Discover a rare waterfront compound designed for the way people truly live in the Hamptons, centered around the water, the outdoors, and effortless gathering with family and friends. Set on nearly a full acre with deep-water dockage, expansive lawns, a heated gunite pool, and multiple structures, 20 Penny Lane offers a waterfront and boating lifestyle rarely found at this price point. Originally renovated and expanded over time, the home blends relaxed coastal comfort with thoughtfully designed living spaces oriented toward the water. The heart of the home is an expansive gourmet kitchen that flows seamlessly into the dining area with wood-burning fireplace and a dramatic vaulted living room filled with natural light. Large glass doors open to a covered porch overlooking the pool, lawn, dock, and open water beyond, creating an easy indoor-outdoor lifestyle throughout the seasons. The upper-level primary suite serves as a peaceful private retreat with water views, its own balcony, and a dedicated office or sitting room with an additional balcony overlooking the property. Two guest suites on the main level provide comfort and privacy for family and visitors, while the lower level offers additional flexible guest accommodations, recreation space, and a full laundry room. A second laundry area within the primary suite adds everyday convenience. A separate cottage of approximately 1,000 square feet adds exceptional versatility to the property. Complete with a wet bar, it functions beautifully as a guest lounge, media room, studio, gym, home office, or creative retreat, a true bonus space that expands how the property can be enjoyed. Outside, the property unfolds into a complete Hamptons waterfront experience. The bulkheaded shoreline and deep-water dock accommodate boats and water toys with ease, while the heated gunite pool, fire pit, covered porch, and sprawling lawn create an ideal setting for entertaining or quiet afternoons by the water. A striking three-car carport, additional barn structure, and mature landscaping complete the compound. Whether your ideal summer revolves around boating, paddle boarding, sunset dinners by the pool, or simply escaping the crowds for a more relaxed waterfront lifestyle, 20 Penny Lane offers a rare opportunity to enjoy the Hamptons from the water outward.