500 Maple Street Winnetka, IL $ 2,395,000
500 Maple Street
$ 2,395,000
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500 Maple Street

Winnetka, IL, 60093
$ 2,395,000
Bedrooms5 Baths3.2 Sq 5,646

Monthly Estimate*

$ 14,746

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Single Family Home for sale in Winnetka, IL

for $2,395,000 with 5 bedrooms and 3 full baths, 2 half baths. This 5,646 square foot home was built in 1920 on a lot size of 0.4.

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!

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Single Family Active

Price

$ 2,395,000

Bedrooms

5

Full Bath

3

Half Bath

2

Property Type

Single Family

Taxes

$ 40,526

Style

Colonial

Lot Size

0.4

Year Built

1920

Town/City

Winnetka

County/Region

Cook

MLS | Web ID

12631320

Features
General
Living Area 5646
Sewer Public Sewer
Heating Radiator(s)
Cooling Small Duct High Velocity
Possession Closing
Roof Shake
Appliances Double Oven Microwave Dishwasher Refrigerator Freezer Disposal Gas Cooktop
Garage Spaces 2
Association Fee Includes None
Architectural Style Colonial
Construction Materials Brick
Year Built 1920
Township New Trier
Tax Year 2024
Ownership Fee Simple
Community Features Park Curbs Sidewalks Street Lights Street Paved
Assoc Fee Paid Per Not Applicable
County Cook
New Construction N
Property Type Residential Detached Single
Other Structures Pergola
Total Rooms 12
Full Baths 3
Status New
Directions Green Bay to Oak East to Maple. Home is on NW corner of Maple and Oak across from Village Green.
High School New Trier Twp H.S. Northfield/Wi
City Winnetka
High School District 203
MLS Area Winnetka
Elementary School Greeley Elementary School
Tax Annual Amount 40526.5
Middle/Junior High School Carleton W Washburne School
Additional Parcels Y/N N
Standard Status Active
Middle/Junior School District 36
Elementary School District 36
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Interior
Interior Amenities Vaulted Ceiling(s) Built-in Features Walk-In Closet(s) Bookcases Historic/Period Mlwk Special Millwork Separate Dining Room
Basement Partially Finished Full
Flooring Hardwood Carpet
Total Fireplaces 2
Fireplace Features Wood Burning Gas Log
Half Baths 2
Laundry Features In Bathroom
Total Bedrooms 5
Below Grade Finished Area 645
Room Type Breakfast Room Office Sitting Room Foyer Mud Room Bedroom 5
Total Baths 5
Bedrooms Possible 5
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Exterior
Exterior Amenities Lighting
Parking Features Brick Driveway Garage Door Opener Yes Garage Owned Detached Garage
Lot Features Corner Lot Landscaped Mature Trees Garden
Water Source Lake Michigan
Total Parking 2
Lot Dimensions 97x160
Lot Size Acres 0.4
Waterfront Y/N N
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* Excluded Features
List By
Compass

Broker

paige.dooley@compass.com

Email

Affordability Calculator

$18,124
Per Month
81%
19%
0%
Monthly Principal & Interest
$14,746
Monthly Property Taxes
$3,377
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
566279 Elementary School
566222 Middle School
New Trier Twp H.S. Northfield/Wi High School
Pricing History
DatePricePrice ChangeDescription
5/18/2026$2,395,000 Listed Price

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500 Maple Street, Winnetka, IL, 60093 is a Single Family Home for sale at $2,395,000 with 5,646 sqft and a lot size of 0.4. 500 Maple Street has 5 bedrooms, 3.2 baths, and was built in 1920. The property's zip code is 60093 which is in Winnetka, IL