$1,725,000
5 Beds
4.5 Baths
6,580 sqft (on 0.27 acres)
555 Cherry St, Winnetka, IL 60093
Est. Mortgage $12,191/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 1892
0.27 acre lot
$262/sqft
2 Car Garage
Local Information
- Map ViewExplore the area around 555 Cherry St.
- Schools2 Elementary Schools2 Middle Schools2 High Schools
- Shop & Eat
-- mins to
About this House
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".
Last check for updates: about 11 hours ago
Listing courtesy of: Howard Meyers, (847) 778-1394
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.
Home Details for 555 Cherry St
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MLS Status: Contingent |
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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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Contingencies: Attorney/Inspection |
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Business Information Ownership: Fee Simple |
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BasementMls Number: 12711173Zillow Contingency Status: Under ContractAttribution Contact: (847) 778-1394Back On Market Date: Fri Aug 07 2026 |
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Source Internet Entire Listing DisplayMRD IDX Comments Reviews: NoMRD Listing On IDX Display: YesMRD Address On VOW Display: YesMRD AVM On IDX Display: NoMRD 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 |
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.
Market trends in Winnetka
Last updated August 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
25
5MoM
Home Value
Trulia Estimate
$1.71MSince last month
Decreased$4K (-0.2%)Since last year
Decreased$105K (-5.8%)Since last sale
Increased$313K (+22.3%)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 +29% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $1.71M |
| August 2026 | $1.72M |
| June 2026 | $2.05M |
| May 2026 | $1.99M |
| April 2026 | $1.99M |
| March 2026 | $1.97M |
| February 2026 | $1.86M |
| January 2026 | $1.84M |
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 |
|---|---|---|---|---|---|---|---|
0.09 | Single-Family Home | $2,825,000 | 09/11/26 | 5 | 4 | 4,212 | |
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 |
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 |
|---|---|---|---|---|---|---|
0.05 | $2,338,200 | 5 | 4 | 5,000 | Off Market | |
0.08 | $2,764,400 | 6 | 4.5 | 4,114 | Off Market | |
0.09 | $1,748,700 | 3 | 3 | 2,458 | Off Market | |
0.09 | $2,825,000 | 5 | 4 | 4,212 | Recently Sold | |
0.10 | $2,857,000 | 6 | 4.5 | 4,251 | Off Market | |
0.05 | $2,661,000 | 6 | 4.5 | 5,800 | Off Market | |
0.13 | $2,775,000 | 5 | 4.5 | 5,065 | Recently Sold | |
0.07 | $2,230,000 | 4 | 3.5 | 3,200 | Off Market | |
0.11 | $3,048,000 | 5 | 6.5 | 5,193 | Off Market | |
0.10 | $4,995,000 | 5 | 7 | 4,450 | Recently Sold | |
0.14 | $2,209,400 | 4 | 3.5 | - | Off Market | |
0.10 | $4,554,000 | 6 | 6.5 | - | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Nov 23, 2022 Source: N/A | Sold | $1,400,000 |
Apr 15, 2021 Source: MRED as distributed by MLS GRID #10993447 | Sold | $1,415,000 |
Mar 6, 2021 Source: Engel & Volkers #10993447 | Pending | $1,475,000 |
Mar 5, 2021 Source: MRED as distributed by MLS GRID #10993447 | Contingent | $1,475,000 |
Mar 5, 2021 Source: MRED as distributed by MLS GRID #10993447 | Listed For Sale | $1,475,000 |
Jul 24, 2020 Source: Agent Provided | ListingRemoved | $1,449,000 |
Feb 24, 2020 Source: Agent Provided | Listed For Sale | $1,449,000 |
Dec 5, 2019 Source: Agent Provided | ListingRemoved | $1,450,000 |
Nov 5, 2019 Source: Agent Provided | PriceChange | $1,450,000 Price decreased by 3% |
Oct 21, 2019 Source: Agent Provided | Listed For Sale | $1,499,000 |
Sep 13, 2004 Source: N/A | Sold | $1,650,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $25,644 | $1,096,450 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Howard Meyers, Compass
Agent Phone: (847) 778-1394
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
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Frequently asked questions about 555 Cherry St
- What is the estimated monthly payment for 555 Cherry St?Based on a $1,725,000 list price with 20% down at today's rates, the estimated monthly payment for 555 Cherry St in Winnetka, IL is approximately $12,358 (about $9,422 principal & interest, $2,861 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Winnetka?Residents describe Winnetka, IL as dog-friendly, pedestrian-friendly, and well-kept. See homes for sale in Winnetka, IL.
- What are the closest schools to 555 Cherry St?The closest schools to 555 Cherry St in Winnetka, IL are Carleton W Washburne School (Middle, rated 8/10), Greeley Elementary School (rated 9/10), New Trier Township H S Northfield (Middle/High).
- What is 555 Cherry St estimated to be worth?Trulia's estimated value for 555 Cherry St in Winnetka, IL is $1,707,700.
- Does 555 Cherry St have air conditioning?Yes, 555 Cherry St in Winnetka, IL has air conditioning.
- Does 555 Cherry St have laundry facilities?Yes, 555 Cherry St in Winnetka, IL has laundry facilities.
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.