145 Woodley, Winnetka IL 60093
$3,999,900

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Property Description

If My Best Friend's Wedding had a sequel...it would be filmed right here. This coastal Colonial estate set on 1.4 acres of lush, manicured grounds on premier Woodley Road offers the ultimate backdrop for timeless North Shore living. Elegant, welcoming, and effortlessly cinematic, it's the kind of home where every day feels like a scene straight out of a movie. A rare generational opportunity, this pristinely cared-for home features over 7,500 square feet of finished space & a floor plan that flows effortlessly from one sunlit room to the next. Wonderful features include a Chef's kitchen that opens to a great room, endless bluestone patios, vibrant gardens, and a sparkling pool oasis, creating an entertainer's dream. Step inside the gracious, light-filled foyer, where your eye is immediately drawn through the elegant living room picture window to the breathtaking private grounds creating instant tranquility. Formal dining room flows gracefully into the heart of the home: an inviting Chef's kitchen where classic design meets casual comfort w/quality custom cabinetry, massive island with seating for 5 and separate breakfast area. Great room accented with skylights and oversized windows naturally brings the outside in. Get cozy around the FP framed by fine built-ins creating the perfect place to unwind as this space is so inviting. To the other end of large first floor is the formal office, the ultimate private retreat with rich wood paneling & built-ins and opens to a cozy sitting room. Best yet, a spectacular sunroom with a full bath and hot tub solarium overlooking the beautiful outdoors. Expansive 2nd floor with five bedrooms including a luxury primary suite with a spacious bedroom, massive walk-in closet & crisp, sunlit white spa bath with dual vanities, soaking tub, and separate shower. 2 family size beds with ensuite neutral baths and the other 2 beds share a hall bath. Full 2nd floor laundry and awesome large play/rec space allows for many other options. Lofted finished space on 3rd level is now storage but can be studio/ 2nd office. The back staircase leads to spacious lower level with second rec room. Completing this exceptional home is a rare 4-car attached garage and an oversized mudroom/utility space waiting for your design touch. Surrounded by enchanted private gardens, sun-drenched interiors, and expansive bluestone patios, 145 Woodley Road captures the essence of quintessential North Shore living-so cinematic, it feels like a movie set... yet it's real, and waiting for you.

Features & Information

Key Details

  • List Price $3,999,900
  • Property Taxes $37,614.17
  • Square Feet 7548
  • Price/ Sq. Ft. $529.93
  • Year Built 1957
  • Parking Type Garage,Space/s
  • Status Pending

Rooms

  • Total Rooms 16
  • Basement P
  • Master Bedroom

  • Master Bath F
  • Room Size 20X17
  • Bedroom 2

  • Room Size 19X14
  • Floor Level 2nd Level
  • Flooring Carpet
  • Bedroom 3

  • Room Size 20X15
  • Floor Level 2nd Level
  • Flooring Carpet
  • Bedroom 4

  • Room Size 13X12
  • Floor Level 2nd Level
  • Flooring Carpet
  • Living Room

  • Room Size 28X20
  • Floor Level Main Level
  • Flooring Hardwood
  • Family Room

  • Room Size 26X20
  • Floor Level Main Level
  • Dining Room

  • Room Size 20X14
  • Floor Level Main Level
  • Flooring Hardwood
  • Kitchen

  • Room Size 25X20
  • Kitchen Type Island,Pantry-Closet,Breakfast Room,Country Kitchen,Custom Cabinetry
  • Floor Level Main Level
  • Flooring Hardwood
  • Basement

  • Basement Description Finished
  • Bathroom(s) in Basement N

Additional Rooms

  • Additional Room 1

  • Additional Room 1 Name 5th Bdrm
  • Additional Room Size 13X12
  • Additional Room Level 2nd Level
  • Additional Room Flooring Carpet
  • Additional Room 2

  • Additional Room 2 Name Playroom
  • Additional Room Size 45X18
  • Additional Room Level 2nd Level
  • Additional Room Flooring Carpet

Interior Features

  • Appliances

  • Appliances Included Oven-Double, Oven/Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Disposal, All Stainless Steel Kitchen Appliances
  • Heating & Cooling

  • Heating Type Gas
  • Air Conditioning Central Air, Zoned
  • Fireplace

  • # of Fireplaces 4
  • Type of Fireplace Wood Burning,Gas Starter

Exterior Features

  • Building Information

  • Age of Building 61-70 Years
  • Exterior Construction Cedar,Shakes,Stone,Wood Siding
  • Foundation Concrete
  • Parking

  • Parking Garage,Space/s
  • # of Cars 12
  • Garage Features Garage Door Opener(s)
  • Parking Details Driveway

Location

  • County Cook
  • Township New Trier
  • Corporate Limits Unincorporated
  • Directions to Property Locust (south Of Hill) To Southern Most Entrance Of Woodley
  • Schools

  • Elementary School District 37
  • School Name Avoca West Elementary Sch
  • Junior High District 37
  • School Name Marie Murphy School
  • High School District: 203
  • School Name New Trier Twp H.S. Northf
  • Property Taxes

  • Tax 37614.17
  • Tax Year 2024
  • Tax Exemptions Homeowner,Senior
  • Parcel Identification Number 05291030180000
  • Lot Information

  • Dimensions 187 x 346
  • Acreage 1.462

Utilities

  • Sewer Sewer-Publ

Listed by: @properties Christie's International Real Estate | Phone: 847.881.0200
Source: MRED as distributed by MLS GRID

Based on information submitted to the MLS GRID as of 2/20/2026 6:32 PM. 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.

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