Real Estate Investment Properties for Sale in Oak Bluffs, MA

Looking for investment property in Oak Bluffs, MA with high ROI ?

Explore a variety of short-term homes & houses in Oak Bluffs, MA. Invest wisely with VRBO & Oak Bluffs, 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 Oak Bluffs, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
8 School House Village Oak Bluffs, MA Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attract...	4 beds \| 4 baths \| 2,336 sq.ft.	$1,690,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 1.37% Airbnb Rental Income: $5355 Traditional Rental Income: $4409 Airbnb ROI: 1.28% Traditional ROI: 1.37%
1 Pease Avenue Oak Bluffs, MA Year-round living nestled in the Martha's Vineyard Camp Meeting Association, this cottage,...	3 beds \| 1 baths \| 574 sq.ft.	$749,000	Airbnb cash on cash: 5.27% Traditional cash on cash: 1.4% Airbnb Rental Income: $6048 Traditional Rental Income: $2146 Airbnb ROI: 5.27% Traditional ROI: 1.4%
35 Double Ox Road Oak Bluffs, MA New Construction To Be Built~The Homes at Lagoon Ridge is a new subdivision of stylish pro...	2 beds \| 4 baths \| 2,558 sq.ft.	$2,275,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 0.7% Airbnb Rental Income: $6815 Traditional Rental Income: $3739 Airbnb ROI: 1.53% Traditional ROI: 0.7%
4 High Meadow Lane Oak Bluffs, MA Classic Post & Beam set in Meadow View Farms This bright and charming four-bedroom home...	4 beds \| 4 baths \| 2,810 sq.ft.	$2,595,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.31% Airbnb Rental Income: $5355 Traditional Rental Income: $4171 Airbnb ROI: 0.36% Traditional ROI: 0.31%
40 Hidden Cove Road #16 Oak Bluffs, MA The living comes easy at this three-bedroom Oak Bluffs condominium in the highly regarded ...	3 beds \| 3 baths \| 2,188 sq.ft.	$1,075,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 2.1% Airbnb Rental Income: $6048 Traditional Rental Income: $3790 Airbnb ROI: 3.16% Traditional ROI: 2.1%
37 Circuit Avenue #4 & 5 Oak Bluffs, MA Downtown Oak Bluffs- TWO Penthouse Condominiums being sold together. Located in the heart ...	3 beds \| 2 baths \| N/A	$1,900,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 0.01% Airbnb Rental Income: $6048 Traditional Rental Income: $3264 Airbnb ROI: 0.91% Traditional ROI: 0.01%
33 Clay Avenue Oak Bluffs, MA East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary thre...	3 beds \| 3 baths \| 2,408 sq.ft.	$1,750,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.78% Airbnb Rental Income: $6048 Traditional Rental Income: $3793 Airbnb ROI: 1.43% Traditional ROI: 0.78%
37 Circuit Avenue #5 Oak Bluffs, MA In the heart of Downtown Oak Bluffs this is 1 of 2 penthouse condominiums in the building ...	1 beds \| 1 baths \| 797 sq.ft.	$950,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 0.18% Airbnb Rental Income: $5097 Traditional Rental Income: $1840 Airbnb ROI: 2.69% Traditional ROI: 0.18%
37 Circuit Avenue #4 Oak Bluffs, MA In the heart of Downtown Oak Bluffs this is one of 2 penthouse condominiums that comes wit...	2 beds \| 1 baths \| 990 sq.ft.	$1,050,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 0.32% Airbnb Rental Income: $6815 Traditional Rental Income: $2103 Airbnb ROI: 3.79% Traditional ROI: 0.32%
30 Franklin Avenue Oak Bluffs, MA Welcome to your dream home! This stunning new construction boasts a coastal feel throughou...	2 beds \| 3 baths \| 2,137 sq.ft.	$2,350,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.45% Airbnb Rental Income: $6815 Traditional Rental Income: $3458 Airbnb ROI: 1.38% Traditional ROI: 0.45%
14 Forest Hill Avenue Oak Bluffs, MA LOCATION, LOCATION, LOCATION..House & Guest House. Turnkey! A short stroll to town where y...	3 beds \| 2 baths \| 788 sq.ft.	$1,300,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 0.78% Airbnb Rental Income: $6048 Traditional Rental Income: $2583 Airbnb ROI: 2.65% Traditional ROI: 0.78%
