5638 S WOODLAWN Avenue Chicago IL 60637 MLS #MRD12446282

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
MLS #:
MRD12446282
Status:
Active
Beds:
6
Baths:
9
Address:
5638 S WOODLAWN Avenue
Type:
Single Family
Neighborhood:
chihydepark
City:
Chicago
Listed Date:
Sep 15, 2025
State:
IL
Finished Sq Ft:
8,000
ZIP:
60637
Year Built:
1911

Schools

School District:
299
Elementary School:
Ray Elementary School
Middle School:
Canter Middle School
High School:
Kenwood Academy High School

Interior

Bathrooms
6 Full Bathrooms, 3 Half Bathrooms
Cooling
Wall Unit(s)
Fireplaces Total
3
Heating
Natural Gas
Laundry Features
In Unit, Laundry Chute, Sink

Exterior

Architectural Style
Traditional
Construction Materials
Brick
Parking Features
Off Alley, On Site, Owned
Parking Spots
3

Financial

HOA Frequency
Not Applicable
HOA Includes
None
Tax Year
2023

Listing Agent & Office

Susan O’Connor
Berkshire Hathaway HomeServices Chicago

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