Real Estate Investment Properties for Sale in Vineyard Haven, MA

Looking for investment property in Vineyard Haven, MA with high ROI ?

Explore a variety of short-term homes & houses in Vineyard Haven, MA. Invest wisely with VRBO & Vineyard Haven, 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 Vineyard Haven, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
169 Clover Hill Drive Vineyard Haven, MA Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home sits on a g...	3 beds \| 2 baths \| 1,809 sq.ft.	$1,350,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.97% Airbnb Rental Income: $3110 Traditional Rental Income: $3257 Airbnb ROI: 0.29% Traditional ROI: 0.97%
50 Lantern Lane Vineyard Haven, MA *NOTE: The seller is offering a $25,000 credit towards the required septic upgrade. Nestle...	3 beds \| 2 baths \| 1,040 sq.ft.	$1,193,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 0.87% Airbnb Rental Income: $3110 Traditional Rental Income: $2812 Airbnb ROI: 0.5% Traditional ROI: 0.87%
36 Ferro Way Vineyard Haven, MA Drone shots and virtual staging coming soon. Welcome to 36 Ferro Way in beautiful Tisbury,...	5 beds \| N/A baths \| 4,032 sq.ft.	$1,630,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 1.13% Airbnb Rental Income: $3929 Traditional Rental Income: $4454 Airbnb ROI: 0.23% Traditional ROI: 1.13%
5 Pine Tree Lane Vineyard Haven, MA Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in...	4 beds \| 3 baths \| 2,730 sq.ft.	$1,999,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0.93% Airbnb Rental Income: $3124 Traditional Rental Income: $4403 Airbnb ROI: -0.14% Traditional ROI: 0.93%
36 Tashmoo Avenue Vineyard Haven, MA This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic ...	4 beds \| 3 baths \| 2,770 sq.ft.	$2,995,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.1% Airbnb Rental Income: $3124 Traditional Rental Income: $3875 Airbnb ROI: -0.43% Traditional ROI: 0.1%
26 Union Court unit: 7 #7 Vineyard Haven, MA Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town li...	2 beds \| N/A baths \| 1,532 sq.ft.	$1,625,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.94% Airbnb Rental Income: $3213 Traditional Rental Income: $3894 Airbnb ROI: 0.01% Traditional ROI: 0.94%
345 Franklin Street Vineyard Haven, MA Charming Cape-style home in Vineyard Haven, ideally located just minutes from Downtown and...	3 beds \| 2 baths \| 1,012 sq.ft.	$949,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 1.73% Airbnb Rental Income: $3110 Traditional Rental Income: $2812 Airbnb ROI: 1.27% Traditional ROI: 1.73%
124 Skiff Avenue unit: A-11 #A-11 Vineyard Haven, MA Newly priced ~ fully renovated building and move-in ready! Outstanding, year-round, two-be...	2 beds \| 1 baths \| 725 sq.ft.	$599,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.03% Airbnb Rental Income: $3213 Traditional Rental Income: $2111 Airbnb ROI: 2.7% Traditional ROI: 2.03%
33 Goethals Way Vineyard Haven, MA A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage re...	5 beds \| 3 baths \| 2,794 sq.ft.	$12,500,000	Airbnb cash on cash: -1.11% Traditional cash on cash: -0.99% Airbnb Rental Income: $3929 Traditional Rental Income: $4394 Airbnb ROI: -1.11% Traditional ROI: -0.99%
124 Skiff Avenue unit: D10 #D10 Vineyard Haven, MA Enjoy effortless year-round living with easy access to Vineyard Haven's downtown shops, re...	3 beds \| 2 baths \| 1,356 sq.ft.	$725,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 2.81% Airbnb Rental Income: $3110 Traditional Rental Income: $3037 Airbnb ROI: 1.87% Traditional ROI: 2.81%
139 Main Street Vineyard Haven, MA Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly...	5 beds \| N/A baths \| 4,372 sq.ft.	$3,750,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.73% Airbnb Rental Income: $3929 Traditional Rental Income: $7989 Airbnb ROI: -0.68% Traditional ROI: 0.73%
10 Putnam Way Vineyard Haven, MA Raised ranch style house on a corner lot near the lagoon. This could be the ''fixer upper'...	3 beds \| 1 baths \| 1,168 sq.ft.	$700,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 1.87% Airbnb Rental Income: $3110 Traditional Rental Income: $2498 Airbnb ROI: 1.72% Traditional ROI: 1.87%
34 Davis Street Vineyard Haven, MA NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this ...	3 beds \| 4 baths \| 2,453 sq.ft.	$2,195,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 0.27% Airbnb Rental Income: $3110 Traditional Rental Income: $2998 Airbnb ROI: -0.03% Traditional ROI: 0.27%
33 Lagoon Pond Road Vineyard Haven, MA Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtf...	3 beds \| 3 baths \| 1,680 sq.ft.	$2,150,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 0.56% Airbnb Rental Income: $3110 Traditional Rental Income: $3454 Airbnb ROI: 0.04% Traditional ROI: 0.56%
159 Lake Street Vineyard Haven, MA Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy an...	5 beds \| 4 baths \| 3,329 sq.ft.	$2,595,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.75% Airbnb Rental Income: $3929 Traditional Rental Income: $5519 Airbnb ROI: -0.26% Traditional ROI: 0.75%
22 Old Lighthouse Road Vineyard Haven, MA This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vi...	5 beds \| 3 baths \| 1,811 sq.ft.	$1,595,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 0.82% Airbnb Rental Income: $3929 Traditional Rental Income: $3631 Airbnb ROI: 0.45% Traditional ROI: 0.82%
51 Lantern Lane Vineyard Haven, MA Find your sweet spot in this charming starter home, ideally located on a quiet street yet ...	2 beds \| 1 baths \| 768 sq.ft.	$835,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 0.97% Airbnb Rental Income: $3213 Traditional Rental Income: $2076 Airbnb ROI: 1.5% Traditional ROI: 0.97%
344 Greenwood Avenue Vineyard Haven, MA This move-in ready four-bedroom, being offered fully furnished, delivers effortless living...	4 beds \| 2 baths \| 1,566 sq.ft.	$1,300,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.28% Airbnb Rental Income: $3124 Traditional Rental Income: $3586 Airbnb ROI: 0.31% Traditional ROI: 1.28%
33 Alyssa Lane Vineyard Haven, MA Country Living so close to Town! Lovely 3/4 Bedroom 2,304 sq ft Colonial Cape with Garage ...	3 beds \| 3 baths \| 2,304 sq.ft.	$1,495,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.09% Airbnb Rental Income: $3110 Traditional Rental Income: $3663 Airbnb ROI: 0.18% Traditional ROI: 1.09%

Real Estate investment in Vineyard-haven, MA

There are 19 properties for sale in the city of Vineyard Haven . The median list price in Vineyard Haven is $1,595,000 and the average price per square foot is $772. In December 2025, the average monthly cash on cash return in Vineyard Haven is 1.00%. The average monthly rental income in Vineyard Haven is $3,520.

Vineyard-haven, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 19 investment properties available for sale in Vineyard-haven.

In 2025, the best neighborhood to buy investment property is Vineyard Haven.

The ROI for Short-Term is higher than the Long-Term in Vineyard-haven with average rental income of $3,124.

Your search for investment property begins and ends here

Investment Property for Sale in Vineyard Haven, MA

169 Clover Hill Drive

Vineyard Haven, MA

3 beds | 2 baths | 1,809