No addressee is listed, but research has determined the addressee is Henry Knox. Written from Milton. Discusses financial exchanges and land deals.

Apologizes for not having written sooner and discusses estimates relating to land deals. Notes he finds it unlikely that the state will cover any differences in quantity, as had been suggested, due to the member's prior voting record on the subject. Informs Isaac he has increased the advancement of his brother's, [Samuel Winslow], cash because of his current situation. Requests that he meets with his cousin, Isaac, and make a determination of whether they will accept Knox's offer on some land (includes part of the Waldo patent). They will need to provide Knox with evidence that there are no existing claims against the land.

Discussing financial issues and difficulties related to the Waldo patent, a large tract of land which Knox owns and which Winslow helps manage. Winslow also discusses his personal affairs.

Discussing financial issues related to Waldo's patent, a large tract of land owned by Knox that previously belonged to his wife's family. Discusses taxes on the land, the desire of the residents of the patent to have their lands surveyed, and settling financial affairs with various tenants.

Discusses details related to Knox's lands in present-day Maine. Refers to business matters between Knox and his late father (also named Isaac Winslow). Relates that Mr. Flucker (Knox's father-in-law), Isaac Winslow, Sr., and Governor James Bowdoin had been involved in glass works together, the General Court had granted them land which they sold, and now he is trying to sort out the details of the ownership and purchase of the land.

Provides information on the members of the Eastern Committee in the Legislature, including General [Rufus] Putnam. Discusses the powers the committee feels it possesses regarding interfering in the Waldo patent land negotiations. Also comments on the financial status of the Flucker estate.