5 Woodley Rd

Winnetka, IL 60093

$3,600,000
Last Sold Price
8
Beds
7,168 Sq. Ft.
$502 / Sq. Ft.
7,168
Sq. Ft.
$502
per Sq. Ft.
Closed 11/14/25
Closed 11/14/25
a front view of a house with a yard and potted plants
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a living room with furniture and a fireplace
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a kitchen with granite countertop a sink stainless steel appliances and cabinets
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a living room with furniture and a fireplace
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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...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.
  1. Listed by Jena Radnay • @properties Christie's International Real Estate
    P: (312)-925-9899 C: (312)-925-9899 jradnay@atproperties.com;jradnay@atproperties.com

Sold By Compass

Property Details for 5 Woodley Road

Area
Winnetka
Subdivision
Woodley Road
Township
New Trier
Ownership
Fee Simple
Num Of Garage Spaces
3.0
Num Of Parking Spaces
8.0
Parking Included in Price
Yes
Air Conditioning Type
Central Air
LISTING UPDATED: 11/17/2025 02:01 AM

Property Details for 5 Woodley Road

StatusClosed
MLS #12452300
Days on Market30
Taxes$35,328 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeDetached Single / 3 Stories
Year Built1938
Lot Size1.46 AC / 63,466 SF
CountyCook County

Location

Add your commute

Building Information for 5 Woodley Road

Stories-Year Built1938Building Size-Lot Size1.46 AC / 63,466 SF

Payment Calculator

$20,490 per month

30 year fixed, 6.15% Interest

Principal and Interest

$17,546

Property Taxes

$2,944

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 5 Woodley Road

General Information
School Information
  • Elementary School District: 37
  • Elementary School: Avoca West Elementary School
  • Jr High Middle School: Marie Murphy School
  • High School District: 203
  • High School: New Trier Twp H.S. Northfield/Wi
  • Middle Or Junior School District: 37
Addtl Parking Information
  • Parking Details: Asphalt, Circular Driveway, Garage Door Opener, Heated Garage, Yes, Garage Owned, Attached, Driveway, Owned, Garage
Location and General Information
  • Front Exposure: North, South, East, West
Taxes and HOA Information
  • Association Fee Frequency: Not Applicable
  • Association Fee Includes: None
  • Master Association Fee($): 3500
  • Master Association Fee: Yes
  • Master Association Fee Frequency: Yearly
  • Additional Parcels: No
Property Information
Interior Features
  • Interior Property Features: Wet Bar, Built-in Features, Walk-In Closet(s), Bookcases, High Ceilings, Special Millwork
  • Num Of Rooms: 17
  • Bedrooms Total: 8
  • Bedrooms (Below Grade): 0
  • Community Features: Curbs, Street Paved
  • Attic: Finished
  • Bath Amenities: Separate Shower,Double Sink,Soaking Tub
  • Fireplace Features: Wood Burning
  • Basement Type: Finished, Partial
  • Bedrooms Possible: 8
  • Air Conditioning: Central Air
  • Electric: Circuit Breakers, 200+ Amp Service
  • Flooring: Hardwood, Carpet
  • Dining Room: Separate
  • Basement Bathrooms: No
  • Fireplace Location: Family Room,Living Room,Basement,Other,Bedroom
  • Room Type: Bedroom 5, Bedroom 6, Bedroom 7, Bedroom 8, Foyer, Sitting Room, Heated Sun Room, Recreation Room, Bonus Room
  • Num of Baths: 5.2
Exterior Features
  • Fencing: Fenced
  • Type: 3 Stories
Utilities / Equipment
  • Sewer: Sewer-Public
  • Water: Lake Michigan
  • Appliances: Range, Microwave, Dishwasher, High End Refrigerator, Freezer, All Stainless Steel Kitchen Appliances, Wine Cooler/Refrigerator
  • Other Equipment: Security System, Sump Pump, Security Cameras
Property/Lot Information
  • Exterior Property Features: Hot Tub
  • New Construction YN: No
  • Rebuilt: No
  • Rehabilitated: Yes
  • Rehab Year: 2001
  • Built Before 1978: Yes
  • Age: 81-90 Years
  • Type Detached: 3 Stories
  • Total Sq Ft: 0
  • Aprox Total Finished Sq Ft: 0
  • Total Finished and Unfin Sq Ft: 0
  • Lot Description: Landscaped Professionally, Mature Trees
  • Lot Size: 1.0-1.99 Acres
  • Lot Dimensions: 237.5 X 64
  • Other Structures: Outdoor Kitchen
  • Waterfront: No
  • Disability Access and/or Equipped: No
  • Construction: Brick
  • Roof Type: Slate
  • Foundation Details: Concrete Perimeter
  • General Information: None
  • Living Area Source: Other
Property and Assessments
  • Public Document Count: 3
  • Document Date: 2025-08-21T17:05:44
  • Photos Count: 48
  • Rural: N
  • OpenHouse Count: 0
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
  • Virtual Tour Date: 09-03-2025
Room Information
Master Bedroom Information
  • Master Bedroom Level: Second
  • Room Type: Master Bedroom
  • Master Bedroom Bath: Full, Double Sink, Tub & Separate Shwr
  • Master Bedroom Dimensions: 22X19
Bedroom #2 Information
  • 2nd Bedroom Level: Second
  • Room Type: Bedroom 2
  • Bedroom #2 Room Dimensions: 20X18
Bedroom #3 Information
  • 3rd Bedroom Level: Second
  • Room Type: Bedroom 3
  • Bedroom #3 Room Dimensions: 19X16
Bedroom #4 Information
  • 4th Bedroom Level: Second
  • Room Type: Bedroom 4
  • Bedroom #4 Room Dimensions: 16X16
Bedroom #5 Information
  • 5th Bedroom Level: Second
  • Room Type: Bedroom 5
  • Bedroom #5 Room Dimensions: 13X17
Bedroom #6 Information
  • 6th Bedroom Level: Third
  • Room Type: Bedroom 6
  • Bedroom #6 Room Dimensions: 20X11
Bedroom #7 Information
  • 7th Bedroom Level: Third
  • Room Type: Bedroom 7
  • Bedroom #7 Room Dimensions: 15X11
Bedroom #8 Information
  • 8th Bedroom Level: Third
  • Room Type: Bedroom 8
  • Bedroom #8 Room Dimensions: 16X11
Dining Room Information
  • Dining Room Level: Main
  • RoomType_DR: Dining Room
  • Dining Room Dimensions: 21X16
Family Room Information
  • Family Room Level: Main
  • RoomType_FR: Family Room
  • Family Room Dimensions: 22X26
Kitchen Information
  • Kitchen Level: Main
  • RoomType_KT: Kitchen
  • Kitchen Dimensions: 25X19
Laundry Information
  • Laundry Level: Second
  • Room Type: Laundry
  • Laundry Dimensions: 11X9
Living Room Information
  • Living Room Level: Main
  • Room Type: Living Room
  • Living Room Dimensions: 32X19
Foyer Information
  • Room Level: Main
  • Room Type: Foyer
  • Dimensions: 13X22
Recreation Room Information
  • Room Level: Basement
  • Room Type: Recreation Room
  • Dimensions: 45X22
Heated Sun Room Information
  • Room Level: Main
  • Room Type: Heated Sun Room
  • Dimensions: 18X15
Bonus Room Information
  • Room Level: Third
  • Room Type: Bonus Room
  • Dimensions: 39X21
Sitting Room Information
  • Room Level: Second
  • Room Type: Sitting Room
  • Dimensions: 10X19

