Pending

$2,395,000

500 Maple Street, Winnetka, IL 60093
5 Beds5 Baths4,508 sqft5 days
500 Maple Street·Winnetka, IL 60093
5Bedrooms
5Bathrooms
4,508Sq Ft
1920Year Built
About This Home

Exceptional East Winnetka Georgian on serene and lush . 4-acre grounds (96x160) with sweeping views of the Village Green. Architecturally significant and award-winning William Aiken classic restored and preserved to the modern standard, including a 2007 addition. Just a short walk to everything - town, train, beaches, school, and more - with your own private backyard garden oasis, this home offers a unique blend of timeless charm and contemporary luxury overlooking the iconic Village Green vistas. This classic architectural gem has been meticulously renovated and lovingly maintained to showcase architectural details, with every graciously scaled room beautifully appointed with breathtaking panoramic views. From the moment you enter the classic foyer with detailed millwork and soaring ceilings, the seamless flow of the home provides an ideal layout for everyday living and formal entertaining. The expansive living room features gorgeous built-in bookshelves, a beautiful wood-burning fireplace (overmantle designed by the homeowner), and glass French doors along every wall, offering incredible natural light and floor-to-ceiling Village Green views. Enjoy stunning vistas at any time of the year from either of the two 4-exposure sunrooms (one off LR and one off DR). A separate formal dining room, conveniently located with access to the kitchen, offers enough space for all of your entertaining needs, and opens to the second sunroom. The family room (2007) is a showstopper with vaulted ceilings and skylights, a handsome stone fireplace (gas), detailed built-in bookshelves, and oversized windows highlighting breathtaking views of the award-winning backyard. The bright kitchen with center island and wall-to-wall built-ins is perfectly positioned between the dining room, family room, and back hall mudroom. The gracious front hall staircase invites you upstairs to find the primary suite with bay window overlooking the gorgeous grounds, private bath, and walk-in closet. Two additional well-sized bedrooms share a Jack-and-Jill bath, as well as a hall bath with washer/dryer offering potential for a full second floor laundry room. Retreat up to the third floor with two bedrooms and a full bath - the ultimate treetop suite! The lower level offers a large finished recreation room that was dug out in 2007 while the expansive unfinished area has unlimited potential and endless possibilities. The backyard is a true private oasis - a sanctuary from the hustle and bustle of everyday life - offering serene tranquility and peaceful moments. Featuring bluestone terraces and limestone pathways, the backyard reveals a true secret garden with lush plantings, 3 waterfalls, a koi pond, and a bridge to the Japanese teahouse / gazebo. This home was thoughtfully renovated in 1989 and updated meticulously over the years, including an award-winning 2007 addition, 2003 detached garage, and updated Marvin windows. Experience elegance and comfort in an A+ location, just steps from town, train, schools, and Maple Beach!

MLS# 12631320Listed May 17, 2026ResidentialColonial
Property Details

Beds & Baths

Total Bedrooms5
Total Bathrooms5
Full Baths3
Half Baths2
Total Rooms12

Size & Structure

Living Area4,508 sqft
Garage Spaces2
Fireplaces2
Year Built1920
Lot Size0.400 acres

Location

CountyCook
TownshipNew Trier
Zip Code60093

Financial

List Price$2,395,000
Price / Sq Ft$531
Annual Taxes (2024)$40,527
Monthly Tax Est.$3,377
Parcel #05211090100000
Interior Features

Appliances

Double OvenMicrowaveDishwasherRefrigeratorFreezerDisposalGas Cooktop

Flooring

HardwoodCarpet

Heating

Radiator(s)

Cooling

Small Duct High Velocity

Basement

Partially FinishedFull

Laundry

In Bathroom

Fireplace

Wood BurningGas Log
Exterior & Lot

Construction

Brick

Roof

Shake

Exterior Features

Lighting

Patio & Porch

Patio

Lot Features

Corner LotLandscapedMature TreesGarden
Utilities & Parking

Sewer

Public Sewer

Water Source

Lake Michigan

Parking

Brick DrivewayGarage Door OpenerYesGarage OwnedDetachedGarage
HOA & Community

HOA Includes

None

Community Features

ParkCurbsSidewalksStreet LightsStreet Paved
Schools
Elementary
Greeley Elementary School
District: 36
Middle School
Carleton W Washburne School
District: 36
High School
New Trier Twp H.S. Northfield/Wi
District: 203
Tax & Financial
Annual Taxes
$40,527
Tax Year 2024
Monthly Tax Est.
$3,377
per month
Price per Sq Ft
$531
per square foot
Property Location

500 Maple Street, Winnetka, IL 60093Cook County

$2,395,000
$531 / sqft
500 Maple Street
5 bd5 ba4,508 sqft
VL
Vittoria Logli
Top Glenview Agent

IL License 475.178467 · (847) 810-8438

Quick Facts
5 days on market
2-car garage
2 fireplaces
0.400 acres
$40,527/yr taxes
$15,964
estimated monthly payment
Principal & Interest
$12,587/mo
Property Tax
$3,377/mo
$2,395,000
20% — $479,000
3%50%
6.875%
3%12%
Loan Amount
$1,916,000
Down Payment
$479,000

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

Listed by
Compass
Agent: Paige Dooley
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Listing Courtesy: MRED as distributed by MLS GRID | @properties Christie's International Real Estate

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