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Sort By: NameBedroomsBathroomsSleepsMaximum 
Star of the Sea
Name: Star of the SeaBedrooms: 3Bathrooms: 3SleepsMaximum: 8$3000/week*
Long Beach! Walk to two of Cape Ann's finest sandy beaches, restaurants and even an ice cream store from this tastefully and comfortably furnished three bedroom, three bath contemporary home. The perfect location for your ultimate Cape Ann vacation!  Learn more...
Changing Tides
Name: Changing TidesBedrooms: 3Bathrooms: 2SleepsMaximum: 5$1000/month + winter; $1900/week summer*
Situated on the shores of the tidal Mill River on a shaded lot of nearly one acre in Gloucester's watery Riverview district, this newly renovated property has a private dock and float. Swim, fish, or row in the dinghy left for your use.  Learn more...
Stowe Farm
Name: Stowe FarmBedrooms: 3Bathrooms: 3SleepsMaximum: 7$6,000/mo summer $5,000/mo shoulder*
Pastoral and privately situated on 200 rolling acres this newly built, 3 bed/3 bath high quality home is part of an historic estate in Essex and close enough to Route 128 to be an easy commute to Boston.  Learn more...
Brier Neck Lookout
Name: Brier Neck LookoutBedrooms: 4Bathrooms: 2SleepsMaximum: 8$3500/wk summer; $2200/wk Sept/Oct*
Views of the Atlantic Ocean abound from the deck of this recently remodeled cottage, perched on a bold granite outcropping at the highest point of Briar Neck. A short stroll will bring you to Good Harbor, one of Gloucester's finest sandy beaches.  Learn more...
Wiley's Way
Name: Wiley's WayBedrooms: 2Bathrooms: 1.5SleepsMaximum: 4$1600/week*
A charming cottage located in Gloucester's fabled artist colony of Rocky Neck, on a quiet side street. Two bedrooms and 1.5 baths. Enjoy the great room and the private and enclosed outside area with seating for four and a grill.  Learn more...
Ocean Bluff
Name: Ocean BluffBedrooms: 4Bathrooms: 3.5SleepsMaximum: 8$2500/mo+ winter or $5,000/wk summer*
Rockport! Swimming pool! This oceanfront home in the coveted 'Avenues' section of Rockport's Pigeon Cove offers glorious views and all the comforts of home in a spacious and very private quiet setting.  Learn more...
Bottom's Up
Name: Bottom's UpBedrooms: 2Bathrooms: 1SleepsMaximum: 4$1000/wk summer*
"Bottom’s Up!” This two bedroom one bath hidden gem is located in the heart of the historic and scenic North Shore in Beverly. Nestled in a cul de sac, it’s a little off the beaten path, while still allowing easy access to Gloucester, Rockport, Manchester  Learn more...
Ocean's Edge
Name: Ocean's EdgeBedrooms: 3Bathrooms: 2.5SleepsMaximum: 8$750/nt+ or $3500/wk winter $5000/wk sum*
Waterfront! Beachfront! This immaculate, sun filled contemporary is perched on the ocean's edge with short path from the property that leads directly onto the sands of Long Beach. Central Air 3 beds/2.5 baths.  Learn more...
Friendly Views
Name: Friendly ViewsBedrooms: 3Bathrooms: 2.5SleepsMaximum: 6$2000/wk sum/$400 nite off 3 nite min*
This gleaming, immaculate home is perched above the sparkling waters of Gloucester's inner harbor. From the comfort of your sun porch or deck, watch the gulls following the fishing boats home with their catch and enjoy the lively nautical scene.  Learn more...
Stone Mansion
Name: Stone MansionBedrooms: 10Bathrooms: 6.5SleepsMaximum: 18$6500/week contact realtor*
Go back in time to the Civil War era when Brig. General Greely Curtis came to Manchester by the Sea to build his mansion on a high bluff overlooking the Atlantic, with the Boston skyline and the Cape Cod shore visible in the distance.  Learn more...
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