Development increased in Windsor Hills, especially north of Loudon Avenue and Alto Road, during the teens and 1920's, with almost all houses built in the single family detached, wood frame and shingle cottage style. A 1916 newspaper advertisement described cottage lots for sale in Windsor Hills as being "restricted against rows of brick buildings, saloons, and all nuisances." A few rowhouses were built in Windsor Hills, with a group of Daylight houses in the 4000 block of Clifton Avenue advertised for sale by James A. Bealmear and Son, in 1929.
The Windsor Hills Improvement Association was formed during the early days of the community, and served primarily a social function for the somewhat isolated early suburban pioneers. After a dormant period, the association revived in the 1950's to fight undesirable zoning changes, to protect property owners from unscrupulous block busting real estate salesmen, and to promote orderly integration of the community.