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

Winnetka, IL, 60093
$ 1,725,000
Bedrooms5 Baths4.1 Sq 6,580

Monthly Estimate*

$ 10,892

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Single Family Home for sale in Winnetka, IL

for $1,725,000 with 5 bedrooms and 4 full baths, 1 half bath. This 6,580 square foot home was built in 1892 on a lot size of 0.265.

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".

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Single Family Active

Price

$ 1,725,000

Bedrooms

5

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 25,644

Style

Victorian

Lot Size

0.265

Year Built

1892

Town/City

Winnetka

County/Region

Cook

MLS | Web ID

12711173

Features
General
Living Area 6580
Sewer Public Sewer
Heating Natural Gas Steam
Cooling Central Air Small Duct High Velocity
Possession Closing
Roof Asphalt
Garage Spaces 2
Association Fee Includes None
Architectural Style Victorian
Construction Materials Cedar
Year Built 1892
Electric 200+ Amp Service
Township New Trier
Tax Year 2024
Ownership Fee Simple
Assoc Fee Paid Per Not Applicable
County Cook
New Construction N
Property Type Residential Detached Single
Total Rooms 12
Full Baths 4
Status New
Directions Sheridan to Cherry West two blocks to home
High School New Trier Twp H.S. Northfield/Wi
City Winnetka
High School District 203
MLS Area Winnetka
Elementary School Greeley Elementary School
Tax Annual Amount 25644.1
Middle/Junior High School The Skokie School
Standard Status Active
Middle/Junior School District 36
Elementary School District 36
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Interior
Basement Partially Finished Partial
Flooring Hardwood
Total Fireplaces 3
Half Baths 1
Total Bedrooms 5
Room Type Great Room Loft Walk In Closet Bedroom 5 Office Foyer Screened Porch
Total Baths 5
Bedrooms Possible 5
Bathroom Separate Shower Soaking Tub
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Exterior
Parking Features Asphalt Heated Garage Yes Garage Owned Attached Garage
Water Source Lake Michigan Public
Total Parking 2
Lot Dimensions 85X157X25X60X127
Lot Size Acres 0.265
Waterfront Y/N N
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* Excluded Features
List By
Compass

Broker

hsmeyers813@gmail.com;howard.meyers@compass.com

Email

Affordability Calculator

$13,029
Per Month
84%
16%
0%
Monthly Principal & Interest
$10,892
Monthly Property Taxes
$2,137
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
566279 Elementary School
567901 Middle School
New Trier Twp H.S. Northfield/Wi High School
Pricing History
DatePricePrice ChangeDescription
7/23/2026$1,725,000 Listed Price

Map


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555 Cherry Street, Winnetka, IL, 60093 is a Single Family Home for sale at $1,725,000 with 6,580 sqft and a lot size of 0.265. 555 Cherry Street has 5 bedrooms, 4.1 baths, and was built in 1892. The property's zip code is 60093 which is in Winnetka, IL