Airbnb Properties for Sale in Oak Bluffs, MA

Looking for a vacation rental investment in Oak Bluffs, MA with high ROI ?

Explore a range of newly added short-term rental homes in Oak Bluffs, MA. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Oak Bluffs, MA

Q: How many Airbnb properties are available for sale in Oak-bluffs?

There are 15 Airbnb properties available for sale in Oak-bluffs

Q: What is the average Airbnb occupancy rate in Oak-bluffs, MA?

In September 2025, the average Airbnb occupancy rate in Oak-bluffs is 25%.

Q: How to get Oak-bluffs, MA Airbnb data?

Airbnb data on vacation rentals in Oak-bluffs, MA is available at Mashvisor. You can access data such as listings, real-time pricing trends, Oak-bluffs, MA market insights, guest information and booking details, seasonality trends and historical Oak-bluffs, MA Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$1,250,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 0.9% Airbnb Rental Income: $4315 Traditional Rental Income: $2817 Airbnb ROI: 1.41% Traditional ROI: 0.9%
37 Circuit Avenue #5 Oak Bluffs, MA Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shop...	1 beds \| 1 baths \| N/A	$935,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.2% Airbnb Rental Income: $3498 Traditional Rental Income: $1840 Airbnb ROI: 1.22% Traditional ROI: 0.2%
37 Circuit Avenue #4 Oak Bluffs, MA Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a s...	2 beds \| 1 baths \| N/A	$985,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 0.39% Airbnb Rental Income: $4315 Traditional Rental Income: $2103 Airbnb ROI: 1.82% Traditional ROI: 0.39%
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.	$1,200,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.06% Airbnb Rental Income: $4315 Traditional Rental Income: $2872 Airbnb ROI: 1.54% Traditional ROI: 1.06%
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: 0.52% Traditional cash on cash: -0.06% Airbnb Rental Income: $3498 Traditional Rental Income: $1921 Airbnb ROI: 0.52% Traditional ROI: -0.06%
37 Circuit Avenue unit: 4 #4 Oak Bluffs, MA Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a s...	2 beds \| 1 baths \| 990 sq.ft.	$985,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.15% Airbnb Rental Income: $4315 Traditional Rental Income: $2319 Airbnb ROI: 2.33% Traditional ROI: 1.15%
37 Circuit Avenue unit: 5 #5 Oak Bluffs, MA Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shop...	1 beds \| 1 baths \| 797 sq.ft.	$935,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 0.92% Airbnb Rental Income: $3498 Traditional Rental Income: $2008 Airbnb ROI: 1.75% Traditional ROI: 0.92%
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: 0.52% Traditional cash on cash: -0.03% Airbnb Rental Income: $3498 Traditional Rental Income: $1963 Airbnb ROI: 0.52% 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: 0.52% Traditional cash on cash: -0.03% Airbnb Rental Income: $3498 Traditional Rental Income: $1963 Airbnb ROI: 0.52% 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: 0.42% Traditional cash on cash: -0.26% Airbnb Rental Income: $4315 Traditional Rental Income: $2155 Airbnb ROI: 0.42% 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: 0.42% Traditional cash on cash: -0.26% Airbnb Rental Income: $4315 Traditional Rental Income: $2155 Airbnb ROI: 0.42% Traditional ROI: -0.26%
4 Quail Run #7 Oak Bluffs, MA Amazing Turnkey End Unit with Kayak & EV Charger! Not to be missed! Island living made eas...	2 beds \| 2 baths \| 1,323 sq.ft.	$941,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1% Airbnb Rental Income: $4315 Traditional Rental Income: $2239 Airbnb ROI: 2.33% Traditional ROI: 1%
1 Onondaga Avenue Oak Bluffs, MA Charming Single Story Cottage on a Beautiful Oak Bluffs Lot - Perfect for Your Vineyard Re...	1 beds \| 1 baths \| 960 sq.ft.	$899,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 1.14% Airbnb Rental Income: $3498 Traditional Rental Income: $2261 Airbnb ROI: 1.69% Traditional ROI: 1.14%
21 Norris Avenue Oak Bluffs, MA An Exciting Opportunity for First-Time Buyers or Island Investors. This long-time family h...	2 beds \| 1 baths \| 1,086 sq.ft.	$800,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 1.44% Airbnb Rental Income: $4315 Traditional Rental Income: $2263 Airbnb ROI: 2.98% Traditional ROI: 1.44%
16 Cottage Oak Bluffs, MA Just steps from the iconic Tabernacle and Trinity Park, this charming cottage is nestled i...	2 beds \| 1 baths \| 954 sq.ft.	$839,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 1.08% Airbnb Rental Income: $4315 Traditional Rental Income: $2089 Airbnb ROI: 2.76% Traditional ROI: 1.08%

