5638 S WOODLAWN Avenue — Chicago, IL 60637
Closed
Chicago, IL 60637

5638 S WOODLAWN Avenue

$3,100,000
6 beds · 9 baths · 8,000 sqft
Listed at $3,100,000 38 days on market $0/yr taxes
01About this home

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.

02Inside the home
03By the numbers
$3,100,000
List price
8,000
Square feet
6
Bedrooms
6 full / 3 half
Bathrooms
1911
Year built
Lot size
3
Garage spaces
$0
Annual taxes
Traditional
Style
38
Days on market
04Features
Heating
Natural Gas
Cooling
Wall Unit(s)
Parking
Off AlleyOwned
Construction
Brick
Sewer
Public Sewer
05Neighborhood
E Elementary school
Ray Elementary School
Chicago, IL
M Middle school
Canter Middle School
Chicago, IL
H High school
Kenwood Academy High School
Chicago, IL
06History

Every event we have for this address, straight from the MLS.

May 14, 2026
SoldThis listing
$2,750,000
Sep 15, 2025
Listed for saleThis listing
Berkshire Hathaway HomeServices Chicago
$3,100,000
Sourced from MRED. Older events appear here as our history backfill completes.
07Ask Dwello

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08See it for yourself

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09Similar homes
Listed by Berkshire Hathaway HomeServices Chicago · Susan O'Connor
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12446282
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