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

Meet your guide

Walker Loetscher

Walker is the former Editor in Chief of InsideHook. Before that, he was the Managing Editor of Howler Magazine. He attended Georgetown University, and lives in the woods with a nice lady and some dogs.