Tucked away on one of East Hampton Village's most desirable streets, this quintessential Sears Roebuck Hamptons cottage beautifully balances timeless character with thoughtful modern updates. Set on a beautifully landscaped and private .39 acre+/- lot, the single-level home offers 1,300 SF+/- of sun-drenched living space across three bedrooms and two full bathrooms. With an open-concept layout and carefully curated finishes, the home delivers both function and charm in equal measure. At the heart of the home, a seamless flow connects the kitchen, dining, and living spaces-anchored by original wainscoting, rich wood floors, and large windows that frame lush garden views. The renovated kitchen, completed during a comprehensive redesign between 2003-2005 by renowned architect Frank Greenwald, opens directly onto an expansive dining deck, ideal for easy indoor-outdoor entertaining. The bedroom wing is anchored by a private, rear-facing primary suite, which enjoys tranquil garden views and direct access to a covered porch. Two additional guest bedrooms are thoughtfully positioned and share a full bath, making the home exceptionally well-suited for guests or family. Modern comforts were introduced during the renovation, including a new boiler, hot water heater, and central air conditioning for year-round livability. Outside, the beautifully manicured grounds feature mature trees, blooming hydrangeas, and layered landscaping that frame a heated gunite pool. Tucked at the back of the property is a charming, grandfathered pool house-technically classified as a non-conforming shed-offering a stylish bonus space complete with half bath, WiFi, TV, and an outdoor shower. Whether used for poolside entertaining, overflow guests, or a quiet work-from-home escape, the pool house expands the property's versatility and appeal. This move-in-ready home also offers expansion potential, with up to 1300 SF+/- of additional buildable space permitted. Peaceful and private, yet moments from the village's shops, restaurants, train, Jitney, and famed ocean beaches, this is a rare offering in one of East Hampton's most coveted locations-equally suited as a serene year-round residence or a picture-perfect summer retreat.