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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.
| DAYS ON MARKET | 1 | LAST UPDATED | 1/12/2026 |
|---|---|---|---|
| YEAR BUILT | 1957 | COMMUNITY | Winnetka |
| GARAGE SPACES | 4.0 | COUNTY | Cook |
| STATUS | Conditional | PROPERTY TYPE(S) | Single Family |
| School District | New Trier Twp H.S. Northfield/Wi |
|---|---|
| Elementary School | Avoca West Elementary School |
| Jr. High School | Marie Murphy School |
| High School | New Trier Twp H.S. Northfield/Wi |
| ADDITIONAL DETAILS | |
| AIR | Central Air, Zoned |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Disposal, Double Oven, Freezer, Microwave, Range, Refrigerator, Stainless Steel Appliance(s), Washer |
| AREA | Winnetka |
| BASEMENT | Finished, Partial, Sump Pump, Yes |
| CONSTRUCTION | Cedar, Shake Siding, Stone, Wood Siding |
| EXTERIOR | Lighting |
| FIREPLACE | Yes |
| GARAGE | Attached Garage, Yes |
| HEAT | Natural Gas |
| INTERIOR | Bookcases, Built-in Features, Dry Bar, Vaulted Ceiling(s), Walk-In Closet(s) |
| LOT | 1.462 acre(s) |
| LOT DESCRIPTION | Garden, Landscaped |
| LOT DIMENSIONS | 187 x 346 |
| PARKING | Asphalt, Garage Door Opener, Attached, Driveway, Garage |
| POOL DESCRIPTION | In Ground |
| SEWER | Public Sewer |
| STYLE | Colonial |
| TAXES | 37614.17 |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision.
Copyright 2026 MRED. All rights reserved.
This IDX solution is (c) Diverse Solutions 2026.