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9 Beds
4 Baths
3,600 sqft

$1,139,999

366 Main St, Gloucester MA, 01930

Price per sqft$316.67
Built in1900
Property size3,600 sqft
Property typeMulti-family

Overview

Active

Listed Aug 16, 2026

Updated 8 days ago

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.

$7,584/mo

Est. mortgage payment based on a $1,139,999 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
73564309

Interior Features

Bedrooms
9
Bathrooms
4
Basement
Yes

Exterior Features

Lot Size
0.1 Acres

Other Property Details

Taxes
$6,624
Tax Frequency
Annually
Waterfront
Yes
55+/Senior Community
No

This listing is provided by Kristi Gjikondi with Gjikondi Realty

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Data last updated 2:53 AM UTC, 9/29/2026

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