Introducing 434 on Main - an exceedingly rare opportunity on Main Street in Amagansett, a vintage .66-acre estate of exceptional character and provenance. Originally built in 1905 on the coveted south side of Main Street, this distinguished property predates local zoning and retains a grace and scale seldom found today. Meticulously restored in 2013-2014, the residence first known as Sunset View Lodge has been thoughtfully reimagined for modern living while honoring its storied past. Currently zoned and operated as an inn, the home offers four beautifully appointed ensuite bedrooms - each with its own private bath - formal living and dining rooms, a wonderful chef's kitchen, a first-floor powder room ideal for guests and entertaining, and both front and back staircases that lend the home a rare sense of privacy and flow. A gracious front porch recalls the leisurely spirit of turn-of-the-century summers, while a newly finished lower level with soaring 9-foot ceilings provides abundant additional space. The grounds are nothing short of enchanting. An early barn structure, now used as a studio and garage, stands as a charming reminder of Amagansett's rural heritage - and once served as the creative studio of acclaimed artist Bill Durham. Known for his expressive use of color and nationally recognized work, including a Pollock-Krasner grant in 1998, Durham's legacy endures in collections such as Guild Hall, infusing this property with rare cultural resonance. Beyond the barn, an expansive sun-filled garden unfolds with intimate seating areas, mature plantings, and a serenity rarely found at the village center. Whether you're seeking an income-producing inn or a gracious private residence, this home offers both. A once-in-a-generation vintage Amagansett estate, just steps to town, moments from the LIRR and Hampton Jitney, and 0.36 miles to the ocean. It truly doesn't get any better. Barn Studio photography has been digitally edited to show rooms unfurnished.