550 Oak St, Winnetka, IL 60093
Property image
Property image
OFF MARKET

$2,325,700

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 5,000 sqft (on 0.42 acres)

550 Oak St, Winnetka, IL 60093

Est. Refi. Payment $16,000/mo*
Refinance Your Home
Currently Off Market - Sold Jul 29, 2025 for $2,201,894

Home Value

Trulia Estimate
$2.33M
Since last month
Decreased$7K (-0.3%)
Since last year
Increased$123K (+5.6%)
Since last sale
Increased$127K (+5.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +47% in the last 10 years
MonthEstimated value
2026
August 2026$2.33M
August 2026$2.33M
July 2026$2.34M
June 2026$2.31M
May 2026$2.3M
April 2026$2.29M
March 2026$2.26M
February 2026$2.21M
January 2026$2.26M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
560 Elm St, Winnetka, IL
0.08
Single-Family Home
$2,775,000
04/27/26
5
4.5
5,065
545 Sheridan Rd, Winnetka, IL
0.14
Single-Family Home
$2,200,000
09/30/25
4
3.5
3,659
500 Maple St, Winnetka, IL
0.25
Single-Family Home
$2,550,000
06/18/26
5
4
5,646
355 Myrtle St, Winnetka, IL
0.28
Single-Family Home
$1,925,000
10/23/25
5
4.5
4,544
386 Fairview Ave, Winnetka, IL
0.22
Single-Family Home
$2,030,000
01/29/26
4
3.5
5,284
519 Cedar St, Winnetka, IL
0.15
Single-Family Home
$3,050,000
10/01/25
6
5.5
4,295
355 Linden St, Winnetka, IL
0.47
Single-Family Home
$2,437,000
05/22/26
5
4.5
5,184

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
520 Oak St, Winnetka, IL 60093
0.05
$2,810,600
6
4.5
4,114
Off Market
514 Oak St, Winnetka, IL 60093
0.07
$1,527,800
3
3
2,458
Off Market
474 Sheridan Rd, Winnetka, IL 60093
0.09
$2,846,500
6
4.5
4,251
Off Market
548 Cherry St, Winnetka, IL 60093
0.09
$2,650,100
6
4.5
5,800
Off Market
560 Elm St, Winnetka, IL 60093
0.08
$2,775,000
5
4.5
5,065
Recently Sold
429 Walnut St, Winnetka, IL 60093
0.11
$2,257,400
4
3.5
3,200
Off Market
597 Oak St, Winnetka, IL 60093
0.09
$3,078,900
5
6.5
5,193
Off Market
525 Ash St, Winnetka, IL 60093
0.13
$4,995,000
5
7
4,450
Recently Sold
568 Elm St, Winnetka, IL 60093
0.10
$2,219,100
4
3.5
-
Off Market
610 Oak St, Winnetka, IL 60093
0.11
$4,614,200
6
6.5
-
Off Market
577 Ash St, Winnetka, IL 60093
0.14
$2,899,700
5
4.5
4,916
Off Market

Local Information

  • Map ViewExplore the area around 550 Oak St.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1894
0.42 acre lot
5,000 sqft
$465/sqft
2 Car Garage

About this House

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.
550 Oak St, Winnetka, IL 60093 is a 5 bedroom, 5 bathroom, 5,000 sqft single-family home built in 1894. It last sold for $2,201,894 on Jul 29, 2025 (38% above the $1,599,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,325,700, with a rent estimate of $6,868/month.
Last check for updates: about 2 hours ago
Listed by Paige Dooley, (847) 446-9600
Compass
Bought with: Jacquelynn Gordon, (847) 533-0835, Compass
Co-Buyer's Agent: Caroline Keehn, Compass
Source: MRED as distributed by MLS GRID, MLS#12349818

Home Details for 550 Oak St

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Unfinished,FullNumber of Rooms: 14Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Dining Room, Exercise Room, Family Room, Kitchen, Laundry, Living Room, Mud Room, Office, Other Room, Play Room, Recreation Room, Screened Porch, Sitting Room, Storage
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 5000 Square Feet
Appliances & Utilities
Appliances: Range, Dishwasher, Refrigerator, Gas Water HeaterDishwasherLaundry: Main Level,Gas Dryer HookupRefrigerator
Heating & Cooling
Heating: Radiator(s)Has CoolingAir Conditioning: Small Duct High VelocityHas HeatingHeating Fuel: Radiator S
Fireplace & Spa
Number of Fireplaces: 5Fireplace: Wood Burning, Family Room, Living Room, Master Bedroom, Basement, Dining RoomHas a Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2Accessibility: No Disability AccessFloors: Hardwood
View
No View

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: ScreenedFencing: FencedFoundation: Brick/Mortar, Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Asphalt,Garage Door Opener,On Site,Garage Owned,Attached,Garage
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1894
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional
Building
Construction Materials: FrameNot a New Construction
Property Information
Parcel Number: 05211180040000

Price & Status

Price
List Price: $1,599,000
Status Change & Dates
Off Market Date: Mon Jun 30 2025Possession Timing: Close Of Escrow

Location

Direction & Address
City: Winnetka
School Information
Elementary School: Greeley Elementary SchoolElementary School District: 36Jr High / Middle School: Carleton W Washburne SchoolJr High / Middle School District: 36High School: New Trier Twp H.S. Northfield/WiHigh School District: 203

