Overview Property Details Payment Calculator Walkability

Add to favorites

Remove from favorites
Send to Friend
Watch changes on this property

Active

366 Main St, Gloucester MA 01930

$1,190,000

Estimated $2,482/month Calculator

Multi Family

Total Units: 3

Price Per Unit: $396,666.67

Total Rent: 102000/year

Estimated CAP Rate:

9 Bedrooms

Baths

3600

Total Parking: 2

4,550 (0.10)

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.

This home has been viewed 3 times

Last Checked: September 15th, 2026 at 8:28am (Source: MLS PIN #73564309)

Gross Income: $102,000

Gross Expenses: $6,624

Net Income Calc: $95,376

Waterfront

Annual Expenses for 366 Main St, Gloucester MA 01930

Total Gross Expenses (Calculated)$6,624/year

APOD AvailableNo

Heating

Electricity

Water

Gas

Insurance

Sewer

Trash Removal

Repair & Maintenance

Management

Miscellaneous

Real Estate Tax6624

Annual Income & Unit Breakdown for 366 Main St, Gloucester MA 01930

Total Gross Income (Calculated)$102,000

Unit 1

Rental Income$0

LeaseN

Bedrooms2

Bathrooms1 Full

Floor1

Levels in Unit1

Rent Includes

Unit 2

Rental Income$0

LeaseY

Bedrooms2

Bathrooms1 Full

Floor2

Levels in Unit1

Rent Includes

Unit 3

Rental Income$0

LeaseY

Bedrooms5

Bathrooms2 Full

Floor3

Levels in Unit2

Rent Includes

General Information for 366 Main St, Gloucester MA 01930

Listing ID73564309

Property TypeMulti Family / 3 Family

Price1190000 ($330.56/SqFt)

Style3 Family

CityGloucester

CountyEssex

Neighborhood(s)Ipswich

Approximate Living Area Total3600

Approximate Lot Size (Acres)0.1

Total Parking2

Garage Parking0

Year Built1900

Year Built SourcePublic Records

Year Built DetailsActual

WaterPublic

SewerPublic Sewer

Electric

Hot Water

Roof Material

BasementFull

Construction Materials

Lot FeaturesGentle Sloping

Foundation Description

Accessible Features

Outdoor Space

ZoningNB

Water Views

Water Views Features

Waterfront1

Waterfront FeaturesRiver

Terms

Disclosures for 366 Main St, Gloucester MA 01930

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourceOther

ExclusionsAll Personal Property.

Financial Data Source

Total Gross Expenses By Broker

Total Gross Income By Broker

Total Net Income By Broker

Short Sale / Forclosure (Bank Owned)

Compensation Based On

Financial Information for 366 Main St, Gloucester MA 01930

Real Estate Taxes6624

Tax Year2026

Assessed Value$711,500

Financial Data Source

Total Gross Expenses By Broker

BostonRealEstate.com Gross Expenses

Total Gross Income By Broker

BostonRealEstate.com Gross Income

Total Net Income By Broker

BostonRealEstate.com Gross NOI

CAP Rate (based on Broker info)

Location Information for 366 Main St, Gloucester MA 01930

Neighborhood(s)Ipswich

Area Amenities

Contact Information for 366 Main St, Gloucester MA 01930

Agent

Name: Kristi Gjikondi

Office

Name: Gjikondi Realty

Phone: 781-558-3465

Payment Calculator

, Interest

Property Taxes 552

Principal & Interest 7332.4

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Gjikondi Realty

Kristi Gjikondi

Agent Phone

Office Phone

(781) 558-3465

Text Agent Call Agent Call Office

Array
(
    [acres] => Approx. 0.1 acres (4,550 SqFt)
    [add_date] => 2026-09-15 08:28:34
    [address] => Main St
    [agent] => Array
        (
            [address] => 30 Chelsea Street
            [city] => Everett
            [id] => CN237355
            [name] => Kristi Gjikondi
            [national_association] => 449649752
            [office] => AN8150
            [state] => MA
            [zip] => 02149
        )

[apod_available] => Array
        (
            [0] => No
        )

[appliances] => Array
        (
        )

[approx_living_area_total] => 3600
    [approx_lot_size_acres] => 0.1
    [approx_lot_size_sqft] => 4550
    [assessed_value] => $711,500
    [association] => 
    [association_fee] => Array
        (
        )

[association_fee_frequency] => Array
        (
        )

[association_fee_includes] => Array
        (
        )

[association_required] => Array
        (
        )

[available_date] => 
    [available_now] => 0
    [basement] => Array
        (
            [0] => Full
        )

[bathrooms] => 
    [bedrooms] => 9
    [building_amenities] => Array
        (
        )

