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.
Closed
$3,600,000
5 Woodley Rd, Winnetka, IL 60093
8beds
7,168sqft
Single Family Residence
Built in 1938
1.46 Acres Lot
$3,637,600 Zestimate®
$502/sqft
$6,976 Estimated rent
Home value
$3,637,600
$3.27M - $4.04M
$6,976/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: November 17, 2025 at 12:01am
Listing courtesy of:
Jena Radnay 312-925-9899,
@properties Christie's International Real Estate
Bought with:
Paige Dooley
Compass
Source: MRED as distributed by MLS GRID,MLS#: 12452300
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 8
- Bathrooms: 7
- Full bathrooms: 5
- 1/2 bathrooms: 2
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 (Hardwood)
- Level: Main
- Area: 315 Square Feet
- Dimensions: 21X15
Sitting room
- Features: Flooring (Carpet)
- Level: Second
- Area: 190 Square Feet
- Dimensions: 10X19
Heating
- Natural Gas
Cooling
- Central Air
Appliances
- Included: Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Stainless Steel Appliance(s), Wine Refrigerator
- Laundry: Upper Level, Sink
Features
- Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, High Ceilings, Special Millwork
- Flooring: Hardwood, Carpet
- Doors: French Doors, Panel Door(s)
- Windows: Drapes, Screens, Shutters, Window Treatments
- 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
Property
Parking
- Total spaces: 8
- Parking features: Asphalt, Circular Driveway, Garage Door Opener, Heated Garage, 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
- Other equipment: Sump Pump
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
Details
- Builder model: Colonial
Utilities & green energy
- Electric: Circuit Breakers, 200+ Amp Service
- Sewer: Public Sewer
- Water: Lake Michigan
Community & neighborhood
Security
- Security features: Security System, Closed Circuit Camera(s)
Community
- Community features: Curbs, Street Paved
Location
- Region: Winnetka
- Subdivision: Woodley Road
Other
Other facts
- Listing terms: Conventional
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 1/26/2026 | Sold | $3,600,000$502/sqft |
Source: Public Record Report a problem | ||
| 11/14/2025 | Sold | $3,600,000-10%$502/sqft |
Source:  MRED as distributed by MLS GRID #12452300 Report a problem | ||
| 10/6/2025 | Contingent | $3,999,900$558/sqft |
Source: MRED as distributed by MLS GRID #12452300 Report a problem | ||
| 9/3/2025 | Price change | $3,999,900-5.9%$558/sqft |
Source: MRED as distributed by MLS GRID #12452300 Report a problem | ||
| 6/16/2025 | Listed for sale | $4,250,000$593/sqft |
Source: MRED as distributed by MLS GRID #12394393 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2023 | $35,328 +5.3% | $193,977 |
| 2022 | $33,546 -34.2% | $193,977 -24.4% |
| 2021 | $50,985 +2.5% | $256,531 |
Find assessor info on the county website
Neighborhood: 60093
Nearby schools
GreatSchools rating
- 9/10Avoca West Elementary SchoolGrades: K-5Distance: 1.5 mi
- 8/10Marie Murphy SchoolGrades: PK,6-8Distance: 0.6 mi
- NANew Trier Township H S NorthfieldGrades: 9Distance: 1 mi
Schools provided by the listing agent
- Elementary: Avoca West Elementary School
- Middle: Marie Murphy School
- High: New Trier Twp H.S. Northfield/Wi
- District: 37
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
$3,637,600
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$3,637,600
- Illinois
- Cook County
- Winnetka
- 60093
- 5 Woodley Rd