Welcome to 58 Woodley Road; a singular combination of space, land, and privacy, in one of Winnetka's most esteemed neighborhoods. A park-like setting punctuated by stone walkways and gardens creates a magical backdrop for the stately brick manse of over 8,000 (above grade) square feet. This residence is a testament to classic design. Beautiful, newly installed white-oak floors, wainscoting, dentil moulding, tray ceilings, custom built-ins and arched doorways lend an air of timeless elegance throughout. Stepping through the grand foyer, the home unfolds with a sense of expansiveness with stunning site-lines to the backyard. Formal and informal entertaining spaces, including a spacious living room and dining room, as well as an enormous family room with French doors opening to the backyard offer a great first floor flow. A beautiful sunroom, adorned with vaulted ceilings, abundant windows and six French doors, invites you to linger over morning coffee or spend a leisurely afternoon amidst the surrounding greenery. A handsome office boasts rich paneling, a fireplace and built-in bookshelves. The traditional-style kitchen, which opens to the family room, is a culinary haven, appointed with an 8-burner Wolf range, a large pantry and spacious center island. An adjoining breakfast room equally captivates with views of the backyard. A large mudroom is every bit a luxury as it offers a sink, a command center, and a second Sub-Zero refrigerator for extra food storage. A thoughtfully redesigned staircase leads upstairs to more private spaces. Expansive and sun-kissed with a dramatic vaulted ceiling, the primary bedroom doubles as a sanctuary with dual walk-in closets, dual baths, and separate water closets. A generously sized shower "room" connects them. Completing this level are three well-appointed ensuite bedrooms, and a separate au pair or in-law "wing" with two rooms, a full bath, and its own staircase and veranda. Two rooms and a full bath reside on the third level, providing the ideal space for a second office, teen hangout, kids playroom, or private guest quarters. The finished basement offers a world of possibilities. Marble flooring sets the stage for an expansive entertainment area, while a dedicated craft room, rec room, and a well-stocked bar with an ice maker cater to every leisure pursuit. A gym and wine cellar ensure there's a space for everyone to enjoy. This finely crafted estate delivers an unparalleled living experience on sought after Woodley Road in Winnetka.
Single-familyProperty Type
1939Year Built
0.93 acresLot Size
$437Est. Price/Sq.Ft.
3 car garageParking
Listed by Dawn McKenna• Coldwell Banker Realty
Bought with Emily Sachs Wong• @properties Christie's International Real Estate
Our renovations are complete and you simply won't believe your eyes! The home, stunningly appointed throughout, is filled with tasteful and stunning architectural details and offers every amenity which every luxury buyer is seeking today. Gorgeous curb appeal in a secluded and park-like one-acre setting in one of Winnetka's most sought after neighborhoods sets this home apart from other high-end homes. A chic, inviting and room-sized foyer sets the tone for this fresh, on-trend, easy-living (yet hugely impressive) home. The first floor includes a handsome, paneled office (loaded with built-ins and a striking fireplace), entertainment-sized living and dining rooms which are wildly fabulous, and a family room/kitchen area unlike any area you've ever seen. Boasting new superior wide-plank oak flooring, white custom kitchen cabinets and more, this area is truly unimaginable with its beauty, functionality and openness to the home's rear patios and lawns. Completing this level is a magnificent sunroom with walls of windows and a volume ceiling, as well as the world's best mudroom complete with a 2nd refrigerator, sink and desk. The second floor includes a primary suite with a spa area which rivals professional spas, three handsomely appointed ensuite bedrooms, and a nanny/in-law "wing" with two rooms, a full bath, and its own staircase (and its own veranda). The third floor includes two rooms and a full bath for more office, teen, or sleeping space. The lower level is where the fun begins: a recreation room & game room adjacent to a full-size bar, and exercise room with an adjacent full bath, a theatre room, wine-cellar, and play room/craft room. The home also has a three-car heated attached garage, myriad outdoor spaces,an unending amount of storage, and newer HVAC systems, mechanical systems, appliances and more. This is a rare opportunity to live in home of this class and caliber. Take a look and experience the "vibe" that sets this home apart from all others.
