Miles Brewton House, Charleston

An architectural heavyweight from the 1760s, this property is a “double house” and is called so because each floor therein boasts four grand rooms neatly split by a central staircase. The house was built for Miles Brewton, a prosperous planter, who made his fortune in the slave trade (the kind history doesn’t brag about these days). Today, however, it’s often praised as one of the finest Georgian-Palladian designs anywhere in the world—subtle flex, 18th-century edition...

That spiky, medieval-looking wrought-iron fence out front (known fancily as “chevaux-de-frise”) is not original, though. It was added in the 1820s, when whispers of a possible slave uprising had the town collectively sleeping with one eye open.

Over the years, this stately home has played host to some rather uninvited guests—first serving as headquarters for British General Henry Clinton during the Revolution, and later housing federal troops after the Civil War. A rather surprising footprint for a “private residence”...

Set on a generous two acres, the property is practically a time capsule, with one of the most complete collections of Georgian outbuildings in the country. Head around to the north side, and you’ll find what’s known as a “plantation lane”—a lineup of working structures including slave quarters, a kitchen, and a pavilion, all linked by a covered walkway.

And just beyond the house, the garden still follows its original 18th-century design—proof that while history here may have been complicated, the landscaping has always been impeccably on point.