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  • $4,250,000

    5 Woodley Rd, Winnetka, IL 60093

    8beds
    7,168sqft
    : 
    Single Family Residence
    Built in 1938
    1.46 Acres Lot
    $-- Zestimate®
    $593/sqft
    $-- HOA

    What's special

    Manicured groundsStately fpFloor-to-ceiling windowsSoaring ceilingsSpacious bedroomEnsuite bedroomsStately white-painted brick colonial
    This estate delivers the ultimate outdoor summer experience. It's time to sip 5pm summer cocktails in a true country club setting with gorgeous vistas of precisely manicured grounds from the tiered entertaining bluestone patios with the soothing sounds of the fountain trickling in the background. And as the sun sets, enjoy evenings under the stars in the tasteful, boutique hotel level hot tub that is the perfect place to gather and relax. It's all here waiting for you at this timeless architectural beauty on prestigious Woodley Road. This stately, white-painted brick Colonial, accented with classic black shutters, never goes out of style. Nestled on over 1.4 acres of meticulously manicured grounds by Midwest Arbor, 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 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. 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. It's time to experience the ultimate summer oasis.
    47 days
    on Zillow
    |
    2,295
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    70
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    Zillow last checked: 7 hours ago

    Listing updated: July 19, 2025 at 09:56am

    Listing courtesy of:

    Jena Radnay 847-881-0200,

    @properties Christie's International Real Estate

    Source: MRED as distributed by MLS GRID,MLS#: 12394393MLS Logo
    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 5 Woodley Rd.

    Next available tour time:Today at 4pm

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 8
    • Bathrooms: 7
    • Full bathrooms: 5
    • 1/2 bathrooms: 2
    Rooms
    • Room types: Bedroom 5, Bedroom 6, Bedroom 7, Bedroom 8, Foyer, Sitting Room, Heated Sun Room, Recreation Room, Bonus Room
    Primary bedroom
    • Features: Flooring (Carpet), Window Treatments (Curtains/Drapes), Bathroom (Full, Double Sink, Tub & Separate Shwr)
    • Level: Second
    • Area: 418 Square Feet
    • Dimensions: 22X19
    Bedroom 2
    • Features: Flooring (Carpet), Window Treatments (Curtains/Drapes)
    • Level: Second
    • Area: 360 Square Feet
    • Dimensions: 20X18
    Bedroom 3
    • Features: Flooring (Carpet), Window Treatments (Curtains/Drapes)
    • Level: Second
    • Area: 304 Square Feet
    • Dimensions: 19X16
    Bedroom 4
    • Features: Flooring (Carpet), Window Treatments (Curtains/Drapes)
    • Level: Second
    • Area: 256 Square Feet
    • Dimensions: 16X16
    Bedroom 5
    • Features: Flooring (Carpet), Window Treatments (Blinds)
    • Level: Second
    • Area: 221 Square Feet
    • Dimensions: 13X17
    Bedroom 6
    • Features: Flooring (Carpet)
    • Level: Third
    • Area: 220 Square Feet
    • Dimensions: 20X11
    Other
    • Level: Third
    • Area: 165 Square Feet
    • Dimensions: 15X11
    Other
    • Level: Third
    • Area: 176 Square Feet
    • Dimensions: 16X11
    Bonus room
    • Features: Flooring (Carpet)
    • Level: Third
    • Area: 819 Square Feet
    • Dimensions: 39X21
    Dining room
    • Features: Flooring (Hardwood), Window Treatments (Curtains/Drapes)
    • Level: Main
    • Area: 336 Square Feet
    • Dimensions: 21X16
    Family room
    • Features: Flooring (Hardwood), Window Treatments (Curtains/Drapes)
    • Level: Main
    • Area: 572 Square Feet
    • Dimensions: 22X26
    Foyer
    • Features: Flooring (Hardwood)
    • Level: Main
    • Area: 286 Square Feet
    • Dimensions: 13X22
    Other
    • Level: Main
    • Area: 270 Square Feet
    • Dimensions: 18X15
    Kitchen
    • Features: Kitchen (Eating Area-Breakfast Bar, Eating Area-Table Space, Island, Breakfast Room, Country Kitchen, Custom Cabinetry), Flooring (Hardwood)
    • Level: Main
    • Area: 475 Square Feet
    • Dimensions: 25X19
    Laundry
    • Features: Flooring (Other)
    • Level: Second
    • Area: 99 Square Feet
    • Dimensions: 11X9
    Living room
    • Features: Flooring (Hardwood), Window Treatments (Curtains/Drapes)
    • Level: Main
    • Area: 608 Square Feet
    • Dimensions: 32X19
    Recreation room
    • Level: Basement
    • Area: 990 Square Feet
    • Dimensions: 45X22
    Sitting room
    • Features: Flooring (Carpet)
    • Level: Second
    • Area: 190 Square Feet
    • Dimensions: 10X19
    Sitting room
    • Features: Flooring (Hardwood)
    • Level: Main
    • Area: 315 Square Feet
    • Dimensions: 21X15
    Heating
    • Natural Gas
    Cooling
    • Central Air
    Appliances
    • Included: Microwave, Dishwasher, High End Refrigerator, Freezer, Stainless Steel Appliance(s), Wine Refrigerator
    • Laundry: Upper Level, Gas Dryer Hookup, Sink
    Features
    • Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, High Ceilings, Special Millwork
    • Flooring: Hardwood, Carpet
    • Windows: Drapes
    • Basement: Finished,Partial
    • Attic: Finished
    • Number of fireplaces: 5
    • Fireplace features: Wood Burning, Family Room, Living Room, Basement, Other, Bedroom
    Interior area
    • Total structure area: 0
    • Total interior livable area: 7,168 sqft
    Video & virtual tour

    Property

    Parking
    • Total spaces: 8
    • Parking features: Asphalt, Circular Driveway, Garage Door Opener, Heated Garage, On Site, Garage Owned, Attached, Driveway, Owned, Garage
    • Attached garage spaces: 3
    • Has uncovered spaces: Yes
    Accessibility
    • Accessibility features: No Disability Access
    Features
    • Stories: 3
    • Has spa: Yes
    • Spa features: Outdoor Hot Tub
    • Fencing: Fenced
    Lot
    • Size: 1.46 Acres
    • Dimensions: 237.5 X 64
    • Features: Landscaped, Mature Trees
    Details
    • Additional structures: Outdoor Kitchen
    • Parcel number: 05291010070000
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Colonial
    • Property subtype: Single Family Residence
    Materials
    • Brick
    • Foundation: Concrete Perimeter
    • Roof: Slate
    Condition
    • New construction: No
    • Year built: 1938
    • Major remodel year: 2001

    Utilities & green energy

    • Electric: Circuit Breakers, 200+ Amp Service
    • Sewer: Public Sewer
    • Water: Lake Michigan

    Community & HOA

    Community
    • Features: Curbs, Street Paved
    • Subdivision: Woodley Road
    HOA
    • Services included: None
    Location
    • Region: Winnetka

    Financial & listing details

    • Price per square foot: $593/sqft
    • Tax assessed value: $1,939,770
    • Annual tax amount: $35,327
    • Date on market: 6/16/2025
    • Ownership: Fee Simple
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