Just moments from the heart of Sag Harbor Village, 166 Bay Street is a turnkey 4-bedroom residence that masterfully blends timeless Hamptons charm with modern amenities. Set on nearly half an acre (rare for Sag Harbor Village!) this beautifully maintained home features a heated gunite pool and a separate, fully equipped pool house-all surrounded by lush landscaping for ultimate privacy and tranquility. A quintessential wraparound front porch welcomes you to this historic gem, leading to a spacious back deck ideal for al fresco dining and outdoor entertaining. Inside, the home is filled with natural light and elegant details. A sun-drenched formal dining room flows seamlessly into a cozy library/formal living room and a separate den with pocket doors-perfect for relaxing evenings or intimate gatherings. The bright, eat-in kitchen is outfitted with premium Sub-Zero and Viking appliances and overlooks the expansive, private backyard and garden. A conveniently located powder room and laundry area are just off the kitchen. Upstairs, the serene primary suite includes an ensuite bathroom, while two additional bedrooms share a well-appointed full bath. The finished attic level-with its own half bath-offers flexible space for an additional bedroom, office, or playroom. Additional storage is available in the full basement, accessible from the kitchen porch. The outdoor amenities are just as compelling as the interior. Incredibly unique for Sag Harbor Village, 166 Bay Street offers a lot size almost triple(!) the size of most lots within the Village. The gated, English garden-inspired pool area is surrounded by mature privet and manicured plantings, providing a peaceful retreat. The renovated pool house features crisp, modern finishes, a full bath, and a slate patio-perfect for summer entertaining or guest accommodations. Combining historic charm, modern amenities, and an unbeatable location close to the shops, restaurants, Bay Beach and marina of Sag Harbor Village, this exceptional property offers effortless Hamptons living at its finest.