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 32 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 28%.

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
2 Upper Douglas Lane Oak Bluffs, MA Are you still looking for a year-round, island home for your family and only finding homes...	4 beds \| 2 baths \| 1,584 sq.ft.	$1,333,333	Airbnb cash on cash: 2.52% Traditional cash on cash: 1.13% Airbnb Rental Income: $6095 Traditional Rental Income: $3162 Airbnb ROI: 2.52% Traditional ROI: 1.13%
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: 3.51% Traditional cash on cash: 1.58% Airbnb Rental Income: $5399 Traditional Rental Income: $2647 Airbnb ROI: 3.51% Traditional ROI: 1.58%
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: 3.49% Traditional cash on cash: 0.9% Airbnb Rental Income: $7212 Traditional Rental Income: $2817 Airbnb ROI: 3.49% Traditional ROI: 0.9%
25 Oak Avenue Oak Bluffs, MA WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenu...	2 beds \| 1 baths \| N/A	$669,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 1.98% Airbnb Rental Income: $7212 Traditional Rental Income: $2316 Airbnb ROI: 7.6% Traditional ROI: 1.98%
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 \| 4 baths \| 2,810 sq.ft.	$2,445,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 0.39% Airbnb Rental Income: $6095 Traditional Rental Income: $4171 Airbnb ROI: 0.7% Traditional ROI: 0.39%
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: 3.93% Traditional cash on cash: 0.2% Airbnb Rental Income: $6332 Traditional Rental Income: $1840 Airbnb ROI: 3.93% 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: 4.45% Traditional cash on cash: 0.39% Airbnb Rental Income: $7212 Traditional Rental Income: $2103 Airbnb ROI: 4.45% Traditional ROI: 0.39%
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.	$2,150,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 0.41% Airbnb Rental Income: $7212 Traditional Rental Income: $3458 Airbnb ROI: 1.59% Traditional ROI: 0.41%
10 Wood Duck Way Oak Bluffs, MA Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully ...	4 beds \| 4 baths \| 1 sq.ft.	$2,395,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 0.43% Airbnb Rental Income: $6095 Traditional Rental Income: $4407 Airbnb ROI: 0.65% Traditional ROI: 0.43%
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: 3.7% Traditional cash on cash: 1.06% Airbnb Rental Income: $7212 Traditional Rental Income: $2872 Airbnb ROI: 3.7% 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: 0.88% Traditional cash on cash: 0.4% Airbnb Rental Income: $6095 Traditional Rental Income: $3918 Airbnb ROI: 0.88% Traditional ROI: 0.4%
4 Dempster Park Oak Bluffs, MA East Chop -- This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled ...	4 beds \| 3 baths \| 1,825 sq.ft.	$2,195,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 0.49% Airbnb Rental Income: $6095 Traditional Rental Income: $3618 Airbnb ROI: 1.11% Traditional ROI: 0.49%
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: 2.22% Traditional cash on cash: -0.06% Airbnb Rental Income: $6332 Traditional Rental Income: $1921 Airbnb ROI: 2.22% Traditional ROI: -0.06%
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.	$3,100,000	Airbnb cash on cash: 0.18% Traditional cash on cash: -0.57% Airbnb Rental Income: $5399 Traditional Rental Income: $2162 Airbnb ROI: 0.18% Traditional ROI: -0.57%
16 Atlantic Avenue Oak Bluffs, MA East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse ...	5 beds \| 3 baths \| 2,577 sq.ft.	$2,495,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 0.09% Airbnb Rental Income: $6402 Traditional Rental Income: $3605 Airbnb ROI: 0.75% Traditional ROI: 0.09%
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: 4.97% Traditional cash on cash: 1.15% Airbnb Rental Income: $7212 Traditional Rental Income: $2319 Airbnb ROI: 4.97% 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: 4.46% Traditional cash on cash: 0.92% Airbnb Rental Income: $6332 Traditional Rental Income: $2008 Airbnb ROI: 4.46% 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: 2.22% Traditional cash on cash: -0.03% Airbnb Rental Income: $6332 Traditional Rental Income: $1963 Airbnb ROI: 2.22% 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: 2.22% Traditional cash on cash: -0.03% Airbnb Rental Income: $6332 Traditional Rental Income: $1963 Airbnb ROI: 2.22% 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: 1.72% Traditional cash on cash: -0.26% Airbnb Rental Income: $7212 Traditional Rental Income: $2155 Airbnb ROI: 1.72% 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: 1.72% Traditional cash on cash: -0.26% Airbnb Rental Income: $7212 Traditional Rental Income: $2155 Airbnb ROI: 1.72% 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: 5.09% Traditional cash on cash: 1% Airbnb Rental Income: $7212 Traditional Rental Income: $2239 Airbnb ROI: 5.09% 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: 4.51% Traditional cash on cash: 1.14% Airbnb Rental Income: $6332 Traditional Rental Income: $2261 Airbnb ROI: 4.51% Traditional ROI: 1.14%
32 Beach Road Oak Bluffs, MA Tucked along a main road in Oak Bluffs, this small yet cozy year-round cottage offers a ch...	3 beds \| 2 baths \| 836 sq.ft.	$1,050,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 1.16% Airbnb Rental Income: $5399 Traditional Rental Income: $2649 Airbnb ROI: 2.86% Traditional ROI: 1.16%
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: 6.22% Traditional cash on cash: 1.44% Airbnb Rental Income: $7212 Traditional Rental Income: $2263 Airbnb ROI: 6.22% Traditional ROI: 1.44%
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.	$1,350,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 1% Airbnb Rental Income: $5399 Traditional Rental Income: $2992 Airbnb ROI: 2.05% Traditional ROI: 1%
11 Onondaga Avenue Oak Bluffs, MA Comfortable Island Home on a Quiet Dead-End Road in Oak Bluffs: Welcome to 11 Onondaga Ave...	3 beds \| 3 baths \| 1,624 sq.ft.	$1,250,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 1.51% Airbnb Rental Income: $5399 Traditional Rental Income: $3473 Airbnb ROI: 2.23% Traditional ROI: 1.51%
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	$1,250,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 1.3% Airbnb Rental Income: $5399 Traditional Rental Income: $3277 Airbnb ROI: 2.19% Traditional ROI: 1.3%
46 Kennebec Avenue Oak Bluffs, MA Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority,...	4 beds \| 2 baths \| 1,305 sq.ft.	$1,495,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 0.8% Airbnb Rental Income: $6095 Traditional Rental Income: $3190 Airbnb ROI: 2.02% Traditional ROI: 0.8%
5 Johns Way Oak Bluffs, MA Property is being offered via Real Estate Auction on Wednesday, September 17 at 12pm on-si...	3 beds \| 2 baths \| 1,365 sq.ft.	$950,600	Airbnb cash on cash: 3.74% Traditional cash on cash: 2.36% Airbnb Rental Income: $5399 Traditional Rental Income: $3091 Airbnb ROI: 3.74% Traditional ROI: 2.36%
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: 5.85% Traditional cash on cash: 1.08% Airbnb Rental Income: $7212 Traditional Rental Income: $2089 Airbnb ROI: 5.85% Traditional ROI: 1.08%
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.	$3,450,000	Airbnb cash on cash: 0.06% Traditional cash on cash: -0.31% Airbnb Rental Income: $6095 Traditional Rental Income: $3705 Airbnb ROI: 0.06% Traditional ROI: -0.31%

