$2,750,000

beds

baths

half baths

8,000

square ft

5638 S Woodlawn Avenue

Chicago, Illinois 60637

Closed / MLS #12446282 / Single Family / Hyde Park

Listing information updated 5/15/2026 at 11:23am

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 Features

Architecture Style:

Traditional

Exterior Type:

Brick

Basement:

Partially Finished,Full

Beds Above Grade:

Cooling System:

Wall Unit(s)

Heating System:

Natural Gas

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

100+ Years

Parking Type:

Off Alley,Yes,Owned

Parking Spaces:

Room Count:

Water Front:

Square Feet:

8,000

Lot Size:

Oversized Chicago Lot

Room Information

Living Room:

17x31 - Main

Dining Room:

22x17 - Main

Kitchen:

17x16 - Main

Family Room:

16x17 - Third

Primary Bedroom:

12x17 - Second Level

2nd Bedroom:

15x21 - Second

3rd Bedroom:

15x20 - Second

4th Bedroom:

13x16 - Second

Bedroom 5:

15x20 - Third Level

Bedroom 6:

13x22 - Third Level

Library:

18x19 - Main Level

Pantry:

6x11 - Main Level

Great Room:

35x32 - Third Level

Taxes & Assessments

Tax Amount:

N/A

Tax Year:

2023

Location

Zip Code:

60637

City:

Chicago

County:

Cook

Schools

School District(s):

299

Elementary School:

Ray Elementary School

Middle School:

Canter Middle School

High School:

Kenwood Academy High School

Architecture Style:

Traditional

Exterior Type:

Brick

Basement:

Partially Finished,Full

Beds Above Grade:

Cooling System:

Wall Unit(s)

Heating System:

Natural Gas

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

100+ Years

Parking Type:

Off Alley,Yes,Owned

Parking Spaces:

Room Count:

Water Front:

Square Feet:

8,000

Lot Size:

Oversized Chicago Lot

Living Room:

17x31 - Main

Dining Room:

22x17 - Main

Kitchen:

17x16 - Main

Family Room:

16x17 - Third

Primary Bedroom:

12x17 - Second Level

2nd Bedroom:

15x21 - Second

3rd Bedroom:

15x20 - Second

4th Bedroom:

13x16 - Second

Bedroom 5:

15x20 - Third Level

Bedroom 6:

13x22 - Third Level

Library:

18x19 - Main Level

Pantry:

6x11 - Main Level

Great Room:

35x32 - Third Level

Tax Amount:

N/A

Tax Year:

2023

Zip Code:

60637

City:

Chicago

County:

Cook

School District(s):

299

Elementary School:

Ray Elementary School

Middle School:

Canter Middle School

High School:

Kenwood Academy High School

Listing Office: Berkshire Hathaway HomeServices Chicago

Listing Office Phone: 312.944.8900

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 5/15/2026 at 11:23am. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.

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5638 S Woodlawn Avenue, Chicago, IL 60637 is a single family home which sold for $2,750,000. 5638 S Woodlawn Avenue features 6 Beds, 6 Baths, 3 Half Baths. This single family home has been listed on @properties Christie's International Real Estate since September 15th, 2025 and was built in 1911. Nearby schools include Ray Elementary School, Canter Middle School, and Kenwood Academy High School. The nearest transit stops include Cottage Grove CTA Green line and 57th Street Metra South Shore line.