Thanks to careful conservation and expansion, this delightful, inviting five-bedroom home—dating to the years just following the Revolutionary War—stands as a reminder of the past while enduring for generations to come.

The history of Long Island is closely interwoven with that of the United States itself. On its east end, the village of Sag Harbor exemplifies these bonds, with roots that began with the Indigenous Algonquin people and led to a well-recognized era as a global whaling hub. After the Revolutionary War, an esteemed lieutenant colonel named John Hulbert—who headed the Bridgehampton Militia—settled here, on Sag Harbor’s Main Street, in a stalwart shingled timber-frame residence. Legend has it that between battles, Hulbert designed a flag—which may have hung on one of these walls—that perhaps served as a prototype for the modern-day Stars and Stripes.

Sag Harbor, New York| Harald Grant, Bruce Grant, Sotheby’s International Realty – Southampton Brokerage

In the centuries since Hulbert’s home’s original construction, painstaking renovations have added eye-catching hallmarks of Colonial and Italianate styles—dormer windows and white storybook trim among them—along with a covered porch. More recently, an impressive comprehensive restoration and redesign—undertaken in agreement with local historic organizations—added striking contemporary elements while preserving the home’s irreplaceable vintage character.

Rugged exposed beams, wide-plank blonde hardwood floors, and period-inspired fixtures and finishes serve as charming reminders of the home’s provenance, but today’s 5,000-square-foot floor plan augments the subtly elegant historic rooms with spaces that are undeniably refined and modern. Chief among them is a dazzling open-plan great room and impressive modern kitchen, where a cathedral window wall admits glorious light and enviable views of the lush lawn and thriving trees and landscaping. Now spanning three levels, the residence also offers five comfortable bedrooms, including an owner’s suite with a luxurious bath offering both a shower and a soaking tub.

On the street side of the estate, a picturesque emerald yard is framed by quintessential Colonial iron fencing, and the dreamy wraparound porch beckons with visions of breezy relaxation. French doors open from the chic interior living and entertaining spaces to a serene secluded bluestone terrace. Another swath of lawn—threaded with stepping stones—unfurls in the backyard toward an azure swimming pool and spa and a one-bedroom guesthouse with its own terrace and warming outdoor fireplace. Thanks to careful conservation and enhancement, this delightful, inviting home in Sag Harbor village and minutes from the historic waterfront stands as a reminder of Sag Harbor’s past while enduring for generations yet to come.

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