• Primary Photo - WINTER RENTAL: Squam Light
  • Building Photo - WINTER RENTAL: Squam Light
    Building Photo - WINTER RENTAL: Squam Light
  • Building Photo - WINTER RENTAL: Squam Light
    Building Photo - WINTER RENTAL: Squam Light
$3,150 Total Monthly Price

31 Chester Square

,

Gloucester, MA 01930

2 Weeks Ago
| Edit
Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
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31 Chester Square
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Beds Baths Average SF
3 Bedrooms 3 Bedrooms 3 Br 2 Baths 2 Baths 2 Ba 1,596 SF

About This Property

Winter Rental: Available October 1, 2025-April 30, 2026 (Utilities Included) Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the perfect off-season home. The bright and airy ground floor has many windows, letting in lots of natural light. The full bathroom on the main level has a shower over tub. A three-season sunroom runs the length of the house with two additional beds. The dining room is classic and formal with a drop leaf table and ceiling fan. Upstairs, there are 3 bedrooms and a full bath with clawfoot tub and shower. All bedrooms have closet space and dressers for storage. The primary bedroom has a queen bed, bedroom two has a full, and the third has two twins. The private back yard has garden furniture and parking both at the top and bottom of the driveway. Take a walk back in history by strolling through the prototypical colonial village with its white clapboard and black shuttered homes and picturesque lanes that were created to accommodate horse-drawn carriages. This is what you come to New England for -- history on the water! Dogs OK. Cats OK. Internet and water/sewer included. Electric and gas heat included up to $400/mo. First, last, & a half month's security deposit due at signing. No smoking. No events or parties.

31 Chester Square is a house located in Essex County and the 01930 ZIP Code. This area is served by the Gloucester School District attendance zone.

Unique Features

  • Clawfoot Tub
  • Refrigerator/Freezer
  • Single-Family
  • Water/Sewer
  • Wi-Fi
  • 2 Car Parking
  • Cat-friendly
  • Gas
  • Hot Water
  • Gas Stove/Range
  • Neighborhood access to swimming
  • Off-street Parking
  • Toaster Oven
  • Utilities Included
  • Winter Rental
  • Coffee Maker
  • Driveway
  • Outdoor Seating
  • Seasonal Rental
  • Three-season Porch
  • Yard/Garden
  • .5 mi or less to Beach
  • Annisquam
  • Electricity
  • Internet
  • Dog-Friendly
  • Heat

House Features

  • Dishwasher
Location
31 Chester Square, Gloucester,
MA 01930
Get Directions
Neighborhood

The coastal area between Boston and New Hampshire, the North Shore is a massive cluster of cities including Salem, Gloucester, Beverly, Essex, Rockport, and more. Rocky coastlines, wetlands, beaches, and harbors fill this area with natural beauty. This historic and cultural region of Massachusetts offers parks, golf courses, museums, historical landmarks, and so much more.

Tour a medieval style castle from the early 1900s, Hammond Castle Museum, on the coast of Gloucester, or visit Castle Hill in Ipswich for 165 acres of land with a historic mansion and access to Crane Beach. Travel over to Historic Downtown Salem to learn about the Salem Witch Trials, and venture to Manchester by the Sea on Cape Ann, the setting for Kenneth Lonergan’s 2016 film Manchester by the Sea, to admire this iconic, scenic beach town.

With so many cities to choose from in the North Shore cluster, there’s something for everyone in this coastal oasis.

Learn more about living in North Shore 

Below are rent ranges for similar nearby apartments

Beds Average Size Lowest Typical Premium
4 Beds 4 Beds 4 Beds 3589 Sq Ft $3,300 — —
Amenities
  • Dishwasher
  • Clawfoot Tub
  • Refrigerator/Freezer
  • Single-Family
  • Water/Sewer
  • Wi-Fi
  • 2 Car Parking
  • Cat-friendly
  • Gas
  • Hot Water
  • Gas Stove/Range
  • Neighborhood access to swimming
  • Off-street Parking
  • Toaster Oven
  • Utilities Included
  • Winter Rental
  • Coffee Maker
  • Driveway
  • Outdoor Seating
  • Seasonal Rental
  • Three-season Porch
  • Yard/Garden
  • .5 mi or less to Beach
  • Annisquam
  • Electricity
  • Internet
  • Dog-Friendly
  • Heat
Education
Colleges & Universities Distance
Colleges & Universities Distance
Gordon College, Wenham
Drive: 20 min 12.5 mi
Endicott College
Drive: 27 min 15.0 mi
Salem State University
Drive: 35 min 20.7 mi
North Shore C.C., Danvers
Drive: 35 min 21.5 mi
31 Chester Square is within 20 minutes or 12.5 miles from Gordon College, Wenham. It is also near Endicott College and Salem State University.
Schools
Rockport Elementary
Public Elementary School
Grades PK-5
263 Students
Nearby
Plum Cove School
Public Elementary School
Grades K-5
226 Students
Attendance Zone
Grades 6-8
594 Students
Attendance Zone
Gloucester High
Public High School
Grades 9-12
769 Students
Attendance Zone
Faith Christian School
Private Elementary & Middle School
Grades PK-8
36 Students
Nearby
The Academy at Penguin Hall
Private High School
Grades 9-12
Nearby
School data provided by The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

Data provided by GreatSchools.org © 2026. All rights reserved.
Transportation

31 Chester Square is near General Edward Lawrence Logan International, located 33.6 miles or 57 minutes away, and Portsmouth International at Pease, located 49.1 miles or 77 minutes away.

Commuter Rail Distance
Commuter Rail Distance
Gloucester
Drive: 9 min 4.3 mi
Rockport
Drive: 12 min 5.9 mi
West Gloucester
Drive: 13 min 6.6 mi
Manchester
Drive: 19 min 10.8 mi
Ipswich
Drive: 28 min 15.2 mi
Airports Distance
Airports Distance
General Edward Lawrence Logan International
 Drive: 57 min 33.6 mi
Portsmouth International at Pease
 Drive: 77 min 49.1 mi

Walkability Near 31 Chester Square Gloucester, MA 01930

Getting Around
Somewhat Walkable
Walkability
20 / 100
Limited Public Transit
Transit
20 / 100
Exceptionally Drivable
Drivability
90 / 100
Fairly Bikeable
Bikeability
50 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
-
Soundscore™
- / 100

Traffic

-

Airport

-

Businesses

-

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 31 Chester Square.

Shopping Centers Distance
Shopping Centers Distance
Gloucester Crossing
Drive: 11 min 5.2 mi
Whistlestop Mall
Drive: 12 min 6.0 mi
The Commons
Drive: 12 min 6.4 mi
31 Chester Square has 3 shopping centers within 6.4 miles, which is about a 12-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Halibut Point State Park
 Drive: 8 min 3.8 mi
Mass Audubon's Eastern Point Wildlife Sanctuary
 Drive: 16 min 7.8 mi
Coolidge Reservation
 Drive: 17 min 8.6 mi
Appleton Farms
 Drive: 28 min 15.3 mi
Sandy Point State Reservation
 Drive: 76 min 35.4 mi
31 Chester Square has 5 parks within 35.4 miles, including Halibut Point State Park, Mass Audubon's Eastern Point Wildlife Sanctuary, and Coolidge Reservation.
Military Bases Distance
Military Bases Distance
Fort Pickering
Drive: 34 min 20.0 mi
Fort Miller
Drive: 43 min 24.2 mi
31 Chester Square is 20.0 miles from Fort Pickering, and is convenient to other military bases, including Fort Miller.

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