555 Cherry St
Winnetka, IL 60093
5 Beds
4.5 Baths
6,580 sqft (on 0.27 acres)
5 Beds
4.5 Baths
6,580 sqft
(on 0.27 acres)
Home Highlights
Parking
2 Car Garage
Outdoor
Patio
Climate Control
Heating & Cooling
Price/Sqft
$262
Local Information
- Map ViewExplore the area around 555 Cherry St.
- Schools2 Elementary Schools2 Middle Schools2 High Schools
- Shop & Eat
-- mins to
Description
Beautifully restored idyllic Victorian home expanded for today's living features a flexible floorplan with easy flow, generously sized rooms, dramatic ceiling heights, detailed millwork and plaster moldings, inlaid floors and an abundance of tall oversized windows. The lushly landscaped property highlighted by majestic oak trees is ideally located on a favorite east Winnetka street near lakefront beaches, shopping, restaurants, Metra, Greeley and New Trier East. The quintessential front porch welcomes you to sit and enjoy the view of the park-like lawn. The front entry opens to the foyer connecting the first floor rooms and a striking staircase. Grandly scaled great room sets the tone for the rest of the home, and offers a wonderful space for gathering and relaxing. The formal living and dining rooms echo the same gracious, comfortable style. An updated white kitchen with granite countertops has top appliances and opens to the family room with doors to the deck and paver patio. Second floor includes a stunning primary suite featuring a gorgeous bedroom filled with light, soaring ceilings, two walk-in closets, a luxurious spa bath and a lofted office above. Three additional bedrooms and two renovated baths complete this level. The third floor has treetop views, a bedroom, office and full bath. The lower level features a laundry room, playroom and storage. Very private back yard with two level deck and separate paver patio. Attached heated garage. Property sold "As- Is".
Home Details for 555 Cherry St
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MLS Status: New |
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Interior Details Basement: Partially Finished,PartialNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Dining Room, Family Room, Foyer, Great Room, Kitchen, Laundry, Living Room, Loft, Office, Screened Porch, Walk In Closet |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 6580 Square Feet |
Heating & Cooling Heating: Natural Gas,SteamHas CoolingAir Conditioning: Central Air,Small Duct High VelocityHas HeatingHeating Fuel: Natural Gas |
Fireplace & Spa Number of Fireplaces: 3Fireplace: Family Room, Living Room, BedroomHas a Fireplace |
Gas & Electric Electric: 200+ Amp Service |
Windows, Doors, Floors & Walls Flooring: Hardwood |
Levels, Entrance, & Accessibility Stories: 3Accessibility: No Disability AccessFloors: Hardwood |
View No View |
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Exterior Home Features Roof: AsphaltPatio / Porch: Patio, Screened |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageHas an Attached GarageParking Spaces: 2Parking: Asphalt,Heated Garage,Yes,Garage Owned,Attached,Garage |
Frontage Not on Waterfront |
Water & Sewer Sewer: Public Sewer |
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Year Built Year Built: 1892Year Renovated: 2015 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Victorian |
Building Construction Materials: CedarNot a New Construction |
Property Information Parcel Number: 05211180100000 |
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Price List Price: $1,725,000Price Per Sqft: $262 |
Status Change & Dates Possession Timing: Close Of Escrow |
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Direction & Address City: Winnetka |
School Information Elementary School: Greeley Elementary SchoolElementary School District: 36Jr High / Middle School: The Skokie SchoolJr High / Middle School District: 36High School: New Trier Twp H.S. Northfield/WiHigh School District: 203 |
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Listing Agent Listing ID: 12711173 |
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Building Area Building Area: 6580 Square Feet |
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HOA Fee Includes: None |
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Lot Area: 0.27 acres |
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Special Conditions: List Broker Must Accompany |
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Business Information Ownership: Fee Simple |
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BasementMls Number: 12711173 |
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Source Internet Entire Listing DisplayMRD IDX Comments Reviews: NoMRD Listing On IDX Display: YesMRD AVM On IDX Display: NoMRD Address On VOW Display: YesMRD Price History On IDX Display: NoMRD Market Time On IDX Display: NoMRD REMARKSINTERNET: YesSource Internet Address DisplayHide Days On Site DisplayHide Price History DisplayMRD Remarks On VOW Display: Yes |
Last check for updates: about 3 hours ago
Listing courtesy of: Howard Meyers, (847) 446-9600
Compass
Susan Meyers, GRI,SRES, (847) 778-1395
Compass
Source: MRED as distributed by MLS GRID, MLS#12711173
Also Listed on MRED as distributed by MLS GRID.
