I think I maybe able to speed your search along. My ancestors purchased land from the estate of a Wing Rogers of Addison County. The land record is for transfering the land from Job Steadman to his son Asa Steadman. The record states “ whereas we Abrms. Rogers and Joseph Rogers Executors of the last will and testament of Winy Rogers late of Ferrisburgh in the County of Addison in the State of Vermont Deceased…order of the court of probate …It appears that Winy Rogers Deceased was in his lifetime and at his death under [?] to deed to Job Stedman of Bristol , county and state forsaid- Therefore we the [?] Rogers and Joseph Rogers Executors as forsaid were liscenced and ordered to deed the following lands to the above said Job Stedman…in Bristol… being the 2nd Division lot drawn to the original eight of Edward Burling Jr…and containing about fifty acres.”. The land was purchased for $176.67. The record is signed by Abrms Rogers and Joseph Rogers and is witnessed by Stephen Rogers and Howland Delony. Recorded in Volume 6 of the Bristol Land Records , I believe on pages 170 and 189. You could start here and work your way backwards to find out when the Rogers family acquired the land.