Find the Chicago home that speaks to you

An Art Deco Masterpiece at the Crown of Astor Street

Occupying the northernmost position on one of Chicago's most storied residential addresses, 1524 N. Astor Street is a rare convergence of architectural pedigree, bespoke craftsmanship, and exceptional privacy. Originally conceived as a mid-century modern residence by noted Chicago architect I. W. Colburn, the home was later reimagined with a refined Art Deco sensibility by two of the city's most respected design firms — Marvin Herman & Associates and Suzanne Lovell Inc. — resulting in approximately 6,500 square feet of interiors that reward close inspection at every turn. From a soaking tub carved from a single block of Noir St. Laurent marble to hand-cast plaster moldings and a dramatic curved staircase with artisan-fabricated bronze and steel balusters, this is a Gold Coast residence of uncommon distinction.

Featured by Jennifer Ames

Gothic Limestone, Panoramic Skies, and Turnkey Perfection

Residence 2203 at the legendary Tribune Tower offers one of Chicago's most architecturally singular living experiences — a fully turnkey three-bedroom-plus-den home where original Gothic limestone frames sweeping views of Lake Michigan, the Chicago River, and the city skyline. Seamlessly blending the Tower's storied 1925 neo-Gothic pedigree with cutting-edge interior design, this residence delivers exquisite custom millwork, a chef's kitchen appointed with Wolf, Sub-Zero, and Miele, and a spa-caliber primary suite — all governed by Crestron home automation. The crown jewel is a professionally landscaped private terrace with an outdoor kitchen, fire table lounge, and built-in dining area, framed by the same soaring limestone arches that have defined this iconic address for a century.

Featured by Ryan Preuett

Limestone Legacy on Lincoln Park's Most Coveted Address

Set on two and a half lots along one of Lincoln Park's most distinguished residential streets, 1838 N. Burling Street is a rare limestone and brick single-family residence that delivers both architectural grandeur and effortless livability. Across five thoughtfully composed levels, the home unfolds from formal entertaining spaces and a chef's kitchen to a primary suite with three fireplaces, a top-floor game room, and a backyard that rivals a private resort — complete with a swimming pool, sport court, outdoor kitchen, and a temperature-controlled glass atrium. This is a home that earns its address in every detail, offering a standard of living that is genuinely difficult to replicate anywhere on Chicago's North Side.

Featured by Ryan Preuett

A Landmark Lake Shore Drive Residence Where Every Level Gathers

Commanding a rare sixty-six-foot frontage along one of Chicago's most celebrated addresses, this limestone-clad single-family residence on Lake Shore Drive offers approximately 9,000 square feet of impeccably curated living across five levels — each one a distinct destination. Seven bedrooms, seven and a half baths, dual rooftop terraces, a sport court, and a custom outdoor kitchen compose a home that is as purposeful in its architecture as it is generous in its spirit. For the discerning buyer seeking a true Chicago estate — one that commands its address without apology — 3026 North Lake Shore Drive stands in a category entirely its own.

Featured by Brant Booker

Magnificent Masonry Estate with Private Basketball Court

This extraordinary 8,000-square-foot custom residence on prestigious North Park Avenue represents the pinnacle of luxury living in Chicago's coveted Old Town/Gold Coast neighborhood. Constructed from exquisite masonry brick and limestone, the home features seven bedrooms, a professional indoor basketball court, and a distinctive turret tower offering panoramic city views. From the chef's kitchen with Wolf appliances to the rooftop deck and geothermal heating, every detail reflects meticulous craftsmanship and thoughtful design.

Featured by Chaz Walters

Georgian Masterpiece with Hollywood Heritage and Modern Luxury

This magnificent 9,126-square-foot Georgian estate, built in 1921, seamlessly blends timeless architectural elegance with contemporary luxury across three thoughtfully designed levels. Featuring five bedrooms, six full bathrooms, and extraordinary entertaining spaces including a home theater, indoor basketball court, and multiple fireplaces, this iconic property offers unparalleled sophistication on over half an acre of meticulously maintained grounds.

Featured by Kevin McCalister

East Lincoln Park Architectural Masterpiece with Private Pool Sanctuary

This extraordinary 9,500-square-foot residence on coveted Orchard Street represents the pinnacle of contemporary luxury living. From the museum-quality marble foyer to the De Giulio kitchen with Wolf and Sub-Zero appliances, every detail reflects uncompromising craftsmanship. The seamless integration of indoor-outdoor living, featuring a private plunge pool and landscaped yard, creates an urban sanctuary mere steps from Lincoln Park's finest amenities.

Featured by Susan Miner

Soaring Full-Floor Sanctuary with 360-Degree Chicago Views

Experience unprecedented urban luxury in this full-floor residence at One Chicago, where nearly 4,000 square feet of meticulously crafted living space unfolds across the 69th floor. Floor-to-ceiling windows frame breathtaking 360-degree panoramas of Lake Michigan and the city skyline, while bespoke finishes and direct elevator access create an unparalleled sense of privacy and sophistication in the heart of Chicago's most coveted neighborhood.

Featured by Nancy Tassone

Historic Art Deco Penthouse Where Chicago's Golden Age Lives

Commanding 7,880 square feet across two extraordinary floors, this duplex penthouse represents the pinnacle of Chicago sophistication within the legendary Palmolive Building. Once home to Hugh Hefner's original Playboy headquarters and later Vince Vaughn's private residence, this meticulously renovated sanctuary seamlessly blends Art Deco heritage with contemporary luxury, featuring soaring 14-foot ceilings, original mahogany paneling, and three private terraces overlooking the magnificent cityscape.

Featured by Brian Loomis

Exceptional Custom Estate on Lincoln Park's Most Coveted Block

Set on an expansive 44-foot-wide lot, this architectural masterpiece represents the pinnacle of custom craftsmanship on one of Chicago's most prestigious addresses. Every element reflects enduring quality and timeless elegance, from the hand-selected water-struck brick facade to the Christopher Peacock kitchen and rooftop terrace with panoramic skyline views.

Featured by Carrie McCormick

Lincoln Park Multigenerational Estate with Private Coach House

This extraordinary Lincoln Park estate redefines luxury family living on an exceptional double lot. Behind original wrought iron gates, the property features a meticulously renovated main residence connected to a private coach house above a five-car garage, creating unprecedented opportunities for multigenerational living. With six bedrooms, sophisticated entertaining spaces, and a wine cellar, this home has been the backdrop for countless family celebrations across its sun-drenched terraced grounds.

Featured by Emily Sachs Wong

Architectural Penthouse Commanding Chicago's Entire 64th Floor

An unparalleled achievement in residential design, this 8,500-square-foot penthouse occupies the entire 64th floor of the prestigious Park Tower, offering 360-degree views of Chicago's magnificent skyline. Meticulously crafted by Marvin Herman & Associates and interior designer Mitchell Turnbough, this extraordinary residence features hand-plastered walls, custom anegre wood paneling, and a dramatic salmon-pink velvet grand salon with polished black granite floors that create an atmosphere of refined luxury and architectural distinction.