189 Main St

Welcome to the legendary Bert Stern House at 189 Main Street — an extraordinary Georgian masterpiece in the heart of Sag Harbor where art, history, glamour, and summer luxury come together in one unforgettable experience. Once home to iconic photographer Bert Stern, whose timeless portraits of Marilyn Monroe changed the world of fashion and photography forever, this residence is more than a summer rental — it is living inside a piece of American creative history.
Behind the classic facade lies nearly 4,000 square feet of soulful elegance, beautifully preserved with original hardwood floors, rich millwork, grand entertaining rooms, and walls adorned with Stern’s legendary imagery. Every corner of the home tells a story — sophisticated yet relaxed, artistic yet effortlessly luxurious.
Spend long summer afternoons by the heated pool surrounded by lush gardens, host unforgettable candlelit dinners beneath the trees, or walk just moments into Sag Harbor Village for world-class restaurants, boutiques, marinas, and sunset strolls along the harbor. Inside, the home offers expansive living spaces, four beautifully appointed bedrooms, a music room with piano, elegant dining areas, multiple workspaces, and the kind of timeless atmosphere that simply cannot be recreated.
This is not just a Hamptons rental.
This is a rare invitation into the lifestyle of an icon.
For those seeking privacy, inspiration, culture, and authentic Sag Harbor charm, The Bert Stern House delivers a summer experience unlike anything else in the Hamptons.