Steeped in Plymouth history, 8 Winter Street is a remarkable historic residence offering a rare opportunity to own a treasured piece of New England's architectural heritage. Known as the Sgt. William Harlow Family Homestead, this distinctive gambrel-roofed Cape reflects generations of history, craftsmanship, and timeless character. Thoughtfully preserved and expanded over the centuries, including a substantial 19th-century addition, the home showcases exquisite period details throughout, including exposed wood beams, wide-plank wood flooring, and five fireplaces. Offering five bedrooms and 3.5 baths, including a first-floor primary suite, the home blends historic charm with modern conveniences, including an automatic gas generator. Listed on the National Register of Historic Places, this extraordinary property is situated on a .48-acre level lot in a desirable in-town location with ocean views, just a short stroll to Stevens Field Beach and Park, and minutes from Plymouth's historic waterfront, shops, and restaurants. A detached two-car carriage-style garage offers possible ADU potential, subject to approvals, while a separate outbuilding offers an inspiring setting for an art studio. A potting shed and gorgeous perennial gardens throughout the grounds create a gardener's dream. Town water , sewer and natural gas. A rare opportunity to embrace historic coastal New England living in the heart of Plymouth.
8 Winter St, Plymouth MA 02360
Plymouth, MA 02360
- Property type
- Single Family Residence
- Status
- Active
- Year built
- 1700
- Lot size
- 0.48 acres
- Living area
- 3,336 sf
- MLS#
- c515dd654a554fc0a02fcfd43291b7f3
- Beds · Baths
- 5 · 4
Plymouth, MA.
Plymouth, Massachusetts, is a market our advisors follow closely — its streets, housing stock and setting each shape what a residence here is worth and how it lives day to day. We are glad to walk you through the locale in detail, and how this particular address sits within it.
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Listings updated Oct 5, 2026



