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
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: 0.37% Traditional cash on cash: 0.03% Airbnb Rental Income: $4971 Traditional Rental Income: $3444 Airbnb ROI: 0.37% Traditional ROI: 0.03%
7 Hawthorne Lane Gloucester, MA Nestled at the end of a quiet side street, this home offers breathtaking views of Gloucest...	4 beds \| 5 baths \| 2,739 sq.ft.	$2,095,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 0.47% Airbnb Rental Income: $5822 Traditional Rental Income: $5325 Airbnb ROI: 0.13% Traditional ROI: 0.47%
32 Witham St B Gloucester, MA Multi-Generation Home or Summer Get-Away, located near the coveted Good Harbor Beach! The ...	5 beds \| 4 baths \| 3,236 sq.ft.	$1,129,990	Airbnb cash on cash: 5.42% Traditional cash on cash: 4.37% Airbnb Rental Income: $8468 Traditional Rental Income: $5765 Airbnb ROI: 5.42% Traditional ROI: 4.37%
24 Cobblestone Ln #405 Gloucester, MA Your Next Right-Sized Move! A Waterfront Condo Designed for Comfort, Mobility & Views.Disc...	2 beds \| 1 baths \| 905 sq.ft.	$385,000	Airbnb cash on cash: 6.88% Traditional cash on cash: 2.51% Airbnb Rental Income: $4971 Traditional Rental Income: $2378 Airbnb ROI: 6.88% Traditional ROI: 2.51%
10 Perkins Rd Gloucester, MA Very special home on the Annisquam River next to the Cut Bridge. This bright, open & magic...	2 beds \| 2 baths \| 1,183 sq.ft.	$640,000	Airbnb cash on cash: 4.64% Traditional cash on cash: 3.02% Airbnb Rental Income: $4971 Traditional Rental Income: $2983 Airbnb ROI: 4.64% Traditional ROI: 3.02%
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.	$659,900	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.28% Airbnb Rental Income: $5194 Traditional Rental Income: $3239 Airbnb ROI: 4.75% Traditional ROI: 3.28%
30 Grapevine Road Gloucester, MA This beautifully redesigned home is move-in ready & packed w/premium features. A new expan...	4 beds \| 4 baths \| 3,600 sq.ft.	$1,595,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.33% Airbnb Rental Income: $5822 Traditional Rental Income: $5634 Airbnb ROI: 1.68% Traditional ROI: 2.33%
3 Bray St Gloucester, MA An amazing Contemporary home overlooking woods & creeks awaits you! The open flow is great...	3 beds \| 2 baths \| 2,680 sq.ft.	$995,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.67% Airbnb Rental Income: $5194 Traditional Rental Income: $3560 Airbnb ROI: 2.29% Traditional ROI: 1.67%
112 Eastern Ave Gloucester, MA 2 Family Greek Revival set on a spacious lot. Unlimited possibilities to update this home...	5 beds \| 2 baths \| 2,876 sq.ft.	$799,000	Airbnb cash on cash: 7.18% Traditional cash on cash: 3.19% Airbnb Rental Income: $8468 Traditional Rental Income: $3898 Airbnb ROI: 7.18% Traditional ROI: 3.19%
24 Cobblestone Ln 603 Gloucester, MA This thoughtfully designed top floor single level unit offers blended modern comfort with ...	2 beds \| 2 baths \| 939 sq.ft.	$410,000	Airbnb cash on cash: 7.83% Traditional cash on cash: 4.73% Airbnb Rental Income: $4971 Traditional Rental Income: $2763 Airbnb ROI: 7.83% Traditional ROI: 4.73%
42 Englewood Rd Gloucester, MA Nestled in the seaside village of Magnolia, this remodeled home blends coastal charm with ...	2 beds \| 2 baths \| 1,012 sq.ft.	$649,900	Airbnb cash on cash: 4.56% Traditional cash on cash: 2.47% Airbnb Rental Income: $4971 Traditional Rental Income: $2685 Airbnb ROI: 4.56% Traditional ROI: 2.47%

Real Estate investment in Gloucester, MA

There are 11 properties for sale in the city of Gloucester . The median list price in Gloucester is $799,000 and the average price per square foot is $391. In September 2025, the average monthly cash on cash return in Gloucester is 3.00%. The average monthly rental income in Gloucester is $3,444.

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

There are 11 investment properties available for sale in Gloucester.

In 2025, 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 $5,194.

Your search for investment property begins and ends here

Investment Property for Sale in Gloucester, MA

73 Rocky Neck Ave 2

Gloucester, MA

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

$1,600,000

Airbnb cash on cash: 0.37%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $4971

Traditional Rental Income: $3444

Airbnb ROI: 0.37%

Traditional ROI: 0.03%

7 Hawthorne Lane

Gloucester, MA

4 beds | 5 baths | 2,739 sq.ft.

$2,095,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $5822

Traditional Rental Income: $5325

Airbnb ROI: 0.13%

Traditional ROI: 0.47%

32 Witham St B

Gloucester, MA

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

$1,129,990

Airbnb cash on cash: 5.42%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $8468

Traditional Rental Income: $5765

Airbnb ROI: 5.42%

Traditional ROI: 4.37%

24 Cobblestone Ln #405

Gloucester, MA

2 beds | 1 baths | 905 sq.ft.

$385,000

Airbnb cash on cash: 6.88%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $4971

Traditional Rental Income: $2378

Airbnb ROI: 6.88%

Traditional ROI: 2.51%

10 Perkins Rd

Gloucester, MA

2 beds | 2 baths | 1,183 sq.ft.

$640,000

Airbnb cash on cash: 4.64%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $4971

Traditional Rental Income: $2983

Airbnb ROI: 4.64%

Traditional ROI: 3.02%

587 Essex Ave

Gloucester, MA

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

$659,900

Airbnb cash on cash: 4.75%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $5194

Traditional Rental Income: $3239

Airbnb ROI: 4.75%

Traditional ROI: 3.28%

30 Grapevine Road

Gloucester, MA

4 beds | 4 baths | 3,600 sq.ft.

$1,595,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 2.33%

Airbnb Rental Income: $5822

Traditional Rental Income: $5634

Airbnb ROI: 1.68%

Traditional ROI: 2.33%

3 Bray St

Gloucester, MA

3 beds | 2 baths | 2,680 sq.ft.

$995,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $5194

Traditional Rental Income: $3560

Airbnb ROI: 2.29%