Richard Singletary lived in Salem, Massachusetts, where he received a land grant in 1637. From Salem he relocated for a time in Newbury, Massachusetts, where he took the oath of a freeman on 7 September 1638. He joined the church there in 1638, having been admitted as an inhabitant of the community in October.

He was probably married at that time, for a record exists indicating that "Goodwife Singletary" died 1638/1639 at Newbury, Massachusetts. He perhaps had a son named William by her.

Soon after, Richard and others were granted permission to build a plantation at Merrimac. In the spring of 1639 the Merrimac plantation site was chosen. Richard Singletary was one of those receiving a grant of land in the Town of Colchester, but evidently did not relocate there until later. This settlement was later renamed Salisbury. Richard married again around 1638 to Susannah COOKE, born ca 1616, and they lived in Newbury for a time.

About 1645, they built a home in Salibury, where Richard was a selectman in 1650. He did not tarry long in Salibury, for by 1652, he had relocated his family to Haverhill, Massachusetts. With this move came an involvement with others in signing a petition asking the court to revoke Robert Pike's sentence. Robert had supported preaching on the Sabbath by unordained ministers, and that was forbidden by the court. He let the court know his disdain for the law and thus was punished for his statement. His supporters were fined for their support and thus, they revoked their support.

In 1653 Richard Singletarry received more land and was a selectman in Haverhill in 1655. Richard and Susanna are recorded as having transferred some of their land holdings to members of their family in 1662 and later.