555 Cherry St, Winnetka, IL 60093
OFF MARKET

555 Cherry St
Winnetka, IL 60093

  • 5 Beds
  • 5 Baths
  • 5,625 sqft (on 0.30 acres)

$1,971,600

Trulia Estimate
as of May 21, 2026
Est. Refi. Payment $13,294/mo*
Refinance Your Home

$1,971,600

Trulia Estimate
as of May 21, 2026
Est. Refi. Payment $13,294/mo*
Refinance Your Home
5 Beds
5 Baths
5,625 sqft
(on 0.30 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Vintage beauty with show stopping curb appeal and amazing street presence screams welcome home! Large scale rooms, hardwood flooring, tons of windows bringing in natural light; this home is loaded with charming details, high ceilings, and a flexible floor plan. Jaw dropping primary suite with new private bath and loft. Three additional bedrooms on 2nd level (one en-suite and the other two share hall bath), third level with 5th bedroom, full bath & study area is a perfect teen suite for those e-schooling. The outdoor space is just as wonderful as the indoors - sweeping wrap around porch, deck, paver patio and lovely green space. Location is A+ making this one a real winner!!! 2021-04-12
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 555 Cherry St

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: Brick
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1892
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Price History for 555 Cherry St

DatePriceEventSource
11/23/2022$1,400,000Sold
N/A
06/07/2021$1,415,000Sold
N/A
03/06/2021$1,475,000PendingEngel & Volkers #10993447
03/05/2021$1,475,000Listed For SaleAgent Provided
07/24/2020$1,449,000ListingRemovedAgent Provided
02/24/2020$1,449,000Listed For SaleAgent Provided
12/05/2019$1,450,000ListingRemovedAgent Provided
11/05/2019$1,450,000PriceChange
Agent Provided
10/21/2019$1,499,000Listed For SaleAgent Provided
09/13/2004$1,650,000Sold
N/A
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Property Tax and Assessment

Year2023
Tax$24,650
Assessment$1,096,440
Home facts updated by county records

Comparable Sales for 555 Cherry St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
548 Cherry St, Winnetka, IL
0.05
Single-Family Home
$2,495,000
08/06/25
6
4.5
5,800
495 Willow Rd, Winnetka, IL
0.20
Single-Family Home
$2,400,000
06/11/25
5
4.5
6,000
560 Elm St, Winnetka, IL
0.13
Single-Family Home
$2,775,000
04/27/26
5
4.5
5,065
500 Sheridan Rd, Winnetka, IL
0.10
Single-Family Home
$1,950,000
03/30/26
4
3.5
5,482
550 Oak St, Winnetka, IL
0.05
Single-Family Home
$2,202,000
07/29/25
5
4
4,172
355 Myrtle St, Winnetka, IL
0.25
Single-Family Home
$1,925,000
10/29/25
5
4.5
3,735
475 Maple St, Winnetka, IL
0.19
Single-Family Home
$1,900,000
07/10/25
4
4
3,524
474 Sheridan Rd, Winnetka, IL
0.10
Single-Family Home
$2,675,000
06/23/25
6
4.5
4,251
556 Willow Rd, Winnetka, IL
0.21
Single-Family Home
$2,000,000
05/08/26
5
4.5
4,023
519 Cedar St, Winnetka, IL
0.17
Single-Family Home
$3,050,000
10/08/25
6
5.5
4,295

Assigned Schools

These are the assigned schools for 555 Cherry St.
View nearby schools on GreatSchools
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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

  • 75 % Say it's quiet

  • 74 % Say car is needed

  • 72 % Say there are community events

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

  • 71 % Say it's walkable to grocery stores

  • 70 % Say neighbors are friendly

  • 67 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • 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
    Flag
  • 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
    Flag
  • Patty E.
    "I want to move here ,whith my kids."
    0
    Flag

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555 Cherry St, Winnetka, IL 60093 is a 5 bedroom, 5 bathroom, 5,625 sqft single-family home built in 1892. This property is not currently available for sale. 555 Cherry St was last sold on Nov 23, 2022 for $1,400,000. The current Trulia Estimate for 555 Cherry St is $1,971,600.