Active
49 Days on market
366 Main St Gloucester — Photo 1 of 21

366 Main St Gloucester — Photo 1 of 21

Recent Drop: $50,001

$1,190,000
$1,139,999

$1,139,999

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.

Key facts

It was listed on August 16, 2026. The price has come down from an original $1,249,000 to $1,139,999 across 2 changes, most recently on September 23, 2026. The annual property taxes are $6,624 (2026 tax year). It sits on a 0.1-acre (4,550 sq ft) lot.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$317/sqft
Local Avg (Gloucester)$644/sqft
51% BelowMarket Average

* Analysis is based on 17 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

Property History

Price Drop
$1,139,999

Was $1,190,000

Sep 23, 2026

MLS® 73564309

Price Drop
$1,190,000

Was $1,249,000

Sep 1, 2026

MLS® 73564309

Listed
$1,249,000

Aug 16, 2026

MLS® 73564309

Questions about this home

When was 366 Main St, Gloucester listed?

366 Main St, Gloucester was listed on August 16, 2026.

Has the price of 366 Main St, Gloucester changed?

The price has come down from an original $1,249,000 to $1,139,999 across 2 changes, most recently on September 23, 2026.

What are the property taxes for 366 Main St, Gloucester?

The annual property taxes for 366 Main St, Gloucester are $6,624 (2026 tax year).

How big is the lot at 366 Main St, Gloucester?

366 Main St, Gloucester sits on a 0.1-acre (4,550 sq ft) lot.

What is the status of 366 Main St, Gloucester?

366 Main St, Gloucester is actively listed for sale.

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

1,060 housing units permitted in the last 12 months (-11% vs the prior 12 months) — 603 in 5+ unit buildings

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

Listing Provided By

Listing Agent: Kristi Gjikondi

Listing Office: Gjikondi Realty

MLS® Number: 73564309