Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage
Diamond Cove Seaside Cottage

Diamond Cove Seaside Cottage

Annisquam, Massachusetts

2 - 6 Keys 3 Bedrooms 6 Guests 2 baths


Our lovely cottage is situated directly on Diamond Cove in Annisquam, a historic seaside village of Gloucester, MA settled in 1631, and a place where families have summered for generations. The 1,800 sq. ft. home offers 3 bedrooms (plus) and 2 bathrooms.

One of our favorite activities is relaxing on the front porch watching the boats go by and enjoying the beautiful views to the New Hampshire and Maine coasts 20 miles away on a clear day. Swim from the rocky beach in front of the house, nap in the hammock on the porch, listen to the waves lapping at the seawall at night. It's a very tranquil location. A five minute walk will take you to a magnificent sandy beach where you can relax in the shadow of the historic Annisquam Lighthouse

Our winterized cottage dates from the 1850's, with the ambiance of vintage property such as a wrap-around covered porch and a stone fireplace, yet completely updated inside. Imagine preparing a meal while watching sailboats cruise across Ipswich bay out your window? The indoor dining area has a beautiful wooden table with four chairs and a padded bench, while outdoor dining options include the porch or front lawn.

Our friends who visit us tell us the house is paradise and we agree! It is a house full of character and comfort. If you love the ocean and magnificent sunsets, this is the place for you!

Should you get tired of relaxing there are many local activities available. Browsing local shops and art galleries at the Rocky Neck art colony, great dining, fishing charters, schooner sailing and whale watching are all within a 15 minute drive. The town of Rockport with it's world famous 'Motif #1' is a short drive away.

Please note there is no cable TV, only WiFi/internet and big TV with Netflix. Book-reading on the front porch is a favorite way to relax the day-away!

Own a Luxury Second Home?

Join our trusted community of like-minded home owners.
Travel within our members-only Exchange Club staying in 11,000 luxury homes, villas, and resorts all over the world.

Get Started

Property Details


Single Family Home with 3 levels
3 bedrooms, 2 baths, 1800 square feet, 168 square meters


Queen, Twin, and Full
6 guests maximum

Nearest airport

Boston Logan Airport
45 minutes by car

Property View

Direct oceanfront on Ipswich Bay. Views for 25 miles West and North. Amazing sunsets!

Property ID



No Pets Allowed
Not Handicap Accessible
View All Amenities

Own a Luxury Second Home?

Apply for Membership

Activities of Interest

  • Arts
  • Fish
  • Hike
  • Watersports
  • Sit on the front porch with a glass of wine and watch the fabulous sunset
  • Relax at Lighthouse Beach or body surf at Good Harbor Beach
  • Hire a fishing charter for Tuna or Stripe bass fishing
  • Visit Cape Ann Art Museum
  • Stroll the shops and art galleries of Rockport
  • Hike the paths of Dogtown
  • Dine at The Market, a farm-to-table gourmet destination
  • Go sailing or whale watching from the USA's oldest seaport, Gloucester

Places of Interest

  • Kids love the Gloucester Maritime Museum and Aquarium
  • Gloucester
  • Annisquam Lighthouse
  • Cape Ann Art Haven
  • Cape Ann Brewing Company
  • Cressey's Beach
  • Gloucester HarborWalk
  • Hammond Castle


Diamond Cove....Fantastic

The location was great and the home was beautiful. We loved the views of the water! We had so much fun with our grandchildren looking for sea glass. The layout worked well for the family and offered privacy for everyone. The communication with the owner was fantastic and made access to the home seamless. Fell in love with the area and would love to come back. The Zopf Family ”

ArleneOctober 2020

Amazing and relaxing

We had a wonderful week in Annisquam, a truly lovely community. The home is extremely charming. The most extraordinary aspect of the house is the porch overlooking the bay. We spent a great deal of our time watching the water and the sky, forgoing sighting trips in order to take turns on the hammock. We hope to return next year. Cecilia Kempton ”

CeciliaAugust 2019

Beautiful views and wonderful people

The cottage is quaint and comfortable and it is obvious that has been much loved and well cared for). Neighbors (and the owner) couldn’t have been nicer and the location (33 minutes from Salem and less than an hour from Boston) couldn’t have been better. And the cool breezes off the ocean were much appreciated on those long hot May days. For anyone looking for a cute place to relax near Salem and Boston, we highly recommend Diamond Cove cottage.”

DavidMay 2019

Loved loved!

Perfect location right on the water...amazing sunsets and tranquility quiet and sweet...a perfect New England get away... Owner super helpful and accommodating..made our stay easy and uneventful.. And just a stone's throw from Boston and nearby towns gave us options every day... Just what the doctor ordered! ”

ClariceMay 2018

Cape Ann rejuvenation

Everyone's heard of Cape Cod, but Cape Ann . . .? It is the undiscovered Cape -- full of quaint New England villages, the freshest of seafood, friendly locals, and breathtaking seaside vistas. Kim and John's cozy waterfront cottage is right in the middle of Cape Ann charm. We could drive to Gloucester's conveniences in just 15-20 minutes, as well as numerous other villages along the coast of Cape Ann. But who'd want to leave the restful porch that overlooks Diamond Cove, with amazing sunset views and peaceful days spent reading and rejuvenating? Kim and John are amazing hosts, greeting and orienting us, available if we had questions, and graciously offering their beautiful home that is now a memory we will forever treasure. ”

TerryJune 2017

Hated to Leave

Kim and John have done a fabulous job at a fabulous place. Gray Cottage has all the charm of an Old Fashioned New England coast Cottage with all the conveniences of a renovated, beautiful space. Right on the water, Gray Cottage location could not be better. Imagine sleeping in the loft bedroom with a huge window, and waking up to the sunshine, sea, and rocky coastline of Gloucester MA. Had a terrific time walking in the neighborhood and exploring the many but varied seaside towns of Cape Ann. The restaurants are better than many I have known in New York City. The cottage was immaculate, well supplied, and fun. We would return in a heartbeat.”

CynthiaSeptember 2016
Show More Less Reviews