An exceptional opportunity to own in the highly sought-after Greenport / North Fork region, where lifestyle, flexibility, and long-term value come together. Whether you are seeking a year-round residence, weekend retreat, or property with extended living possibilities, this well-maintained ranch offers outstanding versatility in one of Long Island's most desirable coastal destinations. Welcome to 395 Linnet Street, also known as 806 Linnet Street, Southold. Designed for today's casual lifestyle, the home features an open-concept layout, 3 bedrooms and 2 full baths on the main level, along with an updated eat-in kitchen showcasing quartz countertops. The expansive backyard creates the perfect setting for entertaining, outdoor dining, or simply enjoying the peaceful North Fork atmosphere. The fully finished lower level with outside entrance (OSE) offers additional bedrooms and baths (all on Certificate of Occupancy), creating exceptional flexibility for extended living, guests, private work-from-home space, recreation, or separate accommodations. Located just minutes from bay beaches, marinas, parks, vineyards, farm stands, acclaimed restaurants, boutique shopping, the historic Greenport waterfront village, LIRR, and Hampton Jitney, this property places you in the center of the North Fork lifestyle that continues to attract homeowners and weekend visitors alike.