Thank you for your reply. As you may know, many family groups during this time moved together from place to place, and often there are many marriages among them. As you noted, many of the Pomfret families were from Roxbury. The Polleys were one of these that moved to Pomfret, Woodstock, Holland and Charlton. Many of these same families also moved to Cortland County, NY around 1800. Again, The Polleys were one of them. Among these was Lucien Polley who married Sarah Ann Allen, the daughter of Timothy Allen and Sally. Though I have no birth date for Timothy, we can guess he was born about 1786 based on the birthdates of his children. I can find no information about his origins in Homer,Cortland County, NY and one train of thought was that he may have been one of the settlers from the upper-mid Connecticut/lower-mid-Massachusetts area (The originals that moved from Roxbury/Dedham/Rehoboth)
In addition, Patience Polley is an ancestor of Lucien mentioned above, another reason to look at this area as a possible area where Timothy came from.
Should you find anything about a Timothy that might fit, I would appreciate a post or an e-mail.