Winnetka
Winnetka, a charming village in Cook County, Illinois, just 16 miles north of downtown Chicago, on the shore of Lake Michigan. Winnetka has around 12,475 friendly folks calling it home. Established in 1904, the Winnetka Park District is the fourth oldest park district in Illinois, maintaining 27 parks, five beaches, and various facilities for golf, ice skating/hockey, paddle, pickleball, and tennis. It is a fabulous community for active people of all ages. With three Metra stations—Hubbard Woods, Winnetka, and Indian Hill—commuting to Chicago is incredibly convenient.
Winnetka hosts many community events that have been continuing for generations. The Winnetka Children’s Fair, set to celebrate its 78th anniversary in June 2024, is a delightful 2-day affair on the Village Green, marking the unofficial start of summer and the end of the school year with rides, games, and a strong sense of community. The Village Green also holds a plaque dedicated to Martin Luther King, Jr., who spoke in Winnetka in 1965, an event that led to the establishment of the non-profit organization Open Communities. Additionally, the annual July 4th parade draws people from surrounding areas to enjoy the hometown parade, featuring marching bands, floats, and local participants.
Meg + Katie’s Very Best Winnetka Adventures:
The Winnetka Music Festival: Now in its 5th year, this 2 day event attracts music lovers from far and wide with bands on several stages, food trucks, and beer tents. Headlining in June 2024 are the bands Milky Chance and Band of Horses, alongside many indie and local acts. It’s definitely a highlight for the community and feels like a block party with friends from near and far!
Hubbard Woods First Friday Art Walk: Experience different art displays, design and new product introductions at participating merchants along Green Bay Road between Tower Road and Scott. Doors are open late, and there is a festive feel as neighbors enjoy art, food and music near Hubbard Woods Park.
Family Campout at Tower Beach: Families will stay overnight at Tower Road Beach on a summer July night. After dark a movie is shown and a campfire will be lit. In the morning, breakfast will be served! Fun for the whole family!
Fun Fact!! The exterior of 671 Lincoln Avenue was featured in the iconic Home Alone movies and remains a popular tourist attraction.
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32 Woodley Road Winnetka, IL 60093
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$4,950,000
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Beds 5 Baths 4 | 3 SqFt 9,908 Property Type House
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VIRTUAL TOUR
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$29,900,000
8 8 Beds
9 | 4 9 | 4 Baths
20,000 SqFt 20,000 SqFt
12680920 Listing No. 12680920
House Property Type: House
VIRTUAL TOUR
(81)
Listing courtesy of @properties Christie's International Real Estate
(14)
$16,900,000
6 6 Beds
8 | 2 8 | 2 Baths
15,000 SqFt 15,000 SqFt
12600188 Listing No. 12600188
House Property Type: House
(14)
Listing courtesy of Village Realty Group Inc
VIRTUAL TOUR
(67)
$7,999,900
6 6 Beds
7 | 2 7 | 2 Baths
10,588 SqFt 10,588 SqFt
12661112 Listing No. 12661112
House Property Type: House
VIRTUAL TOUR
(67)
Listing courtesy of @properties Christie's International Real Estate
VIRTUAL TOUR
(53)
$5,149,000
6 6 Beds
5 | 2 5 | 2 Baths
13,000 SqFt 13,000 SqFt
12465682 Listing No. 12465682
House Property Type: House
VIRTUAL TOUR
(53)
Listing courtesy of @properties Christie's International Real Estate
(50)
$4,999,900
6 6 Beds
4 | 2 4 | 2 Baths
4,159 SqFt 4,159 SqFt
12660037 Listing No. 12660037
House Property Type: House
(50)
Listing courtesy of @properties Christie's International Real Estate
VIRTUAL TOUR
(61)
$4,995,000
6 6 Beds
6 | 3 6 | 3 Baths
7,480 SqFt 7,480 SqFt
12657418 Listing No. 12657418
House Property Type: House
VIRTUAL TOUR
(61)
Listing courtesy of @properties Christie's International Real Estate
(56)
$4,950,000
5 5 Beds
4 | 3 4 | 3 Baths
9,908 SqFt 9,908 SqFt
12283033 Listing No. 12283033
House Property Type: House
(56)
Listing courtesy of @properties Christie's International Real Estate
VIRTUAL TOUR
(43)
$4,200,000
6 6 Beds
6 | 3 6 | 3 Baths
6,950 SqFt 6,950 SqFt
12606067 Listing No. 12606067
House Property Type: House
VIRTUAL TOUR
(43)
Listing courtesy of @properties Christie's International Real Estate
(84)
$3,850,000
7 7 Beds
5 | 1 5 | 1 Baths
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12680669 Listing No. 12680669
House Property Type: House
(84)
Listing courtesy of Jameson Sotheby's International Realty
(38)
$3,495,000
6 6 Beds
7 | 1 7 | 1 Baths
8,303 SqFt 8,303 SqFt
12660928 Listing No. 12660928
House Property Type: House
(38)
Listing courtesy of Coldwell Banker Realty
(71)
$3,200,000
6 6 Beds
4 | 2 4 | 2 Baths
7,914 SqFt 7,914 SqFt
12555408 Listing No. 12555408
House Property Type: House
(71)
Listing courtesy of Compass
(26)
$3,200,000
5 5 Beds
4 | 1 4 | 1 Baths
3,683 SqFt 3,683 SqFt
12682485 Listing No. 12682485
House Property Type: House
(26)
Listing courtesy of @properties Christie's International Real Estate
Open House: Jun 20, 2026, 12:00 PM - 3:00 PM
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