Cook, US
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.
Courtesy Of: Berkshire Hathaway HomeServices Chicago
Feature Highlights
- Built Before 1978
- Basement Bathrooms
General Features
- List Date:
- 09/15/2025
Public Schools
- Elementary School:
- Ray Elementary Schoo
- High School:
- Kenwood Academy High
Interior Features
- Living Area Source:
- Plans
- Bedrooms Possible:
- 6
- Bathrooms Full:
- 6
- Rooms Total:
- 15
- Aprox. Total Finished Sq Ft:
- 8282
Exterior Features and Amenities
- Lot Size Dimensions:
- 61 x 178
- Parking Total:
- 3
Financial
- Purchase Contract Date:
- 2025-10-22
- Days On Market:
- 39
- Tax Year:
- 2023
Other Features
- Elementary School District:
- 299
- High School District:
- 299
- Middle Or Junior School District:
- 299
- Age:
- 100+ Years
Directions
From DuSable Lake Shore Drive take the exit at the Museum of Science and Industry - 57th Drive. Proceed along 57th as it merges into Cornell. Continue through the stoplight at Stony Island, west on the Midway Plaisance to Woodlawn Avenue. At that light take a right and the house will be about 2 blocks north on your left. Street parking, but that is more interesting when school is in session.
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Data last updated: 2025-12-19.
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