320 Woodley Road — Winnetka, IL 60093
Active
▼ $200,000
Winnetka, IL 60093

320 Woodley Road

$5,149,000
5 beds · 7 baths · 13,000 sqft
$200,000 below original 228 days on market $29,578/yr taxes
01About this home

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.

02Inside the home
03By the numbers
$5,149,000
List price
13,000
Square feet
5
Bedrooms
5 full / 2 half
Bathrooms
1973
Year built
0.95 ac
Lot size
3
Garage spaces
$29,578
Annual taxes
Georgian
Style
228
Days on market
04Features
Heating
Natural GasForced AirZoned
Cooling
Central Air
Appliances
RangeMicrowaveDishwasherHigh End RefrigeratorFreezerWasherDryerDisposalRange Hood
Parking
AsphaltCircular DrivewayGarage Door OpenerHeated GarageGarage OwnedAttachedGarage
Construction
Brick
Sewer
Public Sewer
05Neighborhood
H High school
New Trier Twp H.S. Northfield/Wi
Winnetka, IL
  • Five Guys 0.7 mi
  • Irving's Red Hots 0.8 mi
  • Jersey Mike's Subs 0.8 mi
  • AO Sushi 0.8 mi
  • Akai Hana 0.9 mi
  • Lou Malnati's Pizzeria 0.9 mi
  • The Fresh Market 0.8 mi
  • BP Shop 0.8 mi
  • Shell 1.1 mi
  • Family Pantry 1.1 mi
  • 7-Eleven 1.2 mi
  • Lakeside Foods 1.3 mi
  • Thornwood Park 0.6 mi
  • Community Park 1.0 mi
  • Duke Childs Field 1.0 mi
  • Northfield Park 1.1 mi
  • Robert E. Burke Memorial Park 1.1 mi
  • West Park 1.2 mi
  • Dunkin' 0.8 mi
  • Starbucks 1.1 mi
  • Tala Coffee Roasters 1.2 mi
  • Peet's Coffee 1.3 mi
  • Starbucks 1.3 mi
  • Hometown Coffee & Juice 1.3 mi
POI data via Mapbox · OpenStreetMap contributors
06History

Every event we have for this address, straight from the MLS.

Feb 23, 2026
Price reducedThis listing
@properties Christie's International Real Estate
$5,149,000
−$200,000
Sep 12, 2025
Listed for saleThis listing
@properties Christie's International Real Estate
$5,349,000
Sourced from MRED. Older events appear here as our history backfill completes.
07Ask Dwello

Real answers about this home — pricing, schools, what to ask, anything.

08See it for yourself

Stand in the kitchen.
See the light at 4pm.

Photos can only do so much. Pick a time — we'll meet you at the door.

Connect with Ewelina, Anna, or Nadeem — real people on our team, no call centers.
09Similar homes
Listed by @properties Christie's International Real Estate · Susan Maman
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12465682
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