Since your Holland was born about 1757 you can consider that his parents may not have moved from Nansemond VA to the Bertie Precint of Chowan County North Carolina. In 1728 the NC VA border was surveyed and North Carolina gained lands formly considered a part of Viriginia.. so many folks never moved just had line redrawn around them at this time.
Also wish you luck with trying ot figure out which one was father to your ancestor as fires in Nansemond in 1779 caused the loss of many old records and later in 1837 another on got more of them.
You might want to do a first name seach on Dempsey and Theophilus on some of the on line State Archives like NC (MARS)... MARS (Manuscripts Archival Records System) is on line for North Carolina and there are two systems active.... the OLDer one (will be what you use to get to early land records in an indexed formed listing which shows most of the needed information off the originals) and the NEWer one (will have other records on it and some of the wills and items you can view the actual hand written original on line).
Best way to get to it is do a search for -- North Carlina MARS -- and then should get to the Home Page and need to look on right side about middle of screen for a link... from there just follow instructions to the site you may want to check out.... The OLDer one is a pain to work until you play with it a while and get use to it but well worth a look and spending time learning to use it, and to get to Land Records you'll need to learn...
Just remember how much trouble NASA had getting to MARS and relax if you don't get there the first couple of tries... I've been on it about 8 months now and still learning to walk around on MARS.... old and new
In doing a first name search look for possible known related surnames around Holland or for places to come up where the Hollands known to be living... say 1720 to 1790 time zone as to see where either name might come from into your Holland line.
Also by 1757 Bertie County was under the Earl of Granville who had a land office opened Edenton Chowan County North Carolina called Granville Proprietary Land Office opened in 1746 until his death in 1763 and this competed with Charleston South Carolina in granting land warrants in the Carolinas.... after the Earl died the Crown took it all in and Edenton became a district land office and everything went to Charleston South Carolina until American Revolution... as control point for all of the Carolinas under the English Crown.
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