$2,100,000

beds

baths

half bath

3,697

square ft

285 Woodlawn Avenue

Winnetka, Illinois 60093

New / MLS #12798477 / Single Family / Winnetka

Listing information updated 11/3/2026 at 1:43pm

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.

Full Features

Architecture Style:

Other

Exterior Type:

Cedar,Stone

Basement:

Finished,Full

Beds Above Grade:

Beds Below Grade:

Cooling System:

Central Air, Zoned

Heating System:

Gas, Forced Air, Radiant, Sep Heating Systems - 2+, Zoned

Appliances:

Range, Microwave, Dishwasher, Refrigerator, Bar Fridge, Washer, Dryer, Disposal

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

16-20 Years

Roof Type:

Asphalt

Parking Type:

Garage - Asphalt,Yes,Garage Owned,Detached,Garage

Parking Spaces:

Garage:

Detached

Room Count:

Water Front:

Square Feet:

3,697

Lot Size:

.25-.49 Acre

Acreage:

0.26

Internal Features:

Sauna, Hot Tub, Wet Bar

External Features:

Balcony, Patio/Porch

Room Information

Living Room:

21x14 - Main

Dining Room:

14x14 - Main

Kitchen:

21x13 - Main

Family Room:

24x16 - Main

Primary Bedroom:

19x15 - Second Level

2nd Bedroom:

14x12 - Second

3rd Bedroom:

14x19 - Second

4th Bedroom:

14x16 - Second

Breakfast Room:

10x8 - Main Level

Foyer:

14x6 - Main Level

Office:

16x13 - Main Level

Bedroom 5:

15x13 - Basement Level

Recreation Rm:

50x24 - Basement Level

Taxes & Assessments

Tax Amount:

$41,577

Tax Year:

2025

Location

Zip Code:

60093

City:

Winnetka

County:

Cook

Schools

School District(s):

35, 203

Elementary School:

South Elementary School

Middle School:

Central School

High School:

New Trier Twp H.s. Northfield/Wi

Architecture Style:

Other

Exterior Type:

Cedar,Stone

Basement:

Finished,Full

Beds Above Grade:

Beds Below Grade:

Cooling System:

Central Air, Zoned

Heating System:

Gas, Forced Air, Radiant, Sep Heating Systems - 2+, Zoned

Appliances:

Range, Microwave, Dishwasher, Refrigerator, Bar Fridge, Washer, Dryer, Disposal

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

16-20 Years

Roof Type:

Asphalt

Parking Type:

Garage - Asphalt,Yes,Garage Owned,Detached,Garage

Parking Spaces:

Garage:

Detached

Room Count:

Water Front:

Square Feet:

3,697

Lot Size:

.25-.49 Acre

Acreage:

0.26

Internal Features:

Sauna, Hot Tub, Wet Bar

External Features:

Balcony, Patio/Porch

Living Room:

21x14 - Main

Dining Room:

14x14 - Main

Kitchen:

21x13 - Main

Family Room:

24x16 - Main

Primary Bedroom:

19x15 - Second Level

2nd Bedroom:

14x12 - Second

3rd Bedroom:

14x19 - Second

4th Bedroom:

14x16 - Second

Breakfast Room:

10x8 - Main Level

Foyer:

14x6 - Main Level

Office:

16x13 - Main Level

Bedroom 5:

15x13 - Basement Level

Recreation Rm:

50x24 - Basement Level

Tax Amount:

$41,577

Tax Year:

2025

Zip Code:

60093

City:

Winnetka

County:

Cook

School District(s):

35, 203

Elementary School:

South Elementary School

Middle School:

Central School

High School:

New Trier Twp H.s. Northfield/Wi

Listing Office: Baird & Warner

Listing Office Phone: 773.697.5555

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 11/3/2026 at 1:43pm. 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. Some listings have been excluded from this website.

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285 Woodlawn Avenue, Winnetka, IL 60093 is a single family home currently listed at $2,100,000. 285 Woodlawn Avenue features 5 Beds, 5 Baths, 1 Half Bath. This single family home has been listed on @properties Christie's International Real Estate since November 3rd, 2026 and was built in 2007. Nearby schools include South Elementary School, Central School, and New Trier Twp H.s. Northfield/Wi. The nearest transit stops include Hubbard Woods Metra Metra Union Pacific North line.