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Brad Zimmerman
REALTOR®
(815) 985-2830
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500 Maple Street , Winnetka, IL 60093

$2,395,000
  • 500 Maple Street , Winnetka, IL 60093 Main Photo

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New to the Market New
BEDS5 BATHS3 full 2 partial SQUARE FEET5,646 MLS#12631320
STATUSNew PROPERTY TYPEResidential - Single Family SCHOOLDistrict 203

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 a

500 Maple Street | MLS# 12631320

This single family home located at 500 Maple Street , Winnetka, IL 60093 is currently listed for sale with an asking price of $2,395,000. This property was built in 1920 and has 5 bedrooms and 3 full and 2 partial baths with 5646 sq. ft. Maple Street is located within the District 203 school district. Search Winnetka real estate on bzimmerman.gogambino.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Partially Finished, Full
Cooling: Small Duct High Velocity
Fireplaces: 2
Garage: 2
Heating: Radiator(s)
Home Style: Colonial
Lot Size: 0.40 Acres
Roof Type: Shake
Taxes: $40,526
Year Built: 1920

Amenities

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

Feature Descriptions

Additional rooms: Breakfast Room, Office, Sitting Room, Foyer, Mud Room, Bedroom 5
Additional Structures: Pergola
Appliances: Double Oven, Microwave, Dishwasher, Refrigerator, Freezer, Disposal, Gas Cooktop
Association Includes: None
Dining Room: Separate
Exterior: Brick
Fireplace: Wood Burning, Gas Log
Fireplace Location(s): Family Room, Living Room
Laundry: In Bathroom
Lot: Corner Lot, Landscaped, Mature Trees, Garden
Lot Dimensions: 97x160
Parcel#: 05211090100000
Parking: Brick Driveway, Garage Door Opener, Yes, Garage Owned, Detached, Garage
Sewer: Public Sewer
Total Rooms: 12
Township: New Trier
Water: Lake Michigan

Room Sizes

Breakfast Room: 10X10
Office: 18X16
Sitting Room: 18X16
Foyer: 12X9
Mud Room: 14X5
Bedroom 5: 15X13
Bedroom 2: 15X13
Bedroom 3: 15X13
Bedroom 4: 16X16
Dining Room: 15X15
Family Room: 28X17
Kitchen: 16X16
Laundry: 7X5
Living Room: 26X15
Primary Bedroom: 16X15

Local Schools

High School: New Trier Twp H.S. Northfield/Wi
Middle School: Carleton W Washburne School
Elementary School: Greeley Elementary School
School District: District 203

Listed By / Shown By

Listed By

Agency Name: Compass
Agency Phone: 847-446-9600

Shown By

Agent Name: Brad Zimmerman
Agent Phone: (815) 985-2830
Agency Title: Gambino Realtors

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Estimated Payment

$ 14,954.55 per month $10,878.84 Principal & Interest $3,377.17 Property Tax $698.54 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/18/2026. The listing information on this page last changed on 05/18/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 05/18/2026 8:11:14 AM EST) or MRED MLS (last updated Mon 05/18/2026 7:21:07 AM EST) or Rockford Board of Realtors (NWIAR) (last updated Sun 05/17/2026 10:15:19 PM EST) or Northern Illinois Commercial Association Realtors (last updated Sun 05/17/2026 2:10:24 PM EST). Real estate listings held by brokerage firms other than Gambino Realtors may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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