Ambrose Whittlesey House

Old Saybrook, United States

Exterior only

Visible from the street; the inside is private.

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Heritage registerNational Register of Historic Places↗

The Ambrose Whittlesey House at 2 Main Street in Old Saybrook, Connecticut showcases an architectural transition between Georgian and Federal styles across its two-phase construction. Built initially as a modest one-story structure measuring 16 by 30 feet in 1765, the house was substantially enlarged around 1800 with a two-story main block that reflects evolving tastes. The enlarged section displays a plain facade punctuated by a Georgian portico with classically proportioned columns, yet the fanlight above the door and interior detailing lean toward Federal design. The house retains a substantial center chimney of colonial simplicity, containing six flues serving hearths on both floors. This blend of colonial, Georgian, and Federal elements—unusual among surviving Old Saybrook buildings—was likely enhanced when the Georgian portico was added to the later section. The house's owner, Ambrose Whittlesey, descended from an early Saybrook settler and achieved prominence as a sea captain trading with the West Indies and later Spain and Portugal. Listed on the National Register of Historic Places in 1985, the house preserves a valuable record of Connecticut domestic architecture spanning the late eighteenth and early nineteenth centuries.