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.
This home has been viewed 7 times
Last Checked: June 18th, 2026 at 5:13am (Source: MLS PIN #73521436)
Air Conditioning
Waterview
Waterfront
Lead Paint Free
General Information for 65 Leonard Street, Gloucester MA 01930
Listing ID73521436
Property TypeSingle Family / Attached
Price$1,150,000 ($604.63/SqFt)
StyleColonial
CityGloucester
CountyEssex
MLS AreaAnnisquam
Neighborhood(s)Ipswich
Garage Parking0
ZoningR-20
Year Built1717
Year Built SourceOwner
Year Built DetailsApproximate,Renovated Since
Handicap Access / Features0
Interior Features for 65 Leonard Street, Gloucester MA 01930
Approximate Living Area Total1902
Living Area Includes BasementNo
Rooms7
Bedrooms2
Primary En Suite BathroomNo
BasementFull
CoolingSplit
Fireplaces
AppliancesRange
FlooringTile
Electric220 Volts
Exterior Features for 65 Leonard Street, Gloucester MA 01930
Approximate Lot Size (Acres)0.1
Approximate Lot Size (Square Feet)4500
Total Parking2
Garage Parking0
WaterPublic
SewerPublic Sewer
Lot FeaturesGentle Sloping
Parking Features1
Exterior FeaturesPorch
Foundation Area588
Foundation Materials
Construction MaterialsFrame
Approximate Street Frontage16.00
Road Frontage Type
Patio & PorchCovered
Roof MaterialAsphalt/fiberglass Shingles
Utility Connections110 Volts
Water ViewsYes
Water Views FeaturesBay
Waterfront1
Waterfront FeaturesRiver
Pool Features
Horse Permitted0
Horse AmenitiesRiver
Disclosures for 65 Leonard Street, Gloucester MA 01930
Lead PaintNone
UFFI
Living Area Includes BasementNo
Living Area Disclosure
Building Area SourcePublic Records
Special Listing Conditions
ExclusionsTree House
Compensation Based On
Financial Information for 65 Leonard Street, Gloucester MA 01930
Association Fee
Association Fee Frequency
Association Fee Includes
Real Estate Tax15476
Tax Year2026
Assessed Value$1,662,300
Location Information for 65 Leonard Street, Gloucester MA 01930
Elementary SchoolPlum Cove
Middle SchoolO'maley Ms
High SchoolGloucester Hs
Neighborhood(s)Ipswich
MLS AreaAnnisquam
Area AmenitiesWalk/jog Trails
Contact Information for 65 Leonard Street, Gloucester MA 01930