Stunning architectural gem in East Winnetka, where history meets modern sophistication. This magnificent 5+ bedroom, 3.2-bath classic, set on an expansive .4-acre lot, offers a unique blend of timeless charm and contemporary luxury overlooking the serene vistas of the iconic Village Green. Originally designed and built by the renowned architect William A. Otis for his own family, this home stands as one of Winnetka's most architecturally significant properties but his light airy floor plan with soaring ceilings and incredible panoramic vistas is perfect for the most discerning buyers. A thoughtful 2007 addition/house renovation seamlessly integrates timeless architectural elements with today's lifestyle needs, featuring a thoughtfully designed stylized kitchen, breakfast area, and a spacious family room that opens to private back patio and gardens. A grand paneled foyer introduces the home's exquisite original craftsmanship. The soaring beamed ceilings, intricate millwork, and quarter-sawn oak floors set the tone for the elegance that unfolds in each room. The living room, with its impressive fireplace, flows into the sophisticated dining room adorned with custom leaded glass cabinets and a delph-tiled fireplace and the original owners family crest & initials The heart of this home is the expansive kitchen, a culinary masterpiece equipped with marble countertops, bespoke cabinetry, and professional-grade stainless steel appliances & cleverly hidden command central station. The adjoining family room, with its high beamed ceiling and oversized windows, offers a seamless transition to the three-season porch, perfect for entertaining or enjoying tranquil views of the lush gardens and the Village Green. So good to have a mudroom room to attached garage & first floor laundry! The 2nd floor showcases 4+ beautifully appointed bedrooms, each with generous closet space, and a luxurious primary suite. This private retreat features vaulted ceilings, custom windows, dual walk-in closets, and a spa-inspired bathroom with a marble double sink, steam shower, and a private water closet. The lofty third floor provides versatile tree top living complete with oversized bedroom or playroom, smart office, renovated bath, and storage. Surprisingly tall ceilings in the lower level offer an expansive recroom, play room extraordinarily deep exercise room/golf simulator room (part of the addition) with custom climbing wall, and convenient access to the attached garage. Exceptional landscaped grounds offer a breathtaking setting for relaxation and enjoyment. With a spacious stone patio and gardens. This special home is a sanctuary in one of Winnetka's most distinguished neighborhoods. Experience the epitome of comfortable elegance in this jubilant home that is walkable to everything: town, train, parks, beach, schools and the Green Bay trail!
Closed
$3,055,000
644 Oak St, Winnetka, IL 60093
6beds
5,461sqft
Single Family Residence
Built in 1894
0.4 Acres Lot
$3,164,300 Zestimate®
$559/sqft
$7,577 Estimated rent
Home value
$3,164,300
$2.85M - $3.51M
$7,577/mo
Zestimate® history
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List your homeWhat's special
Zillow last checked: 7 hours ago
Listing updated: May 21, 2025 at 02:36am
Listing courtesy of:
Paige Dooley 847-446-9600,
Compass
Bought with:
Non Member
NON MEMBER
Source: MRED as distributed by MLS GRID,MLS#: 12341040
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 3
- 1/2 bathrooms: 2
Primary bedroom
- Features: Flooring (Hardwood), Bathroom (Full)
- Level: Second
- Area: 320 Square Feet
- Dimensions: 20X16
Bedroom 2
- Features: Flooring (Hardwood)
- Level: Second
- Area: 342 Square Feet
- Dimensions: 19X18
Bedroom 3
- Features: Flooring (Hardwood)
- Level: Second
- Area: 247 Square Feet
- Dimensions: 13X19
Bedroom 4
- Features: Flooring (Carpet)
- Level: Second
- Area: 180 Square Feet
- Dimensions: 20X9
Bedroom 5
- Features: Flooring (Carpet)
- Level: Second
- Area: 209 Square Feet
- Dimensions: 19X11
Bedroom 6
- Features: Flooring (Carpet)
- Level: Third
- Area: 408 Square Feet
- Dimensions: 24X17
Breakfast room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 128 Square Feet
