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
25 Salt Island Rd Gloucester, MA Sought-after Brier Neck retreat with sweeping views of the Atlantic and Salt Islandâreac...	4 beds \| 3 baths \| 3,300 sq.ft.	$4,750,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 0.03% Airbnb Rental Income: $3887 Traditional Rental Income: $4656 Airbnb ROI: -0.33% Traditional ROI: 0.03%
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.	$1,600,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 0.03% Airbnb Rental Income: $2177 Traditional Rental Income: $3444 Airbnb ROI: -1.19% Traditional ROI: 0.03%
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: 2.02% Traditional cash on cash: 5.17% Airbnb Rental Income: $2177 Traditional Rental Income: $2763 Airbnb ROI: 2.02% 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: 1.53% Traditional cash on cash: 2.6% Airbnb Rental Income: $3887 Traditional Rental Income: $4283 Airbnb ROI: 1.53% Traditional ROI: 2.6%
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: 1.26% Traditional cash on cash: 3.36% Airbnb Rental Income: $2589 Traditional Rental Income: $3239 Airbnb ROI: 1.26% Traditional ROI: 3.36%
13 Mystic Ave. Gloucester, MA Located in a desirable central Gloucester neighborhood, this light and bright 1900s 2 bedr...	2 beds \| 2 baths \| 1,538 sq.ft.	$575,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 3.66% Airbnb Rental Income: $2177 Traditional Rental Income: $3078 Airbnb ROI: 0.96% Traditional ROI: 3.66%
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: 3.56% Traditional cash on cash: 3.14% Airbnb Rental Income: $5489 Traditional Rental Income: $4059 Airbnb ROI: 3.56% Traditional ROI: 3.14%
14-R Spring St unit: 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.	$435,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 4.04% Airbnb Rental Income: $2177 Traditional Rental Income: $2437 Airbnb ROI: 2.04% Traditional ROI: 4.04%

Real Estate investment in Gloucester, MA

There are 8 properties for sale in the city of Gloucester . The median list price in Gloucester is $743,450 and the average price per square foot is $371. In April 2026, the average monthly cash on cash return in Gloucester is 2.00%. The average monthly rental income in Gloucester is $3,328.

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

There are 8 investment properties available for sale in Gloucester.

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

The ROI for Long-Term is higher than the Short-Term in Gloucester with average rental income of $3,328.

Your search for investment property begins and ends here

Investment Property for Sale in Gloucester, MA

25 Salt Island Rd

Gloucester, MA

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

$4,750,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $3887

Traditional Rental Income: $4656

Airbnb ROI: -0.33%

Traditional ROI: 0.03%

73 Rocky Neck Ave 2

Gloucester, MA

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

$1,600,000

Airbnb cash on cash: -1.19%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $2177

Traditional Rental Income: $3444

Airbnb ROI: -1.19%

Traditional ROI: 0.03%

24 Cobblestone Ln 603

Gloucester, MA

2 beds | 2 baths | 939 sq.ft.

$385,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $2177

Traditional Rental Income: $2763

Airbnb ROI: 2.02%

Traditional ROI: 5.17%

4 Ciaramitaro Ct

Gloucester, MA

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

$1,245,000

Airbnb cash on cash: 1.53%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $3887

Traditional Rental Income: $4283

Airbnb ROI: 1.53%

Traditional ROI: 2.6%

587 Essex Ave

Gloucester, MA

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

$647,900

Airbnb cash on cash: 1.26%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $2589

Traditional Rental Income: $3239

Airbnb ROI: 1.26%

Traditional ROI: 3.36%

13 Mystic Ave.

Gloucester, MA

2 beds | 2 baths | 1,538 sq.ft.

$575,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $2177

Traditional Rental Income: $3078

Airbnb ROI: 0.96%

Traditional ROI: 3.66%

9 Cleveland Pl

Gloucester, MA

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

$839,000

Airbnb cash on cash: 3.56%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $5489

Traditional Rental Income: $4059

Airbnb ROI: 3.56%

Traditional ROI: 3.14%

14-R Spring St unit: 3

Gloucester, MA

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

$435,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $2177

Traditional Rental Income: $2437

Airbnb ROI: 2.04%