An early settler of Sherborn, MA, probably living in the portion of the town later set off to form the town of Holliston in 1724.  (The Underwood Family in America) Settled w side of Chicken Brook 1 m s w of the common in Holliston142

1709;  William Bull deeds 40 acres land at Sherborn in two parcels to a stepson, Joshua Underwood, signing with a mark.  (Middlesex Deeds, book 16 page 261)

1712, purchased part of Hopper's farm in Holliston142

March 9, 1713;  "To all People to whome these presents shall come greeting; Know ye that I Joshua Underwood of Sherborn in the County of Middlesex within her Majesty's province, of the Massachusetts Bay, in New England Bricklayer, For and in consideration of the sum of fifty pounds currant money to me in hand as before the ensearling hereof will and truly paid by my Brother Jonathan Underwood, mariner of Boston, New England, the receipt whereof  I do hereby acknowledge and my selfe am therewith fully satisfied paid and contented and of evry part and parcell thereof do acquitt exonerate and discharge the said Jonathan Underwood my brother his heires, executors, and admst. by these presents have given, granted bargained, sold-conveyed, and confirmed and fully, freely, clearly and absolutely give, grant, bargaine, sell alien and confirm unto him my said brother Jonathan, his heires, Executors, Admst. and assigns a certain parcell of land both upland and medow situate lyiing and being in Sherborn aforesaid containing by estimation one hundred and eighty acres be it more or less as it lyeth abutted and bounded northerly with the land of Mr. William Sheffield of said Town, all other parts of said land being abutted and bounded with ye common or undivided land of said Town of Sherborn.  It being some of the southermost part of that commonly called by the name of Hoping ffarme.  To have and to hold the said granted and bargained premisses with all the appurtanances profits, privileges, and comodities thereto belonging or in any wise appertaining thereto, and I the said Joshua Underwood, his heires, and Assigns that before the ensealing hereof I am the true, sole and lawfull owner of the above granted and bargained premises and am lawfully seized and possessed of the same and have in myselfe full power, good right and lawful authority to grant, bargaine, sell convey, and confirme said bargained premises in manner as above said.  And be the said Jonathan Underwood, his heires, and Assigns shall and may from time to time and at all times forever after the date hereof by force and virtue of these presents, lawfully, peacefully, and quietly hold, have use possess and enjoy the Domised and bargained premises freely and clearly discharged of and from all manner of former and other Gifts, Grants, bargains, Sales, Leases, Mortgages, wills, or any other Incumbrance whatsoever.  Furthermore, I the sd Joshua Underwood for me, my heires, executors, Admst. do covenant and engage the said demised and bargained premises unto him my said brother Jonathan, his heires, and assigns, against all claimes or demands of any person or persons whatsoever hereafter to warrant, secure, and defend herewith do render and give seizure unto the said Jonathan Underwood, my brother of all the above bargained premises.  In witness whereof I have hereunto set my hand and seal this ninth day of March, anno Domini, one thousand seven hundred and thirteen, and in the twelfth year of ye reign of our Sovereign Lady Anne by the Grace of God of Great Brittaine, France and Ireland, queen Defender of the Faith.
                                             Joshua Underwood (seal)
Signed, Sealed, and
Delivered in ye presence
of us.
Edward Gorkin
Joseph Wilson"  (The Underwood Family in America)

1715, drew land in Douglas142
September 8, 1716;  The above property returned to Joshua from brother Jonathan.    (The Underwood Family in America)

1721, rated among 8 highest142

Died intestate. Widow Mercy appointed administratrix.  Widow remarried before petition for settlement signed and her new husband Joshua Fairbank signed the petition along with Eli Jones, Eleazer Fairbanks (guardian toThankful and Mary Underwood), Nathaniel Sheffield (Guardian to Joshua, Joseph, and David Underwood.   Inventory of estate valued at 1447 pounds, 15 shillings - debts amounted to 143 pounds. (The Underwood Family in America)