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For sale
  • $1,249,000

    366 Main St, Gloucester, MA 01930

    9beds
    3,600sqft
    : 
    $7,502/mo
    Get pre-qualified
    3 Family
    Built in 1900
    -- sqft lot
    $1,206,200 Zestimate®
    $347/sqft
    $-- HOA

    What's special

    Modern finishesIn-unit laundryUpdated kitchens and bathroomsThoughtfully renovated throughoutTwo dedicated parking spacesOffering beautiful ocean views
    Rare opportunity to acquire a fully renovated 3-family property in a highly desirable Gloucester location, just minutes from Good Harbor Beach and offering beautiful ocean views. The property combines strong rental fundamentals with the lifestyle appeal of one of the North Shore’s most sought-after coastal markets. The property has been thoughtfully renovated throughout, featuring updated kitchens and bathrooms, modern finishes, in-unit laundry, and two dedicated parking spaces. The flexible three-family configuration provides multiple income streams and makes the property attractive for both long-term rental and seasonal/vacation rental strategies. With its proximity to Good Harbor Beach, Gloucester’s restaurants, harbor, and downtown amenities, the property is well positioned to benefit from strong demand from both year-round tenants and summer visitors. The property also offers excellent potential for an Airbnb/short-term rental strategy, subject to applicable City of Gloucester regulations and permitting requirements. A major component of the investment opportunity is the separate 368R Main Street lot, located directly behind the property. This additional parcel provides meaningful future upside and could potentially support an ADU, additional residential unit, or other development concept, subject to zoning, permitting, utilities, and site requirements. Please reach out for private showings.
    4 days
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    798
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    14
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    Zillow last checked:

    Listing updated:

    Listed by:

    Kristi Gjikondi 781-558-3465,

    Gjikondi Realty 781-558-3465

    Source: MLS PIN,MLS#: 73564309

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 9
      • Bathrooms: 4
      • Full bathrooms: 4
      Features
      • Basement: Partial
      • Has fireplace: No
      Interior area
      • Total structure area: 3,600
      • Total interior livable area: 3,600 sqft
      • Finished area above ground: 3,600

      Property

      Parking
      • Total spaces: 2
      • Parking features: Off Street
      • Uncovered spaces: 2
      Features
      • On waterfront: Yes
      • Waterfront features: Waterfront, Ocean, Harbor, 1/2 to 1 Mile To Beach, Beach Ownership(Public)
      Lot
      • Size: 4,550 Square Feet
      • Features: Other
      Details
      • Parcel number: M:0051 B:0068 L:0000,1896464
      • Zoning: NB

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: 3 Family
      Materials
      • Foundation: Block
      Condition
      • Year built: 1900

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Location
      • Region: Gloucester

      Financial & listing details

      • Price per square foot: $347/sqft
      • Tax assessed value: $711,500
      • Annual tax amount: $6,624
      • Date on market: 8/16/2026
      • Total actual rent: 8500

        Estimated market value

        $1,206,200

        $1.15M - $1.27M

        $2,849/mo

        Price history

        DateEventPrice
        8/16/2026Listed for sale$1,249,000+868.2%$347/sqft
        Source: MLS PIN #73564309 Report a problem
        10/1/1999Sold$129,000$36/sqft
        Source: Agent Provided Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,979 $614,500
        2024$5,979 -3.9%$614,500 +4.6%
        2023$6,223 $587,600
        2022$6,223 +17.5%$587,600 +38%
        2021$5,296 +5.7%$425,700 +4.7%
        2020$5,012 +7.9%$406,500 +11.1%
        2019$4,645 +7.6%$366,000 +9.6%
        2018$4,317 +6.3%$333,900 +8.5%
        2017$4,060 +4.7%$307,800 +8.1%
        2016$3,876 +2%$284,800 +2.3%
        2015$3,800 +4.7%$278,400 -0.4%
        2014$3,629 +2.7%$279,600 -0.1%
        2013$3,532 +0%$279,900 -3.4%
        2012$3,531 +2.4%$289,900 -4.9%
        2011$3,448 +6.5%$304,900 -1.3%
        2010$3,239 -7.2%$308,800 -15.1%
        2009$3,491 -0.3%$363,600 -5.5%
        2008$3,502 -0.6%$384,800 -6%
        2007$3,524 -0.8%$409,300
        2006$3,553 +10.5%$409,300 +14.5%
        2005$3,214 +6.4%$357,500 +13.7%
        2004$3,022 +14%$314,500 +29.9%
        2003$2,652 $242,200
        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

        78 / 100
        Very Walkable
        42 / 100
        Some Transit
        50 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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