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.
Pending
$3,999,900
145 Woodley Rd, Winnetka, IL 60093
5beds
7,548sqft
Est.:
Single Family Residence
Built in 1957
1.46 Acres Lot
$4,140,500 Zestimate®
$530/sqft
$-- HOA
What's special
Sparkling pool oasisSun-drenched interiorsExpansive bluestone patiosCozy sitting roomEnchanted private gardensSeparate breakfast areaVibrant gardens
- 43 days |
- 180 |
- 3 |
Zillow last checked: 8 hours ago
Listing updated: February 06, 2026 at 10:45am
Listing courtesy of:
Jena Radnay 312-925-9899,
@properties Christie's International Real Estate
Source: MRED as distributed by MLS GRID,MLS#: 12542155
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 5
- 1/2 bathrooms: 2
Rooms
- Room types: Bedroom 5, Play Room, Den, Attic, Breakfast Room, Office, Sitting Room, Sun Room, Recreation Room
Primary bedroom
- Features: Flooring (Carpet), Window Treatments (Curtains/Drapes), Bathroom (Full, Double Sink, Tub & Separate Shwr)
- Level: Second
- Area: 340 Square Feet
- Dimensions: 20X17
Bedroom 2
- Features: Flooring (Carpet)
- Level: Second
- Area: 266 Square Feet
- Dimensions: 19X14
Bedroom 3
- Features: Flooring (Carpet)
- Level: Second
- Area: 300 Square Feet
- Dimensions: 20X15
Bedroom 4
- Features: Flooring (Carpet), Window Treatments (Plantation Shutters)
- Level: Second
- Area: 156 Square Feet
- Dimensions: 13X12
Bedroom 5
- Features: Flooring (Carpet), Window Treatments (Plantation Shutters)
- Level: Second
- Area: 156 Square Feet
- Dimensions: 13X12
Other
- Features: Flooring (Carpet)
- Level: Third
- Area: 558 Square Feet
- Dimensions: 31X18
Breakfast room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 154 Square Feet
- Dimensions: 14X11
Den
- Features: Flooring (Hardwood), Window Treatments (Plantation Shutters)
- Level: Second
- Area: 140 Square Feet
- Dimensions: 14X10
Dining room
- Features: Flooring (Hardwood), Window Treatments (Bay Window(s))
- Level: Main
- Area: 280 Square Feet
- Dimensions: 20X14
Family room
- Features: Flooring (Hardwood), Window Treatments (Blinds, Skylight(s))
- Level: Main
- Area: 520 Square Feet
- Dimensions: 26X20
Kitchen
- Features: Kitchen (Island, Pantry-Closet, Breakfast Room, Country Kitchen, Custom Cabinetry), Flooring (Hardwood), Window Treatments (Blinds)
- Level: Main
- Area: 500 Square Feet
- Dimensions: 25X20
Laundry
- Features: Flooring (Other), Window Treatments (Plantation Shutters)
- Level: Second
- Area: 56 Square Feet
- Dimensions: 8X7
Living room
- Features: Flooring (Hardwood), Window Treatments (Bay Window(s))
- Level: Main
- Area: 560 Square Feet
- Dimensions: 28X20
Office
- Features: Flooring (Hardwood), Window Treatments (Curtains/Drapes)
- Level: Main
- Area: 260 Square Feet
- Dimensions: 20X13
Play room
- Features: Flooring (Carpet)
- Level: Second
- Area: 810 Square Feet
- Dimensions: 45X18
Recreation room
- Features: Flooring (Laminate)
- Level: Basement
- Area: 1060 Square Feet
- Dimensions: 53X20
Sitting room
- Features: Flooring (Hardwood), Window Treatments (Curtains/Drapes)
- Level: Main
- Area: 336 Square Feet
- Dimensions: 21X16
Sun room
- Features: Flooring (Terracotta)
- Level: Main
- Area: 182 Square Feet
- Dimensions: 14X13
Heating
- Natural Gas
Cooling
- Central Air, Zoned
Appliances
- Included: Double Oven, Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Disposal, Stainless Steel Appliance(s)
- Laundry: Upper Level, Gas Dryer Hookup, Sink
Features
- Vaulted Ceiling(s), Dry Bar, 1st Floor Bedroom, Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork
- Flooring: Hardwood, Carpet
- Windows: Screens, Skylight(s), Drapes
- Basement: Finished,Partial
- Attic: Finished
- Number of fireplaces: 4
