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.
For sale
Price cut: $50K (9/23)
$1,139,999
366 Main St, Gloucester, MA 01930
9beds
3,600sqft
3 Family
Built in 1900
-- sqft lot
$1,108,800 Zestimate®
$317/sqft
$-- HOA
What's special
Modern finishesIn-unit laundryUpdated kitchens and bathroomsThoughtfully renovated throughoutTwo dedicated parking spacesOffering beautiful ocean views
- 48 days
- 725
- 27
Zillow last checked:
Listing updated:
Listed by:
Kristi Gjikondi 781-558-3465,
Gjikondi Realty 781-558-3465
Source: MLS PIN,MLS#: 73564309
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 9
- Bathrooms: 4
- Full bathrooms: 4
Features
- Basement: Partial
- Has fireplace: No
Interior area
- Total structure area: 3,600
- Total interior livable area: 3,600 sqft
- Finished area above ground: 3,600
Property
Parking
- Total spaces: 2
- Parking features: Off Street
- Uncovered spaces: 2
Features
- On waterfront: Yes
- Waterfront features: Waterfront, Ocean, Harbor, 1/2 to 1 Mile To Beach, Beach Ownership(Public)
Lot
- Size: 4,550 Square Feet
- Features: Other
Details
- Parcel number: M:0051 B:0068 L:0000,1896464
- Zoning: NB
Construction
Type & style
- Home type: MultiFamily
- Property subtype: 3 Family
Materials
- Foundation: Block
Condition
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Location
- Region: Gloucester
Financial & listing details
- Price per square foot: $317/sqft
- Tax assessed value: $711,500
- Annual tax amount: $6,624
- Date on market: 8/17/2026
- Total actual rent: 8500
Estimated market value
$1,108,800
$1.05M - $1.16M
$2,295/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/23/2026 | Price change | $1,139,999-4.2%$317/sqft |
Source: MLS PIN #73564309 Report a problem | ||
| 9/1/2026 | Price change | $1,190,000-4.7%$331/sqft |
Source: MLS PIN #73564309 Report a problem | ||
| 8/16/2026 | Listed for sale | $1,249,000+868.2%$347/sqft |
Source: MLS PIN #73564309 Report a problem | ||
| 10/1/1999 | Sold | $129,000$36/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,979 | $614,500 |
| 2024 | $5,979 -3.9% | $614,500 +4.6% |
| 2023 | $6,223 | $587,600 |
| 2022 | $6,223 +17.5% | $587,600 +38% |
| 2021 | $5,296 +5.7% | $425,700 +4.7% |
| 2020 | $5,012 +7.9% | $406,500 +11.1% |
| 2019 | $4,645 +7.6% | $366,000 +9.6% |
| 2018 | $4,317 +6.3% | $333,900 +8.5% |
| 2017 | $4,060 +4.7% | $307,800 +8.1% |
| 2016 | $3,876 +2% | $284,800 +2.3% |
| 2015 | $3,800 +4.7% | $278,400 -0.4% |
| 2014 | $3,629 +2.7% | $279,600 -0.1% |
| 2013 | $3,532 +0% | $279,900 -3.4% |
| 2012 | $3,531 +2.4% | $289,900 -4.9% |
| 2011 | $3,448 +6.5% | $304,900 -1.3% |
| 2010 | $3,239 -7.2% | $308,800 -15.1% |
| 2009 | $3,491 -0.3% | $363,600 -5.5% |
| 2008 | $3,502 -0.6% | $384,800 -6% |
| 2007 | $3,524 -0.8% | $409,300 |
| 2006 | $3,553 +10.5% | $409,300 +14.5% |
| 2005 | $3,214 +6.4% | $357,500 +13.7% |
| 2004 | $3,022 +14% | $314,500 +29.9% |
| 2003 | $2,652 | $242,200 |
Find assessor info on the county website
Monthly payment
Est. payment



