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550 Oak Street

Winnetka, IL 60093
  • $1,599,000
  • STATUS: Active Under Contract
  • ON SITE: 27 Days
  • MLS #: 12349818
Under Contract
UPDATED: 52 min ago
$1,599,000
  • 5
    BEDS
  • 0.42
    ACRES
  • 3
    BATHS
  • 2
    1/2 BATHS
  • 5,000
    SQFT
  • $320
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1894
County:
Area:

School Information

Elementary School:
School District:
36

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.

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© 2025 Midwest Real Estate Data LLC. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by MTP, MRED or Ani Real Estate. Based on information submitted to the MRED as of 2025-07-20T07:58:52.32 UTC. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED 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. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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550 Oak Street Winnetka, IL 60093

  • Price: $1,599,000
  • Status: Active Under Contract
  • On Site: 27 Days
  • Updated: 52 min ago
  • MLS #: 12349818
5
Beds
3
Baths
2
½ Baths
0.42
Acres
5,000
SQFT
$320
$/SQFT
1894
Built
Neighborhood:
Cook
County:
Cook
Area:
Cook
Elementary School:
Greeley Elementary School
Middle School:
Carleton W Washburne School
High School:
New Trier Twp H.S. Northfield/Wi
School District:
36
Property 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.
Exterior Features

Architectural Style Traditional Foundation Details Brick/MortarConcrete Perimeter Lot Features Corner Lot Lot Size .25-.49 Acre Parking Features AsphaltGarage Door OpenerOn SiteGarage OwnedAttachedGarage Parking Total 2 Roof Asphalt Types 2 Stories Waterfront YN No

Interior Features

Appliances DishwasherRefrigerator Approximate Finished Sq Ft 4496 Attic Pull Down StairUnfinished Basement Bathrooms YN Yes Basement Details UnfinishedFull Bedrooms Below Grade 0 Bedrooms Total 5 Cooling Small Duct High Velocity Dining Room Separate Fireplace Features Wood Burning Fireplace Location Family RoomLiving RoomMaster BedroomBasementDining Room Fireplaces Total 5 Flooring Hardwood Heating Radiator(s) Laundry Features Main LevelGas Dryer Hookup Main Sq Ft 2666 Room Type Mud RoomBedroom 5OfficeSitting RoomScreened PorchPlay RoomExercise RoomStorageRecreation RoomOther Room Rooms Mud Room (Main) Bedroom 5 (Second) Office (Main) Sitting Room (Second) Screened Porch (Main) Play Room (Basement) Exercise Room (Basement) Storage (Basement) Recreation Room (Basement) Other Room (Basement) Bedroom 2 (Second) Bedroom 3 (Second) Bedroom 4 (Second) Dining Room (Main) Family Room (Main) Kitchen (Main) Laundry (Main) Living Room (Main) Master Bedroom (Second) Rooms Total 14 Total Sq Ft 4496 Unfinished Sqft 5983 Upper Square Feet 1830

Property Features

Age 100+ Years Assessor Square Footage 4172 Association Fee Frequency Not Applicable Association Fee Includes None Built Before1978 YN Yes Community Features Sidewalks Contingency Attorney/Inspection Continue To Show Yes Corporate Limits Winnetka Currently Leased No Disability Access And Or Equipped No Electric 200+ Amp Service General Information None Master Association Fee Frequency Not Required Mls Actual Status Contingent New Construction YN No Other Equipment Ceiling Fan(s)Water Heater-Gas Ownership Fee Simple Rebuilt YN No Sewer Public Sewer Special Listing Conditions List Broker Must Accompany Tax Annual Amount 33616 Tax Year 2023 Township New Trier Type Detached Single Water Source Lake Michigan

Listing information © 2025 Midwest Real Estate Data LLC.
Listing provided courtesy of Compass: 847-446-9600.


© 2025 Midwest Real Estate Data LLC. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by MTP, MRED or Ani Real Estate. Based on information submitted to the MRED as of 2025-07-20T07:58:52.32 UTC. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED 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. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Digital Millennium Copyright Act
 
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