OFF MARKET

Off Market Jun 2016 for $2.2M

$3,234,335

Est. refi paymentEst. refi $21,358/mo

•

—

sq ft

21 Woodley Rd, Winnetka, IL 60093

About this home

A New England estate style home with California casual elegance!!! Set on 1.75 acres of private, landscaped property this home has room for it all. A circular drive brings you to the 3.5 car attached garage. Freshly renovated chef's kitchen features custom cabinets, gas range, Sub Zero fridge, dble wall ovens, twin sinks, & dshwshrs, pantry and wet bar - a true dream kitchen! The expansive wood beamed family room will leave you inspired. Large airy dining, and living rooms make entertaining a breeze. 6 BR's, + playroom or possible 7th BR, 1st flr Mstr suite w/ 2 WICs, luxurious Mstr Bath. A large library, 4FPs, 3 stone patios and expansive yard will provide endless outdoor options.

Single-familyProperty Type

1934Year Built

1.7 acresLot Size

3 car garageParking

Listed by Colleen Archer Daugherty • @properties Christie's International Real Estate

Bought with Non Member • NON MEMBER

Redfin checked: 3 minutes ago

•Source:MRED as Distributed by MLS Grid #09133572

Redfin Estimate

$3,234,335

$947K since sold in June 2016$58K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 30.2% higher than the average sale price ($2.48M) of 6 comparable homes.

SOLD JUL 27, 2026
$4,300,000
A
6 beds5 baths4,159 sq ft
936 Sunset Rd, Winnetka, IL 60093
SOLD JUL 27, 2026
$1,255,000
B
5 beds4.5 baths4,440 sq ft
175 Lagoon Dr, Northfield, IL 60093
SOLD JUN 4, 2026
$1,953,000
C
5 beds4.5 baths4,572 sq ft
910 Chippewa Ln, Wilmette, IL 60091
SOLD AUG 12, 2026
$1,950,000
D
5 beds4.5 baths4,176 sq ft
3031 Indianwood Rd, Wilmette, IL 60091
SOLD JAN 5, 2026
$2,995,000
E
5 beds4.5 baths5,180 sq ft
1106 Seneca Rd, Wilmette, IL 60091
SOLD JUL 30, 2026
$2,450,000
F
6 beds5 baths5,458 sq ft
406 Woodley Woods, Winnetka, IL 60093

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Earn from this home

Sell

$1,659,438

Est. take-home

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Est. cash available

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Rent

$4,278/mo

Redfin rental estimate

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Market trends in 60093, IL

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.7%

0.2% MoM

Median sale price

$1.6M

$50K MoM

Avg. days on market

35d

0 days MoM

Recently sold homes

106

1 MoM

New listings for sale

NEW 6 HRS AGO
$529,000
3 beds2 baths— sq ft
140 W Frontage Rd, Northfield, IL 60093
EARLY ACCESS
$7,999,900
6 beds8 baths10,588 sq ft
919 Hill Rd, Winnetka, IL 60093
EARLY ACCESS
$759,000
3 beds4 baths2,612 sq ft
18 Landmark St, Northfield, IL 60093
EARLY ACCESS
$1,649,000
4 beds3 baths3,215 sq ft
870 Prospect Ave, Winnetka, IL 60093
$947,000
3 beds2.5 baths2,314 sq ft
567 Happ Rd, Northfield, IL 60093
$1,350,000
4 beds3 baths2,000 sq ft
640 Winnetka Mews #403, Winnetka, IL 60093
EARLY ACCESS
$3,275,000
7 beds5.5 baths7,649 sq ft
3 Old Hunt Rd, Northfield, IL 60093
EARLY ACCESS
$14,900,000
8 beds9.5 baths16,000 sq ft
81 Locust Rd, Winnetka, IL 60093
See all

Provided by Redfin

Sale history for 21 Woodley Rd

Date

Event

Price

Public Records

Jun 14, 2016

Sold

$2,287,000

MRED as Distributed by MLS Grid #09133572

Jun 1, 2016

Sold (MLS) (Closed Sale)

