Church Square was constructed in the early 1920s by Charles E. Holman and has remained in his family's ownership ever since.

Church Square boasts impressive classical architecture and is situated in the heart of downtown Wellesley.

In the early 1920s, Wellesley was becoming increasingly popular among businessmen commuting to Boston, and Charles recognized the potential for a prosperous shopping center in the area. He purchased land and built a block of stores, with E.A. Davis as the first tenant.

Emma A. Davis, Charles's sister-in-law, founded the store in Brighton in 1904 and later moved it to the eastern end of Wellesley Square. Emma retired in 1922 and sold the business to her nephew, Clarence, who relocated it to Church Square.

In response to the growing popularity of automobiles, Charles and Clarence bought enough property for their new block to include a large parking lot behind the square. Later in the early 1950s, Clarence bought several houses behind Church Square on Abbott Street, tore them down and added another parking area.

To this day, only one other commercial property has a parking lot of significant size. The parking lot has proven to be a big advantage for Church Square and its tenants, making it easy for customers to visit and support their businesses.

Dover Saddlery, a high-quality tenant, opened its first location in Church Square in 1975. Since then, it has expanded into a substantial national corporation with several stores across the country.

Today, Church Square still provides top-notch stores, services, and dining options.