Active5 days on market
$2,100,000
285 Woodlawn Avenue
Winnetka, IL 60093
- Beds
- 4
- Baths
- 5 full · 1 half
- Sqft
- 3,697
- $/sqft
- $568
- Lot
- 0.26 ac
- Built
- 2007
- Type
- Single Family
- MLS#
- MRD12798477
About this home
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.
Payment calculator
Estimated monthly cost for this home
20% · $420K
%
Term
$15,458/mo
- Principal & interest
- $11,381
- Property taxes
- $3,465
- Home insurance (est.)
- $613
Estimate only, not a quote or offer of credit. Rate starts from today's market rate (7.18%, 2026-11-05). Taxes from the listing's MRED record. Talk to a lender for real numbers; a Subdiview agent can introduce you to a good one.
Price & tax history
| Listed Nov 3, 2026 | $2,100,000 |
| 2025 property taxes | $41,578/yr |
From the listing's MRED record. MRED does not publish per-change dates through IDX, so price changes are shown without one rather than guessed.
Schools
Assigned schools per the listing's MRED record. Always verify with the district before you buy.
Elementary
South Elementary School
35
Middle
Central School
35
High school
New Trier Township High School203
See programs, enrollment & homes near this school →
Where it sits
MRED Broker ReciprocityThis listing is part of the MRED data exchange program provided courtesy of Baird & Warner, listed by Antonio Giamberduca.
Information last updated Nov 5, 2026, 3:43 PM.
285 Woodlawn Avenue
Winnetka, IL 60093
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Call 224-385-8779Property details
Sourced from the MRED MLS feed. Last updated when the listing was modified.
- Cooling
- Central Air, Zoned
- Heating
- Gas, Forced Air, Radiant, Sep Heating Systems - 2+, Zoned
- Basement
- Finished, Full
- Appliances
- Range, Microwave, Dishwasher, Refrigerator, Bar Fridge, Washer, Dryer, Disposal
- Rooms total
- 12
- Fireplaces total
- 4
- Interior features
- Sauna, Hot Tub, Wet Bar
- Finished basement
- 1655