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Winnetka, IL, 60093 • 60093 • Cook County
$497/sqft
5Beds
7Baths
7,548Sqft
1.5 acLot
1957Built
Colonial Style
Built 1957 · 69 years of history
Outdoor Living
Patio · Porch
4 Fireplaces
Wood Burning · Gas Starter · Family Room · Living Room · Basement · Den/Library
4-Car Garage
Asphalt · Brick Driveway · Garage Door Opener · Yes · Garage Owned · Attached · Driveway · Owned · Garage
Premium Finishes
Walk-In Closet(s)
Hardwood Floors
Quality flooring throughout
Demand and pricing signals for this listing
183 views
People checking out this listing
3 saves
Buyers have saved this home
44 days on market
Established listing
$497/sqft
Price per square foot
Single Family · Built 1957
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.
Standout features identified
Our analysis highlights sparkling pool oasis, sun-drenched interiors, and expansive bluestone patios as key attractions of this home.
Based on current rates
Est. 6.75% rate · 30yr fixed · $3,000,000 loan
Full calculator →Key facts and listing details
19 categories of property features
19 rooms detailed
Master Bedroom
SecondBedroom2
SecondBedroom3
SecondBedroom4
SecondBedroom5
SecondOther
Market data and value estimates
3 schools rated nearby
Winnetka, IL, 60093
5 events
25 years of records
Local context around this listing
Winnetka, IL • Cook County
Nearby cities
Nearby zip codes
Based on information submitted to the MLS GRID as of 2026. 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. [Click here for more information](/mls-disclaimers/#17)
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