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
3 Kims Way Oak Bluffs, MA Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs ...	3 beds \| 2 baths \| 1,164 sq.ft.	$1,195,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.02% Airbnb Rental Income: $2133 Traditional Rental Income: $2688 Airbnb ROI: 0.03% Traditional ROI: 1.02%
35 Double Ox Road Oak Bluffs, MA NEW CONSTRUCTION ~Welcome to Lagoon Ridge, Oak Bluffs' newest and most sought-after neighb...	3 beds \| 4 baths \| 2,475 sq.ft.	$2,250,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 0.47% Airbnb Rental Income: $2133 Traditional Rental Income: $3739 Airbnb ROI: -0.56% Traditional ROI: 0.47%
12 & 14 Maple Avenue Oak Bluffs, MA Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentl...	4 beds \| 4 baths \| 1,600 sq.ft.	$1,830,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.66% Airbnb Rental Income: $1596 Traditional Rental Income: $3598 Airbnb ROI: -0.78% Traditional ROI: 0.66%
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.	$1,150,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.15% Airbnb Rental Income: $1961 Traditional Rental Income: $2872 Airbnb ROI: -0.18% Traditional ROI: 1.15%
30 Sengekontacket Road Oak Bluffs, MA Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket A...	4 beds \| 3 baths \| 2,262 sq.ft.	$2,195,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 0.4% Airbnb Rental Income: $1596 Traditional Rental Income: $3918 Airbnb ROI: -0.96% Traditional ROI: 0.4%
23 Circuit Ave Extension Oak Bluffs, MA Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Loc...	3 beds \| 1 baths \| 1 sq.ft.	$2,600,000	Airbnb cash on cash: -0.73% Traditional cash on cash: -0.5% Airbnb Rental Income: $2133 Traditional Rental Income: $2162 Airbnb ROI: -0.73% Traditional ROI: -0.5%
4 Canonicus Avenue Oak Bluffs, MA With a striking presence overlooking Nantucket Sound and just moments from the vibrant pul...	6 beds \| 4 baths \| 2,890 sq.ft.	$5,325,000	Airbnb cash on cash: -2% Traditional cash on cash: -1.28% Airbnb Rental Income: $1690 Traditional Rental Income: $4757 Airbnb ROI: -2% Traditional ROI: -1.28%
7 Upper Meadow Lane Oak Bluffs, MA Meadowview Farms - This home is ideal for those who love to host lively gatherings! Set at...	4 beds \| 3 baths \| 3,268 sq.ft.	$1,799,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 1.03% Airbnb Rental Income: $1596 Traditional Rental Income: $4468 Airbnb ROI: -0.96% Traditional ROI: 1.03%
34 Windemere Road Oak Bluffs, MA Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures th...	4 beds \| 2 baths \| 1,399 sq.ft.	$2,579,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.15% Airbnb Rental Income: $1596 Traditional Rental Income: $3594 Airbnb ROI: -0.88% Traditional ROI: 0.15%
26 Winthrop Avenue Oak Bluffs, MA Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece ...	1 beds \| 1 baths \| 803 sq.ft.	$849,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.51% Airbnb Rental Income: $1383 Traditional Rental Income: $1622 Airbnb ROI: -0.32% Traditional ROI: 0.51%
22 Montgomery Square Oak Bluffs, MA Located in the heart of Wesleyan Grove within the historic Martha's Vineyard Camp Meeting ...	3 beds \| 1 baths \| 931 sq.ft.	$895,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 1.22% Airbnb Rental Income: $2133 Traditional Rental Income: $2267 Airbnb ROI: 0.4% Traditional ROI: 1.22%
18 Wood Duck Way Oak Bluffs, MA Turnkey modern home with 4 bedrooms and 3 full baths, filled with natural light from large...	4 beds \| 3 baths \| 1 sq.ft.	$1,800,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.02% Airbnb Rental Income: $1596 Traditional Rental Income: $2809 Airbnb ROI: -1.02% Traditional ROI: -0.02%
37 Circuit Avenue unit: 4 Oak Bluffs, MA In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2...	2 beds \| 1 baths \| 990 sq.ft.	$899,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 0.88% Airbnb Rental Income: $1961 Traditional Rental Income: $1930 Airbnb ROI: 0.3% Traditional ROI: 0.88%
37 Circuit Avenue unit: 5 Oak Bluffs, MA In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location U...	1 beds \| 1 baths \| 798 sq.ft.	$869,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 0.84% Airbnb Rental Income: $1383 Traditional Rental Income: $1826 Airbnb ROI: -0.23% Traditional ROI: 0.84%
68 Front Street Oak Bluffs, MA Nestled at the end of a quiet street, this charming and spacious Cape-style home offers bo...	3 beds \| 3 baths \| 2,695 sq.ft.	$1,795,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 0.87% Airbnb Rental Income: $2133 Traditional Rental Income: $3830 Airbnb ROI: -0.47% Traditional ROI: 0.87%

