Nestled in the heart of downtown Nantucket, a piece of history has found its way into the modern world. 11 Pleasant Street is a historic gem that offers a unique blend of 18th-century heritage and modern luxury. The property is listed by Michael Passaro of The Holly Parker Team at Douglas Elliman for $9,950,000.
Originally constructed in 1750, this Nantucket treasure underwent a meticulous two-year restoration and renovation, courtesy of John Udelson, CEO of Grey Lady Development. The result? A stunning transformation that seamlessly marries historical character with contemporary elegance.
As you step inside, you’ll be greeted by the rich history that envelops the property. This in-town residence boasts 6 bedrooms and 6.5 bathrooms across three spacious floors.

The main level exudes sophistication, featuring a gourmet kitchen with an impressive 11-foot marble island, a cozy living room with a gas fireplace, and a guest bedroom with an en-suite bath.
Climb the graceful staircase to the second floor, where you’ll find four bedrooms, three of which have their own en-suites, and a home office for those seeking a peaceful workspace. The primary bedroom is a true sanctuary, complete with a walk-in closet, a lavish bath, and a covered veranda where you can savor the island’s beauty.

But the surprises don’t end there. Ascend to the third floor and discover an en-suite bedroom and a delightful children’s space, perfect for family gatherings or creating lasting memories.
This historical home also offers modern conveniences, including a gym with a Peleton, a Sonos sound system, central AC/heat, a butler’s pantry, and a laundry room. Step outside to an oversized deck, patio, and a beautifully landscaped corner lot, where you can relax and entertain in style.
For those who appreciate the finer things in life, the furnishings in this residence have been curated by Serena and Lily, available for purchase at an additional cost. It’s a chance to own a piece of reimagined Nantucket history, where the past and present converge in perfect harmony.
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