Skip To Content

5 Woodley Road

Winnetka, IL 60093
  • $4,499,900
  • STATUS: Active
  • ON SITE: 81 Days
  • MLS #: 12287968
UPDATED: 39 min ago
$4,499,900
  • 8
    BEDS
  • 1.46
    ACRES
  • 5
    BATHS
  • 2
    1/2 BATHS
  • 7,168
    SQFT
  • $628
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1938
County:
Area:

School Information

Elementary School:
Middle School:
School District:
37

Description

An eternal architectural beauty set on prestigious Woodley Road, this stately, white-painted brick Colonial accented with black shutters never goes out of style. Nestled on over 1.4 acres of meticulously manicured grounds by Midwest Arbor, these 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a quintessential floor plan designed for modern life. 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 and 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 of 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. New 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.

Monthly Payment Calculator



© 2025 Midwest Real Estate Data LLC. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by MTP, MRED or Keller Williams Success Realty. Based on information submitted to the MRED as of 2025-05-21T06:58:05.827 UTC. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED 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. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Digital Millennium Copyright Act
www.lewkepartners.com/homes/160953469
Print Image

5 Woodley Road Winnetka, IL 60093

  • Price: $4,499,900
  • Status: Active
  • On Site: 81 Days
  • Updated: 39 min ago
  • MLS #: 12287968
8
Beds
5
Baths
2
½ Baths
1.46
Acres
7,168
SQFT
$628
$/SQFT
1938
Built
Neighborhood:
Woodley Road
County:
Cook
Area:
Cook
Elementary School:
Avoca West Elementary School
Middle School:
Marie Murphy School
High School:
New Trier Twp H.S. Northfield/Wi
School District:
37
Property Description
An eternal architectural beauty set on prestigious Woodley Road, this stately, white-painted brick Colonial accented with black shutters never goes out of style. Nestled on over 1.4 acres of meticulously manicured grounds by Midwest Arbor, these 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a quintessential floor plan designed for modern life. 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 and 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 of 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. New 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.
Exterior Features

Architectural Style Colonial Exterior Features Hot Tub Foundation Details Concrete Perimeter Is Parking Included In Price Yes Lot Features LandscapedMature Trees Lot Size 1.0-1.99 Acres Other Structures Outdoor Kitchen Parking Features AsphaltCircular DrivewayGarage Door OpenerHeated GarageOn SiteGarage OwnedAttachedDrivewayOwnedGarage Parking Total 8 Roof Slate Types 3 Stories Waterfront YN No

Interior Features

Appliances RangeMicrowaveDishwasherHigh End RefrigeratorFreezerStainless Steel Appliance(s)Wine Refrigerator Approximate Finished Sq Ft 0 Attic Finished Basement Bathrooms YN No Basement Details FinishedPartial Bathroom Separate ShowerDouble SinkSoaking Tub Bedrooms Below Grade 0 Bedrooms Total 8 Cooling Central Air Dining Room Separate Door Features French DoorsMirrored Closet Door(s) Fireplace Features Wood Burning Fireplace Location Family RoomLiving RoomBasementOtherBedroom Fireplaces Total 5 Flooring HardwoodCarpet Heating Natural Gas Interior Features Wet BarBuilt-in FeaturesWalk-In Closet(s)BookcasesHigh CeilingsSpecial Millwork Laundry Features Upper LevelGas Dryer HookupSink Room Type Bedroom 5Bedroom 6Bedroom 7Bedroom 8FoyerSitting RoomHeated Sun RoomRecreation RoomBonus Room Rooms Bedroom 5 (Second) Bedroom 6 (Third) Bedroom 7 (Third) Bedroom 8 (Third) Foyer (Main) Sitting Room (Main) Heated Sun Room (Main) Sitting Room (Second) Recreation Room (Basement) Bonus Room (Third) Bedroom 2 (Second) Bedroom 3 (Second) Bedroom 4 (Second) Dining Room (Main) Family Room (Main) Kitchen (Main) Laundry (Second) Living Room (Main) Master Bedroom (Second) Rooms Total 17 Total Sq Ft 0 Unfinished Sqft 0 Window Features Window Treatments

Property Features

Additional Parcels YN No Age 81-90 Years Assessor Square Footage 7168 Association Fee Frequency Not Applicable Association Fee Includes None Built Before1978 YN Yes Community Features CurbsStreet Paved Corporate Limits Winnetka Currently Leased No Disability Access And Or Equipped No Electric Circuit Breakers200+ Amp Service General Information None Master Association Fee Frequency Yearly Master Association Fee YN Yes Master Association Fees 3500 Mls Actual Status Active New Construction YN No Ownership Fee Simple Rebuilt YN No Rehab Year 2001 Rural No Sewer Public Sewer Special Listing Conditions None Tax Annual Amount 35327.92 Tax Year 2023 Township New Trier Type Detached Single Water Source Lake Michigan

Listing information © 2025 Midwest Real Estate Data LLC.
Listing provided courtesy of @properties Christie's International Real Estate: 847-881-0200.


© 2025 Midwest Real Estate Data LLC. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by MTP, MRED or Keller Williams Success Realty. Based on information submitted to the MRED as of 2025-05-21T06:58:05.827 UTC. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED 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. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Digital Millennium Copyright Act
 
https://bt-photos.global.ssl.fastly.net/mred/orig_boomver_2_12287968-1.jpg https://bt-photos.global.ssl.fastly.net/mred/orig_boomver_2_12287968-1.jpg https://bt-photos.global.ssl.fastly.net/mred/orig_boomver_2_12287968-1.jpg
Logo
Keller Williams Success Realty
43 E Crystal Lake Ave
Crystal Lake IL, 60014