5638 S Woodlawn Avenue, Chicago, IL 60637 - Photo 1

1/1

$2,750,000

Sold
Closed
Single Family
6 Beds
6 Full Baths
3 Partial Baths
8,000 Sq. Ft.
Updated 6 days ago

1/1

Property Description

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.

Full Property Details

Full Property Details for 5638 S Woodlawn Ave

General

Sold For: $2,750,000
Taxes: (2023)
Status: Closed
Type: Single Family
Source: MRED
MLS ID: 12446282
Added to Site: 249 day(s) ago

Interior

Fireplace: Yes
Fireplace(s): Living Room, Den/Library, Dining Room, Decorative

Rooms

Bathrooms

Total Bathrooms: 9
Full Bathrooms: 6
Half Bathrooms: 3
Basement Baths: Yes

Bedrooms

Total Bedrooms: 6

Parking

Total Spaces: 3
Parking Features: Off-Alley, Yes, Owned

Location

Area: CHI - Hyde Park
County: Cook
Driving 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.

School Information

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

Community

Assoc. Fees Include: None

Heating & Cooling

Cooling Type: Wall Unit(s)
Heating Type: Natural Gas

Utilities

Water: Lake Michigan

Structural Information

Architectural Style: Traditional
Construction: Brick
Exterior Const.: Brick
Basement Desc.: Partially Finished, Full
Square Feet: 8,000
Sq. Ft. Source: Plans
Year Built: 1911
Built Before 1978: Yes
Remodeled/Updated: 2015

Lot Features

Lot Size Range: Oversized Chicago Lot
Lot Dimensions: 61 x 178
Lot Features: Irregular Lot

Financial Considerations

Parking Included: Yes
Assessment Year: 1911
Tax Year: 2023

Disclosures and Reports

Ownership: Fee Simple
Special Conditions: List Broker Must Accompany
Property ID: 20141120170000

Listed by Berkshire Hathaway HomeServices Chicago
Sold by Porter Group Real Estate

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— 5638 S Woodlawn Ave —

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Schools

Schools serving 5638 S Woodlawn Ave

School District:Chicago Public School District 299

Name	Grades	Distance
Ray Elementary School 5631 South Kimbark Avenue, Chicago, IL 60637	7-8	0.1 mi
Kenwood Academy High School 5015 South Blackstone Avenue, Chicago, IL 60615	9-12	0.9 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5638 S Woodlawn Ave

Date

Details

Price

Change

Source

5/14/2026

Sold

$2,750,000

-11.29%

MLS

9/15/2025

Listed

$3,100,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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5638 S Woodlawn Avenue, Chicago, IL 60637 (MLS# 12446282) is a Single Family property that was sold at $2,750,000 on May 14, 2026. Want to learn more about 5638 S Woodlawn Avenue? Do you have questions about finding other Single Family real estate for sale in Hyde Park? You can browse all Hyde Park real estate or contact a Coldwell Banker agent to request more information.

5638 S Woodlawn Ave Chicago, IL 60637