285 Woodlawn Avenue, Winnetka, IL 60093 (MLS # 12798477)

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PRICE $2,100,000 dsIDX morgage calculator
BEDS 4
BATHS 5.5
HOME SIZE 3,697 sqft
LOT SIZE 11,326 sqft

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.

DAYS ON MARKET 1 LAST UPDATED 11/3/2026
YEAR BUILT 2007 COMMUNITY Winnetka
GARAGE SPACES 2.0 COUNTY Cook
STATUS Active PROPERTY TYPE(S) Single Family

SCHOOLS
School District New Trier Twp H.S. Northfield/Wi
Elementary School South Elementary School
Jr. High School Central School
High School New Trier Twp H.S. Northfield/Wi


ADDITIONAL DETAILS
AIR Ceiling Fan(s), Central Air, Zoned
AIR CONDITIONING Yes
APPLIANCES Bar Fridge, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
AREA Winnetka
BASEMENT Finished, Full, Sump Pump, Yes
CONSTRUCTION Cedar, Stone
EXTERIOR Balcony
FIREPLACE Yes
GARAGE Yes
HEAT Forced Air, Radiant, Zoned
INTERIOR Entrance Foyer, Sauna, Wet Bar
LOT 0.26 acre(s)
LOT DESCRIPTION Cul-de-sac, Landscaped, Wooded
LOT DIMENSIONS 50X232
PARKING Asphalt, Detached, Garage
SEWER Public Sewer
STYLE Other
TAXES 41577.8
UTILITIES Cable Available
WATER Public
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

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*Estimate only

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Listed with Baird & Warner
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