By J.P. Anderson By J.P. Anderson | March 26, 2025 | Home & Real Estate, Home & Real Estate, Home & Real Estate Feature,
As the real estate market in Chicago heats up, we spotlight the hottest listings to snatch up now.
The estate’s ivy-covered pool house makes a grand style statement.
The estate’s grounds span nearly nine acres adjacent to Lake Michigan.
One of the home’s comfortable seating rooms.
The Details:
Considered one of the Midwest’s premier estates, this nearly 12,000-square-foot North Shore gem was designed by Drake Hotel architect Benjamin H. Marshall in 1904 and boasts breathtaking landscaping across nearly nine acres. Elevators access all four floors of the main house, which enchants with high ceilings, stunning fireplaces, a bifurcated staircase, handsome library and more including eight bedrooms and 8.2 baths. 930 E. Rosemary Road, Lake Forest
Price: $14,975,000
Contact: Ann Lyon, 847.295.0700, atproperties.com
“From the moment you enter this exquisite all-white, renovated residence, you appreciate its mint condition and exquisite detailing.” –MICHAEL ROSENBLUM
Prime lakefront location in an architecturally significant building puts this Lake Shore Drive property in high demand.
The Details:
Set in the renowned Lucien Lagrange-designed 840 N. Lake Shore Drive across the street from the sylvan surrounds of Streeterville’s Lake Shore Park, this strikingly renovated 10th-floor residence boasts panoramic views throughout its nearly 4,000 square feet of space. The open floor plan puts the home’s luxurious details fully in view, from hardwood flooring throughout to a large foyer/gallery, oversize chef ’s kitchen with expansive center island, laundry room with side-by-side washer/dryer, primary suite with two walk-in closets, and spa-style marble bathroom and more. 840 N. Lake Shore Drive, Unit 1001
Price: $2,897,747
Contact: Michael Rosenblum, 312.286.1634, happilyeveralways.com
Jaw-dropping views and posh amenities beckon in this duplex penthouse on Michigan Avenue.
The Details:
Spanning more than 15,000 feet of luxurious living space place and designed by renowned architect Howard Van Doren Shaw, the meticulously restored Clayton Mark Estate is one of the North Shore’s most iconic residences. The six-bedroom, 9.3-bathroom manor features opulent amenities like a synthetic ice rink and sports court; outside, a lakefront beach stretches more than 400 feet, making for the ultimate in Lake Michigan living. 999 Lake Road, Lake Forest
Price: $12,999,000
Contact: Patrick Milhaupt, 847.849.9828, sothebysrealty.com
“More than just a home, 999 Lake Road is a living landmark, embodying the prestige, history, and natural beauty of Lake Forest’s most coveted waterfront.”–PATRICK MILHAUPT
This 1914 treasure by celebrated architect Howard Van Doren Shaw is a landmark to luxury living on the North Shore.
The Details:
What could be the perfect pied-á-terre or primary city residence awaits in this 6,000-square-foot duplex penthouse in one of the Mag Mile’s most desired addresses. From the living room with lakefront balcony and the large formal dining room to an extraordinary kitchen, floating wood staircase, two laundry rooms and abundant storage space, this is a prize property in the heart of downtown. 950 N. Michigan Ave., Unit 5503-5501
Price: $2,500,000
Contact: Judith Pielet, 312.640.7010, bairdwarner.com
If you’ve always wanted to live on your own grand country estate, this 70-plus-acre property in Barrington Hills is the place.
The Details:
An extraordinary 70-plus-acre estate in Barrington Hills, Hidden Ponds enchants with rolling countryside, forests, two ponds and exquisite gardens and more. Boasting eight bedrooms, Brazilian walnut floors, vaulted ceilings, five fireplaces, the 30,000-square-foot English Country Manor home is the epitome of luxury, and world-class amenities like a walk-in wine cellar, English pub, gym, movie theater and a stunning pool with cabana (not to mention a six-car garage) complete the posh picture. 7 Fox Hunt Road, Barrington
Price: $22,000,000
Contact: John Morrison/Mimi Noyes, 847.381.0300, atproperties.com
“The outside of this one-of-a-kind home is a pleasure for all to see, and the inside offers so many more outstanding features.”–EMILY SACHS WONG
The 900-bottle wine cellar will appeal to any oenophile.
Exposed brick accents add texture to the home.
The Details:
A stunning oasis on the border of Old Town and Lincoln Park, this custom-crafted home on a 45-foot-wide lot sits inside a walled garden, with the entire ground level open to the outdoors. The striking interiors designed by Bruce Fox incorporate natural materials like exposed brick, reclaimed barn wood and steel accents. Luxe amenities like a 900-bottle wine cellar and tasting room, rec room with sauna and bath, and a heated three-car garage complete the scene. 1970 N. Burling St.
Price: $6,995,000
Contact: Emily Sachs Wong, 773.472.0200, atproperties.com
The home’s stately facade hints at the grandeur within.
The elegant foyer welcomes guests with one of the estate’s 18 fireplaces.
A meticulously landscaped courtyard is just the beginning of the lush exterior.
The Details:
Boasting 45 rooms, 16 bedrooms, 17 baths and 18 fireplaces over 25,000 square feet in the heart of the Gold Coast, the Astor Court estate is a jaw-dropping architectural masterpiece that was designed by Howard Van Doren Shaw for the Goodman Family. From the neo-classical/Georgian Revival facade to its magnificent landscaped courtyard, gorgeously appointed 10,000-square-foot main residence and six one-of-a-kind rental units, it presents a unique opportunity to own a grand piece of Chicago history. 1355 N. Astor St.
Price: $21,000,000
Contact: Natasha Motev, 312.952.5650, sothebysrealty.com
“This is a once-in-a-lifetime opportunity to own one of Chicago’s most iconic estates, on the market for the first time in over 40 years.”–NATASHA MOTEV
Photography by: 930 E. Rosemary Road, Lake Forest photos by PALO DOBRIK AND TOM ROSSITER; 840 N. Lake Shore Drive, Unit 1001 PHOTO BY VHT STUDIOS; 999 Lake Road, Lake Forest PHOTO BY: VHT STUDIOS; 950 N. Michigan Ave., Unit 5503-5501 photo by PHIL GOLDMAN; 7 Fox Hunt Road, Barrington PHOTO BY VHT STUDIOS; 1970 N. Burling St. photos BY POSITIVE IMAGE PHOTOGRAPHY INC.; 1355 N. Astor St. photos BY VHT STUDIOS;