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$1,725,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 6,580 Sq. Ft.
  • 2 Car Garage
  • Updated 1 hour ago
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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".

Full Property Details for 555 Cherry St

General

  • Price: $1,725,000
  • Taxes: $25,644 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12711173

Interior

  • Basement: Partially
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Fireplace(s): Family Room, Living Room, Bedroom
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Bathroom Features: Separate Shower, Soaking Tub

Bedrooms

  • Total Bedrooms: 5

Additional Information

  • Other Features: Commuter Bus, Commuter Train

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Asphalt, Heated Garage, Yes, Garage Owned, Attached, Garage

Location

  • Area: Winnetka
  • County: Cook
  • Township: New Trier
  • Driving Directions: Sheridan to Cherry, West two blocks to home

School Information

  • School District: 36
  • Elem School District: 36
  • Midd School District: 36
  • High School District: 203
  • Elementary School: Greeley Elementary School
  • Middle School: The Skokie School
  • High School: New Trier Twp H.S. Northfield/Wi
  • Private School: New Trier Twp H.S. Northfield/Wi

Community

  • Assoc. Fees Include: None

Heating & Cooling

  • Cooling Type: Central Air Conditioning, Small Duct High Velocity
  • Heating Type: Natural Gas, Steam

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan, Public

Structural Information

  • Architectural Info: Victorian
  • Architectural Style: Victorian
  • Construction: Cedar
  • Exterior Const.: Cedar
  • Basement: Yes
  • Basement Desc.: Partially Finished, Partial
  • Roof: Asphalt
  • Sub-Flooring: Hardwood
  • Square Feet: 6,580
  • Sq. Ft. Source: Plans
  • Year Built: 1892
  • Built Before 1978: Yes
  • Remodeled/Updated: 2015

Lot Features

  • Lot Size (Acres): 0.265
  • Lot Size Range: .25 to .49 Acre
  • Lot Dimensions: 85 x 157 x 25 x 60 x 127

Financial Considerations

  • Assessment Year: 1892
  • Tax Amount: $25,644.1
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: List Broker Must Accompany
  • Property ID: 5211180100000

Listed by Compass

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— 555 Cherry St —

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  • Compass

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Schools serving 555 Cherry St

School Districts:Winnetka School District 36, New Trier Township High School District 203
NameGradesDistance
Greeley Elementary School, Winnetka, IL
275 Fairview Avenue, Winnetka, IL 60093
K-40.4 mi
Carleton W Washburne School
515 Hibbard Road, Winnetka, IL 60093
7-81.3 mi
New Trier Township H S Northfield
7 North Happ Road, Northfield, IL 60093
9-2.2 mi
New Trier Township H S Winnetka
385 Winnetka Avenue, Winnetka, IL 60093
10-120.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Tax History for 555 Cherry St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$24,650
—
$191,001
74%
2023
$24,650
-11%
$109,644
-13%
2022
$27,549
14%
$126,225
31%
2021
$24,071
-2%
$96,083
—
2020
$24,539
3%
$96,083
-7%
2018
$23,910
2%
$103,118
-1%
2019
$23,554
2%
$104,438
1%
2017
$23,186
-2%
$103,118
-6%
2016
$23,671
—
$109,412
10%
2015
$23,779
2%
$99,272
—
2014
$23,282
5%
$99,272
—
2013
$22,192
3%
$99,272
-2%
2012
$21,589
—
$101,249
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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555 Cherry Street, Winnetka, IL 60093 (MLS# 12711173) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 555 Cherry Street is currently listed for $1,725,000 and was received on July 23, 2026. Want to learn more about 555 Cherry Street? Do you have questions about finding other Single Family real estate for sale in Winnetka? You can browse all Winnetka real estate or contact a Coldwell Banker agent to request more information.

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