5638 South Woodlawn Avenue represents a unique opportunity to own a piece of Chicago's architectural heritage. Designed in 1911 by celebrated architect Howard Van Doren Shaw for publishing executive Henry Hoyt Hilton and his wife Charlotte, this three-story Federal-style residence embodies timeless elegance and thoughtful design. Shaw, later honored with the American Institute of Architects' Gold Medal, was renowned for his refined use of symmetry, proportion, and classical detail-hallmarks clearly evident here. Meticulously restored and updated, the massive 8, 000-square-foot home blends original grandeur with modern luxury. Historic details - majestic fireplaces, gleaming hardwood detailing, and an elegant main staircase-are complemented by a new chef's kitchen, renovated baths, a reimagined third-floor great room, as well as the practical including a spacious laundry. The lower level adds a workout room, media room, and abundant storage. With six bedrooms, five full ensuite baths, and three half baths, this residence offers both scale and versatility for modern living. Set in the heart of the University of Chicago community, this historic property is as livable as it is significant - a piece of architectural history, seamlessly blending Shaw's timeless vision with contemporary elegance in one of Chicago's most celebrated neighborhoods.

Property Details

PRICE
$3,100,000
BEDROOMS
6
BATHROOMS
9
SQFT
8000
YEAR BUILT
1911
PARKING SPOTS
N/A
MLS #
12446282
FULL ADDRESS
5638 5638 WOODLAWN Avenue
CITY
Chicago, IL
ZIP
60637

Listing Details

Listing Office
Berkshire Hathaway HomeServices Chicago
Listing Agent
Susan O'Connor
Contact
312-944-8900
Last Data Update
2026-05-15T16:14:56Z

Interior

BATHROOMS
9 Full Bathrooms

Schools

School District
299
Elementary School
Ray Elementary School
High School
Kenwood Academy High School

Buy This Home With a Local Expert

22 years. 600+ Chicago closings. Individual, hands-on representation from first tour through close. Ken can be your buyer's agent on this property. Call 773.398.5585 or drop your details below.

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