Great Island

Great Island is a 600-home, 55+ active adult neighborhood tucked inside The Pinehills, a 3,200-acre master-planned community in South Plymouth, Massachusetts. Developed by Del Webb between 2002 and 2015, it's built around a dense pine forest setting and wraps partially around the 77-acre Great Island Pond, with select homesites offering pond views or distant ocean vistas of Plymouth Bay. The community feels distinctly New England — rolling terrain, towering pines, and a thoughtful, village-oriented layout — rather than the stucco-and-palm-tree template of most Del Webb communities elsewhere in the country. The social and physical hub is the Overlook Clubhouse, a private facility reserved for Great Island residents. Inside you'll find an indoor pool, a fitness center with cardio and weight equipment, a grand ballroom, a billiards room, a card room, a craft room, and multiple gathering spaces. A full-time Lifestyle Director programs a continuous calendar of events, classes, trips, and social gatherings, and residents run an active slate of clubs — chess, glee club, yoga, chair yoga, art club, men's group, knitting, chamber music, book groups, a pond swimming club, and activity committees that host seasonal events and speakers. Outdoors, Great Island has tennis courts, bocce courts, and walking trails that wind through the pine woods. The two on-site ponds support kayaking, swimming, fishing, and small-craft boating right from the neighborhood — a rare perk in a Northeast 55+ community. Because Great Island is a neighborhood within The Pinehills, residents also have full access to the broader master plan. That includes the Stonebridge Club (with an outdoor pool, tennis, exercise room, and 80+ clubs open to all Pinehills residents), the walkable Village Green with shops, restaurants, a fresh-food market, TD Bank, professional services, a U.S. Post Office, and the Mirbeau Inn & Spa. Two highly regarded public daily-fee golf courses — one designed by Rees Jones, the other a Nicklaus Design — sit within The Pinehills and are playable without any mandatory golf membership. More than 60 additional public courses are within 35 miles. Homes were offered in attached (villa-style) and detached single-family series, ranging roughly from 1,587 to 2,881 square feet with two or three bedrooms, two-car garages, and optional finished basements. Floor plans are built around active-adult priorities: first-floor primary suites, open-concept main levels, and low-maintenance exteriors. The HOA structure is dual — every Great Island home pays a monthly Great Island HOA assessment covering exterior maintenance, lawn care, snow removal, trash, water, sewer, the clubhouse and pools, plus a separate monthly Pinehills Landowners Association (PHLOA) fee (currently around $68/month) that funds community-wide common areas across the master plan. Location is a real differentiator. The community sits off Beaver Dam Road in the southeast corner of The Pinehills, roughly 45 miles south of Boston and just 7 miles from the Sagamore Bridge to Cape Cod. Historic downtown Plymouth — Plymouth Rock, Plimoth Patuxet Museums, the waterfront, and a working harbor — is a short drive north, and coastal beaches, cranberry bogs, and state forest land are all nearby. It's a genuine four-season community that draws buyers who want New England weather, coastal proximity, and a walkable, amenity-rich retirement setting without leaving the Northeast.