145 Woodley Rd

Winnetka, IL 60093

$3,999,900
Price
5
Beds
7,548 Sq. Ft.
$530 / Sq. Ft.
7,548
Sq. Ft.
$530
per Sq. Ft.
Listed By @propertiesPending
Listed By @propertiesPending

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...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.
  1. Listed by Jena Radnay • @properties Christie's International Real Estate
    P: (312)-925-9899 C: (312)-925-9899 jradnay@atproperties.com;jradnay@atproperties.com

Property Details for 145 Woodley Road

Area
Winnetka
Township
New Trier
Ownership
Fee Simple
Num Of Garage Spaces
4.0
Num Of Parking Spaces
12.0
Parking Included in Price
Yes
Air Conditioning Type
Central Air, Zoned
Num of Interior Fireplaces
4
LISTING UPDATED: 02/06/2026 12:45 PM

Property Details for 145 Woodley Road

StatusPending
MLS #12542155
Days on Market1
Taxes$37,614 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeDetached Single / 3 Stories
Year Built1957
Lot Size1.46 AC / 63,684 SF
CountyCook County

Location

Add your commute

Building Information for 145 Woodley Road

Stories-Year Built1957Building Size-Lot Size1.46 AC / 63,684 SF

Payment Calculator

$22,629 per month

30 year fixed, 6.15% Interest

Principal and Interest

$19,495

Property Taxes

$3,135

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 145 Woodley Road

General Information
School Information
  • Elementary School District: 37
  • Elementary School: Avoca West Elementary School
  • Jr High Middle School: Marie Murphy School
  • High School District: 203
  • High School: New Trier Twp H.S. Northfield/Wi
  • Middle Or Junior School District: 37
Addtl Parking Information
  • Parking Details: Asphalt, Brick Driveway, Garage Door Opener, Yes, Garage Owned, Attached, Driveway, Owned, Garage
Location and General Information
  • Front Exposure: North, South, East, West
Taxes and HOA Information
  • Association Fee Frequency: Not Applicable
  • Association Fee Includes: None
  • Master Association Fee($): 3500
  • Master Association Fee: Yes
  • Master Association Fee Frequency: Yearly
  • Additional Parcels: No
Property Information
Interior Features
  • Interior Property Features: Vaulted Ceiling(s), Hot Tub, Dry Bar, 1st Floor Bedroom, Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork
  • Num Of Rooms: 16
  • Bedrooms Total: 5
  • Bedrooms (Below Grade): 0
  • Community Features: Curbs, Street Paved
  • Attic: Finished
  • Bath Amenities: Separate Shower
  • Fireplace Features: Wood Burning, Gas Starter
  • Basement Type: Finished, Partial
  • Bedrooms Possible: 5
  • Air Conditioning: Central Air, Zoned
  • Electric: Circuit Breakers, Fuses, 200+ Amp Service
  • Flooring: Hardwood, Carpet
  • Dining Room: Separate
  • Basement Bathrooms: No
  • Fireplace Location: Family Room,Living Room,Basement,Den/Library
  • Room Type: Bedroom 5, Play Room, Den, Attic, Breakfast Room, Office, Sitting Room, Sun Room, Recreation Room
  • Num of Baths: 5.2
Exterior Features
  • Fencing: Fenced
  • Patio And Porch Features: Patio, Porch
  • Pool Features: In Ground
  • Type: 3 Stories
Utilities / Equipment
  • Sewer: Sewer-Public
  • Water: Lake Michigan
  • Appliances: Oven-Double, Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Disposal, All Stainless Steel Kitchen Appliances
  • Other Equipment: Security System, Sump Pump, Backup Sump Pump;
Property/Lot Information
  • Exterior Property Features: Hot Tub, Lighting
  • New Construction YN: No
  • Rebuilt: No
  • Rehabilitated: Yes
  • Rehab Year: 2000
  • Built Before 1978: Yes
  • Age: 61-70 Years
  • Type Detached: 3 Stories
  • Total Sq Ft: 0
  • Aprox Total Finished Sq Ft: 0
  • Total Finished and Unfin Sq Ft: 0
  • Lot Description: Landscaped Professionally, Mature Trees, Garden
  • Lot Size: 1.0-1.99 Acres
  • Lot Size Source: Other
  • Lot Dimensions: 187 x 346
  • Other Structures: None
  • Waterfront: No
  • Disability Access and/or Equipped: No
  • Construction: Cedar, Shake Siding, Stone, Wood Siding
  • Roof Type: Shake
  • Foundation Details: Concrete Perimeter
  • General Information: None
  • Living Area Source: Other
  • Assessor Square Footage: 6719
Property and Assessments
  • Public Document Count: 3
  • Document Date: 2026-01-07T14:13:00
  • Photos Count: 75
  • Rural: N
  • OpenHouse Count: 1
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
Room Information
Master Bedroom Information
  • Master Bedroom Level: Second
  • Room Type: Master Bedroom
  • Master Bedroom Bath: Full, Double Sink, Tub & Separate Shwr
  • Master Bedroom Dimensions: 20X17
Bedroom #2 Information
  • 2nd Bedroom Level: Second
  • Room Type: Bedroom 2
  • Bedroom #2 Room Dimensions: 19X14
Bedroom #3 Information
  • 3rd Bedroom Level: Second
  • Room Type: Bedroom 3
  • Bedroom #3 Room Dimensions: 20X15
Bedroom #4 Information
  • 4th Bedroom Level: Second
  • Room Type: Bedroom 4
  • Bedroom #4 Room Dimensions: 13X12
Bedroom #5 Information
  • 5th Bedroom Level: Second
  • Room Type: Bedroom 5
  • Bedroom #5 Room Dimensions: 13X12
Dining Room Information
  • Dining Room Level: Main
  • RoomType_DR: Dining Room
  • Dining Room Dimensions: 20X14
Family Room Information
  • Family Room Level: Main
  • RoomType_FR: Family Room
  • Family Room Dimensions: 26X20
Kitchen Information
  • Kitchen Level: Main
  • RoomType_KT: Kitchen
  • Kitchen Dimensions: 25X20
Laundry Information
  • Laundry Level: Second
  • Room Type: Laundry
  • Laundry Dimensions: 8X7
Living Room Information
  • Living Room Level: Main
  • Room Type: Living Room
  • Living Room Dimensions: 28X20
Recreation Room Information
  • Room Level: Basement
  • Room Type: Recreation Room
  • Dimensions: 53X20
Play Room Information
  • Room Level: Second
  • Room Type: Play Room
  • Dimensions: 45X18
Office Information
  • Room Level: Main
  • Room Type: Office
  • Dimensions: 20X13
Den Information
  • Room Level: Second
  • Room Type: Den
  • Dimensions: 14X10
Attic Room Information
  • Room Level: Third
  • Room Type: Attic
  • Dimensions: 31X18
Breakfast Room Information
  • Room Level: Main
  • Room Type: Breakfast Room
  • Dimensions: 14X11
Sitting Room Information
  • Room Level: Main
  • Room Type: Sitting Room
  • Dimensions: 21X16
Sun Room Information
  • Room Level: Main
  • Room Type: Sun Room
  • Dimensions: 14X13

