500 Maple Street, Winnetka, Illinois 60093

$2,550,000
5
BD
3
Full Baths
2
Half Baths
5,646
SqFt

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Sold Price
$2,550,000
List Price
$2,395,000
Closing Date
Jun 18, 2026
MLS#
12631320
Status
CLOSED
Type
Single Family Residential
Subtype
Residential
Bedrooms
5
Bathrooms
5
Living Area
5,646
County
Cook
City
Winnetka
Neighborhood
Winnetka
Days On Market
Unknown

Property Description

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!

Additional Information

School District
203
Elementary School
Greeley Elementary School
Middle School
Carleton W Washburne School
High School
New Trier Twp H.S. Northfield/Wi
Corporate Limits
Winnetka
Tax Year
2024
Tax Exemptions
Homeowner, Senior
Tax Amount
$40,526
Frequency
Not Applicable
Year Built
1920
Exterior Property Features
Lighting
Exposure
South, East, West
Lot Dimensions
97x160
Lot Size Range
.25-.49 Acre
Garage Spaces
2
Parking Spaces
2
Parking Details
Brick Driveway, Garage Door Opener, Yes, Garage Owned, Detached, Garage
Air Conditioning
Small Duct High Velocity
Heating
Radiator(s)
Sewer
Public Sewer
Interior Property Features
Vaulted Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork, Separate Dining Room
Interior Fireplaces
2
Full Baths
3
Half Baths
2
Basement
Yes

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Listings courtesy of Midwest Real Estate Data as distributed by MLS Grid

Selling Office: Baird & Warner.



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