He made the first recorded land purchase in what is now the state of Maine, then part of Massachusetts, and proceeded to amass so much property that he was called "the great landholder."

While living in Casco (now Portland, Maine), in 1657, he bought from Scitterygusset, a local Native American sagamore, about 200 acres (80.94 hectares) located on the northern side of Capisic Brook.

[7] Indeed, Chief Wesumbe (or Captain Sandy), the sagamore of the Newichewannock Abenaki tribe, warned Small of a planned attempt on his life by renegade tribesmen.

Instead, they decided to erase the debt by killing him at early dawn on a coming day, setting fire to his house and shooting him when he ran out the door.

The purchase comprised what is called the Ossipee Tract – Limington, Limerick, Cornish (formerly named Francisborough after its early proprietor), Newfield, Parsonsfield and Shapleigh (part of which was later set off as Acton),[8] all today in Maine (despite today’s Ossipee being just west across the border in New Hampshire).

Small thereupon sold a half interest in the Ossipee Tract to Major Nicholas Shapleigh, who lived at what is now Eliot, Maine and was then the wealthiest man in the Piscataqua River region.

However, English settlements in the region were destroyed again in 1689 by Abenaki warriors allied with the forces of New France, which resented encroachment into territory it considered part of Acadia.