$3,750,000 SOLD Feb 2026
Listed at $3,999,900

145 Woodley Road, Winnetka, IL 60093

Closed
5 beds 5.5 baths 7,548 sqft (other) Built 1957 Residential MLS #MRD12542155 1 days on market
Listing courtesy of @properties Christie's International Real Estate · 847-881-0200 · MLS #MRD12542155 · Status: Closed
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.

Property details

Interior

Appliances
Double Oven, Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Disposal, Stainless Steel Appliance(s)
Interior features
Vaulted Ceiling(s), Hot Tub, Dry Bar, 1st Floor Bedroom, Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork
Flooring
Hardwood, Carpet
Fireplaces
4
Fireplace details
Wood Burning, Gas Starter
Basement
Finished, Partial
Laundry
Upper Level, Gas Dryer Hookup, Sink
Additional rooms
Bedroom 5, Play Room, Den, Attic, Breakfast Room, Office, Sitting Room, Sun Room, Recreation Room
Total rooms
16

Building & exterior

Style
Colonial
Age
61-70 Years
Exterior
Cedar, Shake Siding, Stone, Wood Siding
Exterior features
Hot Tub, Lighting
Roof
Shake
Foundation
Concrete Perimeter
Windows
Screens, Skylight(s), Drapes
Patio & porch
Patio, Porch
Other structures
None
Exposure
North,South,East,West

Parking

Garage spaces
4
Total spaces
12
Parking details
Asphalt, Brick Driveway, Garage Door Opener, Yes, Garage Owned, Attached, Driveway, Owned, Garage

Lot & location

Lot dimensions
187 x 346
Lot description
Landscaped, Mature Trees, Garden
Township
New Trier
County
Cook

Utilities

Heating
Natural Gas
Cooling
Central Air, Zoned
Water
Lake Michigan
Sewer
Public Sewer
Electricity
Circuit Breakers, Fuses, 200+ Amp Service
Equipment
Security System, Sump Pump, Backup Sump Pump;

HOA & community

Assessment includes
None
Community features
Curbs, Street Paved

Schools

Elementary
Avoca West Elementary School (37)
Junior high
Marie Murphy School (37)
High school
New Trier Twp H.S. Northfield/Wi (203)

Taxes & terms

Annual taxes
$37,614 (2024)
Parcel number (PIN)
05291030180000
PIN
05291030180000
Ownership
Fee Simple
Possession
Closing
Special conditions
None
Listed
1/12/2026
Sold
2/24/2026
Sold price
$3,750,000
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