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Maggie Li

I'm Maggie Li, a Newton, MA real estate agent serving first-time buyers, luxury clients and sellers across Greater Boston in English & Mandarin. Let's find your home.

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  • 1229 Centre Street, Newton Centre, MA, USA
  • (774) 222-0952
  • lyx0402@gmail.com

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© 2026 Maggie Li. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 366 Main St, Gloucester, MA 01930
Active
4 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)$459/sqft
24% BelowMarket Average

* Analysis is based on 13 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

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