Pending

500 Maple Street

Winnetka, IL 60093

$2,395,000 $10,097/Mo

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Overview

Bed

Bath

5,646

Sqft

0.40

Acre(Lot)

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 soa ring 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!

Property Details

Property Type : Residential

Price : $2,395,000

AD Id : 78871703

MLS Id : MRD12631320

Beds : 5

Lot Size : 0.40 Acre

Living Area Size : 5,646

Year Built : 1920

Garage : 2

County : Cook

Map

Features

Bedroom Information

Total Bedroom: 5 Room Types: Breakfast Room, Office, Sitting Room, Foyer, Mud Room, Bedroom 5

Bathroom Information

Total Baths: 5 Full Baths: 3 Half Baths: 2

Room Information

Rooms Total: 12

Interior Features

Vaulted Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork, Separate Dining Room Roof: Shake Appliances: Double Oven, Microwave, Dishwasher, Refrigerator, Freezer, Disposal, Gas Cooktop Laundry Features: In Bathroom

Roofing Information

Shake
Flooring Information

Flooring: Hardwood, Carpet Construction Materials: Brick
Heating & Cooling

Heating: Radiator(s) Cooling: Small Duct High Velocity WaterSource: Lake Michigan

Building Information

Year Built: 1920
Exterior Features

Lighting Construction Materials: Brick

Lot Information

Lot Dimensions: 97x160 Lot Description: Corner Lot, Landscaped, Mature Trees, Garden Lot Acres: 0.4 Lot Size: .25-.49 Acre

Property Information

Property Type: Residential Style: Colonial Sub Type: Detached Single Type Detached: 3 Stories

Listing Price Information

Original List Price:$2395000

Tax Information

Annual Tax: $40526.5 Tax Year: 2024 Parcel Number: 05211090100000 Tax Exemption: Homeowner,Senior

Parking Information

Total Parking: 2 Brick Driveway, Garage Door Opener, Yes, Garage Owned, Detached, Garage

Garage Information

Garage Space: 2

Homeowners Association Information

Included Fees: None

School Information

Elementary School: Greeley Elementary School Junior High School: Carleton W Washburne School Senior High School: New Trier Twp H.S. Northfield/Wi
Utility Information

Sewer: Public Sewer Water Source: Lake Michigan
Location Information

City: Winnetka Direction: Green Bay to Oak, East to Maple. Home is on NW corner of Maple and Oak across from Village Green.

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Nearby Home Value

Address	Estimate	Bed	Bath	Sq. Ft	Lot Size
1380 Westmoor Trail, Winnetka, IL, 60093	$4,995,000	6	9	7,480	7,480 SqFt
972 Elm Street, Winnetka, IL, 60093	$1,329,000	5	4	2,800	2,800 SqFt
1208 Oak Street, Winnetka, IL, 60093	$1,195,000	3	2	2,680	2,680 SqFt
259 Church Road, Winnetka, IL, 60093	$925,000	3	2	--
936 Sunset Road, Winnetka, IL, 60093	$4,999,900	6	6	4,159	4,159 SqFt
1015 Sheridan Road, Winnetka, IL, 60093	$3,495,000	6	8	8,303	8,303 SqFt
870 Bryant Avenue, Winnetka, IL, 60093	$2,100,000	4	4	3,762	3,762 SqFt
919 Hill Road, Winnetka, IL, 60093	$7,999,900	6	9	10,588	10,588 SqFt
1372 Sunview Lane, Winnetka, IL, 60093	$1,650,000	5	5	3,642	3,642 SqFt
478 Sunset Road, Winnetka, IL, 60093	$1,700,000	4	4	3,364	3,364 SqFt

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ByOwner last updated this listing 06/10/2026 @ 06:20

MLS: MRED #12631320 LISTED BY: Paige Dooley, Compass 847-446-9600 SOURCE: Midwest Real Estate Data LLC (MRED) (Listings courtesy of Midwest Real Estate Data LLC (MRED) as distributed by MLS GRID)