Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island's most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main house offers a comfortable and inviting interior, highlighted by a bay window and a spacious open kitchen and dining area with granite countertops, custom cabinetry, and direct access to the deck. A sunken living room offers separation while maintaining an open flow. The main level includes a primary bedroom and an additional bedroom, while the second floor offers a third bedroom, a full bathroom, and flexible living space. The finished lower level offers approximately 790 sq ft of additional finished space, including a recreation area, den, and full bathroom, along with approximately 525 sq ft of unfinished storage. Outdoor living is equally inviting, with a deck off the kitchen leading to the heated pool and patio. The space includes a pool house with half bath, an outdoor shower, and ample room for dining and lounging, surrounded by hydrangeas. A side yard gently rises to a tucked-away bluestone pad, ideal for a future fire pit or outdoor gathering area. The guest house offers its own private setting with living space, a main-level bedroom and additional finished space upstairs, each with its own full bathroom, plus a half bath, one-car garage, and full basement. At the end of 21st Street you'll find direct access to over 150 acres within the Caroline Tuthill Preserve, as well as the Boulevard landing on Sengekontacket Pond - perfect for kayaking, paddle boarding, or boating. Edgartown Village is approximately 1.5 miles away. A unique opportunity with an established rental history - details upon request. Furniture available for separate purchase.