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Nikki Mayer
Hometown Real Estate
7700 W. Belmont Ave
Chicago , IL 60634
Phone:
888 317 9983
Fax:
773 664 0013
Mobile:
708 268 2313
infohometown@gmail.com

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145 Woodley Road
Winnetka, IL 60093
Cook, US
$3,999,900.00 listing calculator
Status: Contingent (For Sale)
Type: Residential
Size: 7,548 Sq. Ft.
Lot Size: 1.46 Acres
Year Built: 1957
Bedrooms: 5
Bathrooms: 7
MLS ID: 12542155


Overview
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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.

Courtesy Of: @properties Christie's International Real Estate


Feature Highlights


  • Built Before 1978

General Features


List Date:
01/12/2026

Public Schools


Elementary School:
Avoca West Elementar
High School:
New Trier Twp H.S. N

Interior Features


Living Area Source:
Other
Bedrooms Possible:
5
Bathrooms Full:
5
Rooms Total:
16

Exterior Features and Amenities


Lot Size Dimensions:
187 x 346
Parking Total:
12

Financial


Purchase Contract Date:
2026-01-12
Days On Market:
1
Tax Annual Amount:
$37,614.17
Tax Year:
2024

Other Features


Elementary School District:
37
High School District:
203
Middle Or Junior School District:
37
Age:
61-70 Years


Directions


Locust (south of Hill) to southern most entrance of Woodley

Availability Calendar


- Available - Unavailable

Rental Rates


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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of MRED LLC. Real Estate listings held by brokerage firms other than Hometown Real Estate are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is 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.
Data last updated: 2026-01-14
.

Copyright 2026 MRED LLC

The information presented here is deemed reliable, though not guaranteed.
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