Chicago Real Estate News & Neighborhood Notes

One of Winnetka’s most beautiful lakefront estates hit the market earlier this year and has now officially sold and closed for $6.3 million.

Edgar Jannotta, chairman emeritus of investment bank William Blair, first listed the blufftop home in January, asking $6.25 million. Built in 1955, the stunning estate features 4 bedrooms. 3,400 square feet, and a charming Cape Cod architectural style with red brick, white trim, and and shingled roof.

Behind the home is a fabulous lawn with sprawling views of Lake Michigan and a winding stairway down the bluff that leads to a private beach.

Records indicate Jannottas paid just over $3.2 million for the property back in 2000, and the new buyer closed on the home on March 1st of this year for over-asking.

Looking for a stunning suburban home? See what luxury estates are currently on the market in Winnetka below...

Search Luxury Winnetka Homes For Sale, Over $1,000,000

• All Listings
• Over $1,000,000

Show Map

Save Search

Sort by:

Price, high to low

$29,900,000

319 Sheridan Road, Winnetka

7 Beds 11 Baths 20,000 SqFt Residential MLS® # 12680920

$16,900,000

915 Sunset Road, Winnetka

6 Beds 9 Baths 15,000 SqFt Residential MLS® # 12600188

New

$3,999,000

1128 Mt. Pleasant Road, Winnetka

5 Beds 7.5 Baths 6,950 SqFt Residential MLS® # 12774096

New

$2,800,000

64 Locust Road, Winnetka

4 Beds 4 Baths 7,500 SqFt Residential MLS® # 12760634

New

$2,749,900

438 Birch Street, Winnetka

4 Beds 4.5 Baths 5,000 SqFt Residential MLS® # 12433803

New

$2,699,900

252 Myrtle Street, Winnetka

4 Beds 5 Baths 5,243 SqFt Residential MLS® # 12767250

$2,699,000

↓ $86,000

82 Woodley Road, Winnetka

6 Beds 5.5 Baths 0 SqFt Residential MLS® # 12680099

Open House

$2,595,000

↓ $80,000

73 Locust Road, Winnetka

5 Beds 5.5 Baths 4,089 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 1pm - 3pm

MLS® # 12688601

$2,569,900

62 Woodley Road, Winnetka

6 Beds 5 Baths 7,000 SqFt Residential MLS® # 12637769

$2,499,000

1192 Chatfield Road, Winnetka

3 Beds 4.5 Baths 3,610 SqFt Residential MLS® # 12732091

$2,250,000

42 Woodley Road, Winnetka

4 Beds 4.5 Baths 4,225 SqFt Residential MLS® # 12673083

Open House

$1,999,000

1288 Sunview Lane, Winnetka

5 Beds 4 Baths 3,914 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 1am - 2:30pm

MLS® # 12755931

$1,725,000

555 Cherry Street, Winnetka

5 Beds 4.5 Baths 6,580 SqFt Residential MLS® # 12711173

$1,400,000

874 Boal Parkway, Winnetka

5 Beds 4.5 Baths 0 SqFt Residential MLS® # 12736036

New

$1,100,000

592 Provident Avenue, Winnetka

4 Beds 1.5 Baths 2,308 SqFt Residential MLS® # 12746221