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$2,600,000
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Property Description
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.
Full Property Details
Full Property Details for 321 Woodland Ave
General
- Sold For: $2,600,000
- Taxes: $29,752 (2023)
- Status: Closed
- Type: Single Family
- Source: MRED
- MLS ID: 12434894
- Added to Site: 157 day(s) ago
Interior
- Interior Features: 1st-Floor Bath, Built-in Features, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Family Room, Living Room
- Appliances: Double Oven, Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Dryer, Disposal
- Flooring: Hardwood, Carpet
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
- Basement Baths: Yes
- Bathroom Features: Separate Shower, Double Sink, Soaking Tub
Bedrooms
- Total Bedrooms: 6
Additional Information
- Other Features: School Bus Service, Commuter Bus, Commuter Train
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: On Site, Garage Owned, Detached, Garage
- Parking On-Site: Yes
Location
- Area: Winnetka
- County: Cook
- Driving Directions: Sheridan to Willow Road, West 1/2 block to Woodland, south to 321 Woodland
School Information
- School District: 36
- Midd School District: 36
- Elementary School: Greeley Elementary School
- Middle School: The Skokie School
- High School: New Trier Twp H.S. Northfield/Wi
- Private School: New Trier Twp H.S. Northfield/Wi
Community
- Assoc. Fees Include: None
Heating & Cooling
- Cooling Type: Central Air Conditioning
- Heating Type: Natural Gas
Utilities
- Water: Public
Structural Information
- Construction: Brick
- Exterior Const.: Brick
- Basement Desc.: Finished, Full, Daylight
- Sub-Flooring: Hardwood, Carpet
- Square Feet: 4,698
- Sq. Ft. Source: Plans
- Year Built: 2000
Lot Features
- Lot Size Range: Less than .25 Acre
- Lot Dimensions: 50 x 180
Financial Considerations
- Parking Included: Yes
- Assessment Year: 2000
- Tax Amount: $29,752
- Tax Year: 2023
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: List Broker Must Accompany
- Property ID: 5214020130000
Listed by @properties Christie's International Real Estate
Sold by @properties Christie's International Real Estate
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Schools
Schools serving 321 Woodland Ave
School Districts:Winnetka School District 36, New Trier Township High School District 203
| Name | Grades | Distance |
|---|---|---|
Greeley Elementary School, Winnetka, IL 275 Fairview Avenue, Winnetka, IL 60093 | K-4 | 0.1 mi |
The Skokie School 520 Glendale Avenue, Winnetka, IL 60093 | 5-6 | 1.4 mi |
Carleton W Washburne School 515 Hibbard Road, Winnetka, IL 60093 | 7-8 | 1.6 mi |
New Trier Township H S Northfield 7 North Happ Road, Northfield, IL 60093 | 9- | 2.4 mi |
New Trier Township H S Winnetka 385 Winnetka Avenue, Winnetka, IL 60093 | 10-12 | 0.4 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 321 Woodland Ave
Date
Details
Price
Change
Source
9/18/2025
Sold
$2,600,000
6.12%
MLS
8/13/2025
Listed
$2,450,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
321 Woodland Avenue, Winnetka, IL 60093 (MLS# 12434894) is a Single Family property that was sold at $2,600,000 on September 18, 2025. Want to learn more about 321 Woodland Avenue? Do you have questions about finding other Single Family real estate for sale in Winnetka? You can browse all Winnetka real estate or contact a Coldwell Banker agent to request more information.

