555 Cherry Street, Winnetka IL 60093
$1,725,000

Request Private Showing

Property 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".

Features & Information

Key Details

  • List Price $1,725,000
  • Property Taxes $25,644
  • Square Feet 6580
  • Year Built 1892
  • Status Active
  • Market Time 22

Rooms

  • Total Rooms 12
  • Number of Bedrooms 5
  • Number of Bathrooms 4.1
  • Primary Bedroom

  • Room Size 24X19
  • Floor Level Second
  • Flooring Hardwood
  • Primary Bathroom Full
  • Bedroom 2

  • Room Size 19X15
  • Floor Level Second
  • Flooring Hardwood
  • Bedroom 3

  • Room Size 21X16
  • Floor Level Second
  • Flooring Hardwood
  • Bedroom 4

  • Room Size 14X13
  • Floor Level Second
  • Flooring Hardwood
  • Bedroom 5

  • Room Size 15X12
  • Floor Level Third
  • Flooring Carpet
  • Living Room

  • Room Size 21X16
  • Floor Level Main
  • Flooring Hardwood
  • Family Room

  • Room Size 19X15
  • Floor Level Main
  • Flooring Hardwood
  • Dining Room

  • Room Size 16X14
  • Floor Level Main
  • Flooring Hardwood
  • Kitchen

  • Room Size 21X15
  • Floor Level Main
  • Flooring Hardwood

Additional Rooms

  • Great Room

  • Room Size 30X16
  • Floor Level Main
  • Flooring Hardwood
  • Loft

  • Room Size 13X12
  • Floor Level Third
  • Walk In Closet

  • Room Size 13X6
  • Floor Level Second
  • Office

  • Room Size 14X10
  • Floor Level Third
  • Flooring Carpet
  • Foyer

  • Room Size 12X6
  • Floor Level Main
  • Flooring Hardwood
  • Screened Porch

  • Room Size 30X10
  • Floor Level Main
  • Laundry

  • Room Size 19X10
  • Floor Level Basement

Interior Features

  • Heating & Cooling

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

  • # of Fireplaces 3
  • Type of Fireplace Family Room, Living Room, Bedroom

Exterior Features

  • Building Information

  • Age of Building 100+ Years
  • Recent Rehab Yes
  • Rehab Year 2015
  • Parking

  • # of Cars 2

Location

  • County Cook
  • Township New Trier
  • Corporate Limits Winnetka
  • Directions to Property Sheridan To Cherry, West Two Blocks To Home
  • Schools

  • Elementary School District 36
  • Junior High District 36
  • High School District: 203
  • School Name New Trier Twp H.S. Northfield/Wi
  • Property Taxes

  • Tax 25644.1
  • Tax Year 2024
  • Tax Exemptions Homeowner
  • Parcel Identification Number 05211180100000
  • Lot Information

  • Lot Size .25-.49 Acre

Listed by Howard Meyers for Compass | Source: MRED as distributed by MLS GRID

Based on information submitted to the MLS GRID as of 8/20/2026 11:32 PM. 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.

Mortgage Calculator

  • List Price${ formatCurrency(listPrice) }
  • Taxes${ formatCurrency(propertyTaxes) }
  • Assessments${ formatCurrency(assessments) }
  • List Price
  • Taxes
  • Assessments
${ formatCurrency(price) }
${ selectedInterestRate }%
${ downPaymentPercent }%

Estimated Monthly Payment

${ formatCurrency(monthlyTotal) } / month

  • Principal & Interest${ formatCurrency(monthlyPrincipal) }
  • Taxes${ formatCurrency(monthlyTaxes) }
  • Assessments${ formatCurrency(monthlyAssessments) }

All calculations are estimates for informational purposes only. Actual amounts may vary.

Share this Listing