
1 Chester Square, Gloucester, MA 01930
What This House Offers
Winter Rental Available: September 15, 2025-June 15, 2026.
This beautifully renovated home is located directly on Lobster Cove in the historic village of... Annisquam. Soak up the beautiful views from the house, deck or private dock of the fabled footbridge which connects the Annisquam peninsula to the banks of mainland Gloucester.
The interior boasts an open-concept kitchen, dining, and living area, highlighted by a wall of waterside windows that flood the space with natural light. The well-applianced kitchen has honed granite countertops and a mix of fir and bamboo floors. On this level, there are three bedrooms including one of two primary suites with private deck, and two full bathrooms and a laundry closet with side-by-side washer/dryer. Upstairs is the second primary bedroom suite featuring a private deck with spectacular views and an ensuite bathroom with a soaking tub and dressing area.
Enjoy views from the deck or warm fall nights around the fire pit in the verdant side yard. Go for a swim, kayak, or paddleboard from the private dock. Walk to Lobster Cove and Annisquam's beaches, or short boat ride to Wingaersheek Beach.
Two-car parking.
First, last, & security due at signing.
Internet and water/sewer included.
Renter responsible for heat (gas), hot water and electric. Cable ready.
No pets. No smoking. No events or parties.
Unit
- $3,975
Total Monthly Price - 4 Beds
- 3 Baths
- 2,004 sq. ft.
- Available Sep 15
Home Features
- Dishwasher
Annisquam Rental on the Water: Chester Square is located in Gloucester, Massachusetts in the 01930 zip code.
Rental Fees and Pet Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
No Pets Allowed
Explore Commute Options
- Drive Time--
- Walk Time--
- Bike Ride Time--
- Public Transit--
Get In Touch
Gloucester, MA 01930
Neighborhood Scores
Walk Score ®
Car-Dependent17 / 100
Transit Score ®
Some Transit26 / 100
Bike Score ®
Somewhat Bikeable3 / 100
Soundscore ™
Active77 / 100
Travel and Transit



Local Education
Primary and Secondary Schools
Plum Cove School
Grades K-5
Public
Rockport Elementary
Grades PK-5
Public
Ralph B O'Maley Middle
Grades 6-8
Public
Faith Christian School
Grades PK-8
Private
The Academy at Penguin Hall
Grades 9-12
Private
Gloucester High
Grades 9-12
Public
Data provided by GreatSchools.org 2024 © 2024. All rights reserved.

Colleges and Universities
School
Commute Time (Distance)
Gordon College, Wenham
Drive: 20 min (12.4 mi)
Endicott College
Drive: 27 min (15 mi)
Discover North Shore, Gloucester, MA
Commuting
With a TransitScore of 26, Annisquam Rental on the Water: Chester Square has some transit, including 5 transit stops within 15.1 miles. Transit options include Gloucester and Rockport.
Parks and Recreation
Recreational activities near Annisquam Rental on the Water: Chester Square are plentiful. Discover 1 park within 3.7 miles, including Halibut Point State Park.
Airports
Living in North Shore provides easy access to General Edward Lawrence Logan International, located just 57 minutes from Annisquam Rental on the Water: Chester Square. Another nearby airport is Portsmouth International at Pease, located 49.1 miles away.
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