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
1 Cottage Park Oak Bluffs, MA The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs wit...	3 beds \| 2 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 Rd Oak Bluffs, MA NEW CONSTRUCTION ~Welcome to Lagoon Ridge, Oak Bluffs' newest and most sought-after neighb...	3 beds \| 3 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%
4 High Meadow Ln Oak Bluffs, MA Classic Post & Beam set in Meadow View Farms This bright and charming four-bedroom home si...	4 beds \| 3 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 \| 6 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%
12 & 14 Maple Ave 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: 0.01% Traditional cash on cash: 0.66% Airbnb Rental Income: $3208 Traditional Rental Income: $3598 Airbnb ROI: 0.01% Traditional ROI: 0.66%
70 Carol Ln 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: 0.35% Traditional cash on cash: 1.15% Airbnb Rental Income: $2648 Traditional Rental Income: $2872 Airbnb ROI: 0.35% 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: -0.55% 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 \| 3 baths \| 5,165 sq.ft.	$2,900,000	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%
47 E Chop Drive unit: #5 #5 Oak Bluffs, MA East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Ca...	1 beds \| 1 baths \| 650 sq.ft.	$1,495,000	Airbnb cash on cash: 0.45% Traditional cash on cash: -0.06% Airbnb Rental Income: $3384 Traditional Rental Income: $1921 Airbnb ROI: 0.45% Traditional ROI: -0.06%
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%
47 E Chop Drive unit: #1 #1 Oak Bluffs, MA East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condomin...	1 beds \| 1 baths \| 731 sq.ft.	$1,495,000	Airbnb cash on cash: 0.45% Traditional cash on cash: -0.03% Airbnb Rental Income: $3384 Traditional Rental Income: $1963 Airbnb ROI: 0.45% Traditional ROI: -0.03%
47 E Chop Drive unit: #2 #2 Oak Bluffs, MA East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cott...	1 beds \| 1 baths \| 736 sq.ft.	$1,495,000	Airbnb cash on cash: 0.45% Traditional cash on cash: -0.03% Airbnb Rental Income: $3384 Traditional Rental Income: $1963 Airbnb ROI: 0.45% Traditional ROI: -0.03%
47 E Chop Drive unit: #3 #3 Oak Bluffs, MA East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highl...	2 beds \| 1 baths \| 802 sq.ft.	$1,995,000	Airbnb cash on cash: -0.33% Traditional cash on cash: -0.26% Airbnb Rental Income: $2648 Traditional Rental Income: $2155 Airbnb ROI: -0.33% Traditional ROI: -0.26%
47 E Chop Drive unit: #4 #4 Oak Bluffs, MA East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condom...	2 beds \| 1 baths \| 879 sq.ft.	$1,995,000	Airbnb cash on cash: -0.33% Traditional cash on cash: -0.26% Airbnb Rental Income: $2648 Traditional Rental Income: $2155 Airbnb ROI: -0.33% Traditional ROI: -0.26%
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%
47 Winemack Avenue Oak Bluffs, MA Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent th...	3 beds \| 2 baths \| N/A	$1,199,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.39% Airbnb Rental Income: $3291 Traditional Rental Income: $3277 Airbnb ROI: 0.74% Traditional ROI: 1.39%
7 Upper Meadow Ln Oak Bluffs, MA Meadowview Farms - This home is ideal for those who love to host lively gatherings! Set at...	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%
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%
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%
26 Winthrop Ave 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: 1.78% Traditional cash on cash: 0.51% Airbnb Rental Income: $3384 Traditional Rental Income: $1622 Airbnb ROI: 1.78% Traditional ROI: 0.51%
35 New York Ave Oak Bluffs, MA An exceptional chance to own one of the few five-unit apartment buildings available on Mar...	7 beds \| 5 baths \| 3,880 sq.ft.	$3,500,000	Airbnb cash on cash: -1.05% Traditional cash on cash: -0.3% Airbnb Rental Income: $4898 Traditional Rental Income: $6347 Airbnb ROI: -1.05% Traditional ROI: -0.3%

Real Estate investment in Oak-bluffs, MA

There are 29 properties for sale in the city of Oak Bluffs . The median list price in Oak Bluffs is $1,910,000 and the average price per square foot is $948. In March 2026, the average monthly cash on cash return in Oak Bluffs is N/A%. The average monthly rental income in Oak Bluffs is $2,984.

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

There are 29 investment properties available for sale in Oak-bluffs.

In 2026, 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 $2,648.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Bluffs, MA

1 Cottage Park

Oak Bluffs, MA

3 beds | 2 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 Rd

Oak Bluffs, MA

3 beds | 3 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%

4 High Meadow Ln

Oak Bluffs, MA

4 beds | 3 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 | 6 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%

12 & 14 Maple Ave

Oak Bluffs, MA

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

$1,830,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $3208

Traditional Rental Income: $3598

Airbnb ROI: 0.01%

Traditional ROI: 0.66%

70 Carol Ln

Oak Bluffs, MA

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

$1,150,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 1.15%

Airbnb Rental Income: $2648

Traditional Rental Income: $2872

Airbnb ROI: 0.35%

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: -0.55%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $2604

Traditional Rental Income: $3918

Airbnb ROI: -0.55%