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
47 Winemack Street Oak Bluffs, MA Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one ...	3 beds \| 2 baths \| 1,302 sq.ft.	$1,100,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 1.15% Airbnb Rental Income: $2832 Traditional Rental Income: $2817 Airbnb ROI: 0.52% Traditional ROI: 1.15%
37 Circuit Avenue #5 Oak Bluffs, MA In-Town Oak Bluffs Condo with Panoramic Water Views Experience the best of island living i...	1 beds \| 1 baths \| 797 sq.ft.	$849,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.16% Airbnb Rental Income: $1959 Traditional Rental Income: $1840 Airbnb ROI: -0.34% Traditional ROI: 0.16%
37 Circuit Avenue #4 Oak Bluffs, MA Intown Oak Bluffs Condo with Panoramic Rooftop Views Discover the charm of island living i...	2 beds \| 1 baths \| 990 sq.ft.	$879,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.42% Airbnb Rental Income: $2807 Traditional Rental Income: $2103 Airbnb ROI: 0.48% Traditional ROI: 0.42%
47 Winemack Avenue Oak Bluffs, MA Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one ...	3 beds \| 2 baths \| 1,302 sq.ft.	$1,100,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 1.6% Airbnb Rental Income: $2832 Traditional Rental Income: $3277 Airbnb ROI: 0.52% Traditional ROI: 1.6%
34 Windemere Road Oak Bluffs, MA Set along the edge of The Lagoon and Brush Pond, this rare offering captures the essence o...	4 beds \| 3 baths \| 1,399 sq.ft.	$2,495,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.18% Airbnb Rental Income: $2597 Traditional Rental Income: $3594 Airbnb ROI: -0.52% Traditional ROI: 0.18%
68 Front Street Oak Bluffs, MA Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous li...	3 beds \| 3 baths \| 2,815 sq.ft.	$1,755,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 0.91% Airbnb Rental Income: $2832 Traditional Rental Income: $3830 Airbnb ROI: -0.1% Traditional ROI: 0.91%
33 Vineyard Avenue Oak Bluffs, MA Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated p...	3 beds \| 3 baths \| 1,439 sq.ft.	$1,695,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.88% Airbnb Rental Income: $2832 Traditional Rental Income: $3377 Airbnb ROI: 0.12% Traditional ROI: 0.88%
44 Tiffany Drive Oak Bluffs, MA Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated ...	4 beds \| 5 baths \| 4,023 sq.ft.	$2,595,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 1.28% Airbnb Rental Income: $2597 Traditional Rental Income: $6787 Airbnb ROI: -0.71% Traditional ROI: 1.28%
3 Troy Street Oak Bluffs, MA Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional p...	3 beds \| 2 baths \| 1,863 sq.ft.	$1,295,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 1.28% Airbnb Rental Income: $2832 Traditional Rental Income: $3331 Airbnb ROI: 0.32% Traditional ROI: 1.28%
11 Beach Road Oak Bluffs, MA Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming tw...	2 beds \| 1 baths \| 560 sq.ft.	$1,745,000	Airbnb cash on cash: -0.08% Traditional cash on cash: -0.26% Airbnb Rental Income: $2807 Traditional Rental Income: $1865 Airbnb ROI: -0.08% Traditional ROI: -0.26%
40 Hidden Cove Road #2 Oak Bluffs, MA Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengek...	3 beds \| 4 baths \| 2,739 sq.ft.	$1,495,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.68% Airbnb Rental Income: $2832 Traditional Rental Income: $4594 Airbnb ROI: -0.07% Traditional ROI: 1.68%
43 Sengekontacket Road Oak Bluffs, MA Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western...	3 beds \| 3 baths \| 2,234 sq.ft.	$5,495,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.79% Airbnb Rental Income: $2832 Traditional Rental Income: $2897 Airbnb ROI: -0.93% Traditional ROI: -0.79%
99 Ocean Avenue Oak Bluffs, MA A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweep...	4 beds \| 3 baths \| 2,600 sq.ft.	$3,700,000	Airbnb cash on cash: -0.85% Traditional cash on cash: -0.28% Airbnb Rental Income: $2597 Traditional Rental Income: $3947 Airbnb ROI: -0.85% Traditional ROI: -0.28%
323 County Road Oak Bluffs, MA This charming Cape-style home is set on a beautifully landscaped lot filled with colorful ...	1 beds \| 2 baths \| 1,428 sq.ft.	$1,095,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 1.05% Airbnb Rental Income: $1959 Traditional Rental Income: $2608 Airbnb ROI: -0.1% Traditional ROI: 1.05%
11 Stanley Street Oak Bluffs, MA Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5...	3 beds \| 2 baths \| 912 sq.ft.	$1,195,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 0.91% Airbnb Rental Income: $2832 Traditional Rental Income: $2580 Airbnb ROI: 0.55% Traditional ROI: 0.91%
2 Winemack Street Oak Bluffs, MA Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs...	3 beds \| 2 baths \| 2,173 sq.ft.	$1,095,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 1.73% Airbnb Rental Income: $2832 Traditional Rental Income: $3255 Airbnb ROI: 0.67% Traditional ROI: 1.73%
27 Beach Road Oak Bluffs, MA WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this w...	5 beds \| 2 baths \| 1,731 sq.ft.	$2,995,000	Airbnb cash on cash: -0.82% Traditional cash on cash: -0.05% Airbnb Rental Income: $2086 Traditional Rental Income: $3669 Airbnb ROI: -0.82% Traditional ROI: -0.05%
33 Island Inn Road #25 F Oak Bluffs, MA Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination ...	1 beds \| 1 baths \| 319 sq.ft.	$260,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 4.59% Airbnb Rental Income: $1959 Traditional Rental Income: $1598 Airbnb ROI: 3.97% Traditional ROI: 4.59%
21 Island Inn Road #38 G Oak Bluffs, MA Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak ...	1 beds \| 2 baths \| 590 sq.ft.	$389,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 2.4% Airbnb Rental Income: $1959 Traditional Rental Income: $1598 Airbnb ROI: 1.97% Traditional ROI: 2.4%
27 Island Inn Road #10C Oak Bluffs, MA Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha's Vineyard ...	1 beds \| 1 baths \| 783 sq.ft.	$310,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 4.35% Airbnb Rental Income: $1959 Traditional Rental Income: $1809 Airbnb ROI: 3.09% Traditional ROI: 4.35%
27 Island Inn Road #9C Oak Bluffs, MA Welcome to 27 Island Inn, Unit 9C, an inviting Martha's Vineyard retreat offering the perf...	1 beds \| 1 baths \| 388 sq.ft.	$287,500	Airbnb cash on cash: 3.45% Traditional cash on cash: 4.18% Airbnb Rental Income: $1959 Traditional Rental Income: $1642 Airbnb ROI: 3.45% Traditional ROI: 4.18%
15 Pequot Avenue Oak Bluffs, MA Oak Bluffs Copeland District -Just One Block from the Beach! Discover the perfect coastal ...	5 beds \| 4 baths \| 161 sq.ft.	$2,150,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.14% Airbnb Rental Income: $2086 Traditional Rental Income: $3167 Airbnb ROI: -0.67% Traditional ROI: 0.14%
51 Winemack Street & 0 Meadow Ave & Nahomon Street Oak Bluffs, MA A unique opportunity to buy two properties on East Chop -- a colonial style 2BR/2BA year-r...	2 beds \| 2 baths \| 1,048 sq.ft.	$1,945,000	Airbnb cash on cash: -0.34% Traditional cash on cash: -0.09% Airbnb Rental Income: $2807 Traditional Rental Income: $2608 Airbnb ROI: -0.34% Traditional ROI: -0.09%
51 Winemack Street Oak Bluffs, MA East Chop -- This colonial style 2BR/2BA year-round home is conveniently located near the ...	2 beds \| 2 baths \| 1,048 sq.ft.	$1,245,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.69% Airbnb Rental Income: $2807 Traditional Rental Income: $2608 Airbnb ROI: 0.29% Traditional ROI: 0.69%

