366 Main St, Gloucester MA 01930

Gloucester, MA 01930
$1,249,000
Est. $7,068/month
9
Beds
4
Baths
3,600
Sq Ft
$347
Price/Sq Ft
0.10
Acres
1900
Year Built
2
Parking
8 hours 55 minutes
Time on Market
For Sale Listed Aug 16, 2026 • MLS# 73564309 Copied! • Updated Aug 16, 2026

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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.

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Recently Sold Nearby

Property History

Property Timeline

🏠
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 8.17%
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
Lead Paint Yes
Seller Disclosures None
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Other
Documents None
County Essex

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:
School District
Gloucester School District local
C-
🎓 Where Graduates Go Class of 2021
42% attend college
31% 4-Year 11% 2-Year 17% Out of State 14% Working
School Safety 2024-25
1.9% Average
1.9% Suspensions 0.5% In-School
3.6% below state avg
E

Elementary Schools

6 schools
Faith Christian School
1.7 mi
Grades PK-08
C
East Veterans Elementary School
0.3 mi | #651 of 824 | Score: 38.2
Dropped 58 spots from last year
-20 below state avg
451 students Diverse
Grades K-05
Gloucester PreSchool
0.7 mi
101 students Moderate
Grades PK
C-
Beeman Memorial School
1.7 mi | #701 of 824 | Score: 35.6
Dropped 172 spots from last year
-22.6 below state avg
292 students Diverse
Grades K-05
C-
West Parish School
3.0 mi | #683 of 824 | Score: 36.5
Dropped 245 spots from last year
-21.7 below state avg
382 students Less Diverse
Grades K-05
B+
Plum Cove School
4.0 mi | #322 of 824 | Score: 50.1
Improved 68 spots from last year
-8.1 below state avg
217 students Less Diverse
Rising School
Grades K-05
M

Middle Schools

1 school
C+
Ralph B O'Maley Middle School
1.4 mi | #238 of 352 | Score: 37.3
Improved 24 spots from last year
-20.9 below state avg
619 students Moderate
Rising School
Grades 06-08
H

High Schools

1 school
C+
Gloucester High School
1.2 mi | #212 of 346 | Score: 50.4
Improved 27 spots from last year
-7.8 below state avg
776 students Moderate
17 sports • 1,070 athletes
Rising School Career Tech Programs Strong Athletics
Grades 09-12
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Monthly Payment Calculator

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Including down payment
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Down: $0
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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

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Current Rate
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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

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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 Aug 16, 2026 6:49 PM 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
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