With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the rear of the property, a private guest house-affectionately known as The Nest-has undergone a similar transformation and offers a private escape. Adjacent to the main home, the charming bunk house completes the ensemble, perfectly complementing this unique and inviting expansive compound. Though the wraparound porch invites you to linger with its endless ocean views, the nearby beaches, boutique shops, acclaimed restaurants, and the contagious energy of Circuit Avenue and the Harbor are all steps away, offering something for everyone to enjoy. For those seeking flexibility, the home's established rental history further highlights the desirability of both the property and its coveted location. An exciting opportunity to own in one of Oak Bluff's iconic settings! The Nest is a 616-square-foot guest house with a private deck, an outdoor shower, and a parking area. The living space is located on the first floor and has a full bath. The upstairs bedroom, with a private balcony, overlooks Farm Pond to Nantucket Sound. The Lilac House - this fun bunk house, perfect for the younger generation, is open-concept, has a full bath, front deck with waterviews, and a private outdoor shower and deck.