Chandler was born on the family farm, Chandler Hill, located on the boundary between Thompson and Woodstock, Connecticut.
He was the son of William Chandler, a farmer, and Jemima Bradbury Chandler of Woodstock.
After his father's death in 1754, Chandler pursued a career as a portrait and ornamental painter.
 A source claims that the artist studied the art of portrait painting in Boston, although there is only circumstantial evidence of this claim and no documentary proof.

In 1772, Chandler married Mary Gleason.
He does not appear to have participated in the Revolutionary War.
 Members of his family did as is demonstrated by the portrait of his brother Samuel in captain's uniform.
 Over time he pursued a variety of visual arts, including gilding, carving and illustrating, as well as portraiture, landscape and house painting.
This variety of skills points to a possible training as an artisan-painter.
 Despite a modest family inheritance, Chandler soon began to experience financial difficulties that would continue throughout his life.

In 1785 Chandler moved to Worcester, Massachusetts, where he remained for five years.
He likely made this move to look for new patrons as he was constantly experiencing financial difficulties.
Here he also worked as a house painter.
During this period his son Charles as well as his wife died, and his remaining children were sent to live with relatives, possibly his sister, since he painted Mrs. Crafts, née Mahitible Chandler in 1781.
His sister had moved with her husband Ebenezer Crafts to Craftsbury, Vermont.

Chandler returned to Chandler Hill where he died on 29 July 1790.
Chandler was so destitute that his estate was left to the selectmen of Thompson to pay for his medical and funeral expenses.
Chandler was born on the family farm, Chandler Hill, located on the boundary between Thompson and Woodstock, Connecticut. He was the son of William Chandler, a farmer, and Jemima Bradbury Chandler of Woodstock. After his father's death in 1754, Chandler pursued a career as a portrait and ornamental painter.  A source claims that the artist studied the art of portrait painting in Boston, although there is only circumstantial evidence of this claim and no documentary proof.
In 1772, Chandler married Mary Gleason. He does not appear to have participated in the Revolutionary War.  Members of his family did as is demonstrated by the portrait of his brother Samuel in captain's uniform.  Over time he pursued a variety of visual arts, including gilding, carving and illustrating, as well as portraiture, landscape and house painting. This variety of skills points to a possible training as an artisan-painter.  Despite a modest family inheritance, Chandler soon began to experience financial difficulties that would continue throughout his life.
In 1785 Chandler moved to Worcester, Massachusetts, where he remained for five years. He likely made this move to look for new patrons as he was constantly experiencing financial difficulties. Here he also worked as a house painter. During this period his son Charles as well as his wife died, and his remaining children were sent to live with relatives, possibly his sister, since he painted Mrs. Crafts, née Mahitible Chandler in 1781. His sister had moved with her husband Ebenezer Crafts to Craftsbury, Vermont. 
Chandler returned to Chandler Hill where he died on 29 July 1790. Chandler was so destitute that his estate was left to the selectmen of Thompson to pay for his medical and funeral expenses.
Winthrop Chandler