$2,286,995

Mar 31, 2016

Pending

—

Feb 8, 2016

Listed (New)

$2,395,000

MRED as Distributed by MLS Grid #09071324

Dec 8, 2015

Listing Removed

—

Oct 23, 2015

Listed (New)

MRED as Distributed by MLS Grid #07245078

Feb 7, 2011

Sold (MLS) (Closed Sale)

$1,775,000

Nov 18, 2010

Contingent

—

Jul 22, 2010

Price Changed (Price Change)

$1,990,000

Feb 8, 2010

Price Changed (Reactivated)

$2,300,000

Feb 8, 2010

Relisted (Reactivated)

—

Nov 3, 2009

Listing Removed

—

Jun 15, 2009

Listed

$2,550,000

+11

A sprawling New England style cedar home in a country setting on 1.7 acres of prof landscaped property. This unique home features a cook's Kitchen with high end appliances, generous formal Living Room & Dining Room. Lrg rustick family rm. w/ vaulted beamed ceiling, 1st flr Mstr Ste, luxurious bath, library. 6+ BR's including a separate 2 BR, 1 ba Guest Suite. 2nd floor play/bonus/computer room. 3+ car garage. 4 FP's

Public Records

Feb 26, 2007

Sold

$3,300,000

MRED as Distributed by MLS Grid #06319688

Oct 26, 2006

Listing Removed

—

Oct 23, 2006

Listed

Public Records

Apr 16, 1999

Sold

$1,875,000

Public Records

Mar 5, 1996

Sold

$1,450,000

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2023

$14,722 (+5.3%)

$43,476 + $37,359

$80,835

2022

$13,979 (−16.8%)

$43,476 + $37,359

$80,835

2021

$16,793 (+2.5%)

$78,376 + $6,120

$84,496

2020

$16,380 (+4.7%)

$78,376 + $6,120

$84,496

2019

$15,642 (−13.4%)

$78,376 + $12,249

$90,625

2018

$18,066 (+2.4%)

$64,545 + $35,316

$99,861

2017

$17,645 (+7.2%)

$64,545 + $35,316

$99,861

2016

$16,461 (−2.4%)

$64,545 + $35,316

$99,861

2015

$16,866 (+2.1%)

$53,019 + $39,549

$92,568

2014

$16,526 (+5.2%)

$53,019 + $39,549

$92,568

2013

$15,712 (+0.9%)

$53,019 + $39,549

$92,568

2012

$15,566 (+5.3%)

$58,782 + $40,073

$98,855

2011

$14,786 (−13.5%)

$58,782 + $40,073

$98,855

2010

$17,100 (+4.5%)

$58,782 + $60,275

$119,057

2009

$16,363 (+2.3%)

$59,935 + $69,147

$129,082

2008

$16,002 (+7.3%)

$95,896 + $39,978

$135,874

2007

$14,912

$95,896 + $39,978

$135,874

Tax history for 21 Woodley Rd

Year

Property tax

Land + Additions

Assessment*

2023

$14,722 (+5.3%)

$43,476 + $37,359

$80,835

2022

$13,979 (−16.8%)

$43,476 + $37,359

$80,835

2021

$16,793 (+2.5%)

$78,376 + $6,120

$84,496

2020

$16,380 (+4.7%)

$78,376 + $6,120

$84,496

2019

$15,642 (−13.4%)

$78,376 + $12,249

$90,625

2018

$18,066 (+2.4%)

$64,545 + $35,316

$99,861

2017

$17,645 (+7.2%)

$64,545 + $35,316

$99,861

2016

$16,461 (−2.4%)

$64,545 + $35,316

$99,861

2015

$16,866 (+2.1%)

$53,019 + $39,549

$92,568

2014

$16,526 (+5.2%)

$53,019 + $39,549

$92,568

2013

$15,712 (+0.9%)

$53,019 + $39,549

$92,568

2012

$15,566 (+5.3%)

$58,782 + $40,073

$98,855

2011

$14,786 (−13.5%)

$58,782 + $40,073

$98,855

2010

$17,100 (+4.5%)

$58,782 + $60,275

$119,057

2009

$16,363 (+2.3%)

$59,935 + $69,147

$129,082

2008

$16,002 (+7.3%)

$95,896 + $39,978

$135,874

2007

$14,912

$95,896 + $39,978

$135,874

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

3.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

1.06 Acres

Year renovated

—

Sq. Ft.

