You might drive right past 408 Allyn Street in Groton without blinking. But stop. Tucked back from the road stands Redwood, a striking wood-frame villa from 1843. Architect Richard Upjohn designed this place. Yes, the same guy who built Manhattan's famous Trinity Church. Here, though, he ditched the heavy stone. Instead, he opted for vertical board-and-batten siding, paint formulated to mimic local stone, and wildly ornate, scroll-sawed bargeboards dripping from the gables. It looks like a romantic illustration snatched straight out of an Andrew Jackson Downing pattern book. That is exactly the point. Redwood practically introduced the rural Gothic Revival style to Connecticut's coastline. Upjohn's design proved that American homes did not have to be symmetrical, boring Greek Revival boxes.

The guy who paid for it, John F. Trumbull, was not some artsy bohemian. He was a hard-nosed Stonington merchant who made his pile of cash in the whaling, sealing, and banking industries. Mystic was booming in the 1840s, choking on whale oil and shipyard dust. Trumbull wanted an escape from the grime. So, he bought land on the quieter Groton side of the river and built this country retreat. It signaled a massive shift in how the local elite spent their money. They started moving away from the crowded waterfront docks to build showcase estates on the surrounding ridges. Redwood still sits on its original acreage, largely unaltered, preserving the exact moment when Connecticut's maritime wealth traded smelly harbor piers for polite, suburban leisure.