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Single Family Residence at 65 Leonard Street, Gloucester MA 01930, Gloucester
Single Family Residence at 65 Leonard Street, Gloucester MA 01930, Gloucester, photo 2 of 39
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Single Family Residence at 65 Leonard Street, Gloucester MA 01930, Gloucester, photo 4 of 39
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39 photos

$1,150,000

65 Leonard Street, Gloucester MA 01930
Gloucester, MA 01930
Listed by John Farrell
Bedrooms
2
Bathrooms
2
Living area
1,902 sqft
Year built
1717

About this home

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.

Highlights

WaterfrontViewFireplace

Property details

MLS #
73521436
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
143
On market date
May 19, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
2
Lot size
0.1 acres

Location

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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Beeman Memorial
1.37 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
324
Student:teacher ratio
10.8:1
District
Gloucester
Middle
Ralph B O'Maley Middle
1.88 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
630
Student:teacher ratio
11.3:1
District
Gloucester
High
Gloucester High
3 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
830
Student:teacher ratio
10.5:1
District
Gloucester

Walkability

Blended score for Gloucester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

51
Somewhat walkable
out of 100
EPA National Walkability Index
11.0 / 20 -- Above average walkable
Google Places amenity density
45 / 100
Restaurants & cafes2
Grocery stores0
Parks4
Schools3
Transit stops3
Pharmacies0

Market position

How this listing compares to current activity in Gloucester, from live MLS data.

On the market 143 days -- 36 more days than Gloucester's current average of 107 days.
For reference, the median list price across 238 active listings in Gloucester right now is $599,000.

Mortgage calculator

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Est. monthly payment
$7,075/mo
$230,000 down
$920,000 loan
Principal & interest$5,967
Property tax (est.)$958
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 17, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.