Closed

$2,995,000

644 Oak Street, Winnetka, IL 60093
6 Beds5 Baths6,780 sqft6 days
644 Oak Street·Winnetka, IL 60093
6Bedrooms
5Bathrooms
6,780Sq Ft
1894Year Built
About This Home

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!

MLS# 12341040Listed April 21, 2025Residential
Property Details

Beds & Baths

Total Bedrooms6
Total Bathrooms5
Full Baths3
Half Baths2
Total Rooms15

Size & Structure

Living Area6,780 sqft
Garage Spaces2
Fireplaces2
Year Built1894
Lot Size0.400 acres

Location

CountyCook
TownshipNew Trier
Zip Code60093

Financial

List Price$2,995,000
Price / Sq Ft$442
Annual Taxes (2023)$45,671
Monthly Tax Est.$3,806
Parcel #05211160060000
Interior Features

Appliances

RangeMicrowaveDishwasherHigh End RefrigeratorBar FridgeFreezerWasherDryerDisposalStainless Steel Appliance(s)

Flooring

Hardwood

Heating

Natural Gas

Cooling

Central Air

Basement

Partially FinishedPartial

Laundry

Gas Dryer HookupSink
Exterior & Lot

Construction

Cedar

Roof

Shake

Exterior Features

BalconyLighting

Patio & Porch

Patio

Lot Features

Mature TreesGarden
Utilities & Parking

Sewer

Public Sewer

Water Source

Lake Michigan

Electric

200+ Amp Service

Parking

ConcreteGarage Door OpenerGarageOn SiteGarage OwnedAttached
HOA & Community

HOA Includes

None

Community Features

ParkCurbsSidewalksStreet LightsStreet Paved
Schools
Elementary
Greeley Elementary School
District: 36
Middle School
Carleton W Washburne School
District: 36
High School
New Trier Twp H.S. Northfield/Wi
District: 203
Tax & Financial
Annual Taxes
$45,671
Tax Year 2023
Monthly Tax Est.
$3,806
per month
Price per Sq Ft
$442
per square foot
Property Location

644 Oak Street, Winnetka, IL 60093 — Cook County

$2,995,000
$442 / sqft
644 Oak Street
6 bd5 ba6,780 sqft
VL
Vittoria Logli
Top Glenview Agent

IL License 475.178467 · (847) 810-8438

Quick Facts
6 days on market
2-car garage
2 fireplaces
0.400 acres
$45,671/yr taxes
$19,546
estimated monthly payment
Principal & Interest
$15,740/mo
Property Tax
$3,806/mo
$2,995,000
20% — $599,000
3%50%
6.875%
3%12%
Loan Amount
$2,396,000
Down Payment
$599,000

* Estimated payment only. Actual rates, taxes, and insurance may vary. Contact a lender for a personalized quote.

Listed by
Compass
Agent: Paige Dooley
Similar Homes

You May Also Like

Keep Exploring

Find Your Perfect Home

Browse available listings in Winnetka and across the North Shore.

Also popular on the North Shore

REALTOR® Logo
Equal Housing Opportunity LogoEqual Housing Opportunity

Listing Courtesy: MRED as distributed by MLS GRID | @properties Christie's International Real Estate

Based on information submitted to the MLS GRID. 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.

© 2026 MLS GRID. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use.