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

$1,909,500

Trulia Estimate
  • 4 Beds
  • 6 Baths
  • 3,122 sqft (on 0.29 acres)

535 Oak St, Winnetka, IL 60093

Est. Refi. Payment $13,487/mo*
Refinance Your Home

Home Value

Trulia Estimate
$1.91M
Since last month
Increased$38K (+2%)
Since last year
Increased$58K (+3.1%)
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 +44% in the last 10 years
MonthEstimated value
2026
September 2026$1.92M
August 2026$1.88M
July 2026$1.92M
June 2026$1.99M
May 2026$2.11M
April 2026$2M
March 2026$1.96M
February 2026$1.91M
January 2026$1.85M
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
545 Sheridan Rd, Winnetka, IL
0.10
Single-Family Home
$2,200,000
09/30/25
4
3.5
3,659
567 Oak St, Winnetka, IL
0.07
Single-Family Home
$2,825,000
09/11/26
5
4
4,212
500 Sheridan Rd, Winnetka, IL
0.02
Single-Family Home
$1,950,000
03/30/26
4
3.5
5,482
519 Cedar St, Winnetka, IL
0.17
Single-Family Home
$3,050,000
10/01/25
6
5.5
4,295
560 Elm St, Winnetka, IL
0.07
Single-Family Home
$2,775,000
04/27/26
5
4.5
5,065
410 Cedar St, Winnetka, IL
0.26
Single-Family Home
$2,527,000
04/27/26
6
5.5
3,504
525 Ash St, Winnetka, IL
0.16
Single-Family Home
$4,995,000
04/27/26
5
7
4,450
335 Fairview Ave, Winnetka, IL
0.35
Single-Family Home
$1,995,000
01/13/26
4
4.5
3,288
529 Cedar St, Winnetka, IL
0.17
Single-Family Home
$2,550,000
04/23/26
5
4
4,307
334 Woodland Ave, Winnetka, IL
0.38
Single-Family Home
$3,005,000
04/23/26
5
4.5
3,748

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
560 Elm St, Winnetka, IL 60093
0.07
$2,775,000
5
4.5
5,065
Recently Sold
567 Oak St, Winnetka, IL 60093
0.07
$2,825,000
5
4
4,212
Recently Sold
550 Oak St, Winnetka, IL 60093
0.05
$2,338,200
5
4
5,000
Off Market
568 Elm St, Winnetka, IL 60093
0.08
$2,199,800
4
3.5
-
Off Market
520 Oak St, Winnetka, IL 60093
0.05
$2,790,400
6
4.5
4,114
Off Market
514 Oak St, Winnetka, IL 60093
0.05
$1,735,400
3
3
2,458
Off Market
550 Sheridan Rd, Winnetka, IL 60093
0.10
$2,332,800
5
4.5
4,443
Off Market
545 Sheridan Rd, Winnetka, IL 60093
0.10
$2,315,700
4
3.5
3,659
Off Market
597 Oak St, Winnetka, IL 60093
0.12
$3,025,600
5
6.5
5,193
Off Market
474 Sheridan Rd, Winnetka, IL 60093
0.08
$2,857,000
6
4.5
4,251
Off Market
610 Oak St, Winnetka, IL 60093
0.15
$4,554,000
6
6.5
-
Off Market
603 Elm St, Winnetka, IL 60093
0.16
$3,882,400
6
6.5
6,713
Off Market

Local Information

  • Map ViewExplore the area around 535 Oak St.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1926
0.29 acre lot
3,122 sqft
$612/sqft
Garage

About this House

This single-family home is located at 535 Oak St, Winnetka, IL. 535 Oak St is in Winnetka, IL and in ZIP code 60093. This property has 4 bedrooms, 6 bathrooms and approximately 3,122 sqft of floor space. This property has a lot size of 0.29 acres and was built in 1926.
535 Oak St, Winnetka, IL 60093 is a 4 bedroom, 6 bathroom, 3,122 sqft single-family home built in 1926. More recently, it was listed as a rental in January 2024 with an asking price of $11,000 per month. That rental listing was removed on February 15, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,909,500, with a rent estimate of $6,182/month.

Home Details for 535 Oak St

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Other, Hardwood
Interior Details
Number of Rooms: 11Types of Rooms: Dining Room
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Other, TileExterior: Stucco
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1926
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Feb 15, 2024
Source: MRED as distributed by MLS GRID #11966451
ListingRemoved
Jan 24, 2024
Source: MRED as distributed by MLS GRID #11966451
Listed For Rent
$11,000
Jun 23, 2019
Source: Agent Provided
ListingRemoved
$7,395
May 22, 2019
Source: Agent Provided
Listed For Rent
$7,395
Aug 19, 2017
Source: Agent Provided
ListingRemoved
$7,395

Market trends in Winnetka

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
25
5MoM

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 535 Oak St

  • What is 535 Oak St estimated to be worth?
    Trulia's estimated value for 535 Oak St in Winnetka, IL is $1,909,500.
  • 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.
  • What are the closest schools to 535 Oak St?
    The closest schools to 535 Oak St in Winnetka, IL are Carleton W Washburne School (Middle, rated 8/10), Greeley Elementary School (rated 9/10), New Trier Township H S Northfield (Middle/High).
  • Does 535 Oak St have air conditioning?
    Yes, 535 Oak St in Winnetka, IL has air conditioning.
  • How big is the lot at 535 Oak St?
    The lot at 535 Oak St in Winnetka, IL is about 0.29 acres (12,600 sq ft).

Explore by feature - Pet Friendly

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16 rentals with a washer/dryer in Winnetka, IL

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