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Pending
    • Price cut: $105K (8/1)
    $995,000

    65 Leonard St, Gloucester, MA 01930

    2beds
    1,902sqft
    : 
    $6,238/mo
    Get pre-qualified
    Single Family Residence
    Built in 1717
    4,500 Square Feet Lot
    $944,600 Zestimate®
    $523/sqft
    $-- HOA

    What's special

    Two fireplacesWaterfront residenceThird-floor bonus spaceSecond-floor laundryBack stairwayWide pine floorsBathroom on each floor
    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.
    94 days
    |
    1,527
    |
    82
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    John Farrell 978-578-5203,

    Coldwell Banker Realty - Beverly 978-927-1111

    Source: MLS PIN,MLS#: 73521436

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Features: Closet, Flooring - Wood
      • Level: Second
      • Area: 190
      • Dimensions: 19 x 10
      Bedroom 2
      • Features: Closet, Flooring - Wood
      • Level: Second
      • Area: 132
      • Dimensions: 11 x 12
      Primary bathroom
      • Features: No
      Bathroom 1
      • Features: Bathroom - With Shower Stall
      • Level: First
      • Area: 21.33
      • Dimensions: 2.67 x 8
      Bathroom 2
      • Features: Bathroom - Tiled With Tub & Shower, Flooring - Wood
      • Level: Second
      • Area: 48
      • Dimensions: 8 x 6
      Kitchen
      • Features: Closet, Flooring - Wood
      • Level: First
      • Area: 128
      • Dimensions: 16 x 8
      Living room
      • Features: Closet, Closet/Cabinets - Custom Built, Flooring - Wood
      • Level: First
      • Area: 294
      • Dimensions: 21 x 14
      Office
      • Features: Bathroom - 3/4, Closet, Flooring - Wood
      • Level: First
      • Area: 56
      • Dimensions: 7 x 8
      Heating
      • Baseboard, Natural Gas
      Cooling
      • None
      Appliances
      • Included: Gas Water Heater, Water Heater, Range, Dishwasher, Refrigerator, Washer, Dryer
      • Laundry: Second Floor
      Features
      • Dining Area, Bathroom - 3/4, Closet, Sun Room, Office, Foyer, Bonus Room, Walk-up Attic, Internet Available - Broadband
      • Flooring: Wood, Tile, Carpet, Pine, Flooring - Wall to Wall Carpet, Flooring - Wood
      • Windows: Skylight, Insulated Windows
      • Basement: Interior Entry,Sump Pump,Concrete,Unfinished
      • Number of fireplaces: 2
      • Fireplace features: Living Room, Master Bedroom
      Interior area
      • Total structure area: 1,902
      • Total interior livable area: 1,902 sqft
      • Finished area above ground: 1,902

      Property

      Parking
      • Total spaces: 2
      • Parking features: Paved Drive, Off Street, Paved
      • Uncovered spaces: 2
      Accessibility
      • Accessibility features: No
      Features
      • Patio & porch: Porch, Patio
      • Exterior features: Porch, Patio, Rain Gutters, Storage, Garden
      • Has view: Yes
      • View description: Scenic View(s), Water, Dock/Mooring, Harbor
      • Has water view: Yes
      • Water view: Dock/Mooring,Harbor,Water
      • Waterfront features: Waterfront, Navigable Water, Harbor, Dock/Mooring, Frontage, Walk to, Direct Access, Ocean, Beach Ownership(Private, Public)
      • Frontage length: 16.00
      Lot
      • Size: 4,500 Square Feet
      • Features: Easements, Flood Plain
      Details
      • Foundation area: 588
      • Parcel number: M:0121 B:0049 L:0000,1899812
      • Zoning: R-20

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      • Attached to another structure: Yes
      Materials
      • Frame, Post & Beam
      • Foundation: Block, Stone, Irregular
      • Roof: Shingle
      Condition
      • Year built: 1717

      Utilities & green energy

      • Electric: Circuit Breakers
      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: for Electric Range
      Green energy
      • Energy generation: Solar

      Community & HOA

      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
      HOA
      • Has HOA: No
      Location
      • Region: Gloucester

      Financial & listing details

      • Price per square foot: $523/sqft
      • Tax assessed value: $1,662,300
      • Annual tax amount: $15,476
      • Date on market: 5/20/2026
      • Road surface type: Paved

        Estimated market value

        $944,600

        $897,000 - $992,000

        $2,947/mo

        Price history

        DateEventPrice
        8/15/2026Pending sale$995,000$523/sqft
        Source: MLS PIN #73521436 Report a problem
        8/2/2026Contingent$995,000$523/sqft
        Source: MLS PIN #73521436 Report a problem
        8/1/2026Price change$995,000-9.5%$523/sqft
        Source: MLS PIN #73521436 Report a problem
        7/24/2026Price change$1,100,000-4.3%$578/sqft
        Source: MLS PIN #73521436 Report a problem
        6/13/2026Price change$1,150,000-8%$605/sqft
        Source: MLS PIN #73521436 Report a problem
        6/2/2026Price change$1,250,000-7.4%$657/sqft
        Source: MLS PIN #73521436 Report a problem
        5/19/2026Listed for sale$1,350,000+332%$710/sqft
        Source: MLS PIN #73521436 Report a problem
        1/4/1993Sold$312,500+19766.5%$164/sqft
        Source: Public Record Report a problem
        5/16/1990Sold$1,573$1/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$12,129 $1,246,600
        2024$12,129 +6.9%$1,246,600 +16.4%
        2023$11,346 $1,071,400
        2022$11,346 +7.3%$1,071,400 +26%
        2021$10,575 +1.2%$850,100 +0.3%
        2020$10,452 +3.8%$847,700 +6.8%
        2019$10,068 +2.4%$793,400 +4.3%
        2018$9,833 +3%$760,500 +5.1%
        2017$9,544 +3.3%$723,600 +6.6%
        2016$9,238 +3.4%$678,800 +3.7%
        2015$8,937 +7.1%$654,700 +1.8%
        2014$8,346 -3%$643,000 -5.6%
        2013$8,601 +7.5%$681,500 +3.7%
        2012$8,003 +3.5%$657,100 -3.9%
        2011$7,734 +5.2%$683,800 -2.5%
        2010$7,353 +2.4%$701,000 -6.3%
        2009$7,180 +4.2%$747,900 -1.2%
        2008$6,890 +4%$757,100 -1.6%
        2007$6,625 -0.8%$769,400
        2006$6,678 +13.8%$769,400 +17.9%
        2005$5,866 +1.6%$652,500 +8.6%
        2004$5,776 +1.1%$601,000 +15.2%
        2003$5,712 +7.8%$521,600 +30.6%
        2001$5,300 +10.3%$399,400 +25.5%
        1999$4,803 $318,300
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 01930

        Getting around

        17 / 100
        Car-Dependent
        26 / 100
        Some Transit
        3 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Plum Cove
        • Middle: O'maley Ms
        • High: Gloucester Hs

        Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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