RDM Group Chicago

644 Oak Street, Winnetka, IL, 60093

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$2,995,000
6 Days On Site

644 Oak Street
Winnetka, IL 60093

For Sale|Single Family Residence|Active
6
Beds
3
Full Baths
2
Partial Baths
5,461
SqFt
$548
/SqFt
1894
Built
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of Compass
Call Now: 312-566-7107
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312-566-7107
644 Oak Street644 Oak Street644 Oak Street644 Oak Street
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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!

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Listing Snapshot
Price 
$2,995,000
Days On Site 
6 Days
Bedrooms 
6
Inside Area (SqFt) 
5,461 sqft
Total Baths 
5
Full Baths 
3
Partial Baths 
2
Lot Size 
0.4 Acres
Year Built 
1894
MLS® Number 
12341040
Status 
Active
Property Tax 
$45,671
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Plans
Friends & Family
Recent Activity
yesterdayListing updated with changes from the MLS®
3 days agoStatus changed to Active
7 days agoListing first seen on site
General Features
Acres 
0.4
Direction Faces 
North
Garage 
Yes
Garage Spaces 
2
Parking 
ConcreteGarage Door OpenerGarageOn SiteAttached
Parking Spaces 
2
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
Interior Features
Appliances 
RangeMicrowaveDishwasherBar FridgeFreezerWasherDryerDisposalStainless Steel Appliance(s)
Basement 
Partially FinishedPartial
Cooling 
Central Air
Electric 
200+ Amp Service
Fireplace 
Yes
Fireplace Features 
Living Room
Fireplaces 
2
Flooring 
Hardwood
Heating 
Natural Gas
Interior 
Entrance FoyerCathedral Ceiling(s)Dry Bar
Laundry Features 
Gas Dryer HookupSink
Window Features 
Skylight(s)
Bedroom 2 
Dimensions - 19X18Level - Second
Bedroom 3 
Dimensions - 13X19Level - Second
Bedroom 4 
Dimensions - 20X9Level - Second
Bedroom 5 
Dimensions - 19X11Level - Second
Bedroom 6 
Dimensions - 24X17Level - Third
Breakfast Room 
Dimensions - 16X8Level - Main
Den 
Dimensions - 12X10Level - Main
Dining Room 
Dimensions - 18X14Level - Main
Enclosed Porch 
Dimensions - 11X30Level - Main
Exercise Room 
Dimensions - 18X15Level - Basement
Family Room 
Dimensions - 18X16Level - Main
Foyer 
Dimensions - 4X9Level - Main
Kitchen 
Dimensions - 19X13Level - MainDescription - Eating Area-Breakfast Bar,Eating Area-Table Space,Island,Pantry-Closet,Breakfast Room,Custom Cabinetry,Granite Counters,Updated Kitchen
Laundry 
Dimensions - 21X4Level - Main
Living Room 
Dimensions - 17X17Level - Main
Master Bedroom 
Dimensions - 20X16Level - Second
Mud Room 
Dimensions - 8X8Level - Main
Office 
Dimensions - 14X16Level - Third
Recreation Room 
Dimensions - 30X22Level - Basement
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Exterior Features
Construction Details 
Cedar
Exterior 
BalconyLighting
Fencing 
Partial
Lot Features 
Garden
Patio And Porch 
PorchPatio
Roof 
Shake
Windows/Doors 
Skylight(s)
Community Features
Community Features 
ParkCurbsSidewalksStreet Lights
MLS Area 
Winnetka
School District 
New Trier Twp H.S. Northfield/Wi
Township 
New Trier
Schools
School District
New Trier Twp H.S. Northfield/Wi
Elementary School
Greeley Elementary School
Middle School
Carleton W Washburne School
High School
New Trier Twp H.S. Northfield/Wi
Listing Courtesy of MRED as distributed by MLS Grid of Compass



Based on information submitted to the MLS GRID as of 2025-04-24 11:33 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last checked: 2025-04-24 11:33 AM UTC
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Neighborhood & Commute
Source: Walkscore
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