[building_area_source] => Array
        (
            [0] => Other
        )

[building_management] => Array
        (
        )

[building_debug] => 
    [building_id] => 
    [building_parent] => 0
    [building_name] => 
    [building_name_from_address] => 
    [building_url] => 
    [buyer_agent_compensation] => 
    [buyer_agent_id] => 
    [buyer_office_id] => 
    [c_style] => Array
        (
            [0] => 3 Family
        )

[c_type] => Array
        (
            [0] => Multi Family
        )

[cap_rate] => 
    [city] => Gloucester
    [community_features] => Array
        (
        )

[compensation_based_on] => Array
        (
        )

[complex_complete] => Array
        (
        )

[construction_materials] => Array
        (
        )

[construction_status] => 
    [cooling] => Array
        (
        )

[cooperating_agent_commission] => Array
        (
        )

[county] => Essex
    [cultivation_acres] => 
    [date_available_note] => 
    [deposit_amount] => Array
        (
        )

[deposit_required] => Array
        (
        )

[deqe] => 
    [description] => 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.
    [disclosures] => 
    [documents_available] => Array
        (
        )

[electric] => Array
        (
        )

[electric_expense] => Array
        (
        )

[elementary_school] => 
    [en_suite_bath] => Array
        (
            [0] => Yes
        )

[energy_features] => 
    [entry_level] => Array
        (
        )

[estimated_monthly_payment] => 
    [exclusions] => Array
        (
            [0] => All Personal Property.
        )

[exterior_features] => Array
        (
        )

[facilitator_compensation] => 
    [fee_paid_by_tennant] => 
    [financial_data_source] => Array
        (
        )

[fireplaces] => Array
        (
        )

[first_month_required] => Array
        (
        )

[floor_number] => 0
    [flooring] => Array
        (
        )

[for_sale_by_owner] => 
    [foundation_area] => 
    [foundation_materials] => Array
        (
        )

[frontage_length] => 
    [full_baths] => 
    [garage_parking] => 0
    [gas] => Array
        (
        )

[gas_expense] => Array
        (
        )

[gross_income] => Array
        (
        )

[half_baths] => 
    [handicap_access] => 
    [heating] => 
    [heating_expense] => Array
        (
        )

[high_school] => 
    [horse_features] => Array
        (
            [0] => River
        )

[horse_permitted] => 0
    [hot_water] => Array
        (
        )

[id] => 
    [insurance_expense] => Array
        (
        )

[insurance_required] => Array
        (
        )

[interior_features] => Array
        (
        )

[last_month_required] => Array
        (
        )

[last_sync_date] => 2026-09-15 08:28:34
    [laundry_features] => Array
        (
        )

[lead_paint] => Array
        (
            [0] => None
        )

[lease_term] => Array
        (
        )

[levels_in_unit] => 4
    [living_area] => 
    [living_area_disclosure] => Array
        (
        )

[living_area_includes_basement] => Array
        (
            [0] => No
        )

[lot_features] => Array
        (
            [0] => Gentle Sloping
        )

[management_expense] => Array
        (
        )

[middle_school] => 
    [miscellaneuos_expense] => Array
        (
        )

[mls_area] => 
    [mls_id] => 73564309
    [neighborhoods] => Ipswich
    [net_income_calc] => 95376
    [net_operating_income] => Array
        (
        )

[number_of_lots] => Array
        (
        )

[number_of_units] => 3
    [office] => Array
        (
            [id] => AN8150
            [name] => Gjikondi Realty
            [phone] => 781-558-3465
        )

[operating_expense] => Array
        (
        )

[optional_fee_includes] => Array
        (
        )

[optional_price] => 0
    [outdoor_space_available] => Array
        (
        )

[owner_occupancy_source] => 
    [parking_features] => Array
        (
            [0] => 1
        )

[pasture_area] => 
    [patio_and_porch] => Array
        (
        )

[perc_test] => Array
        (
        )

[perc_test_date] => 
    [pet_policy] => Array
        (
            [0] => Allowed
        )

[phone] => 
    [pool_features] => Array
        (
        )

[price] => 1190000
    [price_per_sqft] => 330.56
    [price_per_unit] => 396666.66666667
    [private_pool] => 
    [property_sub_type] => Array
        (
            [0] => 3 Family
        )

[real_estate_tax] => 6624
    [references_required] => Array
        (
        )

[rent_includes] => Array
        (
        )

[repair_maintenance_expense] => Array
        (
        )

[road_frontage_type] => Array
        (
        )

[roof_material] => Array
        (
        )

[rooms] => 16
    [schools] => 
    [senior_community] => 
    [sewer] => Array
        (
            [0] => Public Sewer
        )

