8440 Main Road

This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.