Timeless architecture and lush surroundings combine with awe-inspiring views to create an unparalleled setting on Captain's Row, while multiple structures make this one of the most unique properties in the Village of Sag Harbor. Overlooking Otter Pond on a .60 +/- acre parcel, this exceptional waterfront residence has been fully restored with a two story expansion including a primary suite and sunroom/den. The 3,142 +/- sq. ft. home affords 4 bedrooms, along with 5 full and 1 half bathrooms. A testament to the historic charm, the interior features seven fireplaces with one present in each of the paramount spaces across both levels. Designed as the focal point of the home, a chef's kitchen offers multiple dining areas inclusive of a marble island, open hearth cooking fireplace, high-end stainless steel appliances, secondary kitchen and butler's pantry, and a separate bar with close proximity to the formal dining area. With a central staircase, the second level opens to a sitting area with fireplace and television. Part of the extension, the new primary suite includes a spacious bathroom with double vanity, soaking tub, and shower, as well as a private terrace overlooking the pond. The second floor is completed by three guest bedrooms. An unfinished 1,231 +/- sq. ft. lower level and full attic with stairway allocate plenty of room for storage. Also part of the new addition, the naturally lit sunroom/den provides a separate entertaining space and entry to the backyard. Along with the main residence, the property encompasses two separate structures. Set amongst rolling lawn and well-maintained gardens is a detached office/studio in the process of being converted to a guest house and a brand new pool house with full bathroom. Easily accessed by the pool house, the newly constructed 15' x 40' heated gunite pool and spa are surrounded by extensive patio providing ample room for lounging and both covered and uncovered outdoor dining. Thoughtfully positioned on the parcel, these outdoor amenities maximize the panoramic water vistas. Standing as one of the most distinctive properties in Sag Harbor Village, this pondfront offering presents the unique opportunity to own a historic piece of the Hamptons outfitted with modern amenities.