His first wife, Hannah Cowles was born about 1646 and died on February 4, 1690. They were married before 1664 and had the following children:
a daughter, born March 6, 1664, who died without being baptized;
Hannah, b. October 16, 1666;
Elizabeth, b. October 24, 1669;
Joseph, b. March 5, 1672/3
Twin Daughter, b. September 12, 1683, died next day;
Twin daughter, b. September 12, 1683, died September 18, 1683;
He married his second wife, Sarah Foster, on September 24, 1690, at Charlestown. She died on August 30, 1698.
"Capt. Caleb Stanley of Hartford in Connecticut & Mrs. Sarah Long (widow of Mr. Zech. Long, deceased, of Charlestown, m. by Mr. James Russell, Sept. 24, 1690."
They had the following children:
Twin Anna, b. June 24, 1692, baptized on June 19, 1692;
Twin Mary, b. June 24, 1692, baptized on June 19, 1692;
Abigail, b. February 24, 1695; m. James Church;
Ruth, b. July 1, 1696; m. 1st James Bidwill, m. 2nd probably -- Palmer.
Caleb married Mrs. Lydia (Cole) Willson, widow of Deacon John Willson and daughter of John Cole, at Hartford on September 14, 1699. She died in 1732.
The Court of Assistants was established under the General Assembly of the Colony, and Capt. Caleb Stanley, Sr., was appointed a member of this Court. He was elected Constable in 1667 and 1675; and townsman five times, Deputy five or six times, and he held many other governmental posts.  He was called "Capt. Caleb," and, on November 14, 1688, he was assigned safeguard the colony's ammunition.
Caleb signed his Will on March 7, 1716, and died at Hartford on May 5, 1718. The inventory of his estate was valued at £402. 08s. 03p. and included a gold ring and some silver.
Source: S-189Great Migration 1634-1635, R-S. (Online database. AmericanAncestors.org. New England Historic Genealogical Society, 2012.) Originally published as: The Great Migration, Immigrants to New England, 1634-1635, Volume VI, R-S, by Robert Charles Anderson. Boston: New England Historic Genealogical Society, 2009.
Source: S-190Israel P. Warren. The Stanley families of America. Portland, Maine: B. Thurston, 1887. Open Library
Source: S-191Charlestown, MA: Vital Records to 1850. (Online database. AmericanAncestors.org. New England Historic Genealogical Society, 2008.) Originally published as Vital Records of Charlestown, Massachusetts to the year 1850. Compiled and edited by Roger D. Joslyn. 2 vols in 3. Boston: New England Historic Genealogical Society, 1984-1995.
Source: S-192 James Hammond Trumbull The memorial history of Hartford County, Connecticut, 1633-1884: Volume 1 E. L. Osgood, Boston, 1886
Source: S-1880578048 Title: Family Data Collection - Individual Records Author: Edmund West, comp. Publication: Name: Online publication - Provo, UT, USA: Ancestry.com Operations Inc, 2000. Repository: #R-188
Source: S-1880578050 Title: U.S. and International Marriage Records, 1560-1900 Author: Yates Publishing Publication: Name: Online publication - Provo, UT, USA: Ancestry.com Operations Inc, 2004.Original data - This unique collection of records was extracted from a variety of sources including family group sheets and electronic databases. Repository: #R-188
Repository: R-188 Name: Ancestry.com Address: 360 West 4800 North, Provo, UT 84604