Real Estate investment in Oak-bluffs, MA

There are 25 properties for sale in the city of Oak Bluffs . The median list price in Oak Bluffs is $1,185,935 and the average price per square foot is $809. In November 2026, the average monthly cash on cash return in Oak Bluffs is 1.00%. The average monthly rental income in Oak Bluffs is $2,857.

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

There are 25 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 $2,807.

Your search for investment property begins and ends here

Investment Property for Sale in Oak Bluffs, MA

47 Winemack Street

Oak Bluffs, MA

3 beds | 2 baths | 1,302 sq.ft.

$1,100,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 1.15%

Airbnb Rental Income: $2832

Traditional Rental Income: $2817

Airbnb ROI: 0.52%

Traditional ROI: 1.15%

37 Circuit Avenue #5

Oak Bluffs, MA

1 beds | 1 baths | 797 sq.ft.

$849,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $1959

Traditional Rental Income: $1840

Airbnb ROI: -0.34%

Traditional ROI: 0.16%

37 Circuit Avenue #4

Oak Bluffs, MA

2 beds | 1 baths | 990 sq.ft.

$879,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $2807

Traditional Rental Income: $2103

Airbnb ROI: 0.48%

Traditional ROI: 0.42%

47 Winemack Avenue

Oak Bluffs, MA

3 beds | 2 baths | 1,302 sq.ft.

$1,100,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $2832

Traditional Rental Income: $3277

Airbnb ROI: 0.52%

Traditional ROI: 1.6%

34 Windemere Road

Oak Bluffs, MA

4 beds | 3 baths | 1,399 sq.ft.

$2,495,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 0.18%

Airbnb Rental Income: $2597

Traditional Rental Income: $3594

Airbnb ROI: -0.52%

Traditional ROI: 0.18%

68 Front Street

Oak Bluffs, MA

3 beds | 3 baths | 2,815 sq.ft.

$1,755,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 0.91%

Airbnb Rental Income: $2832

Traditional Rental Income: $3830

Airbnb ROI: -0.1%

Traditional ROI: 0.91%

33 Vineyard Avenue

Oak Bluffs, MA

3 beds | 3 baths | 1,439 sq.ft.

$1,695,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 0.88%

Airbnb Rental Income: $2832

Traditional Rental Income: $3377

Airbnb ROI: 0.12%

Traditional ROI: 0.88%

44 Tiffany Drive

Oak Bluffs, MA

4 beds | 5 baths | 4,023 sq.ft.

$2,595,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $2597

Traditional Rental Income: $6787

Airbnb ROI: -0.71%