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5 Woodley Rd, Winnetka, IL

House

Other

Listed price in listed location currency (USD).
$3,999,900

878

MLS® 12452300

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 7168 sqft
Garage Yes
Taxes $35,328
Days Active 55
Lot Size 
Approx. Age 1938
Avg. Price Per Sqft $558
MLS® Number 12452300

Property Address: 5 Woodley Rd, Winnetka, IL, 60093-3735

Average square foot calculated using Size range provided by listing agent.

Description

Reminiscent of the timeless white painted Colonial retreats off the East Coast of Hyannis Port, this Winnetka estate set on 1.4 acres of gracious grounds captures that same coastal charm right here in the North Shore. Set on premier Woodley Road with a beautiful natural canopy of mature trees, this 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a quintessential floor plan designed for modern day living. 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, 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 to the bluestone patio & new tasteful in-ground spa. Thoughtfully designed mudroom with custom cabinetry connects to the heated 3 car 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. 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. From inside to out, 5 Woodley is an all American classic that always continues to only get better with time. This is a phenomenal opportunity to take this graceful & solidly built home to a new level of 2025 luxury.
MLS® Number12452300
Laundry LevelUpper Level, Sink
Central VacNo
FireplaceNo
Acreage1.457
Exterior
GarageYes
Approx. Age1938
BasementFinished, Partial
DrivewayAsphalt, Circular Driveway, Garage Door Opener, Heated Garage, On Site, Garage Owned, Attached, Driveway, Owned, Garage
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Rooms

Change to metres

Living Room:Main Floor19 × 32 ft
Other:Third Floor11 × 20 ft
Family Room:Main Floor26 × 22 ft
Other:Basement22 × 45 ft
Kitchen:Main Floor19 × 25 ft
Other:Main Floor22 × 13 ft
Other:Second Floor19 × 10 ft
Other:Main Floor15 × 18 ft
Laundry:Second Floor9 × 11 ft
Master Bedroom:Second Floor19 × 22 ft
Other:Third Floor11 × 16 ft
Other:Third Floor11 × 15 ft
Bedroom 2:Second Floor18 × 20 ft
Dining Room:Main Floor16 × 21 ft
Bedroom 5:Second Floor17 × 13 ft
Bonus Room:Third Floor21 × 39 ft
Bedroom 3:Second Floor16 × 19 ft
Bedroom 4:Second Floor16 × 16 ft

Similar Listings

Price History

-End Date
Not Sold YetSold Price

Other

Sep 3, 2025List Date
$3,999,900List Price
  • Commute

Commute

Starting Address
Destination Address
5 Woodley Rd, Winnetka, IL

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