Great Island by Del Webb at The Pinehills

Independent Assessment

Great Island is a clear nested-enclave case: multiple independent sources -- Del Webb's own national brand positioning, The Pinehills' own site, and third-party directories -- consistently describe Great Island itself as the age-restricted product, while The Pinehills master plan surrounding it is explicitly mixed-age. That distinction is important because The Pinehills also contains a second, separately built 55+ enclave (Owls Nest, by Toll Brothers) that shares some amenities with Great Island but is a physically and administratively distinct HOA; buyers researching either community should not assume the two share ownership, pricing, or association fees just because they sit inside the same master plan. A minor discrepancy in clubhouse square footage was found across sources (some describe roughly 7,000 square feet, others roughly 12,000 square feet); the larger figure appears more consistently across Del Webb-affiliated and Pinehills-affiliated sources and is treated as the more likely number, though it is not independently verified against an architectural record. Current resale pricing and HOA fees were not independently confirmed and should be checked against live listings.

Who May Find This Community Appealing

Buyers who want an established, fully built-out Del Webb community with a long operating track record -- rather than a brand-new, still-under-construction enclave -- will find Great Island appealing, especially those who value proximity to Plymouth's coastline and historic downtown along with the broader Pinehills master plan's golf, shopping, and dining. It suits buyers comfortable with a resale-only market rather than new-construction pricing and options, and those who want single-level or low-maintenance attached and detached designs within a mature landscape.

Homes, Builders & Development History

Del Webb (a PulteGroup brand) built Great Island in phases between 2002 and 2015, delivering roughly 600 homes in total. The community offers two attached home designs (2 bedrooms, 2 bathrooms, roughly 1,587-2,222 square feet) and three detached floor plans (2-3 bedrooms, roughly 1,986-2,470 square feet), most with open floor plans and first-floor owner's suites designed for single-level living. Some homesites have views of the 77-acre Great Island Pond or, in select locations, glimpses of Plymouth Bay. Construction is complete and all activity is now resale.

Current Pricing & Market Positioning

A current, reconciled price range for active Great Island resale listings was not independently confirmed. Homes originally started in the mid-$300,000s when Del Webb was still selling new construction; more recent secondary market summaries suggest resale activity has climbed well above that starting point, into the high-$600,000s to $900,000-plus range, reflecting both general South Shore appreciation and Great Island's mature, amenity-rich positioning within The Pinehills. Buyers should confirm current pricing directly against live MLS listings or a local agent before budgeting.

New Construction vs. Resale Considerations

Great Island is fully built out with no remaining new-construction inventory from Del Webb; all current activity is resale. Buyers should expect resale-market dynamics -- competitive offers, home-by-home condition variation, and the need for independent inspection -- rather than builder-backed new-home warranties. Buyers should confirm current available inventory and pricing with a local agent experienced in Pinehills-area resales.

Taxes, Insurance & Special Assessments

Homes at Great Island are subject to the Town of Plymouth's property tax administration; Plymouth's residential tax rate has been cited at roughly $12.55 per $1,000 of assessed value for fiscal year 2026, though buyers should confirm the current-year rate directly with the Plymouth Assessor's office, since rates reset annually. The condominium or homeowners association's current insurance coverage and any special-assessment history for Great Island specifically were not independently confirmed; buyers should request the association's current financials before purchasing.

Golf

Great Island does not have its own private golf course, but residents have access to two daily-fee, championship-caliber public courses operated as part of The Pinehills Golf Club, within the surrounding master-planned community. Whether Great Island residents receive preferential tee times or discounted greens fees versus the general public was not confirmed.

Community Layout & Lifestyle

Great Island sits in the southeast section of The Pinehills, off Beaver Dam Road, giving residents a wooded, pond-dotted setting with walking trails and water access while remaining a short distance from The Pinehills' Village Green for shopping, dining, and community events. Life here centers on the Great Island clubhouse -- an indoor pool, fitness center, ballroom, and billiards space -- supplemented by full access to the wider Pinehills master-plan amenities. Because Great Island is a distinct age-restricted neighborhood within a larger, mostly non-age-restricted master plan, residents interact with a broader multigenerational community at Pinehills-wide amenities and events even while living in an age-qualified enclave.

Shopping, Healthcare & Airport Access

Great Island is located in the southeast section of The Pinehills off Beaver Dam Road in Plymouth, Massachusetts, roughly three miles from the Plymouth coastline and historic downtown Plymouth. The Pinehills sits near Route 3, giving reasonably direct highway access toward Boston (roughly 40 miles north) as well as Cape Cod. Buyers should confirm current drive times to specific medical facilities, shopping, and highway access from individual addresses within Great Island.

Age Qualification & Material Ownership Restrictions

Del Webb's own national active-adult brand and The Pinehills' own site both describe Great Island as an over-55 community requiring at least one resident age 55 or older per household, consistent with a standard federal Housing for Older Persons Act (HOPA) 80/20 structure. Massachusetts also maintains its own state-level registration-based exemption for qualifying 55+ housing under Massachusetts General Laws Chapter 151B, Section 4, paragraph 7, which requires biennial registration with the state housing agency; Great Island's specific registration status under that state provision was not independently confirmed, and a recorded declaration or deed restriction was not reviewed. Buyers should confirm the exact current age-verification procedure directly with the Great Island homeowners association.

Tradeoffs & Limitations

Because Great Island is fully sold out of new construction, buyers are competing in an active resale market where pricing, negotiating leverage, and available inventory are less predictable than in a still-selling new-construction community; current asking prices and HOA fees could not be independently confirmed. Buyers should also be careful not to conflate Great Island with the separate Owls Nest enclave nearby, or with the non-age-restricted portions of the broader Pinehills master plan, since eligibility, HOA structure, and amenities differ by neighborhood even though they share the same overall site and some Pinehills-wide amenities like the Stonebridge Club and golf courses.

Comparison With Nearby Communities

Great Island shares its master-planned site with Owls Nest, a smaller (approximately 44-home), newer Toll Brothers Regency-collection 55+ enclave elsewhere within The Pinehills. Both are genuinely and independently age-restricted, and both residents share access to certain Pinehills-wide amenities such as the Stonebridge Club and the two Pinehills Golf Club courses -- but Great Island and Owls Nest are separate, differently administered HOAs with their own clubhouses, price points, and home inventories, and neither is a subset of the other. Within Plymouth, Great Island is also distinct from Thorndike Development's Sawyer's Reach and Summer Reach communities, which sit elsewhere in town near Colony Place and Summer Street respectively and offer a different, more condominium- and townhome-weighted product at different price points.

Current Listings

A connected local agent, or a Pinehills-area real estate office, can provide current available Great Island listings and recent comparable sales.

Is Great Island the same community as Owls Nest at The Pinehills?

No. Both are age-restricted 55+ enclaves inside the same larger Pinehills master plan and share some master-plan amenities, but they are separate, independently built and administered communities with different builders (Del Webb vs. Toll Brothers), different clubhouses, and different home inventories.

Is the entire Pinehills community age-restricted?

No. The Pinehills master plan as a whole is a mixed-age development. Great Island (and separately, Owls Nest) are age-restricted 55+ neighborhoods within it; most of the rest of The Pinehills has no age restriction.

Can I still buy a new-construction home at Great Island?

No. Del Webb completed construction and sold out of Great Island inventory years ago. All current activity is resale.

Does Great Island have its own golf course?

No. Great Island does not have a dedicated private course, but residents have access to two daily-fee public courses operated as part of The Pinehills Golf Club within the surrounding master plan.