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.

Single Family Homes for Sale in Oak Bluffs, MA

Search for Single Family Residential for Sale in Oak Bluffs, Massachusetts. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 19 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1 Cottage Park Oak Bluffs, MA The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs wit...	3 beds \| 3 baths \| 987 sq.ft.	$925,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.58% Airbnb Rental Income: $3291 Traditional Rental Income: $2647 Airbnb ROI: 1.47% Traditional ROI: 1.58%
35 Double Ox Road Oak Bluffs, MA NEW CONSTRUCTION ~Welcome to Lagoon Ridge, Oak Bluffs' newest and most sought-after neighb...	3 beds \| N/A baths \| 2,475 sq.ft.	$2,250,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 0.63% Airbnb Rental Income: $3291 Traditional Rental Income: $3739 Airbnb ROI: 0.06% Traditional ROI: 0.63%
47 Winemack Street Oak Bluffs, MA Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent th...	2 beds \| 1 baths \| 742 sq.ft.	$1,199,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 0.98% Airbnb Rental Income: $2648 Traditional Rental Income: $2817 Airbnb ROI: 0.27% Traditional ROI: 0.98%
4 High Meadow Lane Oak Bluffs, MA Classic Post & Beam set in Meadow View Farms This bright and charming four-bedroom home si...	4 beds \| N/A baths \| 2,810 sq.ft.	$2,260,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.5% Airbnb Rental Income: $2604 Traditional Rental Income: $4171 Airbnb ROI: -0.55% Traditional ROI: 0.5%
267 Barnes Road Oak Bluffs, MA Live the Dream on Martha's Vineyard! Whether you're seeking a year-round residence or a se...	3 beds \| N/A baths \| 4,046 sq.ft.	$4,395,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.15% Airbnb Rental Income: $3291 Traditional Rental Income: $5453 Airbnb ROI: -0.86% Traditional ROI: -0.15%
30 Franklin Avenue Oak Bluffs, MA Welcome to your dream home! This stunning new construction boasts a coastal feel throughou...	2 beds \| 2 baths \| 2,137 sq.ft.	$2,150,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 0.41% Airbnb Rental Income: $2648 Traditional Rental Income: $3458 Airbnb ROI: -0.31% Traditional ROI: 0.41%
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 \| N/A baths \| 1,500 sq.ft.	$1,200,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 1.06% Airbnb Rental Income: $2648 Traditional Rental Income: $2872 Airbnb ROI: 0.29% Traditional ROI: 1.06%
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: -0.55% Traditional cash on cash: 0.4% Airbnb Rental Income: $2604 Traditional Rental Income: $3918 Airbnb ROI: -0.55% Traditional ROI: 0.4%
63 Bayes Hill Rd Oak Bluffs, MA Picture yourself in this beautifully designed custom home offering the ultimate in privacy...	4 beds \| 5 baths \| 5,165 sq.ft.	$3,150,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.81% Airbnb Rental Income: $2604 Traditional Rental Income: $6584 Airbnb ROI: -0.76% Traditional ROI: 0.81%
16 Atlantic Avenue Oak Bluffs, MA East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse ...	5 beds \| 2 baths \| 2,577 sq.ft.	$2,495,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 0.09% Airbnb Rental Income: $4898 Traditional Rental Income: $3605 Airbnb ROI: 0.21% Traditional ROI: 0.09%
44 Iron Hill Road Oak Bluffs, MA Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca...	3 beds \| 2 baths \| 1,496 sq.ft.	$1,250,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 1.15% Airbnb Rental Income: $3291 Traditional Rental Income: $2992 Airbnb ROI: 0.78% Traditional ROI: 1.15%
7 Upper Meadow Lane Oak Bluffs, MA Meadowview Farms - Tucked at the end of a quiet cul-de-sac, this spacious Colonial offers ...	4 beds \| 2 baths \| 3,268 sq.ft.	$1,799,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 1.1% Airbnb Rental Income: $2604 Traditional Rental Income: $4468 Airbnb ROI: -0.39% Traditional ROI: 1.1%
8 Paddock Road Oak Bluffs, MA Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of...	4 beds \| 6 baths \| 3,300 sq.ft.	$5,450,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.33% Airbnb Rental Income: $2604 Traditional Rental Income: $8269 Airbnb ROI: -0.92% Traditional ROI: 0.33%
6 Brewster Avenue Oak Bluffs, MA Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete wit...	4 beds \| 3 baths \| 1,728 sq.ft.	$3,250,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.27% Airbnb Rental Income: $2604 Traditional Rental Income: $3705 Airbnb ROI: -0.84% Traditional ROI: -0.27%
1 jessie leigh mitchell Way Oak Bluffs, MA Welcome to this spacious and well-appointed home offering 2,128 square feet of comfortable...	2 beds \| N/A baths \| 1 sq.ft.	$1,100,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 0.33% Airbnb Rental Income: $2648 Traditional Rental Income: $1983 Airbnb ROI: 0.37% Traditional ROI: 0.33%
311 E Chop Drive Oak Bluffs, MA Arrive by land or sea to 311 East Chop Drive, a truly rare offering that combines panorami...	4 beds \| 2 baths \| 1,800 sq.ft.	$3,000,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.33% Airbnb Rental Income: $2604 Traditional Rental Income: $2976 Airbnb ROI: -0.69% Traditional ROI: -0.33%
7 South Meadow Lane Oak Bluffs, MA Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort,...	4 beds \| 3 baths \| 3,142 sq.ft.	$1,825,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.96% Airbnb Rental Income: $2604 Traditional Rental Income: $4290 Airbnb ROI: -0.4% Traditional ROI: 0.96%
12 Wheelhouse Way Oak Bluffs, MA Custom-built 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful se...	3 beds \| 2 baths \| 1,487 sq.ft.	$1,095,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 1.19% Airbnb Rental Income: $3291 Traditional Rental Income: $2754 Airbnb ROI: 0.99% Traditional ROI: 1.19%
24 School Street Oak Bluffs, MA An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the pu...	2 beds \| 1 baths \| 861 sq.ft.	$875,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 0.97% Airbnb Rental Income: $2648 Traditional Rental Income: $2052 Airbnb ROI: 0.93% Traditional ROI: 0.97%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oak Bluffs, MA