12 Maple Avenue Oak Bluffs, MA Oak Bluffs- Walk to Beach and town center from this East Chop Bungalow. Lovingly restored ...	2 beds \| 2 baths \| 832 sq.ft.	$1,200,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 0.75% Airbnb Rental Income: $6815 Traditional Rental Income: $2383 Airbnb ROI: 3.53% Traditional ROI: 0.75%
14 Maple Avenue Oak Bluffs, MA East Chop-Near Oak Bluffs Center. This antique bungalow was lovingly restored to a modern ...	2 beds \| 2 baths \| 768 sq.ft.	$1,200,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 0.76% Airbnb Rental Income: $6815 Traditional Rental Income: $2392 Airbnb ROI: 3.53% Traditional ROI: 0.76%
40 Hidden Cove #15 Oak Bluffs, MA Enjoy the fabulous amenities in the well-established Hidden Cove community, including the ...	3 beds \| 3 baths \| 1,898 sq.ft.	$999,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 2.3% Airbnb Rental Income: $6048 Traditional Rental Income: $3679 Airbnb ROI: 3.56% Traditional ROI: 2.3%
18 Brunswick Avenue Oak Bluffs, MA Embrace the history and character of this delightful 1870's Oak Bluffs cottage. Formerly t...	3 beds \| 1 baths \| 875 sq.ft.	$1,200,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 0.7% Airbnb Rental Income: $6048 Traditional Rental Income: $2405 Airbnb ROI: 2.9% Traditional ROI: 0.7%
14 High Meadow Lane Oak Bluffs, MA MEADOW VIEW FARM/OAK BLUFFS - Owned by the same family for over 30 years, this sun-drenche...	3 beds \| 3 baths \| 2,528 sq.ft.	$1,579,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 1.19% Airbnb Rental Income: $6048 Traditional Rental Income: $3892 Airbnb ROI: 1.85% Traditional ROI: 1.19%
10 Wood Duck Way Oak Bluffs, MA Experience the serene beauty of this 4-bedroom, 3.5-bathroom pond-front home in the Sengek...	4 beds \| 4 baths \| 3,014 sq.ft.	$2,950,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 0.19% Airbnb Rental Income: $5355 Traditional Rental Income: $4407 Airbnb ROI: 0.15% Traditional ROI: 0.19%
50 Canonicus Avenue Oak Bluffs, MA Coming Soon! Loved by generations, this quintessential Vineyard cottage has been in the sa...	2 beds \| 1 baths \| 952 sq.ft.	$995,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 0.61% Airbnb Rental Income: $6815 Traditional Rental Income: $2115 Airbnb ROI: 4.26% Traditional ROI: 0.61%
9 Leslie's Lane Oak Bluffs, MA This cozy ranch-style home with 3 bedrooms, 1 bath, and easy one-floor living is just off ...	3 beds \| 1 baths \| 816 sq.ft.	$849,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 1.22% Airbnb Rental Income: $6048 Traditional Rental Income: $2217 Airbnb ROI: 4.55% Traditional ROI: 1.22%
13 W Meadow Lane Oak Bluffs, MA UNLOCK THE POTENTIAL WITH THIS SUPERB LOCATION. Meadow View Farm Association is close to F...	4 beds \| 4 baths \| 2,623 sq.ft.	$1,575,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 1.68% Airbnb Rental Income: $5355 Traditional Rental Income: $4702 Airbnb ROI: 1.39% Traditional ROI: 1.68%
57 Netock Avenue Oak Bluffs, MA Charming three-bedroom home just under a mile from downtown Oak Bluffs where the restauran...	3 beds \| 2 baths \| 1,024 sq.ft.	$895,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 1.65% Airbnb Rental Income: $6048 Traditional Rental Income: $2679 Airbnb ROI: 4.25% Traditional ROI: 1.65%
70 Carol Lane Oak Bluffs, MA Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot ...	2 beds \| 3 baths \| 1,500 sq.ft.	$1,250,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 0.96% Airbnb Rental Income: $6815 Traditional Rental Income: $2872 Airbnb ROI: 3.22% Traditional ROI: 0.96%
10 Combra Way Oak Bluffs, MA NEAR OAK BLUFFS HARBOR - This elegantly remodeled classic Cape Style home is under a mile ...	3 beds \| 4 baths \| 2,200 sq.ft.	$1,695,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 1.23% Airbnb Rental Income: $6048 Traditional Rental Income: $4132 Airbnb ROI: 1.69% Traditional ROI: 1.23%

