321 Woodland Avenue, Winnetka, IL 60093
Local realty services provided by:Better Homes and Gardens Real Estate Connections
Upcoming open houses
- Sat, Aug 1612:00 pm - 02:00 pm
- Sun, Aug 1712:00 pm - 02:00 pm
Listed by:carrie mccormick
Office:@properties christie's international real estate
MLS#:12434894
Source:MLSNI
Price summary
- Price:$2,450,000
- Price per sq. ft.:$521.5
About this home
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.
Contact an agent
Home facts
- Year built:2000
- Listing Id #:12434894
- Added:1 day(s) ago
- Updated:August 14, 2025 at 11:45 AM
Rooms and interior
- Bedrooms:6
- Total bathrooms:5
- Full bathrooms:5
- Living area:4,698 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Natural Gas
Structure and exterior
- Year built:2000
- Building area:4,698 sq. ft.
Schools
- High school:New Trier Twp H.S. Northfield/Wi
- Middle school:The Skokie School
- Elementary school:Greeley Elementary School
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$2,450,000
- Price per sq. ft.:$521.5
- Tax amount:$29,752 (2023)
Copyright 2025 Midwest Real Estate Data LLC. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Midwest Real Estate Data LLC. Listing information is deemed reliable but not guaranteed.New listings near 321 Woodland Avenue
- New
$4,250,000Active5 beds 7 baths8,294 sq. ft.977 Sheridan Road, Winnetka, IL 60093
MLS# 12444526Listed by: BAIRD & WARNER - New
$1,349,000Active4 beds 3 baths2,378 sq. ft.1295 Sunview Lane, Winnetka, IL 60093
MLS# 12434570Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE 
$1,795,000Pending5 beds 5 baths5,445 sq. ft.1118 Mount Pleasant Road, Winnetka, IL 60093
MLS# 12430345Listed by: COMPASS- Open Sun, 12 to 2pm
$2,850,000Active6 beds 6 baths7,000 sq. ft.62 Woodley Road, Winnetka, IL 60093
MLS# 12429588Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE 
$1,625,000Pending4 beds 5 baths2,826 sq. ft.1473 Edgewood Lane, Winnetka, IL 60093
MLS# 12422974Listed by: BAIRD & WARNER
$849,000Pending3 beds 3 baths2,187 sq. ft.640 Winnetka Mews #108, Winnetka, IL 60093
MLS# 12420134Listed by: COMPASS
$2,575,000Pending4 beds 5 baths3,973 sq. ft.1300 Hackberry Lane, Winnetka, IL 60093
MLS# 12423973Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE- Open Sat, 11am to 1pm
$875,000Active3 beds 2 baths2,571 sq. ft.38 Brier Street, Winnetka, IL 60093
MLS# 12420221Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE 
$649,000Active3 beds 3 baths1,600 sq. ft.730 Oak Street, Winnetka, IL 60093
MLS# 12412570Listed by: BAIRD & WARNER
Protect your home and budget with an American Home Shield© home warranty. Learn more© 2025 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each Office is Independently Owned and Operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.