Recently Listed Open House 11/7 12pm - 2pm
285 Woodlawn Avenue
Winnetka, IL, 60093 $ 2,100,000
Bedrooms5 Baths5.1 Sq 3,697 Monthly Estimate*
$ 14,504
for $2,100,000 with 5 bedrooms and 5 full baths, 1 half bath. This 3,697 square foot home was built in 2007 on a lot size of 0.26.
Welcome to this exquisite, sun-drenched 4+1 bed, 5.1 bath luxury home on an oversized lot (50x232) at the Winnetka/Glencoe border. Located on a beautiful tree lined cul-de-sac and adjacent to the Green Bay trail, this home sits across the street from Glencoe Park. The moment you walk in, you are greeted by a bright formal living room featuring one of the home's four fireplaces, flanked by an adjacent office adorned with beautiful, oversized bay windows. Designed for seamless modern living, the main level flows into a sophisticated formal dining room, an open-concept kitchen, breakfast room and family room overlooking expansive backyard. The main level features a light, neutral palette and newer light fixtures throughout. The second floor is a private retreat where all four bedrooms feature dedicated en suite baths, and two enjoy the luxury of private decks. All new hardwood flooring throughout this level along with a fresh paint. Spacious primary bedroom features large walk in closet and elegantly renovated bathroom with double vanity and a breathtaking walk in shower. A dedicated second-floor laundry room includes a newer washer/dryer. Fully finished basement adds incredible value with a huge recreation room, a full bath, bar and a flexible 5th bedroom/home gym. Enjoy cozy evenings anchored by the home's 4 distinct fireplaces. The outdoor oasis features an oversized paver patio, massive yard, and an oversized 2-car garage. Impeccably maintained with newer appliances, wine cooler, updated mechanicals, and a central vac system, this home offers total peace of mind. Unbeatable location just minutes from Hubbard Woods shopping, dining, and the Metra train.
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Open House
11/7/2026 12:00 PM - 2:00 PM
285 Woodlawn Avenue Winnetka, IL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesGeneralLiving Area 3697
Sewer Public Sewer Storm Sewer
Heating Gas Forced Air Radiant Sep Heating Systems - 2+ Zoned
Cooling Central Air Zoned
Possession Closing
Roof Asphalt
Appliances Range Microwave Dishwasher Refrigerator Bar Fridge Washer Dryer Disposal
HOA Fee 0
Garage Spaces 2
Association Fee Includes None
Architectural Style Other
Construction Materials Cedar Stone
Year Built 2007
Electric Circuit Breakers 200+ Amp Service
Township New Trier
Tax Year 2025
Ownership Fee Simple
Community Features Park Tennis Court(s) Curbs Sidewalks Street Lights Street Paved
Assoc Fee Paid Per Not Applicable
County Cook
New Construction N
Property Type Residential Detached Single
Total Rooms 12
Full Baths 5
Status New
Directions OLD GREENBAY N OF SCOTT S OF MARY TO WOODLAWN W TO 285
High School New Trier Twp H.S. Northfield/Wi
City Winnetka
High School District 203
MLS Area Winnetka
Elementary School South Elementary School
Tax Annual Amount 41577.8
Middle/Junior High School Central School
Additional Parcels Y/N N
Standard Status Active
Middle/Junior School District 35
Elementary School District 35
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InteriorInterior Amenities Sauna Hot Tub Wet Bar
Basement Finished Full
Total Fireplaces 4
Half Baths 1
Total Bedrooms 4
Below Grade Finished Area 1655
Room Type Breakfast Room Foyer Office Bedroom 5 Recreation Room
Total Baths 6
Bedrooms Possible 5
Bathroom Whirlpool Separate Shower Steam Shower Double Sink
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ExteriorExterior Amenities Balcony
Parking Features Asphalt Yes Garage Owned Detached Garage
Lot Features Cul-De-Sac Landscaped Wooded
Water Source Lake Michigan Public
Total Parking 2
Foundation Details Concrete Perimeter
Lot Dimensions 50X232
Lot Size Acres 0.26
Waterfront Y/N N
Other Equipment TV-Cable Security System Ceiling Fan(s) Sump Pump
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* Excluded FeaturesList Bytony.giamberduca@bairdwarner.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $14,504
- Monthly Property Taxes
- $3,465
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% 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 NearbySingle family listings in Winnetka, IL
Average List Price $2,185,100
Percent of Sale Price 4%
About Winnetka, IL 12,298 Population
-2% Since 2002
$ 182,976 Median Income
45.24 Median Age
46% Households with Children
Trends Information provided by ATTOM Data Solutions.
567131 Elementary School
566083 Middle School
New Trier Twp H.S. Northfield/Wi High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 11/3/2026 | $2,100,000 | | Listed Price |