Gazette Article by: Steve Adams and Cindy Fuller
Appeared in the Gazette: Spring 2005

• High land where nature has provided a perfect setting for homes.
• Beautifully wooded with forest trees.
• New school soon to be built on twelve acres near by [The Skokie School].
• Convenient to the only municipal golf course now available on the North Shore.
• Corner lots at $40 – $45 per foot. Inside lots at $35 per foot.

So read a December 1919 advertisement for 36 new lots in the Winnetka Heights subdivision, the area now bordered by Pine to the south and Westmoor to the north, between Locust and Rosewood. The ad boasts that “you can afford to forget building costs because the advance in land valuation will largely compensate for the present cost of construction.” At about 660 feet above sea level, the Winnetka Heights subdivision is among the highest areas of elevation in Winnetka. Only the areas on Lincoln between Summit and Eldorado and Scott west of Euclid are on slightly higher ground.

Between 1919 and 1928, 100×188 foot lots were sold for about $4,000 each with homes erected at a value of $15,000 to $20,000. Some of those lots have since been divided. Each building was required to be set back from the road by 50 feet, providing a spacious neighborhood feel.

After an October 1920 approval by the Village to begin construction of sidewalks and roads, the neighborhood’s first homes were built at 1015 Pine St. and 635 Rosewood, with full completion of the housing development eight years later. Area street names have interesting origins. Before it was called Rosewood, the street was named Darroch and then Oakridge. Westmoor was originally Fig. According to a presentation given to the Lion’s Club by Village Engineer Frank Windes in 1947, the Village councilman who lived on the new street was asked by Village President Burr what he would like to name the road. Councilman Hawkes responded, “I don’t give a fig.” President Burr replied, “Then Fig it shall be.”

The two interior one-block streets named Starr and Dinsmore (Dinsmore was originally called Ely in 1919) honor the first two Winnetka casualties of World War I. Aviator and First Lieutenant Philip Comfort Starr, son of Chicago lawyer Merritt Starr and his wife Leila, died in action at Ypres, France, on Feb. 20, 1918, at the age of 28. First attending Cornell, Starr was a member of Harvard’s class of 1914, and the first of 11 Winnetkans who would give their lives during WWI, according to the Winnetka Weekly Talk .

Second Lieutenant Dinsmore Ely, son of Dr. and Mrs. James O. Ely, was killed in action while flying over France on April 21, 1918. Previously cited for valor, he died at age 24 in a Paris hospital and was buried at Versailles. In the weeks prior to his final flight, Ely’s plane lost power at several thousand feet and he plunged to the ground into a dense forest, miraculously escaping with only a few scratches. Before enlisting, Ely was a student at MIT.

Most Winnetka Heights’ homes were one of a kind, built specifically for their sites. Many were architect designed by such names as Lowe and Bollenbacher, Oldefest and Berk, John van Bergen, A.E. Hogenson, Mayo and Mayo, S.S. Beman (his father designed Chicago’s Pullman Village) and Russell S. Walcott. Many of the older homes are Tudor Revival, Colonial Revival and Prairie School. The two adjoining “twin houses” on Dinsmore were built by J.H. Jones in 1923 for his two sons, but the sons inhabited them for a very short time before they moved on.

The Winnetka Heights neighborhood has always been family friendly. Raised on Dinsmore, the Ellis children recall many summers of backyard baseball, including the day that a ball was hit through what they remember to be “Winnetka’s largest plate glass window.” With the window valued at almost $1,000 in the late 1960s, the balance of the summer was required to work off the insurance deductible! But despite occasional sporting event surprises, families living in the “Heights” are proud to call this neighborhood home.