Artboard 1? alert-icon? Artboard 1? ? ? delete-icon? edit-icon? email-icon hide-hover-icon? Artboard 1? login-icon-white Artboard 1? next-icon-left next-icon-right-left next-icon-left-ochre next-icon next-icon-right-grey next-icon-right-ochre plus-with-circle-iconP search-fw-icon? search-icon-ochre search-icon-white

366 Main St

Gloucester, MA 01930
$1,139,999
9 Beds
4 Baths
3,600 Living Area
  • Property Description
    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.
  • Highlights
    • Levels: 4
    • Property Class: Residential Income
    • Stories: 4
    • Year Built: 1900
    • Parking Spots: 2
    • Property Type: 3 Family
    • Total Rooms: 16
    • Status: Active
  • Additional Details
    • Basement: Partial
    • Lot Features: Other
    • Total Number of Units: 3
    • Year Built Source: Public Records
    • Foundation: Block
    • SqFt Source: Other
    • Year Built Details: Actual
    • Zoning: Nb
  • Amenities
    • Parking Features: Off Street
    • Waterfront Features: Waterfront, Ocean, Harbor, 1/2 to 1 Mile To Beach, Beach Ownership(Public)
    • Waerfront: Yes
  • Utilities
    • Sewer: Public Sewer
    • Water Source: Public
  • Fees / Taxes
    • Assessed Value: $711,500
    • Taxes: $6,624
    • Tax Year: 2026
    • Total Rent: $8,500

Location

366 Main St, Gloucester, MA 01930

Loading Map...

Similar Listings

Sold
52 Taylor St 1
12 Photos
52 Taylor St Gloucester, MA 01930
$1,199,000
6 Beds 4 Baths 2,790 Sqft
View Details
Sold
5 Washington Sq 1
20 Photos
5 Washington Sq Gloucester, MA 01930
$1,149,000
6 Beds 3 Baths 3,555 Sqft
View Details
Sold
101 Western Ave 1
35 Photos
Sold
5 Marshfield St 1
41 Photos
5 Marshfield St Gloucester, MA 01930
$1,059,999
6 Beds 5 Baths 3,219 Sqft
View Details
Content © 2026 MLS Property Information Network, Inc. The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Gjikondi Realty. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.
  • Request More Information:

    617.262.2500
    When you are ready, please contact us and we will put our unrivaled knowledge of the Boston real estate market to work for you. Whether you are buying a luxury condo or renting a luxury apartment, we pledge to make your experience as stress free and enjoyable as possible.

    Please call, email, or send us a message through the web form below. An LRG Real Estate agent will contact you promptly.

    For More Info Please Call:

    617.262.2500

    or

    Email Us
  • Hidden
  • This field is for validation purposes and should be left unchanged.

By joining you agree to our Terms of Use and Privacy Policy