Twitter
Facebook
Email
|
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.
| DAYS ON MARKET | 28 | LAST UPDATED | 9/3/2025 |
|---|---|---|---|
| TRACT | Woodley Road | YEAR BUILT | 1938 |
| COMMUNITY | Winnetka | GARAGE SPACES | 3.0 |
| COUNTY | Cook | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| School District | New Trier Twp H.S. Northfield/Wi |
|---|---|
| Elementary School | Avoca West Elementary School |
| Jr. High School | Marie Murphy School |
| High School | New Trier Twp H.S. Northfield/Wi |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Freezer, Microwave, Range, Stainless Steel Appliance(s), Wine Refrigerator |
| AREA | Winnetka |
| BASEMENT | Finished, Partial, Sump Pump, Yes |
| CONSTRUCTION | Brick |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Natural Gas |
| INTERIOR | Bookcases, Built-in Features, Entrance Foyer, High Ceilings, Walk-In Closet(s), Wet Bar |
| LOT | 1.457 acre(s) |
| LOT DESCRIPTION | Landscaped |
| LOT DIMENSIONS | 237.5 X 64 |
| PARKING | Asphalt, Circular Driveway, Garage Door Opener, Heated Garage, On Site, Attached, Driveway, Garage |
| SEWER | Public Sewer |
| STYLE | Colonial |
| SUBDIVISION | Woodley Road |
| TAXES | 35327.92 |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
0
P
I
*Estimate only
| SATELLITE VIEW |
| / | |
We respect your online privacy and will never spam you. By submitting this form with your telephone number
you are consenting for Humderto
Garcia to contact you even if your name is on a Federal or State
"Do not call List".
Listed with @properties Christie's International Real Estate
The data relating to real estate for sale on this web site comes in part from the Broker ReciprocitySM Program of MRED. All real estate listings are marked with the Broker ReciprocitySM logo or the MRED Broker ReciprocitySM thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers.
The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision.
Copyright 2025 MRED. All rights reserved.
The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision.
Copyright 2025 MRED. All rights reserved.
This IDX solution is (c) Diverse Solutions 2025.