596 Oak St, Winnetka, IL 60093
Property image
Property image
OFF MARKET

$3,216,200

Trulia Estimate
  • 8 Beds
  • 6 Baths
  • 4,050 sqft (on 0.92 acres)

596 Oak St, Winnetka, IL 60093

Est. Refi. Payment $22,012/mo*
Refinance Your Home
Currently Off Market - Sold Aug 12, 2020 for $1,995,000

Home Value

Trulia Estimate
$3.22M
Since last month
Increased$30K (+0.9%)
Since last year
Increased$378K (+13.3%)
Since last sale
Increased$1M (+61.2%)
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 +49% in the last 10 years
MonthEstimated value
2026
August 2026$3.22M
July 2026$3.19M
June 2026$3.25M
May 2026$3.12M
April 2026$3.11M
March 2026$3.07M
February 2026$2.91M
January 2026$2.8M
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
519 Cedar St, Winnetka, IL
0.09
Single-Family Home
$3,050,000
10/01/25
6
5.5
4,295
560 Elm St, Winnetka, IL
0.11
Single-Family Home
$2,775,000
04/27/26
5
4.5
5,065
410 Cedar St, Winnetka, IL
0.15
Single-Family Home
$2,527,000
04/27/26
6
5.5
3,504
529 Cedar St, Winnetka, IL
0.11
Single-Family Home
$2,550,000
04/23/26
5
4
4,307
500 Maple St, Winnetka, IL
0.17
Single-Family Home
$2,550,000
06/18/26
5
4
5,646
355 Myrtle St, Winnetka, IL
0.32
Single-Family Home
$1,925,000
10/23/25
5
4.5
4,544
545 Sheridan Rd, Winnetka, IL
0.18
Single-Family Home
$2,200,000
09/30/25
4
3.5
3,659
603 Elm St, Winnetka, IL
0.14
Single-Family Home
$3,480,000
09/06/25
6
6.5
6,713
556 Willow Rd, Winnetka, IL
0.26
Single-Family Home
$2,000,000
05/08/26
5
4.5
4,023
646 Prospect Ave, Winnetka, IL
0.44
Single-Family Home
$3,250,000
05/11/26
6
5.5
5,300

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
610 Oak St, Winnetka, IL 60093
0.02
$4,583,200
6
6.5
-
Off Market
475 Cedar St, Winnetka, IL 60093
0.04
$2,602,000
5
4.5
4,438
Off Market
622 Oak St, Winnetka, IL 60093
0.04
$2,973,100
6
5.5
5,183
Off Market
597 Oak St, Winnetka, IL 60093
0.04
$3,033,800
5
6.5
5,193
Off Market
484 Cedar St, Winnetka, IL 60093
0.08
$3,253,800
6
5
-
Off Market
610 Cherry St, Winnetka, IL 60093
0.09
$1,802,300
4
3.5
-
Off Market
644 Oak St, Winnetka, IL 60093
0.09
$3,267,400
6
4
5,461
Off Market
550 Oak St, Winnetka, IL 60093
0.08
$2,325,700
5
4
5,000
Off Market
429 Walnut St, Winnetka, IL 60093
0.10
$2,212,900
4
3.5
3,200
Off Market
636 Cherry St, Winnetka, IL 60093
0.11
$1,959,900
5
4
3,159
Off Market
519 Cedar St, Winnetka, IL 60093
0.09
$3,188,000
6
5.5
4,295
Off Market
642 Cherry St, Winnetka, IL 60093
0.12
$1,862,800
4
3.5
3,256
Off Market

Local Information

  • Map ViewExplore the area around 596 Oak St.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1853
Lot Size
0.92 acres
Living Area
4,050 sqft
Price/Sqft
$794
Parking
Garage

About this House

3 blocks from train and lake
596 Oak St, Winnetka, IL 60093 is a 8 bedroom, 6 bathroom, 4,050 sqft single-family home built in 1853. It last sold for $1,995,000 on Aug 12, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,216,200, with a rent estimate of $6,361/month.

Home Details for 596 Oak St

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 14Types of Rooms: Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Office, Pantry
Heating & Cooling
Heating: Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: WoodGardenLawnPatioPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1853
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.92 acres

Price and Tax history

DateEventPrice
Aug 12, 2020
Source: MRED as distributed by MLS GRID #10701371
Sold
$1,995,000

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

Frequently asked questions about 596 Oak St

  • What is 596 Oak St estimated to be worth?
    Trulia's estimated value for 596 Oak St in Winnetka, IL is $3,216,200.
  • What is the price history for 596 Oak St?
    596 Oak St in Winnetka, IL last sold for $1,995,000 in August 2020.
  • 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 596 Oak St have air conditioning?
    Yes, 596 Oak St in Winnetka, IL has air conditioning.
  • Does 596 Oak St have a pool?
    Yes, 596 Oak St in Winnetka, IL has a pool.

Explore by feature - Pet Friendly

18 pet-friendly rentals in Winnetka, IL

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23 rentals with a washer/dryer in Winnetka, IL

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