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Detached Single · Winnetka, IL
$4,949,000
5 beds · 6 baths · 13,000 sqft
320 Woodley Road, Winnetka, IL, 60093
A brick-and-mortar place to make your own — room to make it home.
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What’s special

Central air3-car garage0.95-acre lotIn-unit laundry
Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof, columned portico, and timeless symmetry. Together, these elements create a striking first impression and set the stage for interiors that exude sophistication at every turn. Step inside the grand "bookmatched" marble-floored foyer, where a dramatic staircase sets a refined tone for the home. To one side, the formal living room offers an inviting gathering space anchored by a marble fireplace, while the formal dining room is perfectly scaled for both intimate dinners and large-scale entertaining. A massive, richly paneled home office with dramatic coffered ceilings offers an impressive and inspiring workspace. At the heart of the home, the gourmet kitchen boasts professional-grade appliances, an oversized island, full wall of pantry storage, and a sunlit breakfast area all overlooking the magnificent pool and grounds. A butler's pantry ideally placed between the kitchen and dining room provides effortless entertaining. Just beyond, the kitchen opens to a cozy family room with a fireplace and wet bar, while French doors lead to an expansive covered terrace framed by graceful curved archways and cooled by ceiling fans. This spectacular outdoor living space features a brand-new outdoor kitchen fully equipped for grilling and al fresco dining, leading to the sparkling pool, surrounding patio and yard, creating a seamless setting for summer entertaining and secluded relaxation. A convenient first-floor laundry/mud room right off the 3-car heated garage with epoxy flooring and 2 powder rooms adds everyday ease. Upstairs, the elegantly appointed primary suite offers dual walk-in closets, a dedicated vanity area, and a spa-inspired bath with separate vanities and radiant heated floors. Four well-proportioned additional bedrooms, each with generous closets and either en-suite or adjoining baths, provide comfortable accommodations for family and guests. This level is further enhanced by expansive linen closets, abundant storage, and a dedicated luggage room. The impeccably finished lower-level rivals any private club, featuring a state-of-the-art home theatre, richly paneled billiards and game room, fully outfitted bar, expansive fitness studio, wine cellar, guest suite, and a dedicated woodshop for refined hobbyists or craftsmen. Located in one of Winnetka's most prestigious locations and served by its award-winning schools, this remarkable estate perfectly balances classic sophistication with modern luxury. Combining architectural pedigree, unparalleled amenities, and impeccably landscaped grounds, this is a home to be cherished for generations. Furniture available for sale.
— the listing agent’s description

The home

5 beds
6 baths
13,000 sqft
Built in 1973
0.95-acre lot
3-car garage
Detached Single
Georgian

What it’ll cost

$381 / sqft
$29,578 taxes / yr
$2,605/mo HOA
7 days on dwello

Estimated monthly payment

$32,827/mo
Principal & interest$26,314
Property taxes$2,465
Homeowners insurance$1,443
HOA dues$2,605
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WED
Jun 3
THU
Jun 4
FRI
Jun 5
SAT
Jun 6
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7 days on dwello
Price history
Listed for sale
Jul 8, 2026
$4,949,000
Earlier records
Listed
Sep 12, 2025
$5,149,000
From MLS records — independently verify.
Property taxes
2025
Annual tax bill (MLS)
$29,578/yr
Assessed value
2026
County assessor
$285,170~$2,851,700 mkt
2025
$285,170~$2,851,700 mkt
2024
$168,375~$1,683,750 mkt
2023
$168,375~$1,683,750 mkt
2022
$181,456~$1,814,560 mkt
2021
$170,580~$1,705,800 mkt
2020
$170,580~$1,705,800 mkt
2019
$203,601~$2,036,010 mkt
Assessed value from the Cook County Assessor (open records). Estimated market ≈ assessed × 10 for residential; not an appraisal — verify with the assessor.

Features

Central AirNatural GasForced AirZonedBrickPublic SewerAsphaltCircular Driveway

Schools

High — New Trier Twp H.S. Northfield/Wi
Assigned schools per the listing — always verify enrollment + boundaries with the district.
Neighborhood
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Nearby places via OpenStreetMap — approximate; verify what matters to you. Map © Mapbox © OpenStreetMap.
MLS listing dataMRED
Listed by Susan Maman · @properties Christie's International Real Estate
Listing last updated Jul 14, 2026 · data refreshed from the MLS Jul 14, 2026, 5:10 AM CT
Based on information submitted to the MLS GRID as of Jul 14, 2026, 5:10 AM CT. Listing data © MRED LLC, distributed by MLS GRID — deemed reliable but not guaranteed; independently verify. Anything shown below this point is not MLS listing data.
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