Cool Property

10 Lakefront Homes on the North Shore

Location, location, location. These lakefront homes have it — and then some.

Chicago’s north shore is the place to find some of the city’s most desirable suburbs, like Winnetka, Glencoe, Highland Park and Lake Forest. Given its proximity to the lake, these north side communities have beautiful (and often pricey) homes nestled along Lake Michigan. We’ve rounded up 10 of the best lakefront homes currently for sale, according to our team at Preview Chicago.


Top 10 Lakefront Homes on Chicago’s North Shore:


70 Harbor St. (Glencoe)

CONTACT: Susan J. Maman (@properties)

LIST PRICE: $5,990,000


12 Cliff Rd (Highland Park) 

CONTACT: Beth Wexler (@properties)

LIST PRICE: $4,600,000


1215 Whitebridge Hill Rd (Winnetka)

CONTACT: Chaz Walters (Hot Property)

LIST PRICE: $9,750,000


67 Laurel Ave (Highland Park)

CONTACT: Michael Lafido (Conlon)

LIST PRICE: $5,772,000


735 Sheridan Rd (Winnetka)

CONTACT: Jena Radnay (@properties)

LIST PRICE: $12,900,000


480 Oak St (Winnetka)

CONTACT: Scott Newman (Newman Realty)

LIST PRICE: $6,250,000


2445 Woodbridge Ln (Highland Park)

CONTACT: Sally Mabadi (Berkshire Hathaway)

LIST PRICE: $6,999,000


1421 Lake Rd (Lake Forest) 

CONTACT: Mona Hellinga (Berkshire Hathaway)

LIST PRICE: $5,495,000


999 Sheridan Rd (Highland Park) 

CONTACT: Geri Emalfarb (@properties)

LIST PRICE: $3,450,000


1419 Waverly Rd (Highland Park)

CONTACT: Merle Styer (Coldwell Banker)

LIST PRICE: $3,000,000


Which lakefront home is your favorite?



Celebrity Homes

SOLD: Cutler & Cavallari take a loss

Jay Cutler has another loss to his name. The former Chicago Bears quarterback said goodbye to his Lake Forest home on Friday — selling for $3.6 million. The home was purchased by Cutler in 2014 for $4.25 million.

The quarterback was released by the Bears in March after eight seasons with the team and now plays with the Miami Dolphins. Cavallari is a reality TV star turned fashion designer, and mother of three, with Cutler.

Cutler and Cavallari initially listed the seven-bedroom home in May at $4.75 million, then reduced their asking price to just below $4.5 million in September. They cut their asking price further to $3.99 million in late October, according to Chicago Tribune.

Located at 561 Circle Lane in Lake Forest, their former Chicago home is nearly 11,000 square feet located on 1.6 acres of land near Lake Michigan. Over the years, Cavallari took to Instagram to share photos inside their home…







See inside the former home of Cutler and Cavallari…



What do you think Cutler’s home is really worth? We chime in here.



Open House

5 Open Houses in the Northern ‘Burbs

Interested in the Northern Suburbs? We’ve rounded up 5 amazing homes located on Chicago’s north side, all available for viewing during upcoming open houses this month. From Long Grove to Lake Forest and beyond, take a look at these 5 north side homes for sale:


3722 Albert Lane, Long Grove


5 Bedrooms / 5.1 Bathrooms

Open House: Sunday, July 16, 1:00 pm – 4:00 pm

Located in the Deerwood Estates subdivision, this beautiful Long Grove home is built with distinction.  A two-story foyer greets you with a grand staircase, travertine flooring, and leads to formal living & dining rooms, featuring Brazilian cherry hardwood floors and white crown molding. A luxury kitchen offers a large island and an eating area overlooking 1.4 acres of spacious land. (Contact: Jane Lee, 847-295-0800)


30 S Sheridan Rd, Lake Forest


5 Bedrooms / 6.1 Bathrooms

Open House: Sunday, July 16, 1:00 pm – 3:00 pm

This 5-bedroom home is located near the coveted east shoreline in Lake Forest. Beyond the brick-clad architectural exterior, inside you’ll find hardwood flooring throughout, all baths updated with heated floors, generous ceiling heights, and a white kitchen with premium appliances. Outside, lawns and gardens are fit with a private stone gate entrance, a bluestone patio and walkways, plus an additional second patio suitable for entertaining. (Contact: Vera Purcell, 847-735-7648)


464 Oakwood Ave, Lake Forest


5 Bedrooms / 4.1 Bathrooms

Open House: Sunday, July 16, 1:00 pm – 3:00 pm

This 5-bedroom home exudes charm. One of the oldest houses in Lake Forest, enjoy both the character of yesteryear and the modern amenities since updated. A stunning new gourmet kitchen offers a place to gather and entertain, in addition to the the double-decked front porch. All in the heart of downtown, a walk-to-everything location. (Contact: Marina Carney, 847-274-5566)


217 E Washington Ave, Lake Bluff


4 Bedrooms / 4.1 Bathrooms

Open House: Sunday July 23, 1:00 pm – 3:00 pm

Located in East Lake Bluff, this beautiful home looks (and lives) like new. Crafted with a designer’s eye, the interior features luxury finishes and plenty of natural light. Two fireplaces add to the charm and warmth of this spacious home. Plus, a recently-finished lower level is complete with a new full bathroom, exercise room and lots of storage. (Contact: Brad Anderson, 847-650-3456)


1096 S Green Bay Road, Lake Forest


5 Bedrooms / 4.1 Bathrooms

This traditional red-brick home is set on a generously sized lot within the Cherokee District. Featuring a desirable open floor plan, with both formal and informal spaces, a family room with vaulted ceilings and stone fireplace. A newly refinished lower level offers additional recreation space, as does a spacious brick paver patio and private backyard for entertaining. (Contact: Chris Downey, 847-340-8499)