The majority of deeds involve lands in Massachusetts, including Boston, Bedford, Worcester, Barnstable, Bellingham, Attleboro, Wrentham, Malden, Nottingham, Lancaster, Watertown, Leominster, and Dorchester. Deeds from 1735 and 1736 involve digging for iron ore in Attleboro. Within Boston, properties mentioned include a lot on Wing's Lane, as well as a Newbury Street property belonging to Dame Hannah Willard, mother of William Clarke; land near Boston Common belonging to Madam Mary Saltonstall; and Bear Tavern. In Maine, deeds dating as early as 1665 involve lands near Kennebunk River. In 1750, deeds were created for Thouts Plantation near Kennebunk River, Damariscove Island, and Squirrel Island. Lands mentioned in New Hampshire include Nottingham (1727) and Monson (1746).

Indentures include the apprenticeship of Thomas Mason to Benjamin Dolbeare in 1740 and the apprenticeship of John McElroy to William Clarke in 1760. Leases and mortgages are also included.

These records concern the sale and detainment of enslaved people in Massachusetts and Jamaica. Included are a bill of sale in 1732 for an enslaved person named Loran from William Richardson to James Dolbeare; a 1736 deed for the sale of an enslaved woman named Dido from Habijah Weld to William Clarke; a 1743 deed for the sale of an enslaved person named Rose from Nathaniel Brown to James Dolbeare; a 1747 indenture for the sale of an enslaved person named Robin to William Clarke from Ebenezer Griggs; a 1774 deed for the sale of an enslaved person named Boston to Benjamin Williams from the estate of Nathaniel Loring; a 1780 bill of sale for an enslaved person named Dick from Thomas and Rebecca Dolbeare to John Dalling; a 1780 deed for an enslaved person named Peggy from William Clarke to Rebecca Dolbeare; and a 1781 deed describing the sale of an enslaved person named Thomas from John Dolbeare to George Ackinson.

Also included are a 1770 promissory note for the safe passage of an enslaved woman named Quasheba on the voyage from Kingston, Jamaica, to Alexandria, Virginia, and a 1778 list of ensalved captives on Buffet's Pen who were delivered to William Clarke.

Wills included are those of Mary Saltonstall, John Dolbeare (1669-1740), Sarah Comer Dolbeare (1675-1744), Edward Gray, William Fisher, Benjamin Dolbeare (1711-1787), and Bernard Dolbeare. Estate inventories are included for the estates of Sarah Comer Dolbeare, Hannah Vincent Dolbeare, Benjamin Dolbeare (1711-1787), Lemuel Robinson, and John Dolbeare (1752-1830). Additional records include probate records, opinions on Sarah Comer Dolbeare's legacy, a letter granting Nathaniel Loring guardianship of Susanna Loring, and the dying words of Thomas Gray.

Of note is a copy of Queen Anne's commission to Joseph Dudley and others in 1704. Also of interest are a 1733 search warrant for James Dolbeare, who was accused of neglecting his sick wife, and the 1738 divorce papers of James Dolbeare and Mary Vallentine Dolbeare; the 1744 and 1757 commissions of William Clarke as surgeon at Castle William; maritime court documents concerning the Brigantine Hiram David; various powers of attorney and inferior court records; and findings from the Council of Seven Churches in Concord related to the conduct of a minister.

The majority of papers included are a mix of personal and business bills, receipts, and accounts of Benjamin Dolbeare and John Dolbeare. Bills and receipts include payments from the sale of land, household goods, food, services rendered, and various funeral costs. Receipts for payments of college bills for Benjamin Dolbeare (1745-1767) while at Harvard are included. Of note is an account for Dr. Thomas Bulfinch that includes costs for doctor's visits related to Mary Townsend's breast cancer surgery.

Business records contain excerpts from John Dolbeare's (1669-1740) bill of lading book, shipping records, and ship registers. Also included are articles of agreement for business partnerships between Joseph Brandon and Benjamin Dolbeare in 1739 and between Thomas Dolbeare and John Dolbeare in 1774.

William Clarke's Louisbourg journal includes entries from King George's War, detailing the arrival of the troops, the construction of the battery, and the siege of Louisbourg. Copies of letters to William Bollan, dated 1745-1746, and extracts from the minutes of a Council of War held at camp in May and June of 1745 before the expedition against Cape Breton are included. The ledger includes accounts and payments related to his medical practice in Boston.

The ledger of Benjamin Dolbeare and Joseph Wise details the merchants' accounts for various goods, including sugar, flour, rum, and broadcloth. Benjamin Dolbeare's memorandum book includes lists of goods from invoices, lists of books, and receipts. Also included are recipes for remedies of colds, sore throat, gravel, consumption, and rheumatism. His 1739 diary details his travels to various sites in England including London, Oxford, Bath, and Bristol, particularly the House of the Duke of Beauford and a description of Oxford University.

John Dolbeare's diaries contain both business and personal entries. In addition to detailing goods to be purchased, voyages, and expenses, he writes about family history, weather, and social calls. Some of these personal entries are written in French. In 1777, although he did not serve in the battle, Dolbeare records details of the Battle of Saratoga, including copies of two letters from Horatio Gates, one discussing Articles of Convention for Gen. John Burgoyne's surrender and one addressed to Burgoyne discussing the exchange of prisoners of war including Ethan Allen. Lists of vessels taken at war due to privateering from 1776 to 1778 are also included. In his later diaries, John Dolbeare lists detailed local election results. He also documents the Louisiana Purchase in 1803 and the Napoleonic Wars from 1805-1809. Dolbeare's Jamaica almanac, printed by Robert Sherlock in 1788, contains his memos and annotations for the year.

Although these volumes primarily consist of John Dolbeare's diary entries and other writings, many had been previously used by others for various purposes. The practice tables contain copies of legal documents from 1769-1772; the diary of 1787-1825 was previously Benjamin Dolbeare's book from Samuel Grainger's Writing School in 1731; the diary of 1795 was previously Benjamin Dolbeare, Jr.'s memorandum book from 1753-1763 and includes a catalog of books and an index of plant species; the diary of 1795-1797 was previously the receipt book of Michael Dennis in 1753; the diary of 1801-1802 was previously the book of James Dolbeare in 1726; and the diary of 1803-1809 was previously used as Benjamin Dolbeare and Joseph Brandon's alphabet book in 1739.

Included are the bill of lading book of John Dolbeare (1669-1740), as well as estate records of Nathaniel Loring, with Benjamin Dolbeare serving as the administrator of his estate.