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.
Closed
$2,750,000
5638 S Woodlawn Ave, Chicago, IL 60637
6beds
8,000sqft
Single Family Residence
Built in 1911
10,858 Square Feet Lot
$2,781,700 Zestimate®
$344/sqft
$3,777 Estimated rent
Home value
$2,781,700
$2.53M - $3.06M
$3,777/mo
Zestimate® history
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List your homeWhat's special
Modern luxuryHistoric detailsThree half bathsOriginal grandeurFederal-style residenceSpacious laundryMedia room
Zillow last checked:
Listing updated:
Listed by:
Susan O'Connor 312-944-8900,
Berkshire Hathaway HomeServices Chicago
Bought with:
David Porter
Porter Group Real Estate
Source: MRED as distributed by MLS GRID,MLS#: 12446282
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 9
- Full bathrooms: 6
- 1/2 bathrooms: 3
Rooms
- Room types: Bedroom 5, Bedroom 6, Exercise Room, Great Room, Library, Office, Pantry, Sitting Room, Terrace, Walk In Closet
Primary bedroom
- Features: Flooring (Carpet), Bathroom (Full)
- Level: Second
- Area: 204 Square Feet
- Dimensions: 12X17
Bedroom 2
- Features: Flooring (Hardwood)
- Level: Second
- Area: 315 Square Feet
- Dimensions: 15X21
Bedroom 3
- Features: Flooring (Hardwood)
- Level: Second
- Area: 300 Square Feet
- Dimensions: 15X20
Bedroom 4
- Features: Flooring (Hardwood)
- Level: Second
- Area: 208 Square Feet
- Dimensions: 13X16
Bedroom 5
- Features: Flooring (Hardwood)
- Level: Third
- Area: 300 Square Feet
- Dimensions: 15X20
Bedroom 6
- Features: Flooring (Hardwood)
- Level: Third
- Area: 286 Square Feet
- Dimensions: 13X22
Dining room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 374 Square Feet
- Dimensions: 22X17
Exercise room
- Level: Basement
- Area: 405 Square Feet
- Dimensions: 27X15
Family room
- Features: Flooring (Hardwood)
- Level: Third
- Area: 272 Square Feet
- Dimensions: 16X17
Great room
- Level: Third
- Area: 1120 Square Feet
- Dimensions: 35X32
Kitchen
- Features: Kitchen (Island, Pantry-Butler, Breakfast Room), Flooring (Hardwood)
- Level: Main
- Area: 272 Square Feet
- Dimensions: 17X16
Laundry
- Level: Second
- Area: 112 Square Feet
- Dimensions: 7X16
Library
- Features: Flooring (Hardwood)
- Level: Main
- Area: 342 Square Feet
- Dimensions: 18X19
Living room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 527 Square Feet
- Dimensions: 17X31
Office
- Features: Flooring (Hardwood)
- Level: Main
- Area: 132 Square Feet
- Dimensions: 12X11
Pantry
- Features: Flooring (Hardwood)
- Level: Main
- Area: 66 Square Feet
- Dimensions: 6X11
Sitting room
- Features: Flooring (Carpet)
- Level: Second
- Area: 210 Square Feet
- Dimensions: 15X14
Other
- Level: Third
- Area: 252 Square Feet
- Dimensions: 14X18
Walk in closet
- Features: Flooring (Carpet)
- Level: Second
- Area: 100 Square Feet
- Dimensions: 10X10
Heating
- Natural Gas
Cooling
- Wall Unit(s)
Appliances
- Laundry: In Unit, Laundry Chute, Sink
Features
- Basement: Partially Finished,Full
- Number of fireplaces: 3
- Fireplace features: Decorative, Living Room, Den/Library, Dining Room
Interior area
- Total structure area: 8,282
- Total interior livable area: 8,000 sqft
- Finished area below ground: 1,323
Property
Parking
- Total spaces: 3
- Parking features: Off Alley, Yes, Owned
Accessibility
- Accessibility features: No Disability Access
Features
- Stories: 3
Lot
- Size: 10,858 Square Feet
- Dimensions: 61 x 178
- Features: Irregular Lot
Details
- Parcel number: 20141120170000
- Special conditions: List Broker Must Accompany
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick
Condition
- New construction: No
- Year built: 1911
- Major remodel year: 2015
Utilities & green energy
- Electric: Circuit Breakers, 200+ Amp Service
- Sewer: Public Sewer
- Water: Lake Michigan
Community & HOA
HOA
- Services included: None
Location
- Region: Chicago
Financial & listing details
- Price per square foot: $344/sqft
- Date on market: 9/15/2025
- Listing terms: Cash
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 5/14/2026 | Sold | $2,750,000-11.3%$344/sqft |
Source:  MRED as distributed by MLS GRID #12446282 Report a problem | ||
| 1/26/2026 | Pending sale | $3,100,000$388/sqft |
Source: MRED as distributed by MLS GRID #12446282 Report a problem | ||
| 10/23/2025 | Contingent | $3,100,000$388/sqft |
Source: MRED as distributed by MLS GRID #12446282 Report a problem | ||
| 9/15/2025 | Listed for sale | $3,100,000+195.2%$388/sqft |
Source: MRED as distributed by MLS GRID #12446282 Report a problem | ||
| 6/3/2015 | Sold | $1,050,000-4.1%$131/sqft |
Source: MRED as distributed by MLS GRID #08383544 Report a problem | ||
| 10/1/2013 | Pending sale | $1,095,000$137/sqft |
Source: Baird & Warner Real Estate #08383544 Report a problem | ||
| 7/12/2013 | Price change | $1,095,000-8.4%$137/sqft |
Source: Baird & Warner Real Estate #08383544 Report a problem | ||
| 10/13/2012 | Pending sale | $1,195,000$149/sqft |
Source: Baird & Warner Real Estate #08144957 Report a problem | ||
| 8/25/2012 | Price change | $1,195,000-14%$149/sqft |
Source: Baird & Warner Real Estate #08144957 Report a problem | ||
| 5/5/2012 | Listed for sale | $1,390,000-7.3%$174/sqft |
Source: Baird & Warner Real Estate #08144957 Report a problem | ||
| 1/6/2011 | Listing removed | $1,500,000$188/sqft |
Source: CENTURY 21 Kennedy, Ryan, Monigal And Assoc., Inc. #07565772 Report a problem | ||
| 7/14/2010 | Price change | $1,500,000+22976.9%$188/sqft |
Source: CENTURY 21 Kennedy, Ryan, Monigal And Assoc., Inc. #07565772 Report a problem | ||
| 9/21/2009 | Listed for sale | $6,500$1/sqft |
Source: Visual Tour #07329067 Report a problem | ||
Public tax history
Tax history is unavailable.
Neighborhood: Hyde Park
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Nearby schools
GreatSchools rating
- 5/10Ray Elementary SchoolGrades: PK-8Distance: 0.1 mi
- 7/10Kenwood Academy High SchoolGrades: 7-12Distance: 0.8 mi
Schools provided by the listing agent
- Elementary: Ray Elementary School
- Middle: Canter Middle School
- High: Kenwood Academy High School
- District: 299
Source: MRED as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$2,781,700
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Estimated market value
$2,781,700
- Illinois
- Cook County
- Chicago
- 60637
- Hyde Park
- 5638 S Woodlawn Ave
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