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Detached Single · Winnetka, IL
$1,725,000
5 beds · 4.5 baths · 6,580 sqft
555 Cherry Street, Winnetka, IL, 60093
A brick-and-mortar place to make your own — room to make it home.
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What’s special

Central air2-car garage
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".
— the listing agent’s description

The home

5 beds
4.5 baths
6,580 sqft
Built in 1892
0.27-acre lot
2-car garage
Detached Single
Victorian

What it’ll cost

$262 / sqft
$25,644 taxes / yr
No HOA
22 days on dwello

Estimated monthly payment

$11,812/mo
Principal & interest$9,172
Property taxes$2,137
Homeowners insurance$503
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WED
Jun 3
THU
Jun 4
FRI
Jun 5
SAT
Jun 6
11:00 am
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22 days on dwello
Price history
Listed for sale
Jul 23, 2026
$1,725,000
Property taxes
2025
Annual tax bill (MLS)
$25,644/yr
Assessed value
2026
County assessor
$191,001~$1,910,010 mkt
2025
$191,001~$1,910,010 mkt
2024
$109,645~$1,096,450 mkt
2023
$109,645~$1,096,450 mkt
2022
$126,226~$1,262,260 mkt
2021
$96,083~$960,830 mkt
2020
$96,083~$960,830 mkt
2019
$104,438~$1,044,380 mkt
Assessed value from the Cook County Assessor (open records). Estimated market ≈ assessed × 10 for residential; not an appraisal — verify with the assessor.

Features

Central AirSmall Duct High VelocityNatural GasSteamCedarPublic SewerAsphaltHeated Garage

Schools

Elementary — Greeley Elementary School
Middle — The Skokie School
High — New Trier Twp H.S. Northfield/Wi
Assigned schools per the listing — always verify enrollment + boundaries with the district.
Neighborhood
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Nearby places via OpenStreetMap — approximate; verify what matters to you. Map © Mapbox © OpenStreetMap.
MLS listing dataMRED
Listed by Howard Meyers · Compass
Listing last updated Aug 13, 2026 · data refreshed from the MLS Aug 13, 2026, 5:09 AM CT
Based on information submitted to the MLS GRID as of Aug 13, 2026, 5:09 AM CT. Listing data © MRED LLC, distributed by MLS GRID — deemed reliable but not guaranteed; independently verify. Anything shown below this point is not MLS listing data.
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