Vacation Rentals in Oak Bluffs

There are 15 vacation rental properties available for sale in the city of Oak Bluffs . The median list price of Airbnb properties available for sale in Oak Bluffs is $1,495,000 and the average price per square foot is $904. The cash on cash return on vacation rentals in Oak Bluffs is 1.00%. The average monthly short term rental income in Oak Bluffs is $3,515.

Oak Bluffs, MA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 15 Airbnb properties available for sale in Oak Bluffs.

In 2025, the best neighborhood to buy short term rental property is Oak Bluffs.

In September 2025, the average Airbnb occupancy rate in Oak Bluffs is 25%.

Airbnb data on vacation rentals in Oak Bluffs, MA is available at Mashvisor. You can access data such as listings, real-time pricing trends, Oak Bluffs, MA market insights, guest information and booking details, seasonality trends and historical Oak Bluffs, MA Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Oak Bluffs, MA

47 Winemack Street

Oak Bluffs, MA

2 beds | 1 baths | 742 sq.ft.

$1,250,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $4315

Traditional Rental Income: $2817

Airbnb ROI: 1.41%

Traditional ROI: 0.9%

37 Circuit Avenue #5

Oak Bluffs, MA

1 beds | 1 baths | N/A

$935,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $3498

Traditional Rental Income: $1840

Airbnb ROI: 1.22%

Traditional ROI: 0.2%

37 Circuit Avenue #4

Oak Bluffs, MA

2 beds | 1 baths | N/A

$985,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $4315

Traditional Rental Income: $2103

Airbnb ROI: 1.82%

Traditional ROI: 0.39%

70 Carol Lane

Oak Bluffs, MA

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

$1,200,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $4315

Traditional Rental Income: $2872

Airbnb ROI: 1.54%

Traditional ROI: 1.06%

47 E Chop Drive unit: #5 #5

Oak Bluffs, MA

1 beds | 1 baths | 650 sq.ft.

$1,495,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $3498

Traditional Rental Income: $1921

Airbnb ROI: 0.52%

Traditional ROI: -0.06%

37 Circuit Avenue unit: 4 #4

Oak Bluffs, MA

2 beds | 1 baths | 990 sq.ft.

$985,000

Airbnb cash on cash: 2.33%

Traditional cash on cash: 1.15%

Airbnb Rental Income: $4315

Traditional Rental Income: $2319

Airbnb ROI: 2.33%

Traditional ROI: 1.15%

37 Circuit Avenue unit: 5 #5

Oak Bluffs, MA

1 beds | 1 baths | 797 sq.ft.

$935,000

Airbnb cash on cash: 1.75%

Traditional cash on cash: 0.92%

Airbnb Rental Income: $3498

Traditional Rental Income: $2008

Airbnb ROI: 1.75%

Traditional ROI: 0.92%

47 E Chop Drive unit: #1 #1

Oak Bluffs, MA

1 beds | 1 baths | 731 sq.ft.

$1,495,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: -0.03%

Airbnb Rental Income: $3498

Traditional Rental Income: $1963

Airbnb ROI: 0.52%