Your Ultimate Guide to Real Estate on Chicago's North Shore

The North Shore’s 10 Most Expensive Properties

Zillow just published its annual “10 Most Expensive Homes for Sale” list so I thought it would be fun to do my own list of the 10 most expensive homes for sale on Chicago’s North Shore. While we can’t compete with the Spelling mansion, which, at a jaw-dropping $150,000,000, holds the top honors on Zillow’s list, we do have some pretty impressive properties right here in our own backyard.

The homes that are currently on the North Shore “top ten” list range in price from $7,900,000 to $28,000,000. One is in Evanston, two are in Winnetka, two are in Highland Park and five are in Lake Forest. Seven of them are lake front properties and all but three were built before 1930. And, assuming you can afford the price tag to buy one of these beauties, be prepared to cough up another $30,000-132,000 a year in property taxes.

68 Locust Rd, Winnetka, IL

1. Modern Chateau
Location: Winnetka
For Sale: $28,000,000

I watched this one go up and it took over two years to build. Designed by Richard Landry, this French chateau style mansion is situated on two acres inside a walled enclave. It’s not on the lake but it has pretty much everything else you could want including 26 rooms, a 9-car garage, pool and exquisite finishes throughout. Architect Richard Landry is known as “Architect to the Stars” and also designed the homes of Rod Stewart, Wayne Gretzky, Tom Brady, and Eddie Murphy, among others.

405 N. Mayflower, Lake Forest, IL

2. The Schweppe Estate
Location: Lake Forest
For Sale: $15,000,000

This gorgeous 27 room manor was built in 1917 and completely restored in the 1980’s by 70 craftsmen from around the U.S. and Europe. The estate’s claim to fame is that it once hosted the Duke and Duchess of Windsor and the heirs to the crown of Sweden.


3.”Little Orchard”
Location: Lake Forest
For Sale: $11,500,000

This 5.4 acre lakefront estate was designed by Howard Van Doren Shaw and built in 1927. It has beautiful gardens and grounds and claims to have the best beach in Lake Forest.

1345 N. Lake Rd4. Mediterranean Classic
Location: Lake Forest
For Sale: $9,990,000

This 20 room home was designed by Howard Van Doren Shaw for Donald McLennan, President of Marsh and McLennan.  Originally built in 1908, it has been renovated and restored. Situated on 3 acres of lake front it has 11,000 square feet of living space and a $134,189 tax bill!

609 Sheridanfront

5. Private Resort
Location: Winnetka
For Sale: $9,000,000

Live in your own private resort with breathtaking lake views, tennis court, swimming pool, boat house and 609Sheridanpoollakeapproximately 150 feet of sandy beach.

1141SheridanRd6. Lakeside Villa
Location: Highland Park
For Sale: $8,750,000

Built in 2006, this sophisticated villa is perched on 2.7 acres of lakefront property and has 272 feet of shoreline. The home has lake views from virtually every one of its 15 rooms. Other features include a 60 foot indoor pool, elevator, tram to beach and four car garage.

1700MeadowLane7. Traditional Elegance
Location: Highland Park
For Sale: $8,500,000

This 13 room private retreat has no waterfront but sits on 8 fabulous acres of land, complete with formal gardens, orchard, coach house.


8. English Manor House
Location: Lake Forest
For Sale: $8,499,000

This 2.4 acre estate was built in 1911 and has been completely restored and renovated by Lake Forest Landmark Development. It has 18 rooms, a Christopher Peacock kitchen, mahogany paneled library, 9 fireplaces and a 4-car heated garage.


9. Tuscan Villa
Location: Lake Forest
For Sale: $7,990,000

This lakefront home with spectacular gardens was designed by David Adler and built in 1917. With almost 3 acres, this home has 14,000 square feet of living space and 21 rooms.


10. Lake Front Paradise
Location: Evanston
For Sale: $7,900,000

This 22 room house was built in 2008 and has all the bells and whistles, including a 70 foot wide sandy beach and a guest casita.

If you’d like me to help you find your own little piece of paradise, please give me a call at 847-687-5957 or send me an email. I’d love to help you.

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  1. North Shore Chicago's Priciest Homes | North Shore Views

    […] September I wrote about the ten most expensive homes for sale on the North Shore of Chicago. Since almost a year has passed, I thought it was time to update the […]

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