For sale Home

Listed Nov 3, 2026

$2,100,000 Est. $13,890/mo

285 Woodlawn Avenue

  • 4

    Beds

  • 6

    Baths

  • 3,697

    Sq ft

The story

  • Basement

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.

Facts & features

Home type

Home

Year built

2007

Price per sq ft

$568

Parking

2-car garage

Included features

  • Fireplace

    4 fireplaces

  • Basement

    Yes

  • Cooling

    Central Air, Zoned

  • Heating

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

  • Appliances

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

  • Roof

    Asphalt

  • Lot Information

    Cul-De-Sac, Landscaped, Wooded

  • Exterior

    Balcony

  • Water Source

    Lake Michigan, Public

  • Sewer

    Public Sewer, Storm Sewer

Mortgage calculator

Estimated monthly payment

$13,890 /mo

7% rate · 30-yr fixed · 20% down

  • Principal & interest $11,177
  • Property tax $2,100
  • Insurance $613

Includes principal, interest, taxes & insurance.

Your Property Journey

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Listing Broker

Baird & Warner

Broker Name

Baird & Warner

Agent

Antonio Giamberduca