500 Maple ST, Winnetka, IL 60093
500 Maple ST, Winnetka, IL 60093
500 Maple ST, Winnetka, IL 60093
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Doug Anderson

Doug Anderson

+1(847) 687-3424
$2,395,000
Est. payment /mo
5 Beds
4 Baths
5,646 SqFt
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Key Details

Property Type Single Family Home

Sub Type Detached Single

Listing Status Active

Purchase Type For Sale

Square Footage 5,646 sqft

Price per Sqft $424

MLS Listing ID 12631320

Style Colonial

Bedrooms 5

Full Baths 3

Half Baths 2

Year Built 1920

Annual Tax Amount $40,526

Tax Year 2024

Lot Size 0.400 Acres

Lot Dimensions 97x160

Property Sub-Type Detached Single

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!

Location

State IL

County Cook

Area Winnetka

Rooms

Basement Partially Finished, Full

Interior

Interior Features Vaulted Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork, Separate Dining Room

Heating Radiator(s)

Cooling Small Duct High Velocity

Flooring Hardwood, Carpet

Fireplaces Number 2

Fireplaces Type Wood Burning, Gas Log

Fireplace Y

Appliance Double Oven, Microwave, Dishwasher, Refrigerator, Freezer, Disposal, Gas Cooktop

Laundry In Bathroom

Exterior

Exterior Feature Lighting

Garage Spaces 2.0

Community Features Park, Curbs, Sidewalks, Street Lights, Street Paved

Waterfront Description Pond

Roof Type Shake

Building

Lot Description Corner Lot, Landscaped, Mature Trees, Garden

Dwelling Type Detached Single

Building Description Brick, No

Sewer Public Sewer

Water Lake Michigan

Level or Stories 3 Stories

Structure Type Brick

New Construction false

Schools

Elementary Schools Greeley Elementary School

Middle Schools Carleton W Washburne School

High Schools New Trier Twp H.S. Northfield/Wi

School District 36 , 36, 203

Others

HOA Fee Include None

Ownership Fee Simple

Special Listing Condition List Broker Must Accompany

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Midwest Real Estate Data (MRED) IDX
© 2026 Listings courtesy of MRED as distributed by MLS GRID. All Rights Reserved.
Listed by Paige Dooley of  Compass 
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Doug Anderson

Doug Anderson

Designated Managing Broker

+1(847) 687-3424

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500 Maple ST