Annisquam Homes for Sale

Welcome to Annisquam, a picturesque village nestled in the heart of Gloucester, Massachusetts, where coastal charm meets New England elegance. Known for its stunning waterfront views and rich maritime history, Annisquam is a hidden gem that offers the perfect blend of tranquility and vibrancy. With its quaint streets lined with historic homes, this charming community is a haven for those seeking a serene lifestyle, yet still within reach of modern conveniences.

Annisquam boasts a unique character, with its iconic lighthouse standing sentinel over the harbor and the lush greenery of nearby parks providing a perfect backdrop for outdoor enthusiasts. Residents enjoy access to beautiful beaches, scenic walking trails, and the renowned Annisquam River, making it an ideal place for kayaking, fishing, or simply soaking in the breathtaking views.

For those considering a move to this enchanting village, there are an array of homes for sale that cater to diverse tastes and lifestyles. From cozy cottages with ocean views to elegant waterfront estates, Annisquam's real estate offerings are as varied as they are appealing. Whether you’re a first-time homebuyer, looking for a summer retreat, or seeking a forever home, Annisquam has something special for everyone.

Explore the charm of Annisquam and discover the perfect home that aligns with your dreams. With its vibrant community, stunning landscapes, and rich history, Annisquam is not just a place to live; it’s a lifestyle waiting to be embraced. Come and experience the magic of Annisquam, where every day feels like a vacation!

Newest Annisquam Homes for Sale

$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

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .