40 Windsor Dr, Oak Brook, IL 60523
Property image
Property image
OFF MARKET

$3,614,500

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 11,845 sqft (on 1.24 acres)

40 Windsor Dr, Oak Brook, IL 60523

Refinance Your Home
Currently Off Market - Sold Mar 31, 2014 for $2,080,000

Home Value

Trulia Estimate
$3.62M
Since last month
Decreased$33K (-0.9%)
Since last year
Increased$345K (+10.5%)
Since last sale
Increased$2M (+73.8%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$3.61M
August 2026$3.59M
July 2026$3.65M
June 2026$3.65M
May 2026$3.53M
April 2026$3.54M
March 2026$3.47M
February 2026$3.35M
January 2026$3.29M
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
19 Bradford Ln, Oak Brook, IL
0.44
Single-Family Home
$2,100,000
04/20/26
5
5.5
5,372
2619 York Rd, Oak Brook, IL
0.22
Single-Family Home
$870,000
01/16/26
5
3
4,337
23 Croydon Ln, Oak Brook, IL
0.31
Single-Family Home
$930,000
01/08/26
5
3.5
4,768
31 Croydon Ln, Oak Brook, IL
0.34
Single-Family Home
$1,000,000
04/14/26
4
3.5
4,453
26 Windsor Dr, Oak Brook, IL
0.18
Single-Family Home
$900,000
10/31/25
4
3
2,501
3005 Coolidge St, Oak Brook, IL
0.65
Single-Family Home
$1,290,000
06/25/26
6
5
3,684
37 Sheffield Ln, Oak Brook, IL
0.28
Single-Family Home
$760,000
04/17/26
4
4.5
2,827
822 Coventry Ln, Oak Brook, IL
1.04
Single-Family Home
$1,754,375
06/05/26
4
5.5
4,900
806 Wildwood Ct, Oak Brook, IL
0.88
Single-Family Home
$1,050,000
03/27/26
5
4.5
3,875
734 Forest Glen Ln, Oak Brook, IL
0.90
Single-Family Home
$1,200,000
06/15/26
6
3.5
4,661

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
41 Windsor Dr, Oak Brook, IL 60523
0.08
$1,858,500
5
5
3,577
Off Market
1 Stafford Ln, Oak Brook, IL 60523
0.09
$2,383,900
5
6.5
6,949
Off Market
18 Brighton Ln, Oak Brook, IL 60523
0.13
$1,210,500
4
3
3,220
Off Market
58 Sheffield Ln, Oak Brook, IL 60523
0.18
$1,017,400
3
-
2,791
Off Market
59 Sheffield Ln, Oak Brook, IL 60523
0.18
$1,424,900
5
4
4,539
For Sale
15 Brighton Ln, Oak Brook, IL 60523
0.18
$1,377,400
4
3.5
3,794
Off Market
6 Brighton Ln, Oak Brook, IL 60523
0.18
$3,630,200
7
7.5
8,724
Off Market
26 Windsor Dr, Oak Brook, IL 60523
0.18
$1,086,400
4
3
2,501
Off Market
15 Croydon Ln, Oak Brook, IL 60523
0.23
$925,000
5
3.5
4,538
For Sale
2619 York Rd, Oak Brook, IL 60523
0.22
$870,000
5
3
4,337
Recently Sold
16 Croydon Ln, Oak Brook, IL 60523
0.26
$1,246,200
3
3.5
2,864
Off Market
36 Croydon Ln, Oak Brook, IL 60523
0.26
$1,406,900
4
3.5
5,600
Off Market

Local Information

  • Map ViewExplore the area around 40 Windsor Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
1.24 acres
Living Area
11,845 sqft
Price/Sqft
$305
Parking
Garage

About this House

Luxury residence of 1 of most sought after award winning interior designers in US. Come view this private estate w/over 1.24 acres of mature landscaped grounds & experience how this visionary designer has created a retreat, allows ultimate natural light in private setting & home design all as 1! Separate private entry w/ home office or related living quarters. Wing w/ many options. Bring your needs, create your environment!
40 Windsor Dr, Oak Brook, IL 60523 is a 5 bedroom, 5 bathroom, 11,845 sqft single-family home built in 1988. It last sold for $2,080,000 on Mar 31, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,614,500, with a rent estimate of $6,489/month.

Home Details for 40 Windsor Dr

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 2

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family Home

Exterior Features

Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.24 acres

Price and Tax history

DateEventPrice
Mar 31, 2014
Source: MRED as distributed by MLS GRID #08346401
Sold
$2,080,000

Market trends in Oak Brook

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50

Around this home

What Locals Say about Oak Brook

At least 62 Trulia users voted on each feature.

  • 81 % Say car is needed

  • 81 % Say it's dog friendly

  • 80 % Say parking is easy

  • 80 % Say there's holiday spirit

  • 79 % Say yards are well-kept

  • 78 % Say it's quiet

  • 74 % Say people would walk alone at night

  • 66 % Say they plan to stay for at least 5 years

  • 65 % Say there's wildlife

  • 56 % Say kids play outside

  • 53 % Say there are sidewalks

  • 45 % Say streets are well-lit

  • 44 % Say it's walkable to restaurants

  • 38 % Say there are community events

  • 37 % Say neighbors are friendly

  • 24 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Gsmrcina
    "Great access to highways to downtown, to the airport and for travel. Access to trains to get Downtown but you need to drive to the depot. No real village downtown but access to the best shopping center in the world. High end stores abound. Costco is the largest in the area."
    0
    Flag
  • Cooleykirkwoodjacqueline
    "there dog friendly and walk there dogs and people are friendly and safe as well i have been living for 20 years hasn't been any problem at all"
    0
    Flag
  • Lisa
    "There are lots of green spaces in the area. Neighbors are very conscience and keep clean. Please do the same. "
    6
    Flag
  • Danielle J.
    "I don’t live in this area, but I frequent here often. Parents should always teach their children the basics about staying safe in all neighborhoods "
    3
    Flag
  • JR
    "Some dog owners may not feel comfortable with the coyotes that are in the area. Sightings are very common."
    3
    Flag
  • Jas G.
    "Beautiful day and planning. AV is very VICTORIA with the Cars. Free rides cheap and Lyft 100 Bentley "
    0
    Flag
  • Makinbile
    "I’ve lived in this area for 14 years and I loved every year of it. Great restaurants, parks, playing fields, bicycle trails and proximity to stores, low crime rates, great schools. The only reason you go to the downtown Chicago is nightlife."
    3
    Flag
  • Makinbile
    "I have lived in oak Brook for 14 years. Great community easy access to highways, proximity to Chicago, great restaurants and stores. Low crime rate and excellent school system "
    1
    Flag
  • George M.
    "Calm, private, comfortable, seasoned and well keep, quality home for an artist, engineer, educator, business person, or nature lover.."
    0
    Flag
  • Maggie W.
    "This is a well established area with huge trees and large lawns. Most of the residents are families and empty nesters. Friendly residents, many of whom can be seen walking their dogs daily. It is a beautiful, serene, secluded enclave only 5 minutes from the Oakbrook Shopping Center and Fortune 500 company offices. A trip into the city during non-rush hours is about 20 minutes."
    2
    Flag
  • KAREN B.
    "As a resident of York Woods in Oak Brook, I have first hand knowledge of the many wonderful things a York Woods lifestyle has to offer. In addition to the award winning schools, low taxes and convenient location, York Woods is an enclave that is enjoying a strong real estate market. "
    0
    Flag
  • KAREN B.
    "As both a local real estate professional and resident of York Woods, I can attest to the many wonderful attributes of York Woods. This area has a great location, location, location. Close to shopping, roads, schools, Fullersburg woods and less than 30 minutes to down town Chicago! "
    0
    Flag
  • MaiT
    "Best schools in IL. Everything is within 2 miles of your home!"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 40 Windsor Dr

  • What is 40 Windsor Dr estimated to be worth?
    Trulia's estimated value for 40 Windsor Dr in Oak Brook, IL is $3,614,500.
  • What is the price history for 40 Windsor Dr?
    40 Windsor Dr in Oak Brook, IL last sold for $2,080,000 in March 2014.
  • Is Oak Brook a buyer's or seller's market?
    Oak Brook is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Oak Brook?
    Residents describe Oak Brook, IL as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Oak Brook, IL.
  • How big is the lot at 40 Windsor Dr?
    The lot at 40 Windsor Dr in Oak Brook, IL is about 1.2 acres.
  • Does 40 Windsor Dr have a garage?
    Yes, 40 Windsor Dr in Oak Brook, IL has a garage.

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