419 Sheridan Rd

Winnetka, IL 60093

$31,250,000
Last Sold Price
7
Beds
13,894 Sq. Ft.
$2,249 / Sq. Ft.
13,894
Sq. Ft.
$2,249
per Sq. Ft.
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Closed 8/29/25
Closed 8/29/25
an aerial view of a house with a swimming pool

Description

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...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.
  1. Listed by Jena Radnay • @properties Christie's International Real Estate
    P: (312)-925-9899 C: (312)-925-9899 jradnay@atproperties.com;jradnay@atproperties.com

Sold By @properties Christie's International Real Estate

Property Details for 419 Sheridan Road

Area
Winnetka
Subdivision
East Winnetka
Township
New Trier
Ownership
Fee Simple
Num Of Garage Spaces
2.0
Num Of Parking Spaces
2.0
Parking Included in Price
Yes
Air Conditioning Type
Central Air
LISTING UPDATED: 09/15/2025 11:20 AM

Property Details for 419 Sheridan Road

StatusClosed
MLS #12134845
Days on Market146
Taxes$392,611 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeDetached Single / 3 Stories
Year Built1928
Lot Size2.30 AC / 100,187 SF
CountyCook County
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Location

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Building Information for 419 Sheridan Road

Stories-Year Built1928Building Size-Lot Size2.30 AC / 100,187 SF

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$190,078 per month

30 year fixed, 6.46% Interest

Principal and Interest

$157,360

Property Taxes

$32,718

HOA Dues

$0

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Property Information for 419 Sheridan Road

