555 Cherry Street
Winnetka, IL, 60093
$1,725,000
5 Beds
5 Baths
6,580 SqFt
0.27 Acres
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MLS #MRD12711173 image #0
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”.

Property Details

Price:
$1,725,000
MLS #:
MRD12711173
Status:
Active Under Contract
Beds:
5
Baths:
5
Type:
Single Family
Neighborhood:
winnetka
Listed Date:
Jul 23, 2026
Finished Sq Ft:
6,580
Year Built:
1892
VictorianWinnetkaWinnetkaGreeley Elementary SchoolThe Skokie SchoolNew Trier Twp H.s. Northfield/wi

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Schools

School District:
203
Elementary School:
Greeley Elementary School
Middle School:
The Skokie School
High School:
New Trier Twp H.S. Northfield/Wi

Interior

Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Small Duct High Velocity
Fireplaces Total
3
Flooring
Hardwood
Heating
Natural Gas, Steam

Exterior

Architectural Style
Victorian
Construction Materials
Cedar
Garage Spaces
2
Parking Features
Asphalt, Heated Garage, Yes, Garage Owned, Attached, Garage
Parking Spots
2
Parking Total
2
Patio And Porch Features
Patio, Screened
Roof
Asphalt

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2024
Taxes
$25,644

Map

Community

Market Summary

Current real estate data for Single Family in Winnetka as of Oct 05, 2026
24
Single Family Listed
60
Avg DOM
577
Avg $ / SqFt
$4,009,279
Avg List Price

Property Summary

    555 Cherry Street Winnetka IL is a Single Family for sale in Winnetka, IL, 60093. It is listed for $1,725,000 and features 5 beds, 5 baths, and has approximately 6,580 square feet of living space, and was originally constructed in 1892. The current price per square foot is $262. The average price per square foot for Single Family listings in Winnetka is $577. The average listing price for Single Family in Winnetka is $4,009,279.

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