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 \| 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.	$1,250,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 0.9% Airbnb Rental Income: $2648 Traditional Rental Income: $2817 Airbnb ROI: 0.22% Traditional ROI: 0.9%
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 \| 3 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 \| 3 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%
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%
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.	$2,700,000	Airbnb cash on cash: -0.35% Traditional cash on cash: -0.51% Airbnb Rental Income: $3291 Traditional Rental Income: $2162 Airbnb ROI: -0.35% Traditional ROI: -0.51%
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: 0.21% 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%
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.	$835,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 1.3% Airbnb Rental Income: $3384 Traditional Rental Income: $2261 Airbnb ROI: 1.78% Traditional ROI: 1.3%
39 Sengekontacket Road Oak Bluffs, MA SPECTACULAR WATERFRONT home with stunning water views from every room and completely renov...	4 beds \| N/A baths \| 2,861 sq.ft.	$4,075,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 0% Airbnb Rental Income: $2604 Traditional Rental Income: $5380 Airbnb ROI: -0.9% Traditional ROI: 0%
35 Tower Ridge Road Oak Bluffs, MA Thoughtfully designed post-and-beam home that blends character with modern comfort and fle...	3 beds \| 4 baths \| 2,558 sq.ft.	$1,895,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.11% Airbnb Rental Income: $3291 Traditional Rental Income: $4440 Airbnb ROI: 0.03% Traditional ROI: 1.11%
4 Canonicus Avenue Oak Bluffs, MA With a striking presence overlooking Nantucket Sound and just moments from the vibrant pul...	6 beds \| 4 baths \| 2,890 sq.ft.	$5,325,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -1.28% Airbnb Rental Income: $4898 Traditional Rental Income: $4757 Airbnb ROI: -1.45% Traditional ROI: -1.28%
44 Iron Hill Road Oak Bluffs, MA Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca...	3 beds \| N/A 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	$1,250,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 1.3% Airbnb Rental Income: $3291 Traditional Rental Income: $3277 Airbnb ROI: 0.68% Traditional ROI: 1.3%
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 \| N/A baths \| 3,268 sq.ft.	$1,850,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 1.04% Airbnb Rental Income: $2604 Traditional Rental Income: $4468 Airbnb ROI: -0.41% Traditional ROI: 1.04%
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%
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: 0.99% Traditional cash on cash: 1.08% Airbnb Rental Income: $2648 Traditional Rental Income: $2089 Airbnb ROI: 0.99% 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.	$3,250,000	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%
41 Trinity Park Oak Bluffs, MA Step back in time with this quintessential Martha's Vineyard Campground Cottage, nestled i...	4 beds \| 1 baths \| 1,154 sq.ft.	$795,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 2.06% Airbnb Rental Income: $2604 Traditional Rental Income: $2759 Airbnb ROI: 1.01% Traditional ROI: 2.06%
26 Hampson Avenue Oak Bluffs, MA Location, Location, Location! This unique property on the beautiful island of Martha's Vin...	2 beds \| 2 baths \| 1,078 sq.ft.	$999,999	Airbnb cash on cash: 0.66% Traditional cash on cash: 1.31% Airbnb Rental Income: $2648 Traditional Rental Income: $2627 Airbnb ROI: 0.66% Traditional ROI: 1.31%
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 \| 3 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%

Real Estate investment in Oak-bluffs, MA

There are 31 properties for sale in the city of Oak Bluffs . The median list price in Oak Bluffs is $1,895,000 and the average price per square foot is $1,021. In November 2025, 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 31 investment properties available for sale in Oak-bluffs.

In 2025, 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 | 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.

$1,250,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $2648

Traditional Rental Income: $2817

Airbnb ROI: 0.22%

Traditional ROI: 0.9%

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 | 3 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 | 3 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%