500 Maple St, Winnetka, IL 60093
Property image
Property image
SOLD
JUN 18, 2026

$2,577,200

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 5,646 sqft (on 0.40 acres)

500 Maple St, Winnetka, IL 60093

Est. Refi. Payment $17,722/mo*
Refinance Your Home
Currently Off Market - Sold Jun 18, 2026 for $2,550,000 (6% above list price)

Home Value

Trulia Estimate
$2.58M
Since last month
Increased$10K (+0.4%)
Since last year
Increased$139K (+5.7%)
Since last sale
Increased$26K (+1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +53% in the last 10 years
MonthEstimated value
2026
August 2026$2.58M
August 2026$2.58M
July 2026$2.57M
June 2026$2.55M
April 2026$2.67M
March 2026$2.64M
February 2026$2.53M
January 2026$2.41M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
560 Elm St, Winnetka, IL
0.23
Single-Family Home
$2,775,000
04/27/26
5
4.5
5,065
355 Linden St, Winnetka, IL
0.32
Single-Family Home
$2,437,000
05/22/26
5
4.5
5,184
519 Cedar St, Winnetka, IL
0.13
Single-Family Home
$3,050,000
10/01/25
6
5.5
4,295
646 Prospect Ave, Winnetka, IL
0.31
Single-Family Home
$3,250,000
05/11/26
6
5.5
5,300
545 Sheridan Rd, Winnetka, IL
0.29
Single-Family Home
$2,200,000
09/30/25
4
3.5
3,659
410 Cedar St, Winnetka, IL
0.19
Single-Family Home
$2,527,000
04/27/26
6
5.5
3,504

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
705 Oak St, Winnetka, IL 60093
0.02
$1,772,600
5
4.5
3,377
Off Market
711 Oak St #401, Winnetka, IL 60093
0.05
$657,600
2
2
1,544
Off Market
711 Oak St #105, Winnetka, IL 60093
0.05
$694,700
3
2
1,960
Off Market
711 Oak St #106, Winnetka, IL 60093
0.05
$589,000
3
2
1,960
Recently Sold
711 Oak St #303, Winnetka, IL 60093
0.05
$794,700
2
2
1,995
Off Market
711 Oak St #408, Winnetka, IL 60093
0.05
$701,000
3
2
1,960
Off Market
475 Maple St, Winnetka, IL 60093
0.07
$2,812,000
5
4
3,524
Off Market
730 Oak St, Winnetka, IL 60093
0.07
$610,000
3
2.5
1,600
Recently Sold
744 Oak St, Winnetka, IL 60093
0.07
$935,700
3
3
1,915
Off Market
736 Oak St, Winnetka, IL 60093
0.07
$795,800
3
2.5
1,600
Off Market
644 Oak St, Winnetka, IL 60093
0.08
$3,267,400
6
4
5,461
Off Market

Local Information

  • Map ViewExplore the area around 500 Maple St.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1920
0.4 acre lot
5,646 sqft
$452/sqft
Garage

About this House

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!
500 Maple St, Winnetka, IL 60093 is a 5 bedroom, 5 bathroom, 5,646 sqft single-family home built in 1920. It last sold for $2,550,000 on Jun 18, 2026 (6% above the $2,395,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,577,200, with a rent estimate of $7,025/month.
Last check for updates: about 3 hours ago
Listed by Paige Dooley, (847) 446-9600
Compass
Bought with: Brenda Mauldin, (312) 961-0000, Baird & Warner
Source: MRED as distributed by MLS GRID, MLS#12631320

Home Details for 500 Maple St

Active Status

MLS Status: Closed

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $2,395,000Price Per Sqft: $452/sqft
Status Change & Dates
Off Market Date: Thu May 21 2026Possession Timing: Close Of Escrow

Location

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

Building

Building Area
Building Area: 5646 Square Feet

Community

Community Features: Park, Curbs, Sidewalks, Street Lights, Street Paved

HOA

HOA Fee Includes: None

Lot Information

Lot Area: 0.40 acres

Listing Info

Special Conditions: List Broker Must Accompany

Offer

Listing Terms: Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: 12631320Attic: FinishedActivation Date: Mon May 18 2026

Additional Information

ParkCurbsSidewalksStreet LightsStreet PavedMRD SHARE WITH CLIENTS: YesSource Internet Entire Listing DisplayMRD IDX Comments Reviews: NoMRD Listing On IDX Display: YesMRD Address On VOW Display: YesMRD AVM On IDX Display: NoMRD 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

