761 Cherry

The beautiful white frame house at 761 Cherry is perhaps one of the most interesting houses in Winnetka. The original builder and owner of this structure was Solymon Densmore, an early Winnetka settler with connections to several properties in this area.

The Densmore family first moved to Winnetka in 1866, first building a house just across the street at 440 Ridge, where Grace Presbyterian Church is now located. In 1868, Solymon Densmore built this structure on the southeast corner of Linden and Cherry at 443 Linden, approximately where 770 Cherry is today.

While this building is a single-family home today, originally, Densmore built it as a fanning mill shop, where he both manufactured and sold mills that used a fan to separate grains and dirt. With its completion, this 1868 building became Winnetka’s first manufacturing building. The mill was successful for the Densmores, allowing them to move from their modest house at 440 Ridge into the large Gothic Victorian at 411 Linden, which is now home to the Winnetka Historical Society. When Solymon died in 1895, the mill building was purchased by the Burkitt family, who converted it into a single family home.

In 1926, Dorothy Sears, daughter of Kenilworth founder Joseph Sears, purchased the house for $100. She moved it across the street to its present location at 761 Cherry and renovated the building into the North Shore Montessori School.

Dorothy first opened the school in 1916 in an empty storefront on Lincoln. She had trained with Maria Montessori, the founder of the Montessori educational philosophy, for several years beforehand. The school temporarily moved to the Winnetka Women’s Club until Dorothy, the school’s director, purchased this property. Dorothy ran the school at 761 Cherry until 1934, when a lack of enrollment caused by the Depression forced her to close. She then converted the building into two apartment units, making a home for herself on the top floor where she lived until the 1960s.

After Dorothy Sears passed away, 761 Cherry was converted back into a single-family home. Today, there is a plaque on the house commemorating its time as the North Shore Montessori School.

Due to its age and original purpose, this house does not have a typical architectural style. It can best be described as a gable-front vernacular building with saltbox wings. Some non-original Colonial Revival elements have been added, including the broken pediment above the door, the bay window, and the windows with shutters. While this structure has been drastically altered and added to over time, the original shape of the structure can still be seen, particularly along the asymmetrical roofline.