Listings Historic Homes

Why live in a mere building, when you could live in a piece of American architectural history?

There are Tudors and townhouses galore in this city, but it’s not every day a bona fide icon hits the market.

For this month’s The Listings, we’ve rounded up five homes — on the market and for the taking — with origins as rich as their oak and mahogany interiors.

From a cantilevered prairie home by an FLW pupil to an apartment boasting a rooftop bar with Wrigley views, these digs have stories to tell.

And so will you, if you decide to bite the bullet.

3338 Prairie Wind Road
Long Grove, Illinois

Asking: $1.2 million
The Vitals: 4 bedrooms, 3 bathrooms, 3,874 square feet
Claim to Fame: FLW protégé Dennis Blair attended the Taliesin school and helped his mentor design the Guggenheim immediately before beginning work on this glass, cedar and bronze home, which sits adjacent a 50-acre nature preserve.
Defining Feature: Various cantilevers make entire swaths of the home — including balconies and at least one bedroom — appear to float among the surrounding canopy.

Image via VHT Studios / Baird & Warner Real Estate

20841 Oak Lane Drive
Olympia Fields

Asking: $669,000
The Vitals: 4 bedrooms, 3 bathrooms, 3,600 square feet
Claim to Fame: The house was built in 1964 by Mies van der Rohe acolyte H.P. Davis Rockwell, and the inspiration is obvious, from the secluded woodland setting to the two-story glass construction.
Defining Feature: Is there any question? It’s gotta be those floor-to-ceiling windows that canvas nearly every corner of the property.

Image via VHT Studios / @property Real Estate

3735 N Wilton Ave #4S
Wrigleyville

Asking: $600,000
Vitals: 2 bedrooms, 2 bathrooms, 1,500 square feet
Claim to Fame: The majesty of this condo is all about the fabled three Ls of real estate: it’s just .3 miles from Wrigley, with the stadium views to prove it.
Defining Feature: That plush seven-seat rooftop bar, with vintage neon beer signs and stellar views of Wrigley (though not directly into the stadium, unfortunately).

Image via BR Lillie Photography / @properties Real Estate

5 Rolling Ridge Rd
Northfield

Asking: $2.9 million
Vitals: 5 bedrooms, 4.5 bathrooms, 5,500 square feet
Claim to Fame: It’s the erstwhile home of contemporary architect Thomas Roszak, who built it in 2002 and subsequently raised three kids there.
Defining Feature: The two-story glass walls that surround the exterior, naturally.

Image via VHT Studios / @properties Real Estate

5026 S Greenwood Ave
Kenwood

Asking: $4.5 million
Vitals: 7 bedrooms, 8.5 bathrooms, 17,769 square feet
Claim to Fame: It’s one of the most famous Victorian homes in all of Chicagoland, the Goodman Mansion was originally constructed in 1892 for a lumber baron who would go on to open the Goodman Theatre.
Defining Feature: There’s almost too much to choose from, but we’ll go with the period-correct Jacobean ceilings that were recently restored with the help of master craftsmen flown in from Europe.

Main image via VHT Studios / Baird & Warner