Building

Building Area
Building Area: 5983 Square Feet

Community

Community Features: Sidewalks

HOA

HOA Fee Includes: None

Lot Information

Lot Area: 0.42 acres

Listing Info

Special Conditions: List Broker Must Accompany

Offer

Listing Terms: Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: 12349818Attic: Pull Down Stair, UnfinishedActivation Date: Sun Jun 22 2025

Additional Information

SidewalksMRD SHARE WITH CLIENTS: YesSource Internet Entire Listing DisplaySource Internet Address DisplayMRD REMARKSINTERNET: Yes

Price and Tax history

DateEventPrice
Jul 29, 2025
Source: MRED as distributed by MLS GRID #12349818
Sold
$2,201,894
Jul 23, 2025
Source: MRED as distributed by MLS GRID #12349818
Pending
$1,599,000
Jul 1, 2025
Source: MRED as distributed by MLS GRID #12349818
Contingent
$1,599,000
Jun 22, 2025
Source: MRED as distributed by MLS GRID #12349818
Listed For Sale
$1,599,000

Market trends in Winnetka

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
30
4MoM

Around this home

What Locals Say about Winnetka

At least 78 Trulia users voted on each feature.

  • 94 % Say people would walk alone at night

  • 90 % Say it's dog friendly

  • 88 % Say kids play outside

  • 88 % Say there's holiday spirit

  • 87 % Say there are sidewalks

  • 82 % Say yards are well-kept

  • 81 % Say it's walkable to restaurants

  • 80 % Say parking is easy

  • 78 % Say there's wildlife

  • 76 % Say it's quiet

  • 74 % Say car is needed

  • 72 % Say there are community events

  • 72 % Say it's walkable to grocery stores

  • 71 % Say they plan to stay for at least 5 years

  • 70 % Say neighbors are friendly

  • 66 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • DRD
    "Great schools and public works. Incredible beaches. Great fire and police systems. Amazing playing fields for kids’ sports. "
    0
    Flag
  • allisonbowersbrown
    "Park district, block parties, parades, fireworks. Neighborhood get together, school and church events. "
    0
    Flag
  • Jillian D.
    "I take the metra and walk to work. It’s easy and about as fast in the train to Chicago as it is in a car. Going west without a car is not as doable though. "
    1
    Flag
  • Acparacchini
    "Great dog beach, easy walk to town with coffee shops, restaurants, etc and bring the dog! 4th of July parade and everyone brings their dogs "
    0
    Flag
  • Phil L. .
    "Great parks, families and restaurants. Easy walk to restaurants , train, and interesting stores. Lots of people out walking, running or on bikes. "
    0
    Flag
  • Jillian D.
    "I take the train and walk. There are usually window seats available on the Metra when I leave winnetka at 7:21. "
    1
    Flag
  • Jillian D.
    "There are lots of green parks for doggos to play at! There’s also lil fountains where you can get water for people and dogs in the summer. "
    2
    Flag
  • Sarahvaile687
    "Winnetka music festival, summer music in the park...there are plenty of events hosted by the community."
    1
    Flag
  • Winnetka mom
    "I’ve lived here for 14 years and Winnetka is the most warm, welcoming neighborhood I’ve ever lived in!"
    1
    Flag
  • Benjamin J. D.
    "They would like it. It’s a great community with tons of parks. Move here! You won’t regret it. It’s like living in a Rockwell painting."
    1
    Flag
  • Mklein
    "Lived here for 22 years. Raised our family here. Would do it again given the chance. Great mix of people from different backgrounds and heritage. Only downfall is politically backwards and cannot get anything done in the village that’s required to stay current with infrastructure or lifestyle. "
    5
    Flag
  • Sbardoni29
    "Wonderful place to live. Gorgeous homes and great apartment living above shops and restaurants. So close to the lake and Metra runs right through city to downtown. "
    0
    Flag
  • Coveyandclay
    "family friendly and perfect for children! parks are wonderful and schools are best in country. park district facilities are top notch"
    0
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  • Coveyandclay
    "great parks and lots of kids playing there all the time. very family friendly. many kids events put on by park district also."
    0
    Flag
  • Erin K. C.
    "Very dog friendly. There is a great private dog beach that is well maintained with a dog wash and passholder only gate. All dogs are required to be well behaved and up to date on all shots. "
    0
    Flag
  • Acparacchini
    "Lived in Winnetka essentially since I was 9! Great place to raise a family. Beautiful homes, great town, great beaches, excellent schools, easy transportation to the city! "
    2
    Flag
  • Gabriel
    "Safe, quiet and architecturally nice. A great place to live and raise a family. Great schools and close to the lake. "
    0
    Flag
  • mtoyama60
    "Wonderful neighborhood close to lake and town and highly rated schools. Family community. Quiet residential street. Great investment."
    0
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  • Patty E.
    "I want to move here ,whith my kids."
    0
    Flag

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026. 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. Click here for more information

Frequently asked questions about 550 Oak St

  • What is 550 Oak St estimated to be worth?
    Trulia's estimated value for 550 Oak St in Winnetka, IL is $2,325,700.
  • What is the price history for 550 Oak St?
    550 Oak St in Winnetka, IL last sold for $2,201,894 in July 2025.
  • Is Winnetka a buyer's or seller's market?
    Winnetka is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Winnetka?
    Residents describe Winnetka, IL as dog-friendly, pedestrian-friendly, and well-kept. See recently sold homes in Winnetka, IL.
  • Does 550 Oak St have air conditioning?
    Yes, 550 Oak St in Winnetka, IL has air conditioning.
  • Does 550 Oak St have laundry facilities?
    Yes, 550 Oak St in Winnetka, IL has laundry facilities.

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