Active Under Contract

$2,100,000

285 Woodlawn Avenue, Winnetka, IL 60093
4 Beds6 Baths5,352 sqft8 days
285 Woodlawn Avenue·Winnetka, IL 60093
4Bedrooms
6Bathrooms
5,352Sq Ft
2007Year Built
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.

MLS# 12798477Listed November 3, 2026ResidentialOther
Property Details

Beds & Baths

Total Bedrooms4
Total Bathrooms6
Full Baths5
Half Baths1
Total Rooms12

Size & Structure

Living Area5,352 sqft
Garage Spaces2
Fireplaces4
Year Built2007
Lot Size0.260 acres

Location

CountyCook
TownshipNew Trier
Zip Code60093

Financial

List Price$2,100,000
Price / Sq Ft$392
Annual Taxes (2025)$41,578
Monthly Tax Est.$3,465
Parcel #05083190180000
Interior Features

Appliances

RangeMicrowaveDishwasherRefrigeratorBar FridgeWasherDryerDisposal

Heating

GasForced AirRadiantSep Heating Systems - 2+Zoned

Cooling

Central AirZoned

Basement

FinishedFull
Exterior & Lot

Construction

CedarStone

Roof

Asphalt

Foundation

Concrete Perimeter

Exterior Features

Balcony

Patio & Porch

Patio

Lot Features

Cul-De-SacLandscapedWooded
Utilities & Parking

Sewer

Public SewerStorm Sewer

Water Source

Lake MichiganPublic

Electric

Circuit Breakers200+ Amp Service

Parking

AsphaltYesGarage OwnedDetachedGarage
HOA & Community
HOA Fee
$0
Not Applicable

HOA Includes

None

Community Features

ParkTennis Court(s)CurbsSidewalksStreet LightsStreet Paved
Schools
Elementary
South Elementary School
District: 35
Middle School
Central School
District: 35
High School
New Trier Twp H.S. Northfield/Wi
District: 203
Tax & Financial
Annual Taxes
$41,578
Tax Year 2025
Monthly Tax Est.
$3,465
per month
Price per Sq Ft
$392
per square foot
Property Location

285 Woodlawn Avenue, Winnetka, IL 60093 — Cook County

$2,100,000
$392 / sqft
285 Woodlawn Avenue
4 bd6 ba5,352 sqft
VL
Vittoria Logli
Top Glenview Agent

IL License 475.178467 · (847) 810-8438

Quick Facts
8 days on market
2-car garage
4 fireplaces
0.260 acres
$41,578/yr taxes
$0 HOA (not applicable)
$14,501
estimated monthly payment
Principal & Interest
$11,036/mo
Property Tax
$3,465/mo
$2,100,000
20% — $420,000
3%50%
6.875%
3%12%
Loan Amount
$1,680,000
Down Payment
$420,000

* Estimated payment only. Actual rates, taxes, and insurance may vary. Contact a lender for a personalized quote.

Listed by
Baird & Warner
Agent: Antonio Giamberduca
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Listing Courtesy: MRED as distributed by MLS GRID | @properties Christie's International Real Estate

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