$1,725,000

beds

baths

half bath

6,580

square ft

555 Cherry Street

Winnetka, Illinois 60093

New / MLS #12711173 / Single Family / Winnetka

Listing information updated 7/23/2026 at 9:23am

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 Features

Architecture Style:

Victorian

Exterior Type:

Cedar

Basement:

Partially Finished,Partial

Beds Above Grade:

Cooling System:

Central Air, Small Duct High Velocity

Heating System:

Natural Gas, Steam

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

100+ Years

Roof Type:

Asphalt

Parking Type:

Garage - Asphalt,Heated Garage,Yes,Garage Owned,Attached,Garage

Parking Spaces:

Garage:

Attached

Room Count:

Water Front:

Square Feet:

6,580

Lot Size:

.25-.49 Acre

Acreage:

0.265

External Features:

Patio/Porch

Room Information

Living Room:

21x16 - Main

Dining Room:

16x14 - Main

Kitchen:

21x15 - Main

Family Room:

19x15 - Main

Primary Bedroom:

24x19 - Second Level

2nd Bedroom:

19x15 - Second

3rd Bedroom:

21x16 - Second

4th Bedroom:

14x13 - Second

Great Room:

30x16 - Main Level

Loft:

13x12 - Third Level

Walk In Closet:

13x6 - Second Level

Bedroom 5:

15x12 - Third Level

Office:

14x10 - Third Level

Taxes & Assessments

Tax Amount:

$25,644

Tax Year:

2024

Location

Zip Code:

60093

City:

Winnetka

County:

Cook

Schools

School District(s):

36, 203

Elementary School:

Greeley Elementary School

Middle School:

The Skokie School

High School:

New Trier Twp H.s. Northfield/Wi

Architecture Style:

Victorian

Exterior Type:

Cedar

Basement:

Partially Finished,Partial

Beds Above Grade:

Cooling System:

Central Air, Small Duct High Velocity

Heating System:

Natural Gas, Steam

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

100+ Years

Roof Type:

Asphalt

Parking Type:

Garage - Asphalt,Heated Garage,Yes,Garage Owned,Attached,Garage

Parking Spaces:

Garage:

Attached

Room Count:

Water Front:

Square Feet:

6,580

Lot Size:

.25-.49 Acre

Acreage:

0.265

External Features:

Patio/Porch

Living Room:

21x16 - Main

Dining Room:

16x14 - Main

Kitchen:

21x15 - Main

Family Room:

19x15 - Main

Primary Bedroom:

24x19 - Second Level

2nd Bedroom:

19x15 - Second

3rd Bedroom:

21x16 - Second

4th Bedroom:

14x13 - Second

Great Room:

30x16 - Main Level

Loft:

13x12 - Third Level

Walk In Closet:

13x6 - Second Level

Bedroom 5:

15x12 - Third Level

Office:

14x10 - Third Level

Tax Amount:

$25,644

Tax Year:

2024

Zip Code:

60093

City:

Winnetka

County:

Cook

School District(s):

36, 203

Elementary School:

Greeley Elementary School

Middle School:

The Skokie School

High School:

New Trier Twp H.s. Northfield/Wi

Listing Office: Compass

Listing Office Phone: 847.446.9600

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 7/23/2026 at 9:23am. 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. Some listings have been excluded from this website.

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555 Cherry Street, Winnetka, IL 60093 is a single family home currently listed at $1,725,000. 555 Cherry Street features 5 Beds, 4 Baths, 1 Half Bath. This single family home has been listed on @properties Christie's International Real Estate since July 23rd, 2026 and was built in 1892. Nearby schools include Greeley Elementary School, The Skokie School, and New Trier Twp H.s. Northfield/Wi. The nearest transit stops include Winnetka Metra Metra Union Pacific North line.