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.	$413,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.77% Airbnb Rental Income: $1611 Traditional Rental Income: $2420 Airbnb ROI: 0.5% Traditional ROI: 3.77%
73 Rocky Neck Ave 2 Gloucester, MA Nestled above the scenic beauty of Smith Cove in Rocky Neck, this enchanting two-bedroom c...	2 beds \| 3 baths \| 1,760 sq.ft.	$1,500,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 0.18% Airbnb Rental Income: $1611 Traditional Rental Income: $3444 Airbnb ROI: -1.46% Traditional ROI: 0.18%
587 Essex Ave Gloucester, MA Step into classic New England charm with this beautifully maintained two-story Colonial, i...	3 beds \| 2 baths \| 1,524 sq.ft.	$647,900	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.36% Airbnb Rental Income: $1907 Traditional Rental Income: $3239 Airbnb ROI: 0.32% Traditional ROI: 3.36%
24 Cobblestone Ln 603 Gloucester, MA This thoughtfully designed, top floor, single level unit offers blended modern comfort wit...	2 beds \| 2 baths \| 939 sq.ft.	$385,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 5.17% Airbnb Rental Income: $1611 Traditional Rental Income: $2763 Airbnb ROI: 0.72% 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.	$1,245,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 2.6% Airbnb Rental Income: $2568 Traditional Rental Income: $4283 Airbnb ROI: 0.58% Traditional ROI: 2.6%
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: -0.58% Traditional cash on cash: 0.03% Airbnb Rental Income: $2568 Traditional Rental Income: $4656 Airbnb ROI: -0.58% Traditional ROI: 0.03%
9 Cleveland Pl Gloucester, MA Great opportunity to own a 3-family property in a convenient location in Gloucester. Ideal...	6 beds \| 3 baths \| 2,596 sq.ft.	$839,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 3.14% Airbnb Rental Income: $4004 Traditional Rental Income: $4059 Airbnb ROI: 1.98% Traditional ROI: 3.14%
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: -0.29% Traditional cash on cash: -0.04% Airbnb Rental Income: $4004 Traditional Rental Income: $4193 Airbnb ROI: -0.29% Traditional ROI: -0.04%
35 Reservoir Rd Gloucester, MA Well-maintained two-family home in a convenient Gloucester location offering strong income...	5 beds \| 2 baths \| 3,120 sq.ft.	$1,199,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 2.29% Airbnb Rental Income: $4004 Traditional Rental Income: $3785 Airbnb ROI: 1.72% Traditional ROI: 2.29%
10 Fremont St Gloucester, MA Tucked into Gloucesterâs iconic Rocky Neck neighborhood, 10 Fremont Street offers the ch...	4 beds \| 4 baths \| 2,200 sq.ft.	$1,899,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 0.37% Airbnb Rental Income: $2568 Traditional Rental Income: $4673 Airbnb ROI: -1.17% Traditional ROI: 0.37%
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: 3.7% Traditional cash on cash: 4.83% Airbnb Rental Income: $4004 Traditional Rental Income: $3779 Airbnb ROI: 3.7% 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: 1.41% Traditional cash on cash: 3.87% Airbnb Rental Income: $1611 Traditional Rental Income: $1881 Airbnb ROI: 1.41% Traditional ROI: 3.87%

Real Estate investment in Gloucester, MA

There are 12 properties for sale in the city of Gloucester . The median list price in Gloucester is $1,019,000 and the average price per square foot is $488. In May 2026, the average monthly cash on cash return in Gloucester is 2.00%. The average monthly rental income in Gloucester is $3,369.

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

There are 12 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 $1,907.

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.

$413,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $1611

Traditional Rental Income: $2420

Airbnb ROI: 0.5%

Traditional ROI: 3.77%

73 Rocky Neck Ave 2

Gloucester, MA

2 beds | 3 baths | 1,760 sq.ft.

$1,500,000

Airbnb cash on cash: -1.46%

Traditional cash on cash: 0.18%

Airbnb Rental Income: $1611

Traditional Rental Income: $3444

Airbnb ROI: -1.46%

Traditional ROI: 0.18%

587 Essex Ave

Gloucester, MA

3 beds | 2 baths | 1,524 sq.ft.

$647,900

Airbnb cash on cash: 0.32%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $1907

Traditional Rental Income: $3239

Airbnb ROI: 0.32%

Traditional ROI: 3.36%

24 Cobblestone Ln 603

Gloucester, MA

2 beds | 2 baths | 939 sq.ft.

$385,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $1611

Traditional Rental Income: $2763

Airbnb ROI: 0.72%

Traditional ROI: 5.17%

4 Ciaramitaro Ct

Gloucester, MA

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

$1,245,000

Airbnb cash on cash: 0.58%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $2568

Traditional Rental Income: $4283

Airbnb ROI: 0.58%

Traditional ROI: 2.6%

25 Salt Island Rd

Gloucester, MA

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

$4,750,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $2568

Traditional Rental Income: $4656

Airbnb ROI: -0.58%

Traditional ROI: 0.03%

9 Cleveland Pl

Gloucester, MA

6 beds | 3 baths | 2,596 sq.ft.

$839,000

Airbnb cash on cash: 1.98%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $4004

Traditional Rental Income: $4059

Airbnb ROI: 1.98%

Traditional ROI: 3.14%

127-131 Eastern Point Blvd

Gloucester, MA

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

$4,595,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: -0.04%

Airbnb Rental Income: $4004

Traditional Rental Income: $4193

Airbnb ROI: -0.29%