56861 Private Rd B (Main)

Tucked away on a private road in the heart of historic Southold, this light-filled coastal home offers a rare combination of privacy, convenience, and North Fork charm. Surrounded by peaceful farm frontage and mature landscaping, this tranquil retreat is just off the North Fork Wine Trail and moments to town and Peconic Bay and Long Island Sound beaches. Its setting captures the very best of life on the North Fork. Designed for easy living and effortless gathering, the six-bedroom home features bright open-concept spaces that flow naturally from one room to the next. Large windows fill the home with natural light, while thoughtful updates and custom details create a warm and welcoming atmosphere throughout. A fully finished lower level provides additional space for recreation, guests, or movie nights after a day at the beach. Upstairs, a dramatic loft-style landing overlooks the main living area below, creating a sense of openness and connection. The primary suite and additional bedrooms open directly to a balcony overlooking the backyard, where summer days are spent poolside and evenings linger long after sunset. Outside, the home unfolds into a private retreat. A heated saltwater 20' x 45' pool with spa, expansive marble patio, and oversized pergola with pizza oven and fireplace create inviting spaces for al fresca dining, entertaining, and quiet relaxation. Beyond the pool, an additional 1/2 acre tree-lined lot offers room for exploration, a firepit to roast s’mores and hotdogs, lawn games with friends, an afternoon snooze on the hammock, or simply extra space and privacy. Two large outdoor sheds keep bikes, games and beach gear easily accessible. Whether enjoying a morning walk to the beach, browsing nearby farm stands, visiting local wineries, or spending an evening in Greenport, this is a home designed to be enjoyed in every season—a place where family and friends naturally gather and where North Fork memories are made.