Real Estate Investment Properties for Sale in Gloucester, MA

Looking for investment property in Gloucester, MA with high ROI ?

Explore a variety of short-term homes & houses in Gloucester, MA. Invest wisely with VRBO & Gloucester, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Gloucester, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
14-R Spring St #3 Gloucester, MA Perfectly positioned in the heart of historic downtown Gloucester, this sun-filled 2-bedro...	2 beds \| 1 baths \| 1,101 sq.ft.	$375,250	Airbnb cash on cash: 2.6% Traditional cash on cash: 4.25% Airbnb Rental Income: $2434 Traditional Rental Income: $2420 Airbnb ROI: 2.6% Traditional ROI: 4.25%
24 Cobblestone Ln 603 Gloucester, MA Valuable benefit for buyers estimated at $36,000, the owner has elected to prepay the 15-y...	2 beds \| 2 baths \| 939 sq.ft.	$385,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 5.17% Airbnb Rental Income: $2434 Traditional Rental Income: $2763 Airbnb ROI: 2.62% Traditional ROI: 5.17%
4 Ciaramitaro Ct Gloucester, MA Panoramic ocean views of Ipswich Bay and less than a mile to Plum Cove Beach! Experience c...	4 beds \| 3 baths \| 3,264 sq.ft.	$1,220,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 2.67% Airbnb Rental Income: $3498 Traditional Rental Income: $4283 Airbnb ROI: 1.3% Traditional ROI: 2.67%
25 Salt Island Rd Gloucester, MA Sought-after Brier Neck retreat with sweeping ocean views is offered publicly for the firs...	4 beds \| 3 baths \| 3,300 sq.ft.	$4,750,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.03% Airbnb Rental Income: $3498 Traditional Rental Income: $4656 Airbnb ROI: -0.4% Traditional ROI: 0.03%
32 Witham Street #B Gloucester, MA Custom 3,200 sq ft townhome located in highly sought after Good Harbor Beach neighborhood....	5 beds \| 4 baths \| 3,236 sq.ft.	$949,900	Airbnb cash on cash: 0.48% Traditional cash on cash: 4.4% Airbnb Rental Income: $2970 Traditional Rental Income: $5753 Airbnb ROI: 0.48% Traditional ROI: 4.4%
127-131 Eastern Point Blvd Gloucester, MA Presenting a rare waterfront Eastern Pt compound spanning 3 contiguous parcels, ideally lo...	5 beds \| 3 baths \| 2,757 sq.ft.	$4,595,000	Airbnb cash on cash: -0.49% Traditional cash on cash: -0.04% Airbnb Rental Income: $2970 Traditional Rental Income: $4193 Airbnb ROI: -0.49% Traditional ROI: -0.04%
163 Atlantic Rd #6 Gloucester, MA Experience coastal living at its finest on Gloucesterâs stunning Back Shore. Wake each m...	3 beds \| 4 baths \| 2,523 sq.ft.	$1,999,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 0.84% Airbnb Rental Income: $2514 Traditional Rental Income: $5769 Airbnb ROI: -1.25% Traditional ROI: 0.84%
302 Western Ave A Gloucester, MA Buyers cold feet is your opportunity!! Built in 2022 and thoughtfully designed with qualit...	2 beds \| 2 baths \| 1,052 sq.ft.	$635,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 4.32% Airbnb Rental Income: $2434 Traditional Rental Income: $3271 Airbnb ROI: 1.9% Traditional ROI: 4.32%
64 Rocky Neck Ave #A Gloucester, MA Dock, Dine & Drift Away at Harbor Haven. This newly-created condominium offers a rare oppo...	1 beds \| 1 baths \| 648 sq.ft.	$995,000	Airbnb cash on cash: -0.65% Traditional cash on cash: -0.05% Airbnb Rental Income: $2087 Traditional Rental Income: $2106 Airbnb ROI: -0.65% Traditional ROI: -0.05%
64 Rocky Neck Ave #B Gloucester, MA Dock, Dine & Drift Away at Harbor Haven. This newly-created condominium offers a rare oppo...	1 beds \| 1 baths \| 650 sq.ft.	$995,000	Airbnb cash on cash: -0.65% Traditional cash on cash: -0.05% Airbnb Rental Income: $2087 Traditional Rental Income: $2106 Airbnb ROI: -0.65% Traditional ROI: -0.05%
43 Woodward Ave Gloucester, MA This beautifully maintained home has been extensively updated, offering true move-in-ready...	4 beds \| 2 baths \| 2,084 sq.ft.	$1,175,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.98% Airbnb Rental Income: $3498 Traditional Rental Income: $3587 Airbnb ROI: 0.19% Traditional ROI: 0.98%
6 Mt Locust Place 2 Gloucester, MA Just moments from beloved Plum Cove Beach, where spectacular sunsets and coastal beauty be...	2 beds \| 1 baths \| 840 sq.ft.	$489,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 3.69% Airbnb Rental Income: $2434 Traditional Rental Income: $2265 Airbnb ROI: 2.75% Traditional ROI: 3.69%
8 Atlantic Rd Gloucester, MA Offered for the first time in over six decades, 8 Atlantic Road is a beloved coastal retre...	4 beds \| 3 baths \| 3,037 sq.ft.	$1,725,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 1.76% Airbnb Rental Income: $3498 Traditional Rental Income: $4540 Airbnb ROI: 0.63% Traditional ROI: 1.76%
5 Pirates Lane 11 Gloucester, MA Experience spectacular sunsets and panoramic harbor views from this sun-filled, west-facin...	2 beds \| 2 baths \| 1,436 sq.ft.	$858,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.55% Airbnb Rental Income: $2434 Traditional Rental Income: $3103 Airbnb ROI: -0.04% Traditional ROI: 1.55%
8 Bickford Way Gloucester, MA This is more than a homeâitâs a coastal lifestyle. Follow the steps to the water and d...	2 beds \| 2 baths \| 1,731 sq.ft.	$2,395,000	Airbnb cash on cash: -1.44% Traditional cash on cash: -0.87% Airbnb Rental Income: $2434 Traditional Rental Income: $3102 Airbnb ROI: -1.44% Traditional ROI: -0.87%
157 Maplewood Ave Gloucester, MA Charming Gloucester home offering incredible potential with sought-after NB zoning, ideal ...	2 beds \| 1 baths \| 912 sq.ft.	$497,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 2.94% Airbnb Rental Income: $2434 Traditional Rental Income: $2280 Airbnb ROI: 1.99% Traditional ROI: 2.94%
77 Norwood Heights Gloucester, MA Perched above Ipswich Bay on a gentle rise in coveted Norwood Heights, this exceptional co...	5 beds \| 7 baths \| 5,526 sq.ft.	$4,895,000	Airbnb cash on cash: -1.74% Traditional cash on cash: -0.4% Airbnb Rental Income: $2970 Traditional Rental Income: $8377 Airbnb ROI: -1.74% Traditional ROI: -0.4%
33 Maplewood Ave #20 Gloucester, MA Turnkey generously sized two (2) bedroom, 1 1/2 bath, 968 sqft townhouse style condominium...	2 beds \| 2 baths \| 968 sq.ft.	$370,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 5.62% Airbnb Rental Income: $2434 Traditional Rental Income: $2702 Airbnb ROI: 3.13% Traditional ROI: 5.62%
3 Pirmi Lane 4 Gloucester, MA Enjoy the convenience of first-floor, end-unit living at Seasons Condominiums, Gloucesterâ...	2 beds \| 2 baths \| 1,414 sq.ft.	$725,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.88% Airbnb Rental Income: $2434 Traditional Rental Income: $3539 Airbnb ROI: 0.36% Traditional ROI: 2.88%
4 Alpine Ct Gloucester, MA Beautiful turnkey two-family home in Gloucester! The first unit features three spacious be...	5 beds \| 2 baths \| 1,920 sq.ft.	$599,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 4.83% Airbnb Rental Income: $2970 Traditional Rental Income: $3779 Airbnb ROI: 2.16% Traditional ROI: 4.83%
445 Western Ave Gloucester, MA Tucked along Western Ave in scenic Gloucester, this 1-bedroom, 1-bath home offers a great ...	1 beds \| 1 baths \| 595 sq.ft.	$315,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 3.87% Airbnb Rental Income: $2087 Traditional Rental Income: $1881 Airbnb ROI: 2.75% Traditional ROI: 3.87%

