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65 Leonard Street Gloucester, MA

65 Leonard Street Gloucester, MA

by John & Cindy Farrell / Tuesday, 19 May 2026 / Published in Featured Real Estate Listings

65 Leonard Street, Gloucester, MA | Historic Annisquam Waterfront Home

One of the oldest surviving homes in Annisquam, this historic First Period Colonial (circa 1717) is part of the property known as “The Old Castle.” Positioned on Lobster Cove, this waterfront residence showcases a seasonal dock providing direct access and exceptional views enjoyed both inside and out.

See the listing details for 65 Leonard Street

The layout offers a bathroom on each floor, second-floor laundry, a back stairway, a first-floor office, and third-floor bonus space. Practical updates include an updated heating system, replaced sunroom windows, basement work, and a repaired seawall.

Key Property Features

  • Waterfront Living: Positioned directly on Lobster Cove, this waterfront residence showcases a seasonal dock providing direct water access.
  • Waterside Sunroom: An all-season sunroom along the water side was added and designed with three walls of full-length windows to watch the cove, with ample space for dining, multiple seating areas, and a TV area.
  • Historic Detail: Original craftsmanship has been preserved, including wide pine floors, woodwork, and two fireplaces (one on each floor).

The Location

Located on Gloucester’s North Shore, the historic village of Annisquam offers a distinct Massachusetts coastal experience. Known for its narrow winding lanes, historic architecture, and community atmosphere, this waterfront neighborhood is surrounded by the waters of the Annisquam River, Ipswich Bay, and Lobster Cove. The property sits just moments from local beaches, the Annisquam Yacht Club, and the Annisquam Harbor Lighthouse.

To experience the waterfront setting of this Annisquam home firsthand, contact John & Cindy Farrell to arrange your private tour. 978-468-9576

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Tagged under: Featured Listings

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