550 Oak Street, Winnetka, Illinois 60093


$2,201,894

Sold
Status: Closed
Sqft: 5,000
Cost/Sqft: $320
Beds: 5
Baths: 5
Year Built: 1894
Property Taxes: $33,616
Days On Market: 93
Lot Size: 0,42
Map
Street View

Description

Opportunity to own and enhance a once-in-a-generation architecturally rich East Winnetka home built in 1894 and set on a beautifully landscaped .42-acre corner lot just steps from town, train, schools, Lake Michigan beaches and the Village Green. Bring your contractor with you to see this solidly built 5000 plus square foot, 5+ bedrooms, 3.2 baths vintage beauty that is surrounded by an iconic white "acorn" picket fence. This home is full of original character with soaring ceilings, fine millwork, original hardwood floors and five handsome wood-burning fireplaces. Expansive, light-filled rooms offer a flexible and gracious layout that could work perfectly for today's lifestyle. Watch the world go by on the oversized, serene, screened porch. Be welcomed by the gracious foyer leading to a stunning living room with custom bookcases and a grand dining room with a fireplace offering a meticulously preserved surround. At the heart of the home is the breathtaking family room affectionately known as "the library" distinguished by walls of built-in bookcases, lofty ceilings, rich woodwork, and a dramatic wall of windows that bathe the space in natural light. This extraordinary room opens to the spacious porch with bead board accents and overlooks the lush, expansive yard. A thoughtfully designed and potential open-concept kitchen connects seamlessly to the rear mudroom/butler's pantry and is flanked by two versatile spaces perfect for use as an office, food pantry or laundry room. Upstairs, the primary suite offers a peaceful retreat with its own sitting room, ample closet space, and a private en-suite bath. Four additional bedrooms and a well-appointed hall bath provide flexibility and endless opportunities for personalization. In addition to a separate alarmed and locked security room with large fireproof safe, the lower level adds the possibility for expanded living ideal for recreation, fitness, hobbies, a shop, or storage. The attic with its lofty ceilings has potential for future living space. Panoramic views abound from nearly every room, framing the private, beautifully landscaped grounds. The expansive yard, enhanced by mature plantings and tranquil green space, is perfect for entertaining, play, or quiet outdoor enjoyment. 550 Oak is more than just a home it is a beloved sanctuary where every detail has been thoughtfully preserved to honor its legacy while elevating its livability. Nestled in one of Winnetka's most distinguished neighborhoods and walkable to all, this is a truly exceptional opportunity to own a piece of Winnetka's storied history - ready to be reimagined for generations to come. *Note the house is in an estate and is being conveyed AS-IS. Please complete all inspections and contractor visits prior to any offer being submitted in order to waive the inspection contingency. Showings begin on Tuesday, June 24th.

Property Specifics

Single Family
1894
No
0.42
Cook
— / Not Applicable
12349818
05211180040000

Nearby Schools

NAME: DISTRICT: DISTANCE:
Grade School
Greeley Elementary School
36
Middle School
Carleton W Washburne School
36 Not in DB
High School
New Trier Twp H.s. Northfield/wi
203 Not in DB

Property History

DATE: EVENT: PRICE: SOURCE:
29 Jul, 2025 Sold $2,201,894 MRED MLS
30 Jun, 2025 Under contract $1,599,000 MRED MLS
22 Jun, 2025 Listed for sale $1,599,000 MRED MLS

Room Specifics

All Bedroom Info:
Total Bedrooms: 5
Bedrooms Above Ground: 5
Bedrooms Below Ground: 0
Second Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Third Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Fourth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Fifth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Bathroom Info:
Full Bathrooms: 5
Partial Bathrooms: 2
Bathroom Amenities: —
Bathroom in Basement: 1
Additional Rooms Info:
Rooms: —
Basement: —
Basement Description: —

Other Specifics

2
140 X 127 X 88 X 10 X 52 X
Pull Down Stair,Unfinished
Not in DB

Tax History

Year Property Taxes
2025 $33,616

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