145 Woodley Road, Winnetka, IL 60093
Local realty services provided by:CENTURY 21 Circle
Listed by: jena radnay
Office: @properties christie's international real estate
MLS#:12542155
Source:MLSNI
Price summary
- Price:$3,999,900
- Price per sq. ft.:$529.93
About this home
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.
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Home facts
- Year built:1957
- Listing ID #:12542155
- Added:1 day(s) ago
- Updated:January 12, 2026 at 10:44 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:7
- Full bathrooms:5
- Half bathrooms:2
- Living area:7,548 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Natural Gas
Structure and exterior
- Roof:Shake
- Year built:1957
- Building area:7,548 sq. ft.
- Lot area:1.46 Acres
Schools
- High school:New Trier Twp H.S. Northfield/Wi
- Middle school:Marie Murphy School
- Elementary school:Avoca West Elementary School
Utilities
- Water:Lake Michigan
- Sewer:Public Sewer
Finances and disclosures
- Price:$3,999,900
- Price per sq. ft.:$529.93
- Tax amount:$37,614 (2024)
Copyright 2026 Midwest Real Estate Data LLC. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Midwest Real Estate Data LLC. Listing information is deemed reliable but not guaranteed.New listings near 145 Woodley Road
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