3,945

Year built

1935

Style

Single Family Residential

County

Cook County

APN

05291000740000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2026.

Single-Family Residence District

The R-3 Single-Family Residence District is intended to provide a semi-urban environment of single-family homes on relatively large lots. This district creates for lot sizes adequate to accommodate individual wells and sewage disposal systems. Schools, recreation and social facilities, religious facilities and public facilities which serve the residents living in the district are allowed. All commercial activities are prohibited, except for selected recreation and sanitary uses.

Permitted uses

Include but are not limited to:

Greenhouse / nursery
Religious facility
Housing-Group
Housing-Single unit
Educational/school
Library
Museum / gallery
Golf related
Cemetery
Park & open space

Property details

Parking

Parking Information
# Of Cars: 3.5
# of Garage Spaces: 3.5
Parking: Garage
Garage Ownership: Owned
Garage On-Site: Yes
Garage Type: Attached
Garage Details: Garage Door Opener(s),Transmitter(s)
Driveway: Asphalt

Interior

Bathroom Information
# of Baths (Full): 4
# of Baths (1/2): 2
Bath Amenities: Whirlpool,Separate Shower,Double Sink

Bedroom Information
# of Bedrooms: 6
# of Bedrooms Possible: 6

Room Information
Room Type: Bedroom 5
Level: Second
Dimensions: 16 x 12
Flooring: Hardwood

Room Information
Room Type: Bedroom 6
Level: Second
Dimensions: 17 x 12
Flooring: Hardwood

Room Information
Room Type: Play Room
Level: Second
Dimensions: 16 x 12
Flooring: Hardwood

Room Information
Room Type: Library
Level: Main
Dimensions: 24 x 17
Flooring: Hardwood

Room Information
Room Type: Foyer
Level: Main
Dimensions: 12 x 09
Flooring: Hardwood

Room Information
Room Type: Bedroom 2
Level: Second
Dimensions: 24 x 12
Flooring: Hardwood

Room Information
Room Type: Bedroom 3
Level: Second
Dimensions: 14 x 11
Flooring: Hardwood

Room Information
Room Type: Bedroom 4
Level: Second
Dimensions: 15 x 12
Flooring: Hardwood

Room Information
Room Type: Dining Room
Level: Main
Dimensions: 23 x 18
Flooring: Hardwood

Room Information
Room Type: Family Room
Level: Main
Dimensions: 35 x 19
Flooring: Hardwood

Room Information
Room Type: Kitchen
Level: Main
Dimensions: 21 x 18
Flooring: Hardwood

Room Information
Room Type: Living Room
Level: Main
Dimensions: 29 x 17
Flooring: Hardwood

Room Information
Room Type: Master Bedroom
Level: Main
Dimensions: 24 x 16
Flooring: Hardwood

Additional Rooms Information
Attic: Unfinished
Dining Room: Separate
Basement: Partial
Basement Description: Unfinished

Interior Features
Interior Features: Vaulted/Cathedral Ceilings, Skylight(s), Bar-Wet
# of Rooms: 12

Equipment
Appliances: Double Oven, Microwave, Dishwasher, Refrigerator, Bar Fridge, Washer, Dryer, Disposal
Humidifier, Security System, Sump Pump, Sprinkler-Lawn

Fireplace Information
# of Fireplaces: 4
Fireplace Location: Family Room,Living Room,Master Bedroom,Other
Fireplace Features: Gas Starter

