285 Woodlawn Avenue Winnetka, IL $ 2,100,000
285 Woodlawn Avenue
$ 2,100,000
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285 Woodlawn Avenue

Winnetka, IL, 60093
$ 2,100,000
Bedrooms5 Baths5.1 Sq 3,697

Monthly Estimate*

$ 14,504

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Single Family Home for sale in Winnetka, IL

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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Single Family Active

Price

$ 2,100,000

Bedrooms

5

Full Bath

5

Half Bath

1

Property Type

Single Family

Taxes

$ 41,577

Style

Lot Size

0.26

Year Built

2007

Town/City

Winnetka

County/Region

Cook

MLS | Web ID

12798477

Features
General
Living 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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Interior
Interior 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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Exterior
Exterior 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 Features
List By
Baird & Warner

Broker

tony.giamberduca@bairdwarner.com

Email

Affordability Calculator

$17,969
Per Month
81%
19%
0%
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.
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Nearby
567131 Elementary School
566083 Middle School
New Trier Twp H.S. Northfield/Wi High School
Pricing History
DatePricePrice ChangeDescription
11/3/2026$2,100,000 Listed Price

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285 Woodlawn Avenue, Winnetka, IL, 60093 is a Single Family Home for sale at $2,100,000 with 3,697 sqft and a lot size of 0.26. 285 Woodlawn Avenue has 5 bedrooms, 5.1 baths, and was built in 2007. The property's zip code is 60093 which is in Winnetka, IL