Real Estate Agent Jean Crosby, Designated Managing Broker and Owner

Jean Crosby, Designated Managing Broker and Owner REALTOR®

(815) 231-2900
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42 Woodley Road, Winnetka, IL 60093

$2,250,000
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  • 42 Woodley Road, Winnetka, IL 60093 Main Photo

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BEDS4 BATHS3 full 3 partial SQUARE FEET4,225 MLS#12783024
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLDistrict 203
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Property Description

Rarely available first floor primary! Unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners. Owner extremely motivated!!!

42 Woodley Road | MLS# 12783024

This single family home located at 42 Woodley Road, Winnetka, IL 60093 is currently listed for sale with an asking price of $2,250,000. This property was built in 1965 and has 4 bedrooms and 3 full and 3 partial baths with 4225 sq. ft. Woodley Road is located within the District 203 school district. Search Winnetka real estate on jean.bhhscrosby.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Finished, Partial
Cooling: Central Air
Fireplaces: 2
Garage: 2
Heating: Natural Gas
Home Style: Contemporary
Lot Size: 0.90 Acres
Roof Type: Shake
Taxes: $25,026
Year Built: 1965

Amenities

Vaulted Ceiling(s)
Dry Bar
1st Floor Bedroom
In-Law Floorplan
1st Floor Full Bath
Bookcases
Granite Counters

Feature Descriptions

Additional rooms: Maid Room, Family Room
Additional Structures: Gazebo, Guest House
Appliances: Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal
Association Includes: None
Dining Room: Separate
Exterior: Frame, Stone
Fireplace Location(s): Family Room, Living Room
Laundry: Main Level
Lot: Corner Lot, Landscaped
Lot Dimensions: 254 x 155
Parcel#: 05291000770000
Parking: Gravel, Garage Door Opener, Yes, Garage Owned, Detached, Garage
Sewer: Public Sewer
Total Rooms: 10
Township: New Trier
Water: Public

Room Sizes

Maid Room: 12X36
Family Room - Down: 30X52
Bedroom 2: 19X23
Bedroom 3: 12X15
Bedroom 4: 12X15
Dining Room: 13X17
Family Room: 23X13
Kitchen: 17X29
Laundry: 9X22
Living Room: 16X23
Primary Bedroom: 23X31

Local Schools

High School: New Trier Twp H.S. Northfield/Wi
Middle School: Marie Murphy School
Elementary School: Avoca West Elementary School
School District: District 203

Listed By / Shown By

Listed By

Agency Name: @properties Christie's International Real Estate
Agency Phone: 847-374-0200

Shown By

Agent Name: Jean Crosby, Designated Managing Broker and Owner
Agent Phone: (815) 231-2900
Agency Title: Berkshire Hathaway HomeServices Crosby Starck Real Estate

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Estimated Payment

$ 7,749.27 per month $5,007.52 Principal & Interest $2,085.50 Property Tax $656.25 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 11/02/2026. The listing information on this page last changed on 11/02/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 11/02/2026 12:17:51 AM EST) or MRED MLS (last updated Mon 11/02/2026 12:09:04 AM EST) or Rockford Board of Realtors (NWIAR) (last updated Sun 11/01/2026 10:16:12 PM EST) or Northern Illinois Commercial Association Realtors (last updated Sun 11/01/2026 2:10:31 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Crosby Starck Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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