Real Estate investment in Gloucester, MA

There are 21 properties for sale in the city of Gloucester . The median list price in Gloucester is $779,597 and the average price per square foot is $410. In June 2026, the average monthly cash on cash return in Gloucester is 2.00%. The average monthly rental income in Gloucester is $3,324.

Gloucester, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 21 investment properties available for sale in Gloucester.

In 2026, the best neighborhood to buy investment property is Gloucester.

The ROI for Short-Term is higher than the Long-Term in Gloucester with average rental income of $2,514.

Your search for investment property begins and ends here

Investment Property for Sale in Gloucester, MA

14-R Spring St #3

Gloucester, MA

2 beds | 1 baths | 1,101 sq.ft.

$375,250

Airbnb cash on cash: 2.6%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $2434

Traditional Rental Income: $2420

Airbnb ROI: 2.6%

Traditional ROI: 4.25%

24 Cobblestone Ln 603

Gloucester, MA

2 beds | 2 baths | 939 sq.ft.

$385,000

Airbnb cash on cash: 2.62%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $2434

Traditional Rental Income: $2763

Airbnb ROI: 2.62%

Traditional ROI: 5.17%

4 Ciaramitaro Ct

Gloucester, MA

4 beds | 3 baths | 3,264 sq.ft.

$1,220,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $3498

Traditional Rental Income: $4283

Airbnb ROI: 1.3%

Traditional ROI: 2.67%

25 Salt Island Rd

Gloucester, MA

4 beds | 3 baths | 3,300 sq.ft.

$4,750,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $3498

Traditional Rental Income: $4656

Airbnb ROI: -0.4%

Traditional ROI: 0.03%

32 Witham Street #B

Gloucester, MA

5 beds | 4 baths | 3,236 sq.ft.

$949,900

Airbnb cash on cash: 0.48%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $2970

Traditional Rental Income: $5753

Airbnb ROI: 0.48%

Traditional ROI: 4.4%

127-131 Eastern Point Blvd

Gloucester, MA

5 beds | 3 baths | 2,757 sq.ft.

$4,595,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: -0.04%

Airbnb Rental Income: $2970

Traditional Rental Income: $4193

Airbnb ROI: -0.49%

Traditional ROI: -0.04%

163 Atlantic Rd #6

Gloucester, MA

3 beds | 4 baths | 2,523 sq.ft.

$1,999,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 0.84%

Airbnb Rental Income: $2514

Traditional Rental Income: $5769

Airbnb ROI: -1.25%

Traditional ROI: 0.84%

302 Western Ave A

Gloucester, MA

2 beds | 2 baths | 1,052 sq.ft.

$635,000

Airbnb cash on cash: 1.9%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $2434

Traditional Rental Income: $3271

Airbnb ROI: 1.9%