366 Main St, Gloucester MA 01930

Gloucester, MA 01930
$1,249,000
$1,190,000
Est. $6,769/month
9
Beds
4
Baths
3,600
Sq Ft
$331
Price/Sq Ft
0.10
Acres
1900
Year Built
2
Parking
20
Days on Market
For Sale Price Drop -$59,000 Listed Aug 16, 2026 • MLS# 73564309 Copied! • Updated Sep 5, 2026

Track this home for price, status, and open-house alerts.

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.

BMN Estimate

Get the number an algorithm can't give you

A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.

Recently Sold Nearby

Property History

Market Insights

1
Price Changes
4.7%
Price Range

Property Timeline

Price Reduced
Sep 1, 2026
$1,190,000 $59,000 (-4.72%)
From $1,249,000 to $1,190,000 (-4.7%)
🏠
Listed for Sale
Aug 16, 2026
$1,249,000
Original listing
Agent: Kristi Gjikondi Office: Gjikondi Realty

Tax History

Year Taxes Assessment
2026 $6,624 $711,500

Financial Details

Annual Property Tax
$6,624
Tax Year 2026
Assessed Value
$711,500

Facts & Features

Home Facts

Type Residential Income
Style 3 Family
Year Built 1900
Living Area 3,600 sq ft
Lot Size 0.10 acres
Stories 4
Bedrooms 9
Full Baths 4
Total Rooms 16

Investment Metrics

Units 3
Unit 1 Rent $2,100/mo · N
Unit 2 Rent $2,500/mo · Y
Unit 3 Rent $3,900/mo · Y
Total Monthly Rent $8,500/mo
Gross Income $102,000
Net Operating Income $102,000
Cap Rate 8.57%
Heating None
Cooling None
Flooring None
Appliances None
Fireplace None
Basement Partial
Laundry None
Features None
Construction None
Architecture None
Roof None
Features None
Pool None
Spa None
Fencing None
Patio/Porch None
Features Off Street
Total Spaces 2
Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $6,624
Assessed Value $711,500
Fee Includes None
Amenities None
Optional Fee Includes None
Down Payment Resource Eligible
Lead Paint Yes
Seller Disclosures None
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Other
Documents None
County Essex
Total market time (incl. prior listings) 20 days

Property Overview

Property Type
3 Family
Listing Type
For Sale
Year Built
1900
Bedrooms
9
Full Bathrooms
4
Living Area
3,600 sq ft
Total Rooms
16
Stories
4
Levels
4

Floor Layout

Interior Features

Flooring:
Appliances:
Interior Features:
Windows:
Basement: Partial
Laundry:
Security:

Construction & Materials

Year Built: 1900
Structure Type:
Exterior Materials:
Roof:
Foundation: Block
Stories: 4

Heating, Cooling & Utilities

Heating:
Cooling:
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features: Other
Road Surface:

Parking & Garage

Total Parking Spaces: 2
Parking Features: Off Street

Special Features

Waterfront: Yes
Waterfront Type: Waterfront, Ocean, Harbor, 1/2 to 1 Mile To Beach, Beach Ownership(Public)
Community Amenities:

Nearby Schools

School information not available for this location.

Monthly Payment Calculator

Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%

Monthly Payment Breakdown

Principal & Interest $0
Property Tax $552
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

Loading map...

Neighborhood

366 Main St, Gloucester MA 01930

Gloucester, MA 01930

Listing Information

Listing Agent Kristi Gjikondi
Listing Office Gjikondi Realty
Office Phone 781-558-3465
Agent MLS ID CN237355
Office MLS ID AN8150
Listing Data Updated Sep 5, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

Steve Novak Real Estate
Steve Novak Real Estate
Ask about this property — free, no obligation.

Similar Homes for Sale

Comparable Properties

Customize Comparable Search

Finding comparable properties...

Market Analytics for Gloucester, MA

Real-time market trends and pricing data for this area

Loading market insights for Gloucester.