Sign up to get new listings emailed daily! JOIN SIGN IN

Rockford, Illinois Homes & Real Estate For Sale
Cell: (815) 222-8800

Real Estate Agent Chad Pierce

Chad Pierce

Cell: (815) 222-8800
Rockford

Refine Search

5638 S Woodlawn Avenue, Chicago, IL 60637

$3,100,000
  • 5638 S Woodlawn Avenue, Chicago, IL 60637 Main Photo

49 Total Photos [Click to View All]

Pending
BEDS6 BATHS6 full 3 partial SQUARE FEET8,000 MLS#12446282
STATUSPending PROPERTY TYPEResidential - Single Family SCHOOLDistrict 299

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.

5638 S Woodlawn Avenue | MLS# 12446282

This single family home located at 5638 S Woodlawn Avenue, Chicago, IL 60637 is currently listed for sale with an asking price of $3,100,000. This property was built in 1911 and has 6 bedrooms and 6 full and 3 partial baths with 8000 sq. ft. S Woodlawn Avenue is located within the District 299 school district. Search Chicago real estate on cpierce.gogambino.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Partially Finished, Full
Cooling: Wall Unit(s)
Fireplaces: 3
Heating: Natural Gas
Home Style: Traditional
Lot Size: 61 x 178
Year Built: 1911

Feature Descriptions

Additional rooms: Bedroom 5,Bedroom 6,Exercise Room, Great Room, Library, Office, Pantry, Sitting Room, Terrace, Walk In Closet
Association Includes: None
Dining Room: Separate
Exterior: Brick
Fireplace: Decorative
Fireplace Location(s): Living Room, Den/Library, Dining Room
Laundry: In Unit, Laundry Chute, Sink
Lot: Irregular Lot
Lot Dimensions: 61 x 178
Parcel#: 20141120170000
Parking: Off Alley, Yes, Owned
Sewer: Public Sewer
Total Rooms: 15
Township: Hyde Park
Water: Lake Michigan

Room Sizes

Bedroom 5: 15X20
Bedroom 6: 13X22
Library: 18X19
Pantry: 6X11
Great Room: 35X32
Exercise Room: 27X15
Sitting Room: 15X14
Office: 12X11
Terrace: 14X18
Walk In Closet: 10X10
Bedroom 2: 15X21
Bedroom 3: 15X20
Bedroom 4: 13X16
Dining Room: 22X17
Family Room: 16X17
Kitchen: 17X16
Laundry: 7X16
Living Room: 17X31
Primary Bedroom: 12X17

Local Schools

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

Listed By / Shown By

Listed By

Agency Name: Berkshire Hathaway HomeServices Chicago
Agency Phone: 312-944-8900

Shown By

Agent Name: Chad Pierce
Agent Phone: Cell: (815) 222-8800
Agency Title: Gambino Realtors

IDX logo

Estimate Your Payment

Estimated Payment

$ 14,985.33 per month $14,081.17 Principal & Interest $0.00 Property Tax (data not provided by mls) $904.17 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/23/2026. The listing information on this page last changed on 04/23/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 04/23/2026 12:00:46 AM EST) or MRED MLS (last updated Wed 04/22/2026 11:58:02 PM EST) or Rockford Board of Realtors (NWIAR) (last updated Wed 04/22/2026 10:15:37 PM EST) or Northern Illinois Commercial Association Realtors (last updated Wed 04/22/2026 2:10:06 PM EST). Real estate listings held by brokerage firms other than Gambino Realtors may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. 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.



Privacy Policy / DMCA Notice / ADA Accessibility