Historic $4 Million Sag Harbor Cottage Is the Ultimate Blend of Old-World Charm and Modern Luxury

A charming Sag Harbor, NY, cottage that was built in 1840 has hit the market for $3.99 million—serving as a shining example of how history and modern magnificence can blend to create a truly picture-perfect abode.

Located on a leafy street in the heart of Sag Harbor Village, 233 Madison Street, which is listed with Susan Lahrman of Saunders & Associates, has been thoughtfully reimagined to offer the best in both old-world charm and cutting edge architectural detail.

While its historic facade may appear modest at first glance, the interior, with its wide-plank floors and carefully restored period details, is anything but.

"This home is truly one of the jewels of Sag Harbor Village; don't let the exterior fool you, as the house is expansive and generous in size and great for entertaining," the listing teases.

Behind its gleaming black front door sits an expanse of space—and a sun-drenched outdoor space that feels almost like a secret garden, tucked away at the back of the property, surrounded by dense trees.

A dramatic double-height living space with original stone floors brings sophisticated character to the first level, while large windows and a dining room open onto the back patio to fill the space with light and create an easy indoor-outdoor flow.

Built-in shelving makes brilliant use of the space within the main living areas, while also offering the perfect place to display art, knickknacks, or a collection of books, with plenty of storage to house an entire library should a future owner wish to show off their tomes.

A fully modernized kitchen designed for both everyday use and entertaining, along with a home office, sitting room, and family room, round out the main level.

Upstairs, three of the home’s four bedrooms offer comfort and privacy, with each situated on their own private level, according to the listing.

Yet it is the primary suite that truly shines as the jewel of the property, offering a bright, sunlit space that boasts enough room for its own seating area.

The three remodeled bathrooms and a simple, cohesive aesthetic running throughout the property make the space equally suited for family living and elegant gatherings.

For those seeking a summer retreat, the property's backyard will no doubt be the most alluring aspect of the home, offering an in-ground heated pool, as well as ample space to relax and spend time with loved ones.

The listing paints an idyllic picture of summer evening hangouts with friends, grilling sessions, and post-beach sunbathing, stating: "The in-ground heated pool with a stone patio, chaise lounge chairs, and umbrellas make this a perfect spot to relax after a day on the beach."

And while the property may seem pint-sized from the front, the description makes clear that it was designed with entertaining at the front of mind.

"Grill and prepare fabulous dinners for your guests while they dip in the pool," it continues.

"All this is just minutes from the Historic Whaling Village of Sag Harbor with its many restaurants, theaters, and shops. Make sure to stroll down to Long Wharf to watch the yachts and have homemade ice cream."

Location is everything in Sag Harbor, and this home delivers the best of both worlds. You’re in the heart of the village, just steps from shops, galleries, and the wharf, yet the property remains a private sanctuary thanks to its hedges and gardens.

"The exterior is simply fabulous, with lovely professionally landscaped grounds with hydrangea flanking both sides of the pool area and fencing on four sides for privacy," the listing continues.

For someone seeking a sophisticated village retreat—one that captures the romance of old-world craftsmanship while offering all the comforts of modern living, this Sag Harbor cottage might just be the perfect place to call home.

Anyone looking for a lucrative rental opportunity may also see a keen investment in the listing—which has previously been offered up to tenants for as much as $75,000 a month, while Sag Harbor's bustling short-term rental market would undoubtedly welcome such a charming abode.