263 Little Plains Road, Southampton, NY

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Set on a tree-lined stretch of Little Plains Road in the heart of Southampton Village, this restored 1920s residence presents an exceptional summer rental offering with a rare blend of historic character and modern comfort. Ideally located south of the highway, the property is just moments-and an easy walk-to both ocean beaches and the shops, restaurants, and conveniences of the village, making it perfectly suited for a seamless Southampton summer. Spanning 4,000 SF+/-, the main residence has been thoughtfully updated while preserving its original proportions and architectural detailing. Light-filled interiors flow through a series of formal and informal living spaces, creating a natural rhythm for relaxed daily living and effortless entertaining. The home offers 5 bedrooms, 4 full bathrooms, and a powder room, with well-separated guest accommodations across multiple levels to ensure comfort and privacy for all.

Enhancing the experience is a three-story accessory structure that lives like its own private retreat. The first level features a screened-in porch with retractable screens that fully open to the pool area, along with an office, half bathroom, living room, and bar-ideal for indoor-outdoor entertaining. The second level offers an additional living room, bedroom, and kitchenette, providing flexible space for guests, extended family, or staff. Surrounded by mature landscaping, the outdoor setting is designed for summer living, with seamless transitions from interior spaces to the pool and grounds. A turnkey village rental with scale, privacy, and unmatched proximity to both Main Street and the ocean, offering an elevated and effortless Hamptons experience.