Annisquam Real Estate

Welcome to Annisquam, a hidden gem nestled within the picturesque city of Gloucester, Massachusetts. This charming coastal village is part of Essex County and offers a unique blend of natural beauty, rich history, and a vibrant community atmosphere. Annisquam is renowned for its stunning waterfront views, with the Annisquam River gracefully flowing into the Atlantic Ocean, providing residents with a serene backdrop for daily life.

The area is characterized by its beautiful, historic homes that reflect the region's maritime heritage, many of which boast breathtaking views of the water. The tranquil streets are lined with lush greenery and colorful gardens, creating a picturesque setting that feels like a step back in time. Annisquam’s artistic spirit is palpable, with local galleries and studios showcasing the work of talented artisans inspired by the stunning coastal landscape.

Outdoor enthusiasts will find plenty to love in Annisquam. The nearby Annisquam Lighthouse, one of the oldest lighthouses in the country, is a must-visit, offering a glimpse into the area’s maritime history. The surrounding parks and beaches provide ample opportunities for kayaking, sailing, and enjoying peaceful walks along the shore.

With its tight-knit community and friendly atmosphere, Annisquam is not just a place to live; it’s a lifestyle. Residents enjoy a slower pace of life, with local shops, cafes, and eateries just a stone’s throw away. Whether you’re seeking a summer retreat or a year-round residence, Annisquam offers a unique blend of coastal charm and community spirit that is truly hard to resist. Come explore the beauty and warmth of Annisquam – your dream home awaits!

Newest Listings in Annisquam

$519,000

2 Beds ⋅ 1 Baths ⋅ 73553100 MLS

Unique opportunity, intriguing potential & select views of Goose Cove. Adjoined properties at 62 & 64 Bennett St S are separately assessed parcels conveyed on 1 deed, offering 2 sep dways on a 20,600± square feet lot. 62 Bennett: 12,470± square ft habitable, single-story home last used as a 1-bdrm home, w/ approx 1465± square ft including the once-finished 2nd flr. The heated 2nd level offers potential to be completed as a spacious 20x22 primary bdrm w/ a deck overlooking Goose Cove. Additional features include a lge 9x37 front deck & multiple storage areas. 64 Bennett: 8149± sq ft lot w/ a separate dway & a 2 story barn/shed accessory bldg w/ a 16x17+- 1st fl & scuttle access to a 14x16+- 2nd fl. Buyers responsible for conducting their own due diligence regarding zoning, development potential, use, & buildability. Property is sold as-is. No warranties/representations made by Listing Agent or Seller. Subject to Conservator being granted a License to Sell. Open House Sunday, 7/26/26, 12-1:30.

62 Bennett St S, Gloucester

$4,895,000

5 Beds ⋅ 7 Baths ⋅ 73535947 MLS

Perched above Ipswich Bay on a gentle rise in coveted Norwood Heights, this exceptional coastal retreat provides sweeping water views, spectacular sunsets & harbor activity. Warm, inviting & architecturally distinctive, this magnificent home features barrel-vaulted ceilings, refined fixtures & finishes throughout, a thoughtfully designed living space including a private guest wing, classic home office, chef’s kitchen w/ pantry, ocean-view sitting rooms & serene primary suite w/ water views from the bedroom & bath. Meticulously landscaped grounds enhance the uniquely private setting. Enjoy afternoon sun & ocean views from the side deck & morning sun on the expansive rear patio designed for entertaining. A detached 3-bay garage w/ lofted space & partially finished full basement offer endless possibilities. Norwood Heights is one of Annisquam's most sought-after enclaves, offering exclusive access to a private beach, walking paths & renowned Lighthouse Beach.

77 Norwood Heights, Gloucester

$1,100,000

2 Beds ⋅ 2 Baths ⋅ 73521436 MLS

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." On Lobster Cove, this waterfront residence showcases a seasonal dock providing direct access. Located on the North Shore in Gloucester, the historic village of Annisquam offers a distinct coastal experience, distinguished by its narrow winding lanes, historic architecture, and a community atmosphere. Exceptional views are enjoyed both inside and out. Original craftsmanship has been preserved, including wide pine floors, woodwork, and two fireplaces. A 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 and multiple seating areas. The layout offers a bathroom on each floor, second-floor laundry, a back stairway, and third-floor bonus space. Practical updates include an updated heating system, replaced sunroom windows, basement work, and a repaired seawall.

65 Leonard Street, Gloucester

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