Winnetka, IL 60093 321 Woodland Avenue

321 Woodland Avenue Winnetka, IL - Image 1321 Woodland Avenue Winnetka, IL - Image 2321 Woodland Avenue Winnetka, IL - Image 3
60 more
321 Woodland Avenue Winnetka, IL - Image 4321 Woodland Avenue Winnetka, IL - Image 5321 Woodland Avenue Winnetka, IL - Image 6321 Woodland Avenue Winnetka, IL - Image 7321 Woodland Avenue Winnetka, IL - Image 8321 Woodland Avenue Winnetka, IL - Image 9321 Woodland Avenue Winnetka, IL - Image 10321 Woodland Avenue Winnetka, IL - Image 11321 Woodland Avenue Winnetka, IL - Image 12321 Woodland Avenue Winnetka, IL - Image 13321 Woodland Avenue Winnetka, IL - Image 14321 Woodland Avenue Winnetka, IL - Image 15321 Woodland Avenue Winnetka, IL - Image 16321 Woodland Avenue Winnetka, IL - Image 17321 Woodland Avenue Winnetka, IL - Image 18321 Woodland Avenue Winnetka, IL - Image 19321 Woodland Avenue Winnetka, IL - Image 20321 Woodland Avenue Winnetka, IL - Image 21321 Woodland Avenue Winnetka, IL - Image 22321 Woodland Avenue Winnetka, IL - Image 23321 Woodland Avenue Winnetka, IL - Image 24321 Woodland Avenue Winnetka, IL - Image 25321 Woodland Avenue Winnetka, IL - Image 26321 Woodland Avenue Winnetka, IL - Image 27321 Woodland Avenue Winnetka, IL - Image 28321 Woodland Avenue Winnetka, IL - Image 29321 Woodland Avenue Winnetka, IL - Image 30321 Woodland Avenue Winnetka, IL - Image 31321 Woodland Avenue Winnetka, IL - Image 32321 Woodland Avenue Winnetka, IL - Image 33321 Woodland Avenue Winnetka, IL - Image 34321 Woodland Avenue Winnetka, IL - Image 35321 Woodland Avenue Winnetka, IL - Image 36321 Woodland Avenue Winnetka, IL - Image 37321 Woodland Avenue Winnetka, IL - Image 38321 Woodland Avenue Winnetka, IL - Image 39321 Woodland Avenue Winnetka, IL - Image 40321 Woodland Avenue Winnetka, IL - Image 41321 Woodland Avenue Winnetka, IL - Image 42321 Woodland Avenue Winnetka, IL - Image 43321 Woodland Avenue Winnetka, IL - Image 44321 Woodland Avenue Winnetka, IL - Image 45321 Woodland Avenue Winnetka, IL - Image 46321 Woodland Avenue Winnetka, IL - Image 47321 Woodland Avenue Winnetka, IL - Image 48321 Woodland Avenue Winnetka, IL - Image 49321 Woodland Avenue Winnetka, IL - Image 50321 Woodland Avenue Winnetka, IL - Image 51321 Woodland Avenue Winnetka, IL - Image 52321 Woodland Avenue Winnetka, IL - Image 53321 Woodland Avenue Winnetka, IL - Image 54321 Woodland Avenue Winnetka, IL - Image 55321 Woodland Avenue Winnetka, IL - Image 56321 Woodland Avenue Winnetka, IL - Image 57321 Woodland Avenue Winnetka, IL - Image 58321 Woodland Avenue Winnetka, IL - Image 59321 Woodland Avenue Winnetka, IL - Image 60321 Woodland Avenue Winnetka, IL - Image 61321 Woodland Avenue Winnetka, IL - Image 62321 Woodland Avenue Winnetka, IL - Image 63321 Woodland Avenue Winnetka, IL - Image 64
Presented By: @properties Christie's International Real Estate
  • MLS# 12434894
  • 08/13/2025
  • Request Tour
  • Request Info
  • Beds • 6
  • Baths • 5
  • SQFT • 4,698
  • Garage • 2

