[3] Born in Boston, then of the Province of Massachusetts Bay, to Scottish ship captain Andrew Craigie and his Nantucket-born wife Elizabeth, Andrew Craigie Jr. attended the Boston Latin School before being appointed by the Committee of Safety of the Province of Massachusetts on 30 April 1775 to take care of its medical stores.

He was listed in a manuscript of "Medical Men in the American Revolution" deposited in the Library of Congress by Dr. J. M. Toner, who gave him the title of "Surg.

"[4] The Provincial Congress of Massachusetts Bay referred to Craigie as the "commissary of medicinal stores" and charged him with providing beds, linen, and other supplies necessary for patient care to the troops gathering around Boston.

He also became a financier and land speculator, buying and selling parcels of property in New England and Ohio, amassing a large fortune in the process.

It is during this early post-war period that he became acquainted with then-Treasury Secretary Alexander Hamilton through his relationships with New York financial promoter William Duer (Continental Congressman) and speculator Daniel Parker.

Parker played the lead role in organizing a business concern to purchase the post-war debt due to France from the United States in 1788.

He held substantial tracts in upstate New York, Oxford, Maine, and in East Cambridge, and speculated in both domestic and foreign money markets.

[6] In 1791 or 1792 (accounts vary), Craigie purchased the Vassall House and farm, comprising approximately 150 acres, which had served as Washington’s headquarters during the war.

Craigie installed gardens, a greenhouse and an icehouse, and held numerous parties and dances at what was described as his "princely bachelor’s establishment.

Craigie and his associates, who formed the Lechemere Point Corporation, benefited from the building boom that followed, spurred on by their efforts to expand the public street grid.

Short-term residents of the home included Washington biographer Jared Sparks, politician and future Massachusetts Governor Edward Everett, and lexicographer Joseph Emerson Worcester.