MRED as Distributed by MLS Grid #11350309
May 16, 2022
Listing Removed
—
MRED as Distributed by MLS Grid #10273000
Apr 27, 2021
Listing Removed
—
MRED as Distributed by MLS Grid #09343584
Dec 1, 2017
Listing Removed
—
MRED as Distributed by MLS Grid #07775882
Mar 20, 2012
Sold (MLS) (Closed Sale)
$1,537,000
$176/sq ft
Dec 23, 2011
Pending
—
Dec 6, 2011
Price Changed (Price Change)
$1,549,900
$177/sq ft
Dec 6, 2011
Relisted (Reactivated)
—
Sep 8, 2011
Price Changed
$1,999,900
$228/sq ft
Aug 26, 2011
Listing Removed
—
Aug 1, 2011
Price Changed (Price Change)
$2,229,900
$255/sq ft
Jun 30, 2011
Price Changed (Price Change)
$2,499,000
$285/sq ft
May 13, 2011
Price Changed (Price Change)
$2,899,900
$331/sq ft
Apr 8, 2011
Listed (New)
$2,999,900
$343/sq ft
Public Records
Apr 5, 2000
Sold
$1,600,000
$183/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$34,569 (+7.2%)
$76,912 + $252,088
$329,000
2022
$32,233 (−42.8%)
$56,672 + $133,136
$189,808
2021
$56,381 (−3.9%)
$68,816 + $182,394
$251,210
2020
$58,695 (+10.7%)
$68,816 + $199,298
$268,114
2019
$53,015 (−9.9%)
$68,816 + $203,399
$272,215
2018
$58,819 (+2.9%)
$56,672 + $231,040
$287,712
2017
$57,166 (+6.2%)
$56,672 + $231,040
$287,712
2016
$53,831 (−7.4%)
$56,672 + $231,040
$287,712
2015
$58,163 (+2.2%)
$46,552 + $235,655
$282,207
2014
$56,913 (−12.3%)
$46,552 + $235,655
$282,207
2013
$64,871 (+364.4%)
$46,552 + $287,905
$334,457
2012
$13,970 (−79.4%)
$51,612 + $26,276
$77,888
2011
$67,890 (+1.7%)
$51,612 + $348,211
$399,823
2010
$66,723 (−10.3%)
$51,612 + $348,211
$399,823
2009
$74,373 (+5.0%)
$52,624 + $456,922
$509,546
2008
$70,822 (+6.9%)
$84,198 + $452,166
$536,364
2007
$66,247
$84,198 + $452,166
$536,364
Tax history for 58 Woodley Rd
Year
Property tax
Land + Additions
Assessment*
2023
$34,569 (+7.2%)
$76,912 + $252,088
$329,000
2022
$32,233 (−42.8%)
$56,672 + $133,136
$189,808
2021
$56,381 (−3.9%)
$68,816 + $182,394
$251,210
2020
$58,695 (+10.7%)
$68,816 + $199,298
$268,114
2019
$53,015 (−9.9%)
$68,816 + $203,399
$272,215
2018
$58,819 (+2.9%)
$56,672 + $231,040
$287,712
2017
$57,166 (+6.2%)
$56,672 + $231,040
$287,712
2016
$53,831 (−7.4%)
$56,672 + $231,040
$287,712
2015
$58,163 (+2.2%)
$46,552 + $235,655
$282,207
2014
$56,913 (−12.3%)
$46,552 + $235,655
$282,207
2013
$64,871 (+364.4%)
$46,552 + $287,905
$334,457
2012
$13,970 (−79.4%)
$51,612 + $26,276
$77,888
2011
$67,890 (+1.7%)
$51,612 + $348,211
$399,823
2010
$66,723 (−10.3%)
$51,612 + $348,211
$399,823
2009
$74,373 (+5.0%)
$52,624 + $456,922
$509,546
2008
$70,822 (+6.9%)
$84,198 + $452,166
$536,364
2007
$66,247
$84,198 + $452,166
$536,364
*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
6
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.93 Acres
Year renovated
—
Sq. Ft.
8,110
Year built
1937
Style
Single Family Residential
County
Cook County
APN
05291000110000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 16, 2026.
R3
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 Garage Spaces: 3
# of Parking (Total): 3
Parking: Garage
Garage Ownership: Owned
Garage On-Site: Yes
Garage Type: Attached
Garage Details: Garage Door Opener(s),Transmitter(s),Heated
Driveway: Gravel
Interior
Bathroom Information
# of Baths (Full): 7
# of Baths (1/2): 3
Bath Amenities: Separate Shower,Steam Shower,Double Sink,Soaking Tub