Price and Tax history

DateEventPrice
Jun 18, 2026
Source: MRED as distributed by MLS GRID #12631320
Sold
$2,550,000
Jun 1, 2026
Source: MRED as distributed by MLS GRID #12631320
Pending
$2,395,000
May 23, 2026
Source: MRED as distributed by MLS GRID #12631320
Contingent
$2,395,000
May 18, 2026
Source: MRED as distributed by MLS GRID #12631320
Listed For Sale
$2,395,000

Market trends in Winnetka

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
30
4MoM

Around this home

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

  • 76 % Say it's quiet

  • 74 % Say car is needed

  • 72 % Say there are community events

  • 72 % Say it's walkable to grocery stores

  • 71 % Say they plan to stay for at least 5 years

  • 70 % Say neighbors are friendly

  • 66 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • DRD
    "Great schools and public works. Incredible beaches. Great fire and police systems. Amazing playing fields for kids’ sports. "
    0
    Flag
  • allisonbowersbrown
    "Park district, block parties, parades, fireworks. Neighborhood get together, school and church events. "
    0
    Flag
  • Jillian D.
    "I take the metra and walk to work. It’s easy and about as fast in the train to Chicago as it is in a car. Going west without a car is not as doable though. "
    1
    Flag
  • Acparacchini
    "Great dog beach, easy walk to town with coffee shops, restaurants, etc and bring the dog! 4th of July parade and everyone brings their dogs "
    0
    Flag
  • Phil L. .
    "Great parks, families and restaurants. Easy walk to restaurants , train, and interesting stores. Lots of people out walking, running or on bikes. "
    0
    Flag
  • Jillian D.
    "I take the train and walk. There are usually window seats available on the Metra when I leave winnetka at 7:21. "
    1
    Flag
  • Jillian D.
    "There are lots of green parks for doggos to play at! There’s also lil fountains where you can get water for people and dogs in the summer. "
    2
    Flag
  • Sarahvaile687
    "Winnetka music festival, summer music in the park...there are plenty of events hosted by the community."
    1
    Flag
  • Winnetka mom
    "I’ve lived here for 14 years and Winnetka is the most warm, welcoming neighborhood I’ve ever lived in!"
    1
    Flag
  • Benjamin J. D.
    "They would like it. It’s a great community with tons of parks. Move here! You won’t regret it. It’s like living in a Rockwell painting."
    1
    Flag
  • Mklein
    "Lived here for 22 years. Raised our family here. Would do it again given the chance. Great mix of people from different backgrounds and heritage. Only downfall is politically backwards and cannot get anything done in the village that’s required to stay current with infrastructure or lifestyle. "
    5
    Flag
  • Sbardoni29
    "Wonderful place to live. Gorgeous homes and great apartment living above shops and restaurants. So close to the lake and Metra runs right through city to downtown. "
    0
    Flag
  • Coveyandclay
    "family friendly and perfect for children! parks are wonderful and schools are best in country. park district facilities are top notch"
    0
    Flag
  • Coveyandclay
    "great parks and lots of kids playing there all the time. very family friendly. many kids events put on by park district also."
    0
    Flag
  • Erin K. C.
    "Very dog friendly. There is a great private dog beach that is well maintained with a dog wash and passholder only gate. All dogs are required to be well behaved and up to date on all shots. "
    0
    Flag
  • Acparacchini
    "Lived in Winnetka essentially since I was 9! Great place to raise a family. Beautiful homes, great town, great beaches, excellent schools, easy transportation to the city! "
    2
    Flag
  • Gabriel
    "Safe, quiet and architecturally nice. A great place to live and raise a family. Great schools and close to the lake. "
    0
    Flag
  • mtoyama60
    "Wonderful neighborhood close to lake and town and highly rated schools. Family community. Quiet residential street. Great investment."
    0
    Flag
  • Patty E.
    "I want to move here ,whith my kids."
    0
    Flag

LGBTQ Local Legal Protections

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

Frequently asked questions about 500 Maple St

  • What is 500 Maple St estimated to be worth?
    Trulia's estimated value for 500 Maple St in Winnetka, IL is $2,577,200.
  • What is the price history for 500 Maple St?
    500 Maple St in Winnetka, IL last sold for $2,550,000 in June 2026.
  • Is Winnetka a buyer's or seller's market?
    Winnetka is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Winnetka?
    Residents describe Winnetka, IL as dog-friendly, pedestrian-friendly, and well-kept. See recently sold homes in Winnetka, IL.
  • Does 500 Maple St have air conditioning?
    Yes, 500 Maple St in Winnetka, IL has air conditioning.
  • Does 500 Maple St have laundry facilities?
    Yes, 500 Maple St in Winnetka, IL has laundry facilities.

Explore by feature - Pet Friendly

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