$1,725,000

555 Cherry Street, Winnetka, IL 60093

Active Under Contract
5 beds 4.5 baths 6,580 sqft (plans) Built 1892 Residential MLS #MRD12711173 30 days on market
Listing courtesy of Compass · 847-446-9600 · MLS #MRD12711173 · Status: Active Under Contract
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

Interior

Flooring
Hardwood
Fireplaces
3
Basement
Partially Finished, Partial
Additional rooms
Great Room, Loft, Walk In Closet, Bedroom 5, Office, Foyer, Screened Porch
Total rooms
12

Building & exterior

Style
Victorian
Age
100+ Years
Exterior
Cedar
Roof
Asphalt
Patio & porch
Patio, Screened

Parking

Garage spaces
2
Total spaces
2
Parking details
Asphalt, Heated Garage, Yes, Garage Owned, Attached, Garage

Lot & location

Lot dimensions
85X157X25X60X127
Township
New Trier
County
Cook

Utilities

Heating
Natural Gas, Steam
Cooling
Central Air, Small Duct High Velocity
Water
Lake Michigan, Public
Sewer
Public Sewer
Electricity
200+ Amp Service

HOA & community

Assessment includes
None

Schools

Elementary
Greeley Elementary School (36)
Junior high
The Skokie School (36)
High school
New Trier Twp H.S. Northfield/Wi (203)

Taxes & terms

Annual taxes
$25,644 (2024)
Parcel number (PIN)
05211180100000
PIN
05211180100000
Ownership
Fee Simple
Possession
Closing
Special conditions
List Broker Must Accompany
Listed
7/23/2026

Rooms

RoomSizeLevelFlooring
Great Room30X16MainHardwood
Loft13X12Third
Walk In Closet13X6Second
Bedroom 515X12ThirdCarpet
Office14X10ThirdCarpet
Foyer12X6MainHardwood
Screened Porch30X10Main
Bedroom 219X15SecondHardwood
Bedroom 321X16SecondHardwood
Bedroom 414X13SecondHardwood
Dining Room16X14MainHardwood
Family Room19X15MainHardwood
Kitchen21X15MainHardwood
Laundry19X10Basement
Living Room21X16MainHardwood
Master Bedroom24X19SecondHardwood

What would this home cost per month?

Using this listing's actual tax bill (2024) — adjust anything.

Rates move daily — edit to today's quote. Under 20% down adds PMI automatically.

Estimated monthly payment
$0
Principal & interest
Property taxes
Insurance
PMI (under 20% down)
HOA / assessments

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