Property History for 145 Woodley Road

DateEvent & SourcePriceAppreciation
Jan 12, 2026

Pending

MRED #12542155

—
Jan 12, 2026

Contingent

MRED #12542155

—
Jan 12, 2026

Listed (Active)

MRED #12542155

$3,999,900—
DateEvent & SourcePrice
01/12/2026

Pending

MRED #12542155

—
01/12/2026

Contingent

MRED #12542155

—
01/12/2026

Listed (Active)

MRED #12542155

$3,999,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 145 Woodley Road

Taxable ValueLand$102,469Additions$102,500Total$204,969
Tax Record2023$36,243 ($3,020 / month)
Home Facts
Beds6Baths6.5Total Finished SqFt6,719 SqFtAbove Grade Finished SqFt6,719 SqFtStories2Lot Size63,685 SqFtStyleSingle Family ResidenceYear Built1958CountyCOOKAPN05-29-103-018Fireplace TypeHas Fireplace

Schools near 145 Woodley Road

This home is within Avoca School District 37.
Rating
School
Type
Grades
Distance
Avoca West Elementary School
Public - K to 5
Marie Murphy School
Public - 6 to 8
New Trier Township H S Northfield
Public - 9
New Trier Township High School Winnetka
Public - 10 to 12
Rating
School
Distance
Avoca West Elementary School
PublicK to 5

Marie Murphy School
Public6 to 8

New Trier Township H S Northfield
Public9

New Trier Township High School Winnetka
Public10 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Based on information from one of the following Multiple Listing Services: Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 02/06/2026 12:45 PM. 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.