Real Estate investment in Oak-bluffs, MA

There are 23 properties for sale in the city of Oak Bluffs . The median list price in Oak Bluffs is $1,250,000 and the average price per square foot is $751. In December 2024, the average monthly cash on cash return in Oak Bluffs is 1.00%. The average monthly rental income in Oak Bluffs is $3,264.

Oak-bluffs, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 23 investment properties available for sale in Oak-bluffs.

In 2024, the best neighborhood to buy investment property is Oak Bluffs.

The ROI for Short-Term is higher than the Long-Term in Oak-bluffs with average rental income of $6,048.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Bluffs, MA

8 School House Village

Oak Bluffs, MA

4 beds | 4 baths | 2,336 sq.ft.

$1,690,000

Airbnb cash on cash: 1.28%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $5355

Traditional Rental Income: $4409

Airbnb ROI: 1.28%

Traditional ROI: 1.37%

1 Pease Avenue

Oak Bluffs, MA

3 beds | 1 baths | 574 sq.ft.

$749,000

Airbnb cash on cash: 5.27%

Traditional cash on cash: 1.4%

Airbnb Rental Income: $6048

Traditional Rental Income: $2146

Airbnb ROI: 5.27%

Traditional ROI: 1.4%

35 Double Ox Road

Oak Bluffs, MA

2 beds | 4 baths | 2,558 sq.ft.

$2,275,000

Airbnb cash on cash: 1.53%

Traditional cash on cash: 0.7%

Airbnb Rental Income: $6815

Traditional Rental Income: $3739

Airbnb ROI: 1.53%

Traditional ROI: 0.7%

4 High Meadow Lane

Oak Bluffs, MA

4 beds | 4 baths | 2,810 sq.ft.

$2,595,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $5355

Traditional Rental Income: $4171

Airbnb ROI: 0.36%

Traditional ROI: 0.31%

40 Hidden Cove Road #16

Oak Bluffs, MA

3 beds | 3 baths | 2,188 sq.ft.

$1,075,000

Airbnb cash on cash: 3.16%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $6048

Traditional Rental Income: $3790

Airbnb ROI: 3.16%

Traditional ROI: 2.1%

37 Circuit Avenue #4 & 5

Oak Bluffs, MA

3 beds | 2 baths | N/A

$1,900,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 0.01%

Airbnb Rental Income: $6048

Traditional Rental Income: $3264

Airbnb ROI: 0.91%

Traditional ROI: 0.01%

33 Clay Avenue

Oak Bluffs, MA

3 beds | 3 baths | 2,408 sq.ft.

$1,750,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $6048

Traditional Rental Income: $3793

Airbnb ROI: 1.43%

Traditional ROI: 0.78%

37 Circuit Avenue #5

Oak Bluffs, MA

1 beds | 1 baths | 797 sq.ft.

$950,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 0.18%

Airbnb Rental Income: $5097

Traditional Rental Income: $1840

Airbnb ROI: 2.69%