International Real Estate

    Bought with:

    Jena Radnay

    @properties Christie's International Real Estate

    Source: MRED as distributed by MLS GRID,MLS#: 12134845MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 7
    • Bathrooms: 13
    • Full bathrooms: 9
    • 1/2 bathrooms: 4
    Primary bedroom
    • Features: Flooring (Hardwood), Window Treatments (Blinds, Curtains/Drapes), Bathroom (Full)
    • Level: Second
    • Area: 391 Square Feet
    • Dimensions: 23X17
    Bedroom 2
    • Features: Flooring (Hardwood), Window Treatments (Blinds)
    • Level: Second
    • Area: 342 Square Feet
    • Dimensions: 19X18
    Bedroom 3
    • Features: Flooring (Hardwood), Window Treatments (Blinds)
    • Level: Second
    • Area: 255 Square Feet
    • Dimensions: 17X15
    Bedroom 4
    • Features: Flooring (Hardwood), Window Treatments (Blinds)
    • Level: Second
    • Area: 192 Square Feet
    • Dimensions: 12X16
    Bedroom 5
    • Features: Flooring (Hardwood)
    • Level: Second
    • Area: 240 Square Feet
    • Dimensions: 15X16
    Bedroom 6
    • Features: Flooring (Hardwood)
    • Level: Third
    • Area: 238 Square Feet
    • Dimensions: 14X17
    Other
    • Features: Flooring (Hardwood)
    • Level: Third
    • Area: 210 Square Feet
    • Dimensions: 14X15
    Bar entertainment
    • Features: Flooring (Other)
    • Level: Main
    • Area: 30 Square Feet
    • Dimensions: 3X10
    Breakfast room
    • Features: Flooring (Hardwood), Window Treatments (Screens)
    • Level: Main
    • Area: 195 Square Feet
    • Dimensions: 13X15
    Dining room
    • Features: Flooring (Hardwood), Window Treatments (Display Window(s))
    • Level: Main
    • Area: 276 Square Feet
    • Dimensions: 23X12
    Exercise room
    • Features: Flooring (Other)
    • Level: Basement
    • Area: 525 Square Feet
    • Dimensions: 21X25
    Family room
    • Features: Flooring (Hardwood)
    • Level: Main
    • Area: 638 Square Feet
    • Dimensions: 29X22
    Foyer
    • Features: Flooring (Marble)
    • Level: Main
    • Area: 288 Square Feet
    • Dimensions: 16X18
    Kitchen
    • Features: Kitchen (Island, Pantry-Butler, Pantry-Closet, Breakfast Room, Custom Cabinetry, Updated Kitchen), Flooring (Hardwood), Window Treatments (Curtains/Drapes)
    • Level: Main
    • Area: 255 Square Feet
    • Dimensions: 17X15
    Laundry
    • Features: Flooring (Other)
    • Level: Basement
    • Area: 375 Square Feet
    • Dimensions: 25X15
    Library
    • Features: Flooring (Hardwood), Window Treatments (Display Window(s))
    • Level: Second
    • Area: 156 Square Feet
    • Dimensions: 12X13
    Living room
    • Features: Flooring (Hardwood), Window Treatments (Bay Window(s), Curtains/Drapes)
    • Level: Main
    • Area: 561 Square Feet
    • Dimensions: 33X17
    Play room
    • Features: Flooring (Hardwood)
    • Level: Third
    • Area: 812 Square Feet
    • Dimensions: 29X28
    Heating
    • Natural Gas, Forced Air, Radiant Floor
    Cooling
    • Central Air
    Appliances
    • Included: Double Oven, Microwave, Dishwasher, Refrigerator, High End Refrigerator, Stainless Steel Appliance(s), Wine Refrigerator, Cooktop, Oven, Humidifier, Multiple Water Heaters
    • Laundry: Gas Dryer Hookup, Electric Dryer Hookup, In Unit, Laundry Chute, Multiple Locations, Sink
    Features
    • Vaulted Ceiling(s), Cathedral Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, High Ceilings, Historic/Period Mlwk, Special Millwork
    • Flooring: Hardwood
    • Doors: French Doors, Mirrored Closet Door(s), Storm Door(s), Panel Door(s), Pocket Door(s)
    • Windows: Bay Window(s), Blinds, Display Window(s), Curtains/Drapes, Screens, Screens, Drapes
    • Basement: Finished,Full
    • Attic: Finished
    • Number of fireplaces: 7
    • Fireplace features: Wood Burning, Gas Starter, Family Room, Living Room, Master Bedroom, Basement, Other, Den/Library
    Interior area
    • Total structure area: 0
    • Total interior livable area: 13,894 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Brick Driveway, Circular Driveway, Side Driveway, Heated Driveway, Garage Door Opener, Heated Garage, On Site, Garage Owned, Attached, Garage
    • Attached garage spaces: 2
    • Has uncovered spaces: Yes
    Accessibility
    • Accessibility features: No Disability Access
    Features
    • Stories: 3
    • Patio & porch: Patio
    • Exterior features: Boat Slip, Outdoor Grill
    • Pool features: In Ground
    • Has spa: Yes
    • Spa features: Outdoor Hot Tub
    • Fencing: Fenced
    • Has view: Yes
    • View description: Water, Back of Property
    • Water view: Water,Back of Property
    • Waterfront features: Beach Access, Lake Front
    Lot
    • Size: 2.30 Acres
    • Dimensions: 273X435X236X441
    • Features: Landscaped, Mature Trees
    Details
    • Additional structures: Gazebo, Pergola, Pool House, RV/Boat Storage, Boat House
    • Additional parcels included: 05212020030000
    • Parcel number: 05212020040000
    • Special conditions: None
    • Other equipment: Intercom, Sump Pump, Sprinkler-Lawn, Backup Sump Pump;, Generator

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: French Provincial
    • Property subtype: Single Family Residence
    Materials
    • Stone
    • Foundation: Concrete Perimeter
    • Roof: Slate
    Condition
    • New construction: No
    • Year built: 1928
    • Major remodel year: 2002
    Details
    • Builder model: FRENCH

    Utilities & green energy

    • Electric: Circuit Breakers, Fuses, 200+ Amp Service
    • Sewer: Public Sewer
    • Water: Lake Michigan, Public

    Community & neighborhood

    Security
    • Security features: Security System, Fire Sprinkler System, Closed Circuit Camera(s)
    Community
    • Community features: Pool, Water Rights, Gated, Street Lights
    Location
    • Region: Winnetka
    • Subdivision: East Winnetka

    HOA & financial

    HOA
    • Services included: None

    Other

    Other facts
    • Has irrigation water rights: Yes
    • Listing terms: Conventional
    • Ownership: Fee Simple
    Services availability