Welcome to 27 Howard St, Sag Harbor, where you have the rare opportunity to own a historically charming townhouse-style home that exudes elegance and luxury on one of the most prestigious streets in the Village. Originally built in 1824, on the highest point of Howard's Street, this turn-key Captain's home is meticulously renovated with modern amenities and it is the closest walking distance street to Sag Harbor Village that is not in a flood zone. It offers 2,950 square feet of intelligently designed living space, featuring a beautiful custom-made chef's kitchen with an eat-in dining area and banquet, a front room parlor, a bright living room that overlooks the beautifully landscaped rear garden, 4 generously appointed bedrooms, and 4.5 bathrooms, perfect for those seeking a one of a kind, spacious and comfortable home in the heart of Sag Harbor Village. Upon entering, you'll be greeted by an array of architectural elements, including built-ins and decorative moldings, casement windows (some originally restored) with remote control window treatments, all allowing for an abundance of natural light to illuminate each room. The beautiful, knotted hardwood floors throughout complement the charm of this home. There are 2 gas fireplaces, one in the parlor and one in the primary bedroom, ideal for cozy evenings. The custom closets, some hidden, offer ample storage space, while the bathrooms are appointed with beautiful marble, a double sink vanity, and a luxurious soaking tub for relaxation in the primary bathroom. The fully finished lower level with 10 ft ceilings, offers tremendous light throughout the lower level. Three bedrooms are appointed on the lower level, one ensuite and one that is shared. A stackable washer/dryer is available on the lower level and in the primary bedroom suite. Step outside to discover a private oasis. Soak in the spa while admiring your incredible home, and then plunge into the saltwater gunite pool to cool off while listening to the waterfall feature that comes off the spa. The pool house offers a large sauna, kitchenette, full bathroom, and a spacious seating area, complete with a loft-like area. Seven-foot ceiling storage space is available underneath the pool house. Use the pool house as an office or to cool off from the heat. The backyard also features an outdoor shower, exterior speakers, and landscape lighting, perfect for outdoor entertaining and dining. Additional amenities include a backup generator, central vacuum, state-of-the-art water filtration system, and on-site parking for three cars. Don't miss the opportunity to call this exquisite property your home. Book your showing today and experience the epitome of luxury living in Sag Harbor Village.