3 Family at 366 Main St, Gloucester MA 01930, Gloucester
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21 photos

$1,139,999

366 Main St, Gloucester MA 01930
Gloucester, MA 01930
Listed by Kristi Gjikondi
Bedrooms
9
Bathrooms
4
Living area
3,600 sqft
Year built
1900

About this home

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

Waterfront

Property details

MLS #
73564309
Property type
3 Family
Subdivision
N/A
Status
Active
Days on market
45
On market date
August 16, 2026
Stories
4
Total bathrooms
4
Garage spaces
N/A
Parking spaces
2
Lot size
0.1 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Veterans Memorial
0.25 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
216
Student:teacher ratio
8.6:1
District
Gloucester
Middle
Ralph B O'Maley Middle
1.32 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
630
Student:teacher ratio
11.3:1
District
Gloucester
High
Gloucester High
1.21 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
830
Student:teacher ratio
10.5:1
District
Gloucester

Walkability

Blended score for Gloucester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

89
Highly walkable
out of 100
EPA National Walkability Index
16.3 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores12
Parks9
Schools12
Transit stops20
Pharmacies4

Market position

How this listing compares to current activity in Gloucester, from live MLS data.

On the market 45 days -- 59 fewer days than Gloucester's current average of 104 days.
For reference, the median list price across 236 active listings in Gloucester right now is $589,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$7,015/mo
$228,000 down
$911,999 loan
Principal & interest$5,915
Property tax (est.)$950
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 2 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.