William Raveis
Buy
Property SearchSearch all available MLS listingsSet AlertsGet notified about new listingsNeighborhood GuidesExplore local communities & data
Newton, MA
Boston, MA
Weston, MA
Needham, MA
Wellesley, MA
Brookline, MA
View All Neighborhoods →
Featured PropertiesBrowse our exclusive local listings
Sell
Home ValuationGet a free, instant estimateMy ListingsBrowse my active market properties
Insights
About
Meet the AgentMy background and experienceClient StoriesRead reviews from past clients
Contact Me
Buy
Property Search
Set Alerts
Neighborhood Guides
Newton, MA
Newton CentreWabanChestnut HillWest NewtonNewton CornerNewtonvilleNewton HighlandsAuburndaleNewton Upper FallsNewton Lower Falls
Boston, MA
Weston, MA
Needham, MA
Wellesley, MA
Brookline, MA
View All Neighborhoods →
Featured Properties
Sell
Home Valuation
My Listings
Insights
About
Meet the Agent
Client Stories
Contact Me

Rozita Taba

I'm Rozita Taba, a Newton, MA real estate agent serving buyers and sellers across Greater Boston. Luxury specialist, Farsi-speaking—let's find your next move.

Explore

  • Home
  • About
  • Home Search
  • Set Alerts
  • My Active Listings
  • Home Valuation
  • Insights
  • Testimonials
  • Contact
  • Privacy Policy

Contact

  • 1229 Centre Street, Newton Centre, MA, USA
  • (617) 877-8839
  • rozita@oandcteam.com

Brokerage

William Raveis

© 2026 Rozita Taba. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 366 Main St, Gloucester, MA 01930
Active
17 Days on market
366 Main St Gloucester — Photo 1 of 21

366 Main St Gloucester — Photo 1 of 21

$1,249,000

366 Main St, Gloucester, MA 01930

Gloucester, MA 01930

Beds

9

Baths

4

SqFt

3,600

Style

3 Family

Built

1900

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$347/sqft
Local Avg (Gloucester)$478/sqft
27% BelowMarket Average

* Analysis is based on 14 actively listed and recently sold comparable properties strictly within Gloucester, MA.

Property Details

Financials

Original Price$1,249,000
Annual Taxes$6,624

Parking

Garage0
Off-Street2

Interior Specifications

Total Rooms16
FireplacesNone
Flooring--
BasementPartial

Climate & Utilities

Heating--
Cooling--
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
Roof--
FoundationBlock
ZoningNB

Property & Lot

Acres0.1
SqFt Lot4,550
Lot FeaturesOther

Geography

Population

30,075

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$84K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

36.0%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Essex County

992 housing units permitted in the last 12 months (-15% vs the prior 12 months) — 515 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

Full Gloucester, MA market report ZIP 01930 market data
Listing Provided By

Listing Agent: Kristi Gjikondi

Listing Office: Gjikondi Realty

MLS® Number: 73564309

Browse More Homes in Gloucester

Explore other active listings in the area.

  • 105 Centennial Ave
    $518,000
    105 Centennial Ave
    Gloucester, MA
    3 bd1 ba990 sqft
  • 4 Langsford St
    $750,000
    4 Langsford St
Gloucester, MA
2 bd2 ba1,321 sqft
  • 38R Bass Ave
    $549,000
    38R Bass Ave
    Gloucester, MA
    2 bd2 ba1,244 sqft
  • 20 Marble Street
    $699,000
    20 Marble Street
    Gloucester, MA
    4 bd2 ba1,933 sqft
  • 12 Andrews Street
    $1,375,000
    12 Andrews Street
    Gloucester, MA
    5 bd5 ba3,578 sqft
  • 20 Shepherd St
    $799,000
    20 Shepherd St
    Gloucester, MA
    6 bd3 ba2,904 sqft