Sag Harbor

Once a booming international port and major whaling center, so much so that Congress declared it the first official port of entry for the new United States in 1789, Sag Harbor has a long and storied history. It has an abundance of historic buildings to match, the oldest of which predates the American Revolution. Toward late 1800s, Sag Harbor became a summer destination for New York’s wealthy elite. People fell in love with it over the years, and today the village, which is split between the towns of Southampton and East Hampton, offers its fewer than 3,000 residents a vibrant waterfront lifestyle whose quaint, walkable downtown provides easy access to shopping and nearly endless dining options year-round. “People are drawn to Sag Harbor because of the lifestyle and being so close to the water—there’s water all around you there,” says Vincent Horcasitas, a broker at Saunders & Associates. “You have great boating and amazing restaurants. People love being there because it’s probably the most vigorous town out here in the wintertime for locals. There are more people, it’s livelier, it just has a more vibrant vibe.”

Sag Harbor’s homes are a mixture of new construction and older homes, some of which date back as far as the 1800s. One of its more famous homes, the Nathan P. Howell house, was originally designed and built in 1833 in a Greek Revival style before being updated to fit more of an Italianate Revival style in the 1850s. Most homes in the village, though, are colonial-style homes, with a growing collection of Contemporary and Modern homes among new constructions. All these homes have one thing in common: luxury. Amenities like private pools are commonplace in the community, and buying a home here often comes with a hefty price tag. According to Horcasitas, home prices start at around $2 million and can easily climb to $20 million. In Sag Harbor and the neighboring village of North Haven, which is entirely residential and functions almost as an extension of Sag Harbor, home prices climb as high as $50 million. Inventory in the neighborhood is incredibly low, with just a fraction of the usual number of homes on the market, but demand remains high. “There’s a lot of competition,” Horcasitas says. “Things that are priced right sell and have lots of action on them.”

Horcasitas also says that Sag Harbor’s schools are another draw for many residents. The village is served by the Sag Harbor Union Free School District, which has a B on Niche and consists of just two schools. Students begin their education at Sag Harbor Elementary School, which has a B-plus on Niche, before moving on to Pierson Middle/High School in sixth grade. This school has a B on Niche and a student-to-teacher ratio of 8:1.

When the weather is good, residents spend a lot of time out on the water or relaxing at one of Sag Harbor’s many beaches. Havens Beach is a popular residents-only beach that offers calm water, beautiful views and a playground. The village is bracketed by nature preserves, so it also provides plenty of ways to enjoy the outdoors without getting your feet wet. Elizabeth A. Morton National Wildlife Refuge is a beautiful spot to hike, enjoy nature and get glimpses of wildlife. Locals head to Mashashimuet Park to enjoy its playground, watch local baseball and softball games or challenge each other to a round of tennis or pickleball.

Sag Harbor’s walkable downtown is active all year, even during the cold months. Locals often pick up groceries at Schiavoni’s Market, which has served the community since 1932, and grab a morning coffee at their favorite of the village’s many coffee shops. Restaurants in Sag Harbor are a dime a dozen, but The Corner Bar is a longstanding spot for friends to meet up to enjoy dinner and drinks. They also love Lulu Kitchen & Bar’s Mediterranean menu and Sag Pizza’s wood-fired pies. When they truly want to spoil themselves, Le Bilboquet is a go-to spot for waterfront fine dining. For many, Sag Harbor’s beauty and year-round activity make it a beautiful and vibrant place to call home during any season.