145 Woodley Road Winnetka, IL $ 3,999,900
145 Woodley Road
$ 3,999,900
Share Save

145 Woodley Road

Winnetka, IL, 60093
$ 3,999,900
Bedrooms5 Baths5.2 Sq 7,548

Monthly Estimate*

$ 24,628

145 Woodley Road, Winnetka, IL 60093 - Image 1
145 Woodley Road, Winnetka, IL 60093 - Image 2
145 Woodley Road, Winnetka, IL 60093 - Image 3
145 Woodley Road, Winnetka, IL 60093 - Image 4
145 Woodley Road, Winnetka, IL 60093 - Image 5
145 Woodley Road, Winnetka, IL 60093 - Image 6
145 Woodley Road, Winnetka, IL 60093 - Image 7
145 Woodley Road, Winnetka, IL 60093 - Image 8
145 Woodley Road, Winnetka, IL 60093 - Image 9
145 Woodley Road, Winnetka, IL 60093 - Image 10
145 Woodley Road, Winnetka, IL 60093 - Image 11
145 Woodley Road, Winnetka, IL 60093 - Image 12
145 Woodley Road, Winnetka, IL 60093 - Image 13
145 Woodley Road, Winnetka, IL 60093 - Image 14
145 Woodley Road, Winnetka, IL 60093 - Image 15
145 Woodley Road, Winnetka, IL 60093 - Image 16
145 Woodley Road, Winnetka, IL 60093 - Image 17
145 Woodley Road, Winnetka, IL 60093 - Image 18
145 Woodley Road, Winnetka, IL 60093 - Image 19
145 Woodley Road, Winnetka, IL 60093 - Image 20
145 Woodley Road, Winnetka, IL 60093 - Image 21
145 Woodley Road, Winnetka, IL 60093 - Image 22
145 Woodley Road, Winnetka, IL 60093 - Image 23
145 Woodley Road, Winnetka, IL 60093 - Image 24
145 Woodley Road, Winnetka, IL 60093 - Image 25
145 Woodley Road, Winnetka, IL 60093 - Image 26
145 Woodley Road, Winnetka, IL 60093 - Image 27
145 Woodley Road, Winnetka, IL 60093 - Image 28
145 Woodley Road, Winnetka, IL 60093 - Image 29
145 Woodley Road, Winnetka, IL 60093 - Image 30
145 Woodley Road, Winnetka, IL 60093 - Image 31
145 Woodley Road, Winnetka, IL 60093 - Image 32
145 Woodley Road, Winnetka, IL 60093 - Image 33
145 Woodley Road, Winnetka, IL 60093 - Image 34
145 Woodley Road, Winnetka, IL 60093 - Image 35
145 Woodley Road, Winnetka, IL 60093 - Image 36
145 Woodley Road, Winnetka, IL 60093 - Image 37
145 Woodley Road, Winnetka, IL 60093 - Image 38
145 Woodley Road, Winnetka, IL 60093 - Image 39
145 Woodley Road, Winnetka, IL 60093 - Image 40
145 Woodley Road, Winnetka, IL 60093 - Image 41
145 Woodley Road, Winnetka, IL 60093 - Image 42
145 Woodley Road, Winnetka, IL 60093 - Image 43
145 Woodley Road, Winnetka, IL 60093 - Image 44
145 Woodley Road, Winnetka, IL 60093 - Image 45
145 Woodley Road, Winnetka, IL 60093 - Image 46
145 Woodley Road, Winnetka, IL 60093 - Image 47
145 Woodley Road, Winnetka, IL 60093 - Image 48
145 Woodley Road, Winnetka, IL 60093 - Image 49
145 Woodley Road, Winnetka, IL 60093 - Image 50
145 Woodley Road, Winnetka, IL 60093 - Image 51
145 Woodley Road, Winnetka, IL 60093 - Image 52
145 Woodley Road, Winnetka, IL 60093 - Image 53
145 Woodley Road, Winnetka, IL 60093 - Image 54
145 Woodley Road, Winnetka, IL 60093 - Image 55
145 Woodley Road, Winnetka, IL 60093 - Image 56
145 Woodley Road, Winnetka, IL 60093 - Image 57
145 Woodley Road, Winnetka, IL 60093 - Image 58
145 Woodley Road, Winnetka, IL 60093 - Image 59
145 Woodley Road, Winnetka, IL 60093 - Image 60
145 Woodley Road, Winnetka, IL 60093 - Image 61
145 Woodley Road, Winnetka, IL 60093 - Image 62
145 Woodley Road, Winnetka, IL 60093 - Image 63
145 Woodley Road, Winnetka, IL 60093 - Image 64
145 Woodley Road, Winnetka, IL 60093 - Image 65
145 Woodley Road, Winnetka, IL 60093 - Image 66
145 Woodley Road, Winnetka, IL 60093 - Image 67
145 Woodley Road, Winnetka, IL 60093 - Image 68
145 Woodley Road, Winnetka, IL 60093 - Image 69
145 Woodley Road, Winnetka, IL 60093 - Image 70
145 Woodley Road, Winnetka, IL 60093 - Image 71
145 Woodley Road, Winnetka, IL 60093 - Image 72
145 Woodley Road, Winnetka, IL 60093 - Image 73
145 Woodley Road, Winnetka, IL 60093 - Image 74
145 Woodley Road, Winnetka, IL 60093 - Image 75
View a Virtual Tour

