Date
Details
Price
Change
Source
1/12/2026
Listed
$3,999,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/75
$3,999,900 Contingent
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Property Description
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.
Full Property Details
Full Property Details for 145 Woodley Rd
General
- Price: $3,999,900
- HOA FEE: $3,500
- Taxes: $37,614 (2024)
- Status: Contingent
- Type: Single Family
- Source: MRED
- MLS ID: 12542155
- Updated: 1/12/2026
- Added to Site: 5 day(s) ago
Rental Information
- Complex Features: Curbs, Street Paved
Interior
- Basement: Finished, P
- 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
- Fireplace: Yes
- Number of Fireplaces: 4
- Fireplace(s): Family Room, Living Room, Basement, Den/Library, Wood-Burning, Gas Starter
- Appliances: Double Oven, Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Disposal, Stainless Steel Appliance(s)
- Flooring: Hardwood, Carpet
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 5
- Half Bathrooms: 2
- Bathroom Features: Separate Shower
Bedrooms
- Total Bedrooms: 5
Additional Information
- Equipment: Security System, Sump Pump, Backup Sump Pump
Exterior
- Exterior Features: Hot Tub, Lighting
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 4
- Total Spaces: 12
- Parking Features: Asphalt, Brick Driveway, Garage Door Opener, Yes, Garage Owned, Attached, Driveway, Owned, Garage
Location
- Area: Winnetka
- County: Cook
- Township: New Trier
- Driving Directions: Locust (south of Hill) to southern most entrance of Woodley
School Information
- School District: 37
- Elem School District: 37
- Midd School District: 37
- High School District: 203
- Elementary School: Avoca West Elementary School
- Middle School: Marie Murphy School
- High School: New Trier Twp H.S. Northfield/Wi
- Private School: New Trier Twp H.S. Northfield/Wi
Community
- Assoc. Fees Include: None
Heating & Cooling
- Cooling Type: Central Air Conditioning, Zoned
- Heating Type: Natural Gas
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan
Structural Information
- Architectural Info: Colonial
- Architectural Style: Colonial
- Construction: Cedar, Shake Siding, Stone, Wood Siding
- Exterior Const.: Cedar, Shake Siding, Stone, Wood Siding
- Basement: Yes
- Basement Desc.: Finished, Partial
- Foundation: Concrete Perimeter
- Roof: Shake
- Windows: Screens, Skylight(s), Drapes
- Sub-Flooring: Hardwood, Carpet
- Square Feet: 7,548
- Sq. Ft. Source: Other
- Year Built: 1957
- Built Before 1978: Yes
- Remodeled/Updated: 2000
Additional Structures
- Other Structures: None
Lot Features
- Lot Size (Acres): 1.462
- Lot Size Range: 1.0 to 1.99 Acres
- Lot Dimensions: 187 x 346
- Fence: Yes
- Lot Features: Landscaped, Mature Trees, Garden
- Fencing (Description): Fenced
Financial Considerations
- Master Assoc. Fee: $3,500
- Assoc Fee Desc.: 3500
- Transfer Fees: $3,500
- Other Assoc Fees: $3,500
- Parking Included: Yes
- Assessment Year: 1957
- Tax Amount: $37,614.17
- Tax Year: 2024
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 5291030180000
Listed by @properties Christie's International Real Estate
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Schools
Schools serving 145 Woodley Rd
School Districts:Avoca School District 37, New Trier Township High School District 203
| Name | Grades | Distance |
|---|---|---|
Marie Murphy School 2921 Illinois Road, Wilmette, IL 60091 | 6-8 | 0.2 mi |
Avoca West Elementary School 235 Beech Drive, Glenview, IL 60025 | K-5 | 1.2 mi |
New Trier Township H S Northfield 7 North Happ Road, Northfield, IL 60093 | 9- | 1 mi |
New Trier Township H S Winnetka 385 Winnetka Avenue, Winnetka, IL 60093 | 10-12 | 1.4 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 145 Woodley Rd
Tax History
Tax History for 145 Woodley Rd
Year
Property Taxes
Change
Tax Assessment
Change
2023
$36,243
2%
$204,969
—
2022
$35,447
-23%
$204,969
-12%
2021
$46,315
3%
$233,034
—
2020
$45,175
2%
$233,034
-9%
2019
$44,199
-8%
$256,082
-4%
2018
$48,014
2%
$265,398
—
2017
$46,895
—
$265,398
—
2016
$46,875
-10%
$265,398
—
2015
$51,889
2%
$266,072
—
2014
$50,850
5%
$266,072
—
2013
$48,327
6%
$266,072
-1%
2012
$45,487
—
$269,330
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 145 Woodley Rd
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- Single Family
- Active
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- 7Beds
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- Single Family
- Active
- Updated 4 days ago
- 5Beds
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- Single Family
- Closed
- 6Beds
- 7Total Baths
- 7,500Sq. Ft.
Listed by Matan Aharoni
145 Woodley Road, Winnetka, IL 60093 (MLS# 12542155) is a Single Family property with 5 bedrooms, 5 full bathrooms and 2 partial bathrooms. 145 Woodley Road is currently listed for $3,999,900 and was received on January 12, 2026. Want to learn more about 145 Woodley Road? Do you have questions about finding other Single Family real estate for sale in Winnetka? You can browse all Winnetka real estate or contact a Coldwell Banker agent to request more information.