1 Cottage Park

Oak Bluffs, MA

3 beds | 3 baths | 987 sq.ft.

$925,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $3291

Traditional Rental Income: $2647

Airbnb ROI: 1.47%

Traditional ROI: 1.58%

35 Double Ox Road

Oak Bluffs, MA

3 beds | N/A baths | 2,475 sq.ft.

$2,250,000

Airbnb cash on cash: 0.06%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $3291

Traditional Rental Income: $3739

Airbnb ROI: 0.06%

Traditional ROI: 0.63%

47 Winemack Street

Oak Bluffs, MA

2 beds | 1 baths | 742 sq.ft.

$1,199,000

Airbnb cash on cash: 0.27%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $2648

Traditional Rental Income: $2817

Airbnb ROI: 0.27%

Traditional ROI: 0.98%

4 High Meadow Lane

Oak Bluffs, MA

4 beds | N/A baths | 2,810 sq.ft.

$2,260,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $2604

Traditional Rental Income: $4171

Airbnb ROI: -0.55%

Traditional ROI: 0.5%

267 Barnes Road

Oak Bluffs, MA

3 beds | N/A baths | 4,046 sq.ft.

$4,395,000

Airbnb cash on cash: -0.86%

Traditional cash on cash: -0.15%

Airbnb Rental Income: $3291

Traditional Rental Income: $5453

Airbnb ROI: -0.86%

Traditional ROI: -0.15%

30 Franklin Avenue

Oak Bluffs, MA

2 beds | 2 baths | 2,137 sq.ft.

$2,150,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $2648

Traditional Rental Income: $3458

Airbnb ROI: -0.31%

Traditional ROI: 0.41%

70 Carol Lane

Oak Bluffs, MA

2 beds | N/A baths | 1,500 sq.ft.

$1,200,000

Airbnb cash on cash: 0.29%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $2648

Traditional Rental Income: $2872

Airbnb ROI: 0.29%

Traditional ROI: 1.06%

30 Sengekontacket Road

Oak Bluffs, MA

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

$2,195,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $2604

Traditional Rental Income: $3918

Airbnb ROI: -0.55%