[2] With a fortune accumulated from his cigar business, Bond became involved in real estate.

He was one of the most active dealers and largest holders of real estate in Boston.

In 1908, Bond began work on the construction of a theater on Tremont Street in Boston, which was to be known as the Lyric Theatre.

His second wife was Isabelle "Belle" Bacon of Washington, D.C. She and Bond had five children: Edith Louise (Stearns), Mildred Mary (Rogers), Kenneth Bacon, Charles Lawrence and Priscilla Isabelle.

[1] He maintained a residence in Cliftondale until 1899, when he moved to a home on Commonwealth Avenue in Boston.

[2] A patron of the arts, he provided funding for the training of many vocal artists, including Geraldine Farrar.

[2] However, it was reported that Bond left a note in his bedroom which read, "I have been killed by my friends and enemies.

"[4][7][8] At the time of his death, it was believed that Bond's real estate ventures threatened his fortune.

The Washington Post reported that Bond's dissatisfaction with the trustees' actions may have caused him to take his life.