Single Family Home for sale in Winnetka, IL

for $3,999,900 with 5 bedrooms and 5 full baths, 2 half baths. This 7,548 square foot home was built in 1957 on a lot size of 1.462.

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.

See more

Single Family Contingent

Price

$ 3,999,900

Bedrooms

5

Full Bath

5

Half Bath

2

Property Type

Single Family

Taxes

$ 37,614

Style

Colonial

Lot Size

1.462

Year Built

1957

Town/City

Winnetka

County/Region

Cook

MLS | Web ID

12542155

Features
General
Living Area 7548
Sewer Public Sewer
Heating Natural Gas
Cooling Central Air Zoned
Possession Closing
Roof Shake
Appliances Double Oven Range Microwave Dishwasher Refrigerator Freezer Washer Disposal Stainless Steel Appliance(s)
Garage Spaces 4
Association Fee Includes None
Architectural Style Colonial
Construction Materials Cedar Shake Siding Stone Wood Siding
Year Built 1957
Electric Circuit Breakers Fuses 200+ Amp Service
Township New Trier
Tax Year 2024
Ownership Fee Simple
Community Features Curbs Street Paved
Assoc Fee Paid Per Not Applicable
County Cook
New Construction N
Property Type Residential Detached Single
Contingency Attorney/Inspection
Other Structures None
Total Rooms 16
Full Baths 5
Status Contingent
Directions Locust (south of Hill) to southern most entrance of Woodley
High School New Trier Twp H.S. Northfield/Wi
City Winnetka
High School District 203
MLS Area Winnetka
Elementary School Avoca West Elementary School
Tax Annual Amount 37614.17
Middle/Junior High School Marie Murphy School
Additional Parcels Y/N N
Virtual Tour https://hdph.dmwre.com/x2527012
Standard Status Active Under Contract
Middle/Junior School District 37
Elementary School District 37
See more
Interior
Interior Amenities Vaulted Ceiling(s) Hot Tub Dry Bar 1st Floor Bedroom Built-in Features Walk-In Closet(s) Bookcases Historic/Period Mlwk Special Millwork
Basement Finished Partial
Flooring Hardwood Carpet
Total Fireplaces 4
Fireplace Features Wood Burning Gas Starter
Half Baths 2
Laundry Features Upper Level Gas Dryer Hookup Sink
Total Bedrooms 5
Room Type Bedroom 5 Play Room Den Attic Breakfast Room Office Sitting Room Sun Room Recreation Room
Total Baths 7
Bedrooms Possible 5
Bathroom Separate Shower
See more
Exterior
Exterior Amenities Hot Tub Lighting
Parking Features Asphalt Brick Driveway Garage Door Opener Yes Garage Owned Attached Driveway Owned Garage
Lot Features Landscaped Mature Trees Garden
Water Source Lake Michigan
Total Parking 12
Foundation Details Concrete Perimeter
Lot Dimensions 187 x 346
Lot Size Acres 1.462
Waterfront Y/N N
Other Equipment Security System Sump Pump Backup Sump Pump;
See more
* Excluded Features
List By
@Properties Christie's International Real Estate

Broker

jradnay@atproperties.com;jradnay@atproperties.com

Email

Affordability Calculator

$27,763
Per Month
89%
11%
0%
Monthly Principal & Interest
$24,628
Monthly Property Taxes
$3,135
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
565834 Elementary School
567821 Middle School
New Trier Twp H.S. Northfield/Wi High School
Pricing History
DatePricePrice ChangeDescription
1/12/2026$3,999,900 Listed Price

Map


See all

145 Woodley Road, Winnetka, IL, 60093 is a Single Family Home for sale at $3,999,900 with 7,548 sqft and a lot size of 1.462. 145 Woodley Road has 5 bedrooms, 5.2 baths, and was built in 1957. The property's zip code is 60093 which is in Winnetka, IL