500 Maple St
Winnetka, IL 60093
5 Beds
4 Baths
5,646 sqft (on 0.40 acres)
5 Beds
4 Baths
5,646 sqft
(on 0.40 acres)
Local Information
© Google
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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!
Home Highlights
Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
$424
Listed
No Info
Home Details for 500 Maple St
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MLS Status: Contingent |
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Interior Details Basement: Partially Finished,FullNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Breakfast Room, Dining Room, Family Room, Foyer, Kitchen, Laundry, Living Room, Mud Room, Office, Sitting Room |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 5646 Square Feet |
Appliances & Utilities Appliances: Double Oven, Microwave, Dishwasher, Refrigerator, Freezer, Disposal, Gas CooktopDishwasherDisposalLaundry: In BathroomMicrowaveRefrigerator |
Heating & Cooling Heating: Radiator(s)Has CoolingAir Conditioning: Small Duct High VelocityHas HeatingHeating Fuel: Radiator S |
Fireplace & Spa Number of Fireplaces: 2Fireplace: Wood Burning, Gas Log, Family Room, Living RoomHas a FireplaceNo Spa |
Windows, Doors, Floors & Walls Window: Bay Window(s), Display Window(s), Plantation Shutters, Screens, Skylight(s)Flooring: Hardwood, Carpet |
Levels, Entrance, & Accessibility Stories: 3Accessibility: No Disability AccessFloors: Hardwood, Carpet |
View No View |
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Exterior Home Features Roof: ShakePatio / Porch: PatioOther Structures: PergolaExterior: Lighting |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Brick Driveway,Garage Door Opener,Yes,Garage Owned,Detached,Garage |
Frontage Waterfront: PondNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (below surface): 645 Square Feet |
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Year Built Year Built: 1920Year Renovated: 1990 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: BrickNot a New ConstructionNo Additional Parcels |
Property Information Parcel Number: 05211090100000 |
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Price List Price: $2,395,000Price Per Sqft: $424 |
Status Change & Dates Possession Timing: Close Of Escrow |
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Direction & Address City: Winnetka |
School Information Elementary School: Greeley Elementary SchoolElementary School District: 36Jr High / Middle School: Carleton W Washburne SchoolJr High / Middle School District: 36High School: New Trier Twp H.S. Northfield/WiHigh School District: 203 |
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Listing Agent Listing ID: 12631320 |
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Building Area Building Area: 5646 Square Feet |
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Community Features: Park, Curbs, Sidewalks, Street Lights, Street Paved |
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HOA Fee Includes: None |
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Lot Area: 0.40 acres |
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Special Conditions: List Broker Must Accompany |
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Contingencies: Attorney/Inspection |
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Business Information Ownership: Fee Simple |
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BasementMls Number: 12631320Zillow Contingency Status: Under ContractAttic: FinishedActivation Date: Mon May 18 2026 |
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ParkCurbsSidewalksStreet LightsStreet PavedMRD SHARE WITH CLIENTS: YesSource Internet Entire Listing DisplayMRD IDX Comments Reviews: NoMRD Listing On IDX Display: YesMRD AVM On IDX Display: NoMRD Address On VOW Display: YesMRD Price History On IDX Display: NoMRD Market Time On IDX Display: NoMRD REMARKSINTERNET: YesSource Internet Address DisplayHide Days On Site DisplayHide Price History DisplayMRD Remarks On VOW Display: Yes |
Last check for updates: about 19 hours ago
Listing courtesy of: Paige Dooley, (847) 446-9600
Compass
Caroline Keehn
Compass
Source: MRED as distributed by MLS GRID, MLS#12631320
Also Listed on MRED as distributed by MLS GRID.
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Property Tax and Assessment
| Year | 2023 |
|---|---|
| Tax | $38,955 |
| Assessment | $1,739,990 |
Home facts updated by county records
Comparable Sales for 500 Maple St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $1,900,000 | 07/10/25 | 5 | 4 | 3,524 | |
0.23 | Single-Family Home | $2,775,000 | 04/27/26 | 5 | 4.5 | 5,065 | |
0.25 | Single-Family Home | $2,201,894 | 07/29/25 | 5 | 4 | 5,000 | |
0.28 | Single-Family Home | $2,495,000 | 06/27/25 | 6 | 4.5 | 5,800 | |
0.32 | Single-Family Home | $2,437,000 | 05/22/26 | 5 | 4.5 | 5,184 | |
0.13 | Single-Family Home | $3,050,000 | 10/01/25 | 6 | 5.5 | 4,295 | |
0.18 | Single-Family Home | $3,480,000 | 09/06/25 | 6 | 6.5 | 6,713 | |
0.31 | Single-Family Home | $3,250,000 | 05/11/26 | 6 | 5.5 | 5,300 |
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Assigned Schools
These are the assigned schools for 500 Maple St.
- New Trier Township High School Winnetka
- 10-12
- Public
- 2730 Students
8/10GreatSchools RatingParent Rating AverageNew Trier high school is full of students who bully others relentlessly. The administration sweeps all sorts of problems under the rugs. They really only care about students who are athletes and parents who donate money. Many move here because of the schools. Our family can’t wait to leave because of how awful the administration and teachers have treated my children.Parent Review1mo ago - New Trier Township H S Northfield
- 9
- Public
- 880 Students
NAGreatSchools RatingParent Rating AverageIf it was good enough for Charlton Heston, it's good enough for you.Other Review2y ago - The Skokie School
- 5-6
- Public
- 354 Students
8/10GreatSchools RatingParent Rating AverageHorrible school. Avoid if you have academically gifted kids.Parent Review3y ago - Carleton W Washburne School
- 7-8
- Public
- 364 Students
8/10GreatSchools RatingParent Rating AverageNot good. Very rude entrance monitors. Education is ok, all teachers don’t care.Student Review1y ago - Greeley Elementary School
- K-4
- Public
- 340 Students
9/10GreatSchools RatingParent Rating AverageGreeley is a absolute gem! Parents, teachers and staff all are a community like no other. They have worked tremendously hard to keep the students engaged and receive an experience that balances all areas of growth and learning. A kudos to the dedication, diligence and tenacity of all of the teachers who go beyond for the students. As a new parent adjusting from city to burbs coupled with all that we had to adjust during the last year, beyond none, the teachers are our continued heroes!Parent Review5y ago 
Check out schools near 500 Maple St.
What Locals Say about Winnetka
At least 78 Trulia users voted on each feature.
94 % Say people would walk alone at night
90 % Say it's dog friendly
88 % Say kids play outside
88 % Say there's holiday spirit
87 % Say there are sidewalks
82 % Say yards are well-kept
81 % Say it's walkable to restaurants
80 % Say parking is easy
78 % Say there's wildlife
75 % Say it's quiet
74 % Say car is needed
72 % Say there are community events
71 % Say they plan to stay for at least 5 years
71 % Say it's walkable to grocery stores
70 % Say neighbors are friendly
67 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Paige Dooley, Compass
Agent Phone: (847) 446-9600
Based on information submitted to the MLS GRID as of 2026. 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. Click here for more information
500 Maple St, Winnetka, IL 60093 is a 5 bedroom, 5 bathroom, 5,646 sqft single-family home built in 1920. This property is currently available for sale and was listed by MRED as distributed by MLS GRID. The MLS # for this home is MLS# 12631320.