Welcome to 366 Montauk Highway in Eastport, a timeless Victorian Gem at the Gateway to the Hamptons! If you love historic charm and yearn for serenity away from the hustle and bustle, this home offers the perfect blend of character, privacy and accessibility. Just .25 miles to the water, 5.5 miles to West Hampton Beach and 2.6 miles to the LIRR Speonk train station, this home is perfectly located! When you arrive enjoy the convenience of a circular driveway or pull into the oversized detached 2 car garage. Step through the front door into a charming enclosed front porch, where you can enjoy quiet mornings and breezy afternoons. The grand foyer showcases inlaid wood floors and a stately winding wood staircase. The large living room and dining room features an abundance of oversized windows for natural light. Octagonal walls, 8.5 ft ceilings, hidden pocket doors, and a back staircase, are among some of the architectural details rarely found in newer homes. Enjoy an eat-in kitchen and a den with access to the backyard, where you can enjoy entertaining on a ground level deck, and a fully fenced portion of the property. Upstairs there are 4 bedrooms, another full bath with an inviting clawfoot tub, and a unique bonus room that you can enter from the back staircase. Need more room? there is a full attic, just waiting to be finished into an additional living space with endless possibilities. The full basement with high ceilings allows for storage and any additional needs. Come tour this one-of-a-kind home that's waiting for its next owner to make it their own. Who will be the lucky ones? © 2025 OneKey™ MLS, LLC