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.
New
$2,450,000
321 Woodland Ave, Winnetka, IL 60093
6beds
4,698sqft
Est.:
Single Family Residence
Built in 2000
9,000 Square Feet Lot
$-- Zestimate®
$521/sqft
$-- HOA
What's special
Gas fireplaceBeautifully landscaped groundsGreen lawn spaceIsland with breakfast barJack-and-jill bathroomMature treesWalk-in pantry
- 3 days
- on Zillow |
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Zillow last checked: 7 hours ago
Listing updated: August 14, 2025 at 02:17am
Listing courtesy of:
Carrie McCormick 773-472-0200,
@properties Christie's International Real Estate
Source: MRED as distributed by MLS GRID,MLS#: 12434894

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Tour with a buyer's agent
Tour with a buyer's agent
Open houses
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 5
Rooms
- Room types: Bedroom 5, Bedroom 6, Breakfast Room, Den, Foyer, Mud Room, Deck, Workshop
Primary bedroom
- Features: Flooring (Carpet), Bathroom (Full)
- Level: Second
- Area: 400 Square Feet
- Dimensions: 16X25
Bedroom 2
- Features: Flooring (Carpet)
- Level: Second
- Area: 182 Square Feet
- Dimensions: 14X13
Bedroom 3
- Features: Flooring (Carpet)
- Level: Second
- Area: 238 Square Feet
- Dimensions: 14X17
Bedroom 4
- Features: Flooring (Carpet)
- Level: Second
- Area: 196 Square Feet
- Dimensions: 14X14
Bedroom 5
- Features: Flooring (Carpet)
- Level: Lower
- Area: 462 Square Feet
- Dimensions: 22X21
Bedroom 6
- Features: Flooring (Other)
- Level: Lower
- Area: 192 Square Feet
- Dimensions: 12X16
Breakfast room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 130 Square Feet
- Dimensions: 13X10
Deck
- Level: Main
- Area: 345 Square Feet
- Dimensions: 23X15
Den
- Features: Flooring (Hardwood)
- Level: Main
- Area: 140 Square Feet
- Dimensions: 14X10
Dining room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 224 Square Feet
- Dimensions: 14X16
Family room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 286 Square Feet
- Dimensions: 22X13
Foyer
- Features: Flooring (Hardwood)
- Level: Main
- Area: 224 Square Feet
- Dimensions: 28X8
Kitchen
- Features: Kitchen (Eating Area-Table Space, Island), Flooring (Hardwood)
- Level: Main
- Area: 252 Square Feet
- Dimensions: 14X18
Laundry
- Features: Flooring (Other)
- Level: Main
- Area: 35 Square Feet
- Dimensions: 5X7
Living room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 294 Square Feet
- Dimensions: 14X21
Mud room
- Features: Flooring (Other)
- Level: Main
- Area: 40 Square Feet
- Dimensions: 5X8
Other
- Features: Flooring (Other)
- Level: Lower
- Area: 182 Square Feet
- Dimensions: 14X13
Heating
- Natural Gas
Cooling
- Central Air
Appliances
- Included: Double Oven, Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Dryer, Disposal
- Laundry: Upper Level, In Unit
Features
- 1st Floor Full Bath, Built-in Features, Walk-In Closet(s)
- Flooring: Hardwood, Carpet
- Basement: Finished,Full,Daylight
- Number of fireplaces: 2
- Fireplace features: Family Room, Living Room
Interior area
- Total structure area: 4,698
- Total interior livable area: 4,698 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: On Site, Garage Owned, Detached, Garage
- Garage spaces: 2
Accessibility
- Accessibility features: No Disability Access
Features
- Stories: 2
- Patio & porch: Deck, Patio
Lot
- Size: 9,000 Square Feet
- Dimensions: 50 x 180
Details
- Parcel number: 05214020130000
- Special conditions: List Broker Must Accompany
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Brick
Condition
- New construction: No
- Year built: 2000
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Park, Tennis Court(s), Curbs, Sidewalks, Street Lights, Street Paved
HOA
- Services included: None
Location
- Region: Winnetka
Financial & listing details
- Price per square foot: $521/sqft
- Tax assessed value: $1,316,490
- Annual tax amount: $29,752
- Date on market: 8/13/2025
- Ownership: Fee Simple
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