- Fireplace features: Wood Burning, Gas Starter, Family Room, Living Room, Basement, Den/Library
Interior area
- Total structure area: 0
- Total interior livable area: 7,548 sqft
Video & virtual tour
Property
Parking
- Total spaces: 12
- Parking features: Asphalt, Brick Driveway, Garage Door Opener, Yes, Garage Owned, Attached, Driveway, Owned, Garage
- Attached garage spaces: 4
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: No Disability Access
Features
- Stories: 3
- Patio & porch: Patio, Porch
- Exterior features: Lighting
- Pool features: In Ground
- Has spa: Yes
- Spa features: Outdoor Hot Tub, Indoor Hot Tub
- Fencing: Fenced
Lot
- Size: 1.46 Acres
- Dimensions: 187 x 346
- Features: Landscaped, Mature Trees, Garden
Details
- Additional structures: None
- Parcel number: 05291030180000
- Special conditions: None
- Other equipment: Sump Pump, Backup Sump Pump;
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Cedar, Shake Siding, Stone, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Shake
Condition
- New construction: No
- Year built: 1957
- Major remodel year: 2000
Utilities & green energy
- Electric: Circuit Breakers, Fuses, 200+ Amp Service
- Sewer: Public Sewer
- Water: Lake Michigan
Community & HOA
Community
- Features: Curbs, Street Paved
- Security: Security System
HOA
- Services included: None
Location
- Region: Winnetka
Financial & listing details
- Price per square foot: $530/sqft
- Tax assessed value: $2,049,690
- Annual tax amount: $37,614
- Date on market: 1/12/2026
- Ownership: Fee Simple
Estimated market value
$4,140,500
$3.93M - $4.43M
$7,824/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 2/6/2026 | Pending sale | $3,999,900$530/sqft |
Source:  MRED as distributed by MLS GRID #12542155 Report a problem | ||
| 1/12/2026 | Contingent | $3,999,900$530/sqft |
Source: MRED as distributed by MLS GRID #12542155 Report a problem | ||
| 1/12/2026 | Listed for sale | $3,999,900+2.6%$530/sqft |
Source: MRED as distributed by MLS GRID #12542155 Report a problem | ||
| 5/3/1989 | Sold | $3,900,000$517/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2023 | $36,243 +2.2% | $204,969 |
| 2022 | $35,447 -23.5% | $204,969 -12% |
| 2021 | $46,315 +2.5% | $233,034 |
| 2020 | $45,175 +2.2% | $233,034 -9% |
| 2019 | $44,199 -7.9% | $256,082 -3.5% |
| 2018 | $48,014 +2.4% | $265,398 |
| 2017 | $46,895 +0% | $265,398 |
| 2016 | $46,875 -9.7% | $265,398 -0.3% |
| 2015 | $51,889 +2% | $266,072 |
| 2014 | $50,851 +5.2% | $266,072 |
| 2013 | $48,327 +6.2% | $266,072 -1.2% |
| 2012 | $45,487 -11.9% | $269,330 -16.2% |
| 2011 | $51,628 +3.7% | $321,496 |
| 2010 | $49,778 +0.5% | $321,496 -11.3% |
| 2009 | $49,509 -2.2% | $362,502 -11.4% |
| 2008 | $50,608 -5.1% | $409,353 -9.3% |
| 2007 | $53,349 +25.4% | $451,377 +48.5% |
| 2006 | $42,530 +0.6% | $303,999 |
| 2005 | $42,257 +2.3% | $303,999 |
| 2004 | $41,304 +7.4% | $303,999 +18.8% |
| 2003 | $38,475 -1.7% | $255,832 |
| 2002 | $39,148 +26.5% | $255,832 |
| 2001 | $30,946 +1.8% | $255,832 +30.9% |
| 2000 | $30,398 +0.8% | $195,447 |
| 1999 | $30,156 | $195,447 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$27,260/mo
Principal & interest
$20627
Property taxes
$6633
Climate risks
Neighborhood: 60093
Nearby schools
GreatSchools rating
- 9/10Avoca West Elementary SchoolGrades: K-5Distance: 1.3 mi
- 8/10Marie Murphy SchoolGrades: PK,6-8Distance: 0.2 mi
- NANew Trier Township H S NorthfieldGrades: 9Distance: 1 mi
Schools provided by the listing agent
- Elementary: Avoca West Elementary School
- Middle: Marie Murphy School
- High: New Trier Twp H.S. Northfield/Wi
- District: 37
Source: MRED as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 60093