Vacation Rentals in Oak Bluffs

There are 32 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 $915. The cash on cash return on vacation rentals in Oak Bluffs is 2.00%. The average monthly short term rental income in Oak Bluffs is $6,214.

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

There are 32 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 28%.

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

2 Upper Douglas Lane

Oak Bluffs, MA

4 beds | 2 baths | 1,584 sq.ft.

$1,333,333

Airbnb cash on cash: 2.52%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $6095

Traditional Rental Income: $3162

Airbnb ROI: 2.52%

Traditional ROI: 1.13%

1 Cottage Park

Oak Bluffs, MA

3 beds | 3 baths | 987 sq.ft.

$925,000

Airbnb cash on cash: 3.51%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $5399

Traditional Rental Income: $2647

Airbnb ROI: 3.51%

Traditional ROI: 1.58%

47 Winemack Street

Oak Bluffs, MA

2 beds | 1 baths | 742 sq.ft.

$1,250,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $7212

Traditional Rental Income: $2817

Airbnb ROI: 3.49%

Traditional ROI: 0.9%

25 Oak Avenue

Oak Bluffs, MA

2 beds | 1 baths | N/A

$669,000

Airbnb cash on cash: 7.6%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $7212

Traditional Rental Income: $2316

Airbnb ROI: 7.6%

Traditional ROI: 1.98%

4 High Meadow Lane

Oak Bluffs, MA

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

$2,445,000

Airbnb cash on cash: 0.7%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $6095

Traditional Rental Income: $4171

Airbnb ROI: 0.7%

Traditional ROI: 0.39%

37 Circuit Avenue #5

Oak Bluffs, MA

1 beds | 1 baths | N/A

$935,000

Airbnb cash on cash: 3.93%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $6332

Traditional Rental Income: $1840

Airbnb ROI: 3.93%

Traditional ROI: 0.2%

37 Circuit Avenue #4

Oak Bluffs, MA

2 beds | 1 baths | N/A

$985,000

Airbnb cash on cash: 4.45%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $7212

Traditional Rental Income: $2103

Airbnb ROI: 4.45%

Traditional ROI: 0.39%

30 Franklin Avenue

Oak Bluffs, MA

2 beds | 3 baths | 2,137 sq.ft.

$2,150,000

Airbnb cash on cash: 1.59%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $7212

Traditional Rental Income: $3458

Airbnb ROI: 1.59%