$1,250,000
65 Leonard Street
Gloucester, MA, 01930
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.
Property Details
Price:
$1,250,000
MLS #:
73521436
Status:
Active
Beds:
2
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
annisquam
Listed Date:
May 19, 2026
Finished Sq Ft:
1,902
Total Sq Ft:
1,902
Lot Size:
4,500 sqft / 0.10 acres (approx)
Year Built:
1717
Schools
Elementary School:
Plum Cove
Middle School:
O’maley Ms
High School:
Gloucester Hs
Interior
Above Grade Finished Area
1902
Appliances
Gas Water Heater, Water Heater, Range, Dishwasher, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms
Cooling
None
Fireplaces Total
2
Flooring
Wood, Tile, Carpet, Pine, Flooring – Wall to Wall Carpet, Flooring – Wood
Heating
Baseboard, Natural Gas
Interior Features
Dining Area, Bathroom – 3/4, Closet, Sun Room, Office, Foyer, Bonus Room, Walk-up Attic, Internet Available – Broadband
Laundry Features
Second Floor
Exterior
Accessibility Features
No
Architectural Style
Colonial
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Marina, Private School, Public School, T-Station
Construction Materials
Frame, Post & Beam
Exterior Features
Porch, Patio, Rain Gutters, Storage, Garden
Lot Features
Easements, Flood Plain
Open Parking Spaces
2
Open Parking YN
1
Parking Features
Paved Drive, Off Street, Paved
Parking Spots
2
Parking Total
2
Patio And Porch Features
Porch, Patio
Roof
Shingle
View
Scenic View(s)
Waterfront Features
Waterfront, Navigable Water, Harbor, Dock/Mooring, Frontage, Walk to, Direct Access, Ocean, Beach Ownership(Private,Public)
Window Features
Skylight, Insulated Windows
Financial
Tax Year
2026
Taxes
$15,476
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Gloucester as of Jun 04, 2026
56
Single Family Listed
53
Avg DOM
601
Avg $ / SqFt
$1,407,843
Avg List Price
Community
- Address65 Leonard Street Gloucester MA
- CityGloucester
- CountyEssex
- Zip Code01930
Subdivisions in Gloucester
Similar Listings Nearby
Property Summary
- 65 Leonard Street Gloucester MA is a Single Family for sale in Gloucester, MA, 01930. It is listed for $1,250,000 and features 2 beds, 2 baths, and has approximately 1,902 square feet of living space, and was originally constructed in 1717. The current price per square foot is $657. The average price per square foot for Single Family listings in Gloucester is $601. The average listing price for Single Family in Gloucester is $1,407,843. To schedule a showing of MLS#73521436 at 65 Leonard Street in Gloucester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Coldwell Banker Realty – Beverly. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
65 Leonard Street
Gloucester, MA