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$4,499,900
47 Days On Site

5 Woodley Road
Winnetka, IL 60093

For Sale|Single Family Residence|Active
8
Beds
5
Full Baths
2
Partial Baths
7,168
SqFt
$628
/SqFt
1938
Built
Subdivision:
Woodley Road
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of @properties Christie's International Real Estate
Call Now: 847.967.0022
Is this the home for you? We can help make it yours.
847.967.0022
5 Woodley Road5 Woodley Road5 Woodley Road5 Woodley Road
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An eternal architectural beauty set on prestigious Woodley Road, this stately, white-painted brick Colonial accented with black shutters never goes out of style. Nestled on over 1.4 acres of meticulously manicured grounds by Midwest Arbor, these 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a quintessential floor plan designed for modern life. Elegance unfolds the moment you step into the grand reception foyer crowned by a cascading wrought-iron staircase serving as the gateway to the home's formal spaces. Sunlit living room, anchored by a stately FP and framed by floor-to-ceiling windows, flows effortlessly into a dreamy sunroom wrapped in grasscloth wallpaper-offering serene views of the lush backyard. Tucked off the solarium a richly paneled library with FP creating the ultimate private retreat. Elegant dining room with French doors opening to the expansive terraces sets the stage for seamless indoor-outdoor entertaining. At the heart of the home is the expansive Chef's kitchen, designed for both culinary excellence & effortless hosting. Chefs' kitchen with great space, custom cabinetry, island with breakfast bar seating, desk command center, top of the line appliances and separate breakfast area, and fully loaded butler's pantry with wine fridge, sink, and custom cabinetry. Off the kitchen, Ralph Lauren-inspired family room w/ warm chestnut paneling, FP, bay window, and French doors opening of to the bluestone patio & new tasteful in-ground spa. Thoughtfully designed mudroom with custom cabinetry connects to the heated three-car heated garage, perfectly positioned as a discreet backdoor drop zone. Gracious 2nd floor is anchored by the private primary suite wing-offering a serene sanctuary with a spacious bedroom, sitting room with FP, and currently set up as his-and-her baths with an additional den (or bedroom). 3 additional ensuite bedrooms on this level, one tucked away on the north wing with a light-filled art studio. New fully equipped 2nd floor laundry also on this level. Third floor with soaring ceilings, large rec space, and three oversized bedrooms with a full bath offer endless possibilities. The lower level provides even more versatility, with a spacious rec room/gym, custom wine cellar, and ample storage. This classic all-American compound blends timeless sophistication with modern comfort-ready to be cherished for generations to come.

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Listing Snapshot
Price 
$4,499,900
Days On Site 
47 Days
Bedrooms 
8
Inside Area (SqFt) 
7,168 sqft
Total Baths 
7
Full Baths 
5
Partial Baths 
2
Lot Size 
1.457 Acres
Year Built 
1938
MLS® Number 
12287968
Status 
Active
Property Tax 
$35,327.92
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Other
Friends & Family
Recent Activity
2 weeks agoListing updated with changes from the MLS®
4 weeks agoStatus changed to Active
2 months agoListing first seen on site
General Features
Acres 
1.457
Attached Garage 
Yes
Direction Faces 
East
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
3
Parking 
DrivewayAttached
Parking Spaces 
8
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
Style 
Colonial
Interior Features
Appliances 
RangeMicrowaveDishwasherFreezerStainless Steel Appliance(s)Wine Refrigerator
Basement 
Partial
Cooling 
Central Air
Electric 
Circuit Breakers200+ Amp Service
Fireplace 
Yes
Fireplace Features 
Family RoomLiving RoomWood Burning
Fireplaces 
5
Flooring 
Hardwood
Heating 
Natural Gas
Interior 
Wet BarEntrance FoyerBuilt-in FeaturesWalk-In Closet(s)BookcasesHigh Ceilings
Laundry Features 
Gas Dryer HookupSink
Spa 
Yes
Window Features 
Window Treatments
Bedroom 2 
Dimensions - 20X18Level - Second
Bedroom 3 
Dimensions - 19X16Level - Second
Bedroom 4 
Dimensions - 16X16Level - Second
Bedroom 5 
Dimensions - 13X17Level - Second
Bedroom 6 
Dimensions - 20X11Level - Third
Bedroom 7 
Dimensions - 15X11Level - Third
Bedroom 8 
Dimensions - 16X11Level - Third
Bonus Room 
Dimensions - 39X21Level - Third
Dining Room 
Dimensions - 21X16Level - Main
Family Room 
Dimensions - 22X26Level - Main
Foyer 
Dimensions - 13X22Level - Main
Heated Sun Room 
Dimensions - 18X15Level - Main
Kitchen 
Dimensions - 25X19Level - MainDescription - Eating Area-Breakfast Bar,Eating Area-Table Space,Island,Breakfast Room,Country Kitchen,Custom Cabinetry
Laundry 
Dimensions - 11X9Level - Second
Living Room 
Dimensions - 32X19Level - Main
Master Bedroom 
Dimensions - 22X19Level - Second
Recreation Room 
Dimensions - 45X22Level - Basement
Sitting Room 
Dimensions - 21X15Level - Main
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Exterior Features
Construction Details 
Brick
Fencing 
Fenced
Lot Features 
Landscaped
Other Structures 
Outdoor Kitchen
Roof 
Slate
Spa 
Yes
Windows/Doors 
Window Treatments
Community Features
Community Features 
Curbs
MLS Area 
Winnetka
School District 
New Trier Twp H.S. Northfield/Wi
Township 
New Trier
Schools
School District
New Trier Twp H.S. Northfield/Wi
Elementary School
Avoca West Elementary School
Middle School
Marie Murphy School
High School
New Trier Twp H.S. Northfield/Wi
Listing Courtesy of MRED as distributed by MLS Grid of @properties Christie's International Real Estate



Based on information submitted to the MLS GRID as of 2025-04-03 06:44 PM UTC. 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.
Last checked: 2025-04-03 06:44 PM UTC
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Neighborhood & Commute
Source: Walkscore
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