The parent family of Obadiah Gildersleeve, Sr. is the Birth Family.
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 | Lt. Richard Gildersleeve, III (1660-1717)
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 | Experience Ellison (1657-1690)
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| Manasseh Gildersleeve (1678-1703) |
| Ann Gildersleeve (1682- )  |
| Reuben Gildersleeve (1700- ) |
| Zophar Gildersleeve (1706-1776) |
| Reuben Gildersleeve (1690- ) |
| Thomas Gildersleeve (1680-1747)
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| Bridget Gildersleeve (1719-1772) |
| Mary Gildersleeve (1722-1772) |
| Obadiah Gildersleeve, Sr. (1728-1816) |
| Philip Gildersleeve, > (1726-1760) |
| Richard Gildersleeve (1717-1780) |
| Benjamin Gildersleeve (1724-1784) |
| Henry Gildersleeve (1729- ) |
| Elizabeth Gildersleeve (1723-1772) |
| Experience Gildersleave (1730- ) |