Market trends in Winnetka
Last updated June 2026
Avg. sale price
$1.93M
Sale-to-List Price
—
Price per sq ft
$511
Available listings
34
8MoM
Price History for 555 Cherry St
| Date | Price | Event | Source |
|---|---|---|---|
| 11/23/2022 | $1,400,000 | Sold | N/A |
| 04/15/2021 | $1,415,000 | Sold | MRED as distributed by MLS GRID #10993447 |
| 03/06/2021 | $1,475,000 | Pending | Engel & Volkers #10993447 |
| 03/05/2021 | $1,475,000 | Contingent | MRED as distributed by MLS GRID #10993447 |
| 03/05/2021 | $1,475,000 | Listed For Sale | MRED as distributed by MLS GRID #10993447 |
| 07/24/2020 | $1,449,000 | ListingRemoved | Agent Provided |
| 02/24/2020 | $1,449,000 | Listed For Sale | Agent Provided |
| 12/05/2019 | $1,450,000 | ListingRemoved | Agent Provided |
| 11/05/2019 | $1,450,000 | PriceChange | Agent Provided |
| 10/21/2019 | $1,499,000 | Listed For Sale | Agent Provided |
| 09/13/2004 | $1,650,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | |
| Assessment | $1,096,450 |
Home facts updated by county records
Comparable Sales for 555 Cherry St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.05 | Single-Family Home | $2,201,894 | 07/29/25 | 5 | 4 | 5,000 | |
0.13 | Single-Family Home | $2,775,000 | 04/27/26 | 5 | 4.5 | 5,065 | |
0.19 | Single-Family Home | $2,030,000 | 01/29/26 | 4 | 3.5 | 5,284 | |
0.25 | Single-Family Home | $1,925,000 | 10/23/25 | 5 | 4.5 | 4,544 | |
0.40 | Single-Family Home | $1,425,000 | 11/07/25 | 5 | 3.5 | 3,822 | |
0.25 | Single-Family Home | $2,550,000 | 06/18/26 | 5 | 4 | 5,646 | |
0.18 | Single-Family Home | $2,200,000 | 09/30/25 | 4 | 3.5 | 3,659 | |
0.17 | Single-Family Home | $3,050,000 | 10/01/25 | 6 | 5.5 | 4,295 |
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Assigned Schools
These are the assigned schools for 555 Cherry St.
- New Trier Township High School Winnetka
- 10-12
- Public
- 2730 Students
8/10GreatSchools RatingParent Rating AverageNew Trier high school is full of students who bully others relentlessly. The administration sweeps all sorts of problems under the rugs. They really only care about students who are athletes and parents who donate money. Many move here because of the schools. Our family can’t wait to leave because of how awful the administration and teachers have treated my children.Parent Review3mo ago - New Trier Township H S Northfield
- 9
- Public
- 880 Students
NAGreatSchools RatingParent Rating AverageIf it was good enough for Charlton Heston, it's good enough for you.Other Review2y ago - The Skokie School
- 5-6
- Public
- 354 Students
8/10GreatSchools RatingParent Rating AverageHorrible school. Avoid if you have academically gifted kids.Parent Review3y ago - Carleton W Washburne School
- 7-8
- Public
- 364 Students
8/10GreatSchools RatingParent Rating AverageNot good. Very rude entrance monitors. Education is ok, all teachers don’t care.Student Review1y ago - Greeley Elementary School
- K-4
- Public
- 340 Students
9/10GreatSchools RatingParent Rating AverageGreeley is a absolute gem! Parents, teachers and staff all are a community like no other. They have worked tremendously hard to keep the students engaged and receive an experience that balances all areas of growth and learning. A kudos to the dedication, diligence and tenacity of all of the teachers who go beyond for the students. As a new parent adjusting from city to burbs coupled with all that we had to adjust during the last year, beyond none, the teachers are our continued heroes!Parent Review5y ago 
Check out schools near 555 Cherry St.
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
71 % Say they plan to stay for at least 5 years
71 % Say it's walkable to grocery stores
70 % Say neighbors are friendly
66 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Howard Meyers, Compass
Agent Phone: (847) 446-9600
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
555 Cherry St, Winnetka, IL 60093 is a 5 bedroom, 5 bathroom, 6,580 sqft single-family home built in 1892. This property is currently available for sale and was listed by MRED as distributed by MLS GRID. The MLS # for this home is MLS# 12711173.