Sag Harbor, situated towards the end of the South Fork of Long Island, is filled with a vibrant history, culture, and sought after real estate. Algonquin Indians were the first settlers in the areas and named the two square miles “Weg-quae-and-auke” which translates to the land or place at the end of the hill; a name fitting to this day as the village’s main street sits on a slope. Although the Hamptons have seen a significant transformation from luxury real estate to upscale shops, the village of Sag Harbor has retained its charm. The New York Times explains that “despite the flood of big money that continues to sweep the East End from Quogue to Montauk, [Main Street] retains its small-town aura.”

However, the small village has not been immune to change. The area’s real estate has become highly desirable as New Yorkers look for an escape from the City with excellent views of Gardiners Bay, Northwest Harbor, Sag Harbor Bay, and Noyac Bay. Sag Harbor is known for its shingled houses from the 1900s, but buyers have transformed a portion of the real estate market by developing more modern and larger homes. Older homes sell at around $600,000 but the new luxury homes on the waterfronts can go anywhere up to $30 million. The median price is around $1.65 million, and for larger, more modern homes with spacious outdoors buyers pay over $3 million. Although many buyers purchase homes for weekends and holidays, the area does not have a high renters market like in other parts of the Hamptons. Sag Harbor attracts New Yorkers who want to invest in the area and not just for the summer months.

This small village vibe keeps the culture rich. John Steinbeck lived in Sag Harbor in the late years of his life and the village influenced his works such as The Winter of Our Discontent where he wrote: “grab anything that goes by. It may not come around again.” Although Steinbeck could not have predicted the real estate boom in the Hamptons, he definitely had a point. As we have previously discussed, property in the Hamptons is running scarce as free parcels of land have been preserved for agricultural purposes and parks instead of the development of new holiday homes. In Sag Harbor, developers have had to work with the community and compromise on plans. A parcel of land has been split to develop a thirteen-unit condo but also keep enough space for the new John Steinbeck Waterfront Park. Sag Harbor Partnership board member, April Gornik, notes that this is “a compromise well worth making, and, frankly, I just give the village mayor and the Village Board of Trustees credit for having persisted in maintaining obviously friendly talks with the developer. I also give the developer credit for recognizing that this means so much to the community.” Although land in Sag Harbor has become an attraction to developers and buyers, the small village is eager to protect its charm.