Property History for 5 Woodley Road

DateEvent & SourcePriceAppreciation
Nov 14, 2025

Sold

MRED #12452300

$3,600,000—
Oct 2, 2025

Pending

MRED #12452300

—
Oct 2, 2025

Contingent

MRED #12452300

—
Sep 3, 2025

Listed (Active)

MRED #12452300

$3,999,900—
Sep 3, 2025

Cancelled

MRED #12394393

$4,250,000—
Jun 16, 2025

Cancelled

MRED #12378929

$4,250,000—
Jun 16, 2025

Listed (Active)

MRED #12394393

$4,250,000—
Jun 4, 2025

Contingent

MRED #12378929

—
May 30, 2025

Cancelled

MRED #12287968

$4,499,900—
May 30, 2025

Listed (Active)

MRED #12378929

$4,250,000—
Feb 28, 2025

Listed (Active)

MRED #12287968

$4,499,900—
DateEvent & SourcePrice
11/14/2025

Sold

MRED #12452300

$3,600,000
10/02/2025

Pending

MRED #12452300

—
10/02/2025

Contingent

MRED #12452300

—
09/03/2025

Listed (Active)

MRED #12452300

$3,999,900
09/03/2025

Cancelled

MRED #12394393

$4,250,000
06/16/2025

Cancelled

MRED #12378929

$4,250,000
06/16/2025

Listed (Active)

MRED #12394393

$4,250,000
06/04/2025

Contingent

MRED #12378929

—
05/30/2025

Cancelled

MRED #12287968

$4,499,900
05/30/2025

Listed (Active)

MRED #12378929

$4,250,000
02/28/2025

Listed (Active)

MRED #12287968

$4,499,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5 Woodley Road

Taxable ValueLand$96,977Additions$97,000Total$193,977
Tax Record2023$35,328 ($2,944 / month)
Home Facts
Beds5Baths4Total Finished SqFt7,168 SqFtAbove Grade Finished SqFt7,168 SqFtStories2Lot Size63,467 SqFtStyleSingle Family ResidenceYear Built1938CountyCOOKAPN05-29-101-007Fireplace TypeHas Fireplace

Schools near 5 Woodley Road

This home is within Avoca School District 37.
Rating
School
Type
Grades
Distance
Avoca West Elementary School
Public - K to 5
Marie Murphy School
Public - 6 to 8
New Trier Township H S Northfield
Public - 9
New Trier Township H S Winnetka
Public - 10 to 12
Rating
School
Distance
Avoca West Elementary School
PublicK to 5

Marie Murphy School
Public6 to 8

New Trier Township H S Northfield
Public9

New Trier Township H S Winnetka
Public10 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Based on information from one of the following Multiple Listing Services: Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 11/17/2025 02:01 AM. 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.