Properties

Features
: Radiator(s)
: Small Duct High Velocity
: Full , Partially Finished
: Gas Log , Wood Burning
: Patio
: Garage Door Opener , Garage Owned , Garage , Detached , Brick Driveway , Yes
: Lighting
2
: Carpet , Hardwood
: Walk-In Closet(s) , Separate Dining Room , Built-in Features , Bookcases , Special Millwork , Historic/Period Mlwk , Vaulted Ceiling(s)
: In Bathroom
: Public Sewer
: Pond
: Skylight(s) , Screens , Display Window(s) , Bay Window(s) , Plantation Shutters
: Colonial
Appliances
: Microwave , Refrigerator , Dishwasher , Double Oven , Freezer , Disposal , Gas Cooktop
Address Map
US
IL
Cook
Winnetka
60093
Maple
500
Street
W88° 16' 12.8''
N42° 6' 16.8''
Green Bay to Oak, East to Maple. Home is on NW corner of Maple and Oak across from Village Green.
Winnetka
Winnetka
Neighborhood
Greeley Elementary School
Greeley Elementary School
36
New Trier Twp H.S. Northfield/Wi
203
36
Carleton W Washburne School
Additional Information
: Curbs , Street Paved , Park , Sidewalks , Street Lights
: Brick
2
: Corner Lot , Landscaped , Mature Trees , Garden
97x160
: Lake Michigan
Compass
Paige Dooley
Financial
Not Applicable
: None
40526.5
Listing Information
Caroline Keehn
6147
Compass
39577
6147
MRED
: List Broker Must Accompany
Listing Information
47376
6147
Compass
Contingent
2026-05-23T17:29:02Z
2026-05-23T17:28:51Z
Property Description

Exceptional East Winnetka Georgian on serene and lush . 4-acre grounds (96×160) 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!

Residential For Sale

500 Maple Street, Winnetka, Illinois 60093

  • Bedrooms : 5
  • Bathrooms : 5
  • Square Footage: 5,646 Sqft
$2,395,000
Listing ID#12631320
QR Code
Basic Details
Property Type : Residential
Listing Type : For Sale
Listing ID : 12631320
Price : $2,395,000
Bedrooms : 5
Rooms : 12
Bathrooms : 5
Half Bathrooms : 2
Square Footage : 5,646 Sqft
Year Built : 1920
Lot Size : 0.40 Acre
Full Bathrooms : 3
Listing Status : Active Under Contract
Roof
Roof : Shake
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