Home Details

On the market for the first time ever, this 6 bedroom, 5 bath, 4698 SQFT Winnetka home is not to be missed! Custom-built 25 years ago by Dennis McKenna, this charming brick home is set on beautifully landscaped grounds with mature trees and a bluestone inlaid path that divides the front yard, leading right to the front door. The entry foyer welcomes you home and separates the space evenly between the formal living and dining rooms. The formal living room features a gas fireplace and large windows allowing in natural light from two exposures, including a bay window overlooking the front yard. The living room opens to a den that could easily serve as a home office. The spacious formal dining room, elegantly outfitted with a chandelier and bay window, is the perfect setting for entertaining large or small dinner parties. For more informal dining, an open kitchen / family room is lined with walls of windows ushering in an abundance of natural light and overlooking the backyard. The kitchen features quartz counters, 42-inch cabinets, stainless steel appliances, a butler's pantry, a separate walk-in pantry, a built-in desk, an island with breakfast bar, and a cozy breakfast nook. The kitchen opens to a fantastic family room space complete with gas fireplace, Sonos surround system, and two sets of sliding glass doors opening onto the back deck. The entire main level is covered in hardwood flooring. A mud room is located off the side entrance to the home and includes a built-in bench and storage, laundry hook-ups, and sink. A full bath with a shower completes this level. Four bedrooms are conveniently located on the second floor. At the top of the staircase, a skylight floods the space with natural light. The graciously sized primary suite has a vaulted ceiling, a bay window with ample space for a sitting room, two custom walk-in closets, and a luxurious, spa-like ensuite bath with an oversized shower, separate soaking tub, double sink, and water closet. The second and third bedrooms are connected by a Jack-and-Jill bathroom with two sinks and a tub/shower. The fourth bedroom has a walk-in closet and is conveniently located across the hall from a full bathroom. A laundry room with oversized appliances, a sink, and cabinet and counter space completes this level. The lower level features a recreation room, two additional bedrooms (one currently set up as a gym), a full bath with tub/shower, and a workshop/hobby room. The backyard is a true oasis and features two levels of deck space updated in 2022 with Aztec decking. A bluestone patio has a fire pit surrounded by a low, rounded brick wall, which provides additional seating near the fire. Copious green lawn space is whimsically separated by a curved stone pathway leading to the two-car garage (complete with 220V Tesla charger) and a 3-car parking pad. The exterior comes complete with an irrigation system, outdoor lighting, and a gas line for grills. The Sonos surround system, Nest, and AV system will stay with the home.
Presented By: @properties Christie's International Real Estate

Interior Features for 321 Woodland Avenue

Bedrooms

Bedrooms Possible6
Total Bedrooms6

Bathrooms

BathroomSeparate Shower, Double Sink, Soaking Tub
Half Baths
Total Baths5

Other Interior Features

LivingAreaSourcePlans
BasementFinished, Full, Daylight
FlooringHardwood, Carpet
Interior Amenities1st Floor Full Bath, Built-in Features, Walk-In Closet(s)
Laundry FeaturesUpper Level, In Unit
Total Fireplaces2

Other Rooms

Room TypeBedroom 5, Bedroom 6, Breakfast Room, Den, Foyer, Mud Room, Deck, Workshop

General for 321 Woodland Avenue

AppliancesDouble Oven, Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Dryer, Disposal
Assoc Fee Paid PerNot Applicable
Association Fee IncludesNone
CityWinnetka
Community FeaturesPark, Tennis Court(s), Curbs, Sidewalks, Street Lights, Street Paved
Construction MaterialsBrick
ContingencyAttorney/Inspection
CoolingCentral Air
CountyCook
DirectionsSheridan to Willow Road, West 1/2 block to Woodland, south to 321 Woodland
Elementary SchoolGreeley Elementary School
Elementary School District36
Full Baths5
Garage Spaces2
HeatingNatural Gas
High SchoolNew Trier Twp H.S. Northfield/Wi
High School District203
MLS AreaWinnetka
Middle/Junior High SchoolThe Skokie School
Middle/Junior School District36
ModificationTimestamp2025-08-20T21:35:02.360Z
New ConstructionNo
OwnershipFee Simple
PossessionClosing
Property TypeResidential
Property TypeDetached Single
SewerPublic Sewer
Standard StatusActive Under Contract
StatusContingent
Tax Annual Amount29752
Tax Year2023
Total Rooms13
TownshipNew Trier
Virtual TourClick here
Year Built2000

Exterior for 321 Woodland Avenue

Lot Dimensions50 x 180
Parking FeaturesOn Site, Garage Owned, Detached, Garage
Total Parking2
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Schools

Elementary School Greeley Elementary School
Middle School The Skokie School Middle School
High School New Trier Twp H.S. Northfield/Wi

Client Care

Price $2,450,000
MLS#12434894
List Date 08/13/2025
Property Type Contingent
Phone 847.485.2500
Request Tour
Request Info
Visit My Website

Similar Properties to 321 Woodland Avenue