Real Estate investment in Oak-bluffs, MA

There are 15 properties for sale in the city of Oak Bluffs . The median list price in Oak Bluffs is $1,799,000 and the average price per square foot is $1,185. In April 2026, the average monthly cash on cash return in Oak Bluffs is 1.00%. The average monthly rental income in Oak Bluffs is $2,809.

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

There are 15 investment properties available for sale in Oak-bluffs.

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

The ROI for Long-Term is higher than the Short-Term in Oak-bluffs with average rental income of $2,809.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Bluffs, MA

3 Kims Way

Oak Bluffs, MA

3 beds | 2 baths | 1,164 sq.ft.

$1,195,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 1.02%

Airbnb Rental Income: $2133

Traditional Rental Income: $2688

Airbnb ROI: 0.03%

Traditional ROI: 1.02%

35 Double Ox Road

Oak Bluffs, MA

3 beds | 4 baths | 2,475 sq.ft.

$2,250,000

Airbnb cash on cash: -0.56%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $2133

Traditional Rental Income: $3739

Airbnb ROI: -0.56%

Traditional ROI: 0.47%

12 & 14 Maple Avenue

Oak Bluffs, MA

4 beds | 4 baths | 1,600 sq.ft.

$1,830,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $1596

Traditional Rental Income: $3598

Airbnb ROI: -0.78%

Traditional ROI: 0.66%

70 Carol Lane

Oak Bluffs, MA

2 beds | 3 baths | 1,500 sq.ft.

$1,150,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: 1.15%

Airbnb Rental Income: $1961

Traditional Rental Income: $2872

Airbnb ROI: -0.18%

Traditional ROI: 1.15%

30 Sengekontacket Road

Oak Bluffs, MA

4 beds | 3 baths | 2,262 sq.ft.

$2,195,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $1596

Traditional Rental Income: $3918

Airbnb ROI: -0.96%

Traditional ROI: 0.4%

23 Circuit Ave Extension

Oak Bluffs, MA

3 beds | 1 baths | 1 sq.ft.

$2,600,000

Airbnb cash on cash: -0.73%

Traditional cash on cash: -0.5%

Airbnb Rental Income: $2133

Traditional Rental Income: $2162

Airbnb ROI: -0.73%

Traditional ROI: -0.5%

4 Canonicus Avenue

Oak Bluffs, MA

6 beds | 4 baths | 2,890 sq.ft.

$5,325,000

Airbnb cash on cash: -2%

Traditional cash on cash: -1.28%

Airbnb Rental Income: $1690

Traditional Rental Income: $4757

Airbnb ROI: -2%

Traditional ROI: -1.28%

7 Upper Meadow Lane

Oak Bluffs, MA

4 beds | 3 baths | 3,268 sq.ft.

$1,799,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: 1.03%

Airbnb Rental Income: $1596

Traditional Rental Income: $4468

Airbnb ROI: -0.96%