- Dimensions: 16X8
Den
- Features: Flooring (Hardwood)
- Level: Main
- Area: 120 Square Feet
- Dimensions: 12X10
Dining room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 252 Square Feet
- Dimensions: 18X14
Enclosed porch
- Features: Flooring (Hardwood)
- Level: Main
- Area: 330 Square Feet
- Dimensions: 11X30
Exercise room
- Features: Flooring (Sustainable)
- Level: Basement
- Area: 270 Square Feet
- Dimensions: 18X15
Family room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 288 Square Feet
- Dimensions: 18X16
Foyer
- Features: Flooring (Hardwood)
- Level: Main
- Area: 36 Square Feet
- Dimensions: 4X9
Kitchen
- Features: Kitchen (Eating Area-Breakfast Bar, Eating Area-Table Space, Island, Pantry-Closet, Breakfast Room, Custom Cabinetry, Granite Counters, Updated Kitchen), Flooring (Hardwood)
- Level: Main
- Area: 247 Square Feet
- Dimensions: 19X13
Laundry
- Features: Flooring (Hardwood)
- Level: Main
- Area: 84 Square Feet
- Dimensions: 21X4
Living room
- Features: Flooring (Hardwood)
- Level: Main
- Area: 289 Square Feet
- Dimensions: 17X17
Mud room
- Features: Flooring (Ceramic Tile)
- Level: Main
- Area: 64 Square Feet
- Dimensions: 8X8
Office
- Features: Flooring (Hardwood)
- Level: Third
- Area: 224 Square Feet
- Dimensions: 14X16
Recreation room
- Features: Flooring (Wood Laminate)
- Level: Basement
- Area: 660 Square Feet
- Dimensions: 30X22
Heating
- Natural Gas
Cooling
- Central Air
Appliances
- Included: Range, Microwave, Dishwasher, High End Refrigerator, Bar Fridge, Freezer, Washer, Dryer, Disposal, Stainless Steel Appliance(s)
- Laundry: Gas Dryer Hookup, Sink
Features
- Cathedral Ceiling(s), Dry Bar
- Flooring: Hardwood
- Windows: Skylight(s)
- Basement: Partially Finished,Partial
- Attic: Unfinished
- Number of fireplaces: 2
- Fireplace features: Living Room, Dining Room
Interior area
- Total structure area: 6,780
- Total interior livable area: 5,461 sqft
Property
Parking
- Total spaces: 2
- Parking features: Concrete, Garage Door Opener, Garage, On Site, Garage Owned, Attached
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: No Disability Access
Features
- Stories: 3
- Patio & porch: Patio
- Exterior features: Balcony, Lighting
- Fencing: Partial
Lot
- Size: 0.40 Acres
- Dimensions: 83 X 197
- Features: Mature Trees, Garden
Details
- Parcel number: 05211160060000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Cedar
- Roof: Shake
Condition
- New construction: No
- Year built: 1894
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Public Sewer
- Water: Lake Michigan
Community & neighborhood
Community
- Community features: Park, Curbs, Sidewalks, Street Lights, Street Paved
Location
- Region: Winnetka
Other
Other facts
- Listing terms: Cash
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 5/19/2025 | Sold | $3,055,000+2%$559/sqft |
Source:  MRED as distributed by MLS GRID #12341040 Report a problem | ||
| 4/26/2025 | Contingent | $2,995,000$548/sqft |
Source: MRED as distributed by MLS GRID #12341040 Report a problem | ||
| 4/21/2025 | Listed for sale | $2,995,000+185.2%$548/sqft |
Source: MRED as distributed by MLS GRID #12341040 Report a problem | ||
| 2/10/1998 | Sold | $1,050,000+82.1%$192/sqft |
Source: Public Record Report a problem | ||
| 1/20/1994 | Sold | $576,666$106/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2023 | $45,671 +6.2% | $196,999 |
| 2022 | $42,996 -3.2% | $196,999 +15.1% |
| 2021 | $44,436 +1.6% | $171,222 |
Find assessor info on the county website
Neighborhood: 60093
Nearby schools
GreatSchools rating
- 5/10Greeley Elementary SchoolGrades: K-4Distance: 0.5 mi
- 5/10Carleton W Washburne SchoolGrades: 7-8Distance: 1.1 mi
- 10/10New Trier Township High School WinnetkaGrades: 10-12Distance: 0.9 mi
Schools provided by the listing agent
- Elementary: Greeley Elementary School
- Middle: Carleton W Washburne School
- High: New Trier Twp H.S. Northfield/Wi
- District: 36
Source: MRED as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$3,164,300
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$3,164,300
- Illinois
- Cook County
- Winnetka
- 60093
- 644 Oak St