The PINNACLE of lake living on the North Shore ...there is nothing more majestic than 445 Sheridan. Magically set on the premier in-town "Sheridan to Shore" block in Winnekta, this Spanish influenced Villa proves that land & location have only gotten more valuable with time. Behind the scrolled wrought iron gate entrance, a magnificent rare gem sits on over 2.2 acres, as there are only a handful of lakefront lots over 2 acres, with a breathtaking sandy beach that historically has remained large, stretching over 165 feet. Incredible manicured resort level grounds accented with a full 2 story cabana house by notable architect Paul Konstant with elevator, custom bar w/ mahogany coffered wood ceilings, 2 full kitchens and 2 beds/ 2 baths. Be prepared to be taken away by the hotel-level pool experience with the sound of the fountain in the background allowing for the most peaceful & tranquil setting. Built in 1912, the main house is glorious and reminiscent of the time where entertaining on Lake Michigan was a true way of life. Grand foyer entrance that allows the perfect postcard view of the lake with a double atrium staircase accented with braided columns, matching arched casings, and fireplace. Served once as the reception hallway, this is one of the best rooms in the house with the sunrises and lake breezes through the screened-in french doors that lead to the cocktail patio. Terrace steps down to the exquisite table land which leads to a flat, full length patio from north to south perched above the beach. This is the most captivating place on the entire property with a flash of not believing this is really Lake Michigan. Short way down from patio to the beach making this property the ideal place to bring a whole new level of entertainment to fruition. Almost all rooms on the 3 floors face the water allowing for incredible natural light from the lake reflections. Formal spaces on 1st floor set up for how parties used to flow. Grand living room with imperial ceiling details, 10 foot ceilings, curved corners with display areas leads to informal family room with panoramic views. Enchanting dining room with intricate hand molded ceiling, 5 chandeliers and separate solarium breakfast area allowing dining to informal to formal. Separate kitchen, walk in pantry, office space is the ideal place to take this new home to 2022 standards. 2nd floor just rehabbed with primary master suite side with sitting room, w-i-c, spa bath and bed with 180 degree views of lake. 3 additional beds with new quartz baths. 3rd floor was the formal ballroom with exquisite lake views, ripe for all new living space. Elevator to all 4 floors. Lower level hides one of the best speakeasy bars out of a Hollywood movie set. If these walls could only talk, the stories would write a book with a custom bar, built-in lounging booths couches, custom plastered mosaic ceiling with hand painted & mirrored tiles. Huge rec room with billiards area, sauna and full bath. 445 Sheridan brings endless opportunities for those that see the value in what this estate is... the pinnacle of lakefront living, once owned by notable Chicagoian W. Clement Stone and now ready for the next new chapter of success and beauty.
Single-familyProperty Type
1918Year Built
2.22 acresLot Size
$2,425Est. Price/Sq.Ft.
2 garage spacesParking
Listed by Jena Radnay• @properties Christie's International Real Estate
Bought with Jena Radnay• @properties Christie's International Real Estate
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
4
Baths
5.5
Stories
2
Lot width
—
Lot depth
—
Lot size
2.22 Acres
Year renovated
—
Sq. Ft.
8,609
Year built
1911
Style
Single Family Residential
County
Cook County
APN
05212020010000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 16, 2026.
R2
Single-Family Residential District
The requirements set forth in this chapter, together with other provisions set forth in the Building Code of the Village, have been adopted in order to provide for a single-family residential environment of relatively small estate character, where the degree of improvements upon an individual parcel of land is generally subordinate to the landscape. Due to the mature character of development within this district, such requirements are also intended to assure that future modifications to existing structures, or the replacement of existing structures with new structures, will not alter the scale and general character of established neighborhoods. In this regard, the requirements set forth in this chapter are further intended to foster development which is compatible, in general, with the character of existing single-family development within the immediate neighborhood with respect to external architectural scale, landscaping and other site improvements.
Permitted uses
Include but are not limited to:
Housing-Single unit
Property details
Parking
Parking Information
# of Garage Spaces: 2
# of Parking (Total): 8
Parking Features: Asphalt, Circular Driveway, Garage Door Opener, Garage Owned, Detached, Driveway, Electric Gate, Owned, Garage