[sewer_expense] => Array
        (
        )

[short_sale] => Array
        (
        )

[special_listing_conditions] => Array
        (
        )

[state] => Massachusetts
    [state_code] => MA
    [status] => Array
        (
            [0] => Active
        )

[street_number] => 366
    [structure_type] => Array
        (
        )

[style] => Array
        (
        )

[subagent_compensation] => 
    [tag_accessible_features] => 
    [tag_air_conditioning] => 
    [tag_association_pool] => 
    [tag_beach_access] => 
    [tag_beach_front] => 
    [tag_elevator] => 
    [tag_equestrian] => 
    [tag_garage_parking] => 
    [tag_generator] => 
    [tag_green_features] => 
    [tag_laundry] => 
    [tag_lead_paint_free] => 1
    [tag_loft] => 
    [tag_pet_friendly] => 
    [tag_pre_construction] => 
    [tag_private_outdoor_space] => 
    [tag_private_pool] => 
    [tag_professional_management] => 
    [tag_recently_renovated] => 
    [tag_senior_community] => 
    [tag_townhouse] => 
    [tag_waterfront] => 1
    [tag_waterview] => 
    [tax_year] => 2026
    [team] => 
    [team_agents] => Array
        (
        )

[terms] => Array
        (
        )

[timber_acres] => 
    [title_5] => 
    [total_gross_expense] => 6624
    [total_gross_income] => 102000
    [total_parking] => 2
    [trash_expense] => Array
        (
        )

[travel_routes] => 
    [uffi] => Array
        (
        )

[unit_1_bathrooms] => 1 Full
    [unit_1_bedrooms] => 2
    [unit_1_floor] => 1
    [unit_1_lease] => Array
        (
            [0] => N
        )

[unit_1_levels] => 1
    [unit_1_rent] => Array
        (
        )

[unit_2_bathrooms] => 1 Full
    [unit_2_bedrooms] => 2
    [unit_2_floor] => 2
    [unit_2_lease] => Array
        (
            [0] => Y
        )

[unit_2_levels] => 1
    [unit_2_rent] => Array
        (
        )

[unit_3_bathrooms] => 2 Full
    [unit_3_bedrooms] => 5
    [unit_3_floor] => 3
    [unit_3_lease] => Array
        (
            [0] => Y
        )

[unit_3_levels] => 2
    [unit_3_rent] => Array
        (
        )

[unit_4_bathrooms] => 
    [unit_4_bedrooms] => 
    [unit_4_floor] => 
    [unit_4_lease] => Array
        (
        )

[unit_4_levels] => 
    [unit_4_rent] => Array
        (
        )

[unit_level] => 
    [unit_number] => 
    [units_owner_occupied] => 
    [unparsed] => 366 Main St, Gloucester MA 01930
    [utilities] => Array
        (
        )

[view] => Array
        (
        )

[water] => Array
        (
            [0] => Public
        )

[water_expense] => Array
        (
        )

[water_views] => Array
        (
        )

[water_views_features] => Array
        (
        )

[waterfront] => 1
    [waterfront_features] => Array
        (
            [0] => River
        )

[year_built] => 1900
    [year_built_details] => Actual
    [year_built_source] => Public Records
    [year_renovated] => 
    [zip] => 3369
    [zips] => 
    [zoning] => NB
    [zoning_details] => 
    [media] => Array
        (
            [0] => https://www.bostonrealestate.com/wp-content/uploads/WPL/821204/MLS1.jpg
            [1] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=2
            [2] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=3
            [3] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=4
            [4] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=5
            [5] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=6
            [6] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=7
            [7] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=8
            [8] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=9
            [9] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=10
            [10] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=11
            [11] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=12
            [12] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=13
            [13] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=14
            [14] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=15
            [15] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=16
            [16] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=17
            [17] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=18
            [18] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=19
            [19] => https://media.mlspin.com/photo.aspx?mls=73564309&w=1024&h=768&n=20
        )

[raw] => 
)

EXIT

18 More Photos

Active

366 Main St, Gloucester MA 01930

$1,190,000

Annual Expenses for 366 Main St, Gloucester MA 01930

Annual Income & Unit Breakdown for 366 Main St, Gloucester MA 01930

General Information for 366 Main St, Gloucester MA 01930

Disclosures for 366 Main St, Gloucester MA 01930

Financial Information for 366 Main St, Gloucester MA 01930

Location Information for 366 Main St, Gloucester MA 01930

Contact Information for 366 Main St, Gloucester MA 01930

Agent

Office

Payment Calculator

Exclusive Listing Agent

Gjikondi Realty

Kristi Gjikondi