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$2,395,000 Just Listed
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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!
Full Property Details
Full Property Details for 500 Maple St
General
- Price: $2,395,000
- Taxes: $40,526 (2024)
- Status: Active
- Type: Single Family
- Source: MRED
- MLS ID: 12631320
Rental Information
- Complex Features: Park, Curbs, Sidewalks, Street Lights, Street Paved
Interior
- Basement: Partially
- Interior Features: Vaulted Ceiling(s), Built-in Features, Walk-In Closet(s), Bookcases, Historic/Period Mlwk, Special Millwork, Separate Dining Room
- Fireplace: Yes
- Number of Fireplaces: 2
- Fireplace(s): Family Room, Living Room, Wood-Burning, Gas Log
- Appliances: Double Oven, Microwave, Dishwasher, Refrigerator, Freezer, Disposal, Gas Cooktop
- Flooring: Hardwood, Carpet
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 3
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 5
Additional Information
- Other Features: School Bus Service
Exterior
- Exterior Features: Lighting
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: Brick Driveway, Garage Door Opener, Yes, Garage Owned, Detached, Garage
Location
- Area: Winnetka
- County: Cook
- Township: New Trier
- Driving Directions: Green Bay to Oak, East to Maple. Home is on NW corner of Maple and Oak across from Village Green.
School Information
- School District: 36
- Elem School District: 36
- Midd School District: 36
- High School District: 203
- Elementary School: Greeley Elementary School
- Middle School: Carleton W Washburne School
- High School: New Trier Twp H.S. Northfield/Wi
- Private School: New Trier Twp H.S. Northfield/Wi
Community
- Assoc. Fees Include: None
Heating & Cooling
- Cooling Type: Small Duct High Velocity
- Heating Type: Radiator(s)
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan
Structural Information
- Architectural Info: Colonial
- Architectural Style: Colonial
- Construction: Brick
- Exterior Const.: Brick
- Basement: Yes
- Basement Desc.: Partially Finished, Full
- Roof: Shake
- Windows: Bay Window(s), Display Window(s), Plantation Shutters, Screens, Skylight(s)
- Sub-Flooring: Hardwood, Carpet
- Square Feet: 5,646
- Sq. Ft. Source: Estimated
- Year Built: 1920
- Built Before 1978: Yes
- Remodeled/Updated: 1990
Additional Structures
- Other Structures: Pergola
Lot Features
- Lot Size (Acres): 0.4
- Lot Size Range: .25 to .49 Acre
- Lot Dimensions: 97 x 160
- Lot Features: Corner Lot, Landscaped, Mature Trees, Garden
Water Features
- Water Front Desc.: Pond
Financial Considerations
- Assessment Year: 1920
- Tax Amount: $40,526.5
- Tax Year: 2024
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: List Broker Must Accompany
- Property ID: 5211090100000
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Schools
Schools serving 500 Maple St
School Districts:Winnetka School District 36, New Trier Township High School District 203
| Name | Grades | Distance |
|---|---|---|
Greeley Elementary School, Winnetka, IL 275 Fairview Avenue, Winnetka, IL 60093 | K-4 | 0.6 mi |
Carleton W Washburne School 515 Hibbard Road, Winnetka, IL 60093 | 7-8 | 1.1 mi |
New Trier Township H S Northfield 7 North Happ Road, Northfield, IL 60093 | 9- | 2.1 mi |
New Trier Township H S Winnetka 385 Winnetka Avenue, Winnetka, IL 60093 | 10-12 | 0.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Tax History
Tax History for 500 Maple St
Year
Property Taxes
Change
Tax Assessment
Change
2023
$38,955
6%
$173,999
—
2022
$36,632
-10%
$173,999
6%
2021
$40,853
—
$163,411
—
2020
$40,941
1%
$163,411
-8%
2019
$40,620
16%
$177,621
19%
2018
$35,102
-4%
$149,781
-6%
2017
$36,448
4%
$160,173
—
2016
$34,909
3%
$160,173
14%
2015
$33,963
2%
$140,663
—
2014
$33,247
5%
$140,663
—
2013
$31,697
13%
$140,663
8%
2012
$28,051
—
$130,811
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 500 Maple St
500 Maple Street, Winnetka, IL 60093 (MLS# 12631320) is a Single Family property with 5 bedrooms, 3 full bathrooms and 2 partial bathrooms. 500 Maple Street is currently listed for $2,395,000 and was received on May 17, 2026. Want to learn more about 500 Maple Street? Do you have questions about finding other Single Family real estate for sale in Winnetka? You can browse all Winnetka real estate or contact a Coldwell Banker agent to request more information.

