O'Neil Property Group
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$2,395,000
23 Days On Site

500 Maple Street
Winnetka, IL 60093

For Sale|Single Family Residence|Active Under Contract
5
Beds
5
Total Baths
3
Full Baths
2
Partial Baths
5,646
SqFt
$424
/SqFt
1920
Built
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of Compass
500 Maple Street500 Maple Street500 Maple Street500 Maple Street
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Monthly Payment (Est.)

$10,927
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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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Listing Snapshot
Price 
$2,395,000
Days On Site 
23 Days
Bedrooms 
5
Inside Area (SqFt) 
5,646 sqft
Total Baths 
5
Full Baths 
3
Partial Baths 
2
Lot Size 
0.4 Acres
Year Built 
1920
MLS® Number 
12631320
Status 
Active Under Contract
Property Tax 
$40,526.5
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Estimated
Friends & Family
Recent Activity
yesterdayListing updated with changes from the MLS®
yesterdayStatus changed to Active Under Contract
3 weeks agoListing first seen on site
General Features
Acres 
0.4
Direction Faces 
East
Garage 
Yes
Garage Spaces 
2
Parking 
Garage Door OpenerDetachedGarageDriveway
Parking Spaces 
2
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Below 
645
SqFt Total 
3863
Style 
Colonial
Interior Features
Appliances 
Double OvenMicrowaveDishwasherRefrigeratorFreezerDisposalGas Cooktop
Basement 
Partially FinishedFull
Fireplace 
Yes
Fireplace Features 
Family RoomLiving RoomWood BurningGas Log
Fireplaces 
2
Flooring 
HardwoodCarpet
Heating 
Hot Water
Interior 
Entrance FoyerVaulted Ceiling(s)Built-in FeaturesWalk-In Closet(s)Bookcases
Laundry Features 
In Bathroom
Window Features 
Bay Window(s)Display Window(s)Plantation ShuttersScreensSkylight(s)
Bedroom 2 
Dimensions - 15X13Level - Second
Bedroom 3 
Dimensions - 15X13Level - Second
Bedroom 4 
Dimensions - 16X16Level - Third
Bedroom 5 
Dimensions - 15X13Level - Third
Breakfast Room 
Dimensions - 10X10Level - Main
Dining Room 
Dimensions - 15X15Level - Main
Family Room 
Dimensions - 28X17Level - Main
Foyer 
Dimensions - 12X9Level - Main
Kitchen 
Dimensions - 16X16Level - MainDescription - Eating Area-Breakfast Bar,Island
Laundry 
Dimensions - 7X5Level - Second
Living Room 
Dimensions - 26X15Level - Main
Master Bedroom 
Dimensions - 16X15Level - Second
Mud Room 
Dimensions - 14X5Level - Main
Office 
Dimensions - 18X16Level - Main
Sitting Room 
Dimensions - 18X16Level - Main
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Exterior Features
Construction Details 
Brick
Exterior 
Lighting
Lot Features 
Corner LotLandscapedGarden
Other Structures 
Pergola
Patio And Porch 
Patio
Roof 
Shake
Waterfront Features 
Pond
Windows/Doors 
Bay Window(s)Display Window(s)Plantation ShuttersScreensSkylight(s)
Community Features
Community Features 
ParkCurbsSidewalksStreet Lights
MLS Area 
Winnetka
School District 
New Trier Twp H.S. Northfield/Wi
Township 
New Trier
Schools
School District
New Trier Twp H.S. Northfield/Wi
Elementary School
Greeley Elementary School
Middle School
Carleton W Washburne School
High School
New Trier Twp H.S. Northfield/Wi
Listing Courtesy of MRED as distributed by MLS Grid of Compass



Based on information submitted to the MLS GRID as of 2026-05-24 06:41 PM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last checked: 2026-05-24 06:41 PM UTC
MRED DMCA Copyright Information Copyright © 2026 Midwest Real Estate Data LLC. All rights reserved.

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