$1,190,000
Original price: $1,249,000
9 Beds
4 Baths
3,600 sqft
366 Main St, Gloucester, MA 01930
Est. Mortgage $7,406/mo*
Get Pre-QualifiedHome Highlights
Multi-Family
Built in 1900
$331/sqft
2 Parking Spaces
Local Information
- Map ViewExplore the area around 366 Main St.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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.
Last check for updates: about 4 hours ago
Listing courtesy of Kristi Gjikondi, (781) 558-3465
Gjikondi Realty, (781) 558-3465
Source: MLS PIN, MLS#73564309
Also Listed on MLS PIN.
Home Details for 366 Main St
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Interior Details Basement: PartialNumber of Rooms: 16 |
Beds & Baths Number of Bedrooms: 9Number of Bathrooms: 4Number of Bathrooms (full): 4 |
Dimensions and Layout Living Area: 3600 Square Feet |
Fireplace & Spa No FireplaceNo Spa |
Levels, Entrance, & Accessibility Number of Stories: 4 |
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Exterior Home Features Foundation: Block |
Parking & Garage Open Parking Spaces: 2No GarageParking Spaces: 2Parking: Off Street |
Frontage WaterfrontWaterfront: Waterfront, Ocean, Harbor, 1/2 to 1 Mile To Beach, Beach Ownership(Public)On Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 3600 |
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Days on Market: 37 |
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Year Built Year Built: 1900 |
Property Type / Style Property Type: Residential IncomeProperty Subtype: 3 Family |
Building Does Not Include Home Warranty |
Property Information Parcel Number: M:0051 B:0068 L:0000, 1896464 |
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Price List Price: $1,190,000Price Per Sqft: $331 |
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MLS Status: Active |
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Direction & Address City: Gloucester |
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Listing Agent Listing ID: 73564309 |
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Building Area Building Area: 3600 Square Feet |
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Not Senior Community |
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Lot Area: 4550 sqft |
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BasementMls Number: 73564309Above Grade Unfinished Area: 3600 |
Around this home
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.
What Locals Say about Gloucester
At least 179 Trulia users voted on each feature.
88 % Say it's dog friendly
82 % Say people would walk alone at night
72 % Say yards are well-kept
72 % Say there's holiday spirit
71 % Say car is needed
68 % Say there are sidewalks
68 % Say there's wildlife
68 % Say parking is easy
65 % Say neighbors are friendly
64 % Say streets are well-lit
62 % Say it's walkable to restaurants
60 % Say they plan to stay for at least 5 years
60 % Say kids play outside
59 % Say it's walkable to grocery stores
52 % Say it's quiet
46 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
Market trends in Gloucester
Last updated August 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
82
7MoM
Home Value
Trulia Estimate
$1.15MSince last month
Decreased$101K (-8.1%)Since last year
Increased$198K (+20.9%)Since last sale
Increased$1M (+788.4%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +206% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $1.15M |
| August 2026 | $1.25M |
| July 2026 | $961K |
| June 2026 | $993K |
| May 2026 | $999K |
| April 2026 | $1M |
| March 2026 | $1.01M |
| February 2026 | $993K |
| January 2026 | $964K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Multi-Family Home | $1,100,000 | 11/25/25 | 6 | 4 | 2,790 | |
0.23 | Multi-Family Home | $580,000 | 11/07/25 | 5 | 2 | 2,636 | |
0.27 | Multi-Family Home | $600,000 | 01/16/26 | 4 | 2 | 2,214 | |
0.47 | Multi-Family Home | $760,000 | 05/19/26 | 6 | 3 | 2,598 | |
0.65 | Multi-Family Home | $980,000 | 10/17/25 | 9 | 6 | 4,330 | |
0.34 | Multi-Family Home | $550,000 | 01/06/26 | 4 | 3 | 1,991 | |
0.31 | Multi-Family Home | $600,000 | 04/29/26 | 4 | 2 | 1,750 | |
0.42 | Multi-Family Home | $860,000 | 02/05/26 | 5 | 3 | 2,131 | |
0.28 | Multi-Family Home | $645,000 | 02/04/26 | 6 | 2 | 1,848 | |
0.55 | Multi-Family Home | $750,000 | 12/29/25 | 5 | 3 | 2,228 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.00 | - | 7 | 4 | 2,336 | Off Market | |
0.02 | $249,900 | - | - | - | For Sale | |
0.07 | $198,300 | 2 | 1 | 680 | Off Market | |
0.07 | $289,400 | 2 | 1 | 726 | Off Market | |
0.07 | $344,500 | 2 | 1 | 821 | Off Market | |
0.11 | $673,900 | 5 | 2.5 | 2,222 | Off Market | |
0.12 | $234,300 | 1 | 1 | 480 | Off Market | |
0.13 | $470,000 | 3 | 1 | 1,498 | Recently Sold | |
0.14 | $795,700 | 1 | 2 | 2,266 | Off Market | |
0.14 | $665,700 | 3 | 1.5 | 1,474 | Off Market | |
0.14 | $556,700 | 2 | 1.5 | 1,050 | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Sep 1, 2026 Source: MLS PIN #73564309 | PriceChange | $1,190,000 Price decreased by 5% |
Aug 16, 2026 Source: MLS PIN #73564309 | Listed For Sale | $1,249,000 |
Oct 1, 1999 Source: N/A | Sold | $129,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $5,979 | $614,500 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Kristi Gjikondi, Gjikondi Realty, (781) 558-3465
Agent Phone: (781) 558-3465
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
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New Listings near 366 Main St
NEWOPEN SAT, 11:30-1PMMichael V. Cannuscio, The Agency Marblehead
0.64 ACRESThe Murray Brown Group, RE/MAX Beacon
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NEWOPEN SAT, 10-12PMIda Doane, J. Barrett & Company
OPEN SUN, 11-1PMMargaret Maher, William Raveis R.E. & Home Services
2.41 ACRESMichael Selbst, Gibson Sotheby's International Realty
Nancy Goodick, Gibson Sotheby's International Realty
0.25 ACRESKristin Francoeur, Gibson Sotheby's International Realty
0.32 ACRESLillian LoGrasso, J. Barrett & Company
Joseph Maher, Maher Realty Group LLC
Kimberly Tipert Noyes, Engel & Volkers By the Sea- See more homes for sale inGloucester
Frequently asked questions about 366 Main St
- What is the estimated monthly payment for 366 Main St?Based on a $1,190,000 list price with 20% down at today's rates, the estimated monthly payment for 366 Main St in Gloucester, MA is approximately $7,517 (about $6,470 principal & interest, $972 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Gloucester?Residents describe Gloucester, MA as dog-friendly, well-kept, and pedestrian-friendly. See homes for sale in Gloucester, MA.
- What are the closest schools to 366 Main St?The closest schools to 366 Main St in Gloucester, MA are East Veterans Elementary School (rated 5/10), Gloucester High School (rated 4/10), Ralph B O'Maley Innovation Middle School (rated 5/10).
- What is 366 Main St estimated to be worth?Trulia's estimated value for 366 Main St in Gloucester, MA is $1,146,100.
- Does 366 Main St have parking?Yes, 366 Main St in Gloucester, MA has on-site parking.
366 Main St, Gloucester, MA 01930 is a 9 bedroom, 4 bathroom, 3,600 sqft multi-family built in 1900. This property is currently available for sale and was listed by MLS PIN on Aug 16, 2026. The MLS # for this home is MLS# 73564309.