Exterior

Exterior Features
Exterior Features: Patio

Building Information
Living Area Source: Not Reported
Exterior Building Type: Cedar
Age: 81-90 Years
Built Before 1978 (Y/N): Yes
Roof: Shake

Property Information
Property Type: Detached Single
Property Type: 2 Stories
Ownership: Fee Simple
Rehab (Y/N): No
Parcel Number: 05291000740000

Lot Information
Dimensions: 249 X 255 X 304 X 283
Lot Size: 1.0-1.99 Acres
Lot Features: Corner Lot, Landscaped

Financial

Tax Information
Tax Annual Amount: $29,552.12
Tax Year: 2014
Tax Exemptions: Homeowner

Financial Information
Finance Code: Cash
Special Service Area: N

Utilities

Utility Information
Water Source: Public
Sewer: Public Sewer
Electric: 200+ Amp Service

Heating & Cooling
Heating: Forced Air, Zoned
Cooling: Central Air, Zoned

Location

Community Information
Community Features: Street Paved

Homeowners Association Information
Association Fee: $1,817
Association Fee Frequency: Annually

School Information
Elementary School District: 37
Elementary School: AVOCA WEST ELEMENTARY SCHOOL
Middle Or Junior School District: 37
Middle Or Junior School: MARIE MURPHY SCHOOL
High School District: 203
High School: NEW TRIER TWP H.S. NORTHFIELD/WINNETKA

Location Information
Subdivision Name: WOODLEY ROAD
Township: NEW TRIER
Corporate Limits: WINNETKA
Directions: Woodley Rd entrance off Hill just West of Locust-take 1st left fork

Public facts

Beds: 6
Baths: 3.5
Sq. Ft.: 3,945
Stories: 1.5
Lot Size: 1.06 acres
Style: Single Family Residential
Year Built: 1935
Year Renovated: —
County: Cook County
APN: 05291000740000

Home facts updated by county records on Jul 12, 2026

Other

Listing Information
Holds Earnest Money: Yes
Possession: Closing

Around this home

Schools

Avoca West Elementary School

Public K-5 • Assigned • 1.3mi

10/10

Marie Murphy School

Public PreK-8 • Assigned • 0.4mi

9/10

New Trier Township H S Northfield

Public 9 • Assigned • 0.9mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

6/10 Flood Factor

Estimated 67-75% chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

2/10 Heat Factor

7 days above 98° expected this year, 14 days in 30 years

2/10 Wind Factor

1% chance of strong winds in next 30 years

3/10 Air Factor

4 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Winnetka, IL • 60093

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 10.3 hours in June and 3.3 hours in December, placing it below the U.S. average for solar exposure.

10.3 hrs

3.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.07M – $3.72M

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New listings for sale in 60093

NEW 6 HRS AGO

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Home values near 21 Woodley Rd

Data from public records.

Address	Redfin Estimate
301 Woodley Road, Winnetka, IL 4 Beds \| 4.5 Baths \| 4992 Sq. Ft.	$2,271,923
25 Woodley Road, Winnetka, IL 5 Beds \| 6 Baths \| - Sq. Ft.	$3,514,987

Address	Redfin Estimate
16 Woodley Road, Winnetka, IL 5 Beds \| 3.5 Baths \| 3780 Sq. Ft.	$1,887,841
29 Woodley Road, Winnetka, IL 7 Beds \| 7 Baths \| 7000 Sq. Ft.	$3,799,571

Address	Redfin Estimate
302 Woodley Road, Winnetka, IL 5 Beds \| 4.5 Baths \| - Sq. Ft.	$3,064,714
75 Woodley Road, Winnetka, IL 3 Beds \| 3.5 Baths \| 4411 Sq. Ft.	$2,038,198

Property information provided by MRED as Distributed by MLS Grid when last listed in 2016. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 60093, IL

Sale history for 21 Woodley Rd

Tax history for 21 Woodley Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 60093

Home values near 21 Woodley Rd

More real estate resources