General Information
School Information
  • Elementary School District: 36
  • Elementary School: Greeley Elementary School
  • High School District: 203
  • High School: New Trier Twp H.S. Northfield/Wi
  • Middle Or Junior School District: 36
Addtl Parking Information
  • Parking Details: Brick Driveway, Circular Driveway, Side Driveway, Heated Driveway, Garage Door Opener, Heated Garage, On Site, Garage Owned, Attached, Garage
Location and General Information
  • Front Exposure: North, South, East, West, Lake/Water
Taxes and HOA Information
  • Association Fee Frequency: Not Applicable
  • Association Fee Includes: None
  • Master Association Fee: No
  • Master Association Fee Frequency: Not Required
  • Additional Parcels: Yes
Property Information
Interior Features
  • Interior Property Features: Vaulted Ceiling(s), Cathedral Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, High Ceilings, Historic/Period Mlwk, Special Millwork
  • Num Of Rooms: 15
  • Bedrooms Total: 7
  • Bedrooms (Below Grade): 0
  • Door Features: French Doors,Mirrored Closet Door(s),Storm Door(s),Panel Door(s),Pocket Door(s)
  • Window Features: Bay Window(s),Blinds,Display Window(s),Curtains/Drapes,Screens
  • Community Features: Pool, Water Rights, Gated, Street Lights
  • Attic: Finished
  • Bath Amenities: Whirlpool,Separate Shower,Steam Shower,Double Sink
  • Fireplace Features: Wood Burning, Gas Starter
  • Basement Type: Finished, Full
  • Bedrooms Possible: 7
  • Air Conditioning: Central Air
  • Electric: Circuit Breakers, Fuses, 200+ Amp Service
  • Flooring: Hardwood
  • Dining Room: Separate
  • Basement Bathrooms: Yes
  • Fireplace Location: Family Room,Living Room,Master Bedroom,Basement,Other,Den/Library
  • Room Type: Breakfast Room, Foyer, Exercise Room, Library, Play Room, Bedroom 5, Bedroom 6, Bedroom 7
  • Num of Baths: 9.4
Exterior Features
  • Fencing: Fenced
  • Patio And Porch Features: Patio
  • Pool Features: In Ground
  • Type: 3 Stories,Coach House
Utilities / Equipment
  • Sewer: Sewer-Public
  • Water: Lake Michigan, Public
  • Appliances: Oven-Double, Microwave, Dishwasher, Refrigerator, High End Refrigerator, All Stainless Steel Kitchen Appliances, Wine Cooler/Refrigerator, Cooktop, Oven, Humidifier
  • Other Equipment: Security System, Intercom, Fire Sprinklers, Sump Pump, Sprinkler-Lawn, Backup Sump Pump;, Generator, Multiple Water Heaters, Security Cameras
Property/Lot Information
  • Exterior Property Features: Hot Tub, Boat Slip, Outdoor Grill
  • New Construction YN: No
  • Rebuilt: No
  • Rehabilitated: Yes
  • Rehab Year: 2002
  • Built Before 1978: Yes
  • Age: 91-100 Years
  • Type Detached: 3 Stories, Coach House
  • Total Sq Ft: 0
  • Aprox Total Finished Sq Ft: 0
  • Total Finished and Unfin Sq Ft: 0
  • Lot Description: Landscaped Professionally, Mature Trees
  • Lot Size: 2.0-2.99 Acres
  • Lot Size Source: Other
  • Lot Dimensions: 273X435X236X441
  • Other Structures: Gazebo, Pergola, Pool House, RV/Boat Storage, Boat House
  • Waterfront: Yes
  • Disability Access and/or Equipped: No
  • Exterior Building Type: Stone
  • Construction: Stone
  • Roof Type: Slate
  • Foundation Details: Concrete Perimeter
  • General Information: None
  • Living Area Source: Assessor
Property and Assessments
  • Public Document Count: 0
  • Photos Count: 53
  • OpenHouse Count: 0
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
Room Information
Master Bedroom Information
  • Master Bedroom Level: Second
  • Room Type: Master Bedroom
  • Master Bedroom Bath: Full
  • Master Bedroom Dimensions: 23X17
Bedroom #2 Information
  • 2nd Bedroom Level: Second
  • Room Type: Bedroom 2
  • Bedroom #2 Room Dimensions: 19X18
Bedroom #3 Information
  • 3rd Bedroom Level: Second
  • Room Type: Bedroom 3
  • Bedroom #3 Room Dimensions: 17X15
Bedroom #4 Information
  • 4th Bedroom Level: Second
  • Room Type: Bedroom 4
  • Bedroom #4 Room Dimensions: 12X16
Bedroom #5 Information
  • 5th Bedroom Level: Second
  • Room Type: Bedroom 5
  • Bedroom #5 Room Dimensions: 15X16
Bedroom #6 Information
  • 6th Bedroom Level: Third
  • Room Type: Bedroom 6
  • Bedroom #6 Room Dimensions: 14X17
Bedroom #7 Information
  • 7th Bedroom Level: Third
  • Room Type: Bedroom 7
  • Bedroom #7 Room Dimensions: 14X15
Dining Room Information
  • Dining Room Level: Main
  • RoomType_DR: Dining Room
  • Dining Room Dimensions: 23X12
Family Room Information
  • Family Room Level: Main
  • RoomType_FR: Family Room
  • Family Room Dimensions: 29X22
Kitchen Information
  • Kitchen Level: Main
  • RoomType_KT: Kitchen
  • Kitchen Dimensions: 17X15
Laundry Information
  • Laundry Level: Basement
  • Room Type: Laundry
  • Laundry Dimensions: 25X15
Living Room Information
  • Living Room Level: Main
  • Room Type: Living Room
  • Living Room Dimensions: 33X17
Foyer Information
  • Room Level: Main
  • Room Type: Foyer
  • Dimensions: 16X18
Play Room Information
  • Room Level: Third
  • Room Type: Play Room
  • Dimensions: 29X28
Exercise Room Information
  • Room Level: Basement
  • Room Type: Exercise Room
  • Dimensions: 21X25
Bar or Entertainment Room Information
  • Room Level: Main
  • Room Type: Bar/Entertainment
  • Dimensions: 3X10
Breakfast Room Information
  • Room Level: Main
  • Room Type: Breakfast Room
  • Dimensions: 13X15
Library Room Information
  • Room Level: Second
  • Room Type: Library
  • Dimensions: 12X13

Property History for 419 Sheridan Road

DateEvent & SourcePriceAppreciation
Aug 29, 2025

Sold

MRED #12134845

$31,250,000—
DateEvent & SourcePrice
08/29/2025

Sold

MRED #12134845

$31,250,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 419 Sheridan Road

Taxable ValueLand$414,689Additions$515,051Total$929,740
Tax Record2021$240,425 ($20,035 / month)
Home Facts
Beds8Baths6.5Total Finished SqFt13,894 SqFtAbove Grade Finished SqFt13,894 SqFtStories2Lot Size75,398 SqFtStyleSingle Family ResidenceYear Built1929CountyCOOKAPN05-21-202-004Fireplace TypeHas Fireplace

Schools near 419 Sheridan Road

This home is within Winnetka School District 36.
Rating
School
Type
Grades
Distance
Greeley Elementary School
Public - K to 4
The Skokie School
Public - 5 to 6
Carleton W Washburne School
Public - 7 to 8
New Trier Township H S Northfield
Public - 9
Rating
School
Distance
Greeley Elementary School
PublicK to 4

The Skokie School
Public5 to 6

Carleton W Washburne School
Public7 to 8

New Trier Township H S Northfield
Public9

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Based on information from one of the following Multiple Listing Services: Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 09/15/2025 11:20 AM. 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.