25 Pennacook Avenue, DowntownOak Bluffs, MA 02557Price: $2,180,000

A unique offering in the heart of the historic Copeland District of downtown Oak Bluffs. This cherished main residence and guest house, embody the timeless charm that defines this beloved community. Just minutes from Circuit Ave, the ferries and harbor, and a block from Inkwell Beach. This home invites you to experience the essence of Oak Bluffs! The main house, dating back to the 1850s, has been well maintained, preserving its period architectural details while incorporating modern updates, including an updated kitchen with a walk-in pantry. At the heart of the home, a classic stone fireplace anchors the living and dining areas, creating an inviting gathering space. On the second floor, the primary suite gives a sense of grandeur and charm, with a vaulted ceiling, chandelier and multiple closets. The bathroom includes a soaking tub and separate water closet. Two more bedrooms and a shared full bath provide comfortable accommodations for family and visitors. The second floor is thoughtfully centered around a laundry area, complete with an additional third shower for added convenience. The guest cottage is a sweet retreat~ built in 1999. The first floor features a full kitchen, living room, and half bath, along with a convenient stackable washer and dryer. Upstairs, the second floor offers a one-bedroom layout with an adjoining dressing room or office area that leads to a full bath. Hardwood floors run throughout and forced hot water heating allows for comfortable year-round use. The guest house and the main house share the rear deck, and an outdoor shower that's perfect for island living. The properties are connected to town sewer and equipped for year-round use with a heating and A/C Viessmann system for efficiency. When in bloom, blue hydrangeas frame the properties, enhancing their classic Vineyard charm. Both homes feature quintessential front porches, ideal for greeting neighbors and enjoying the island community. This an opportunity to become a part of this enduring legacy and create lasting memories for generations to come. With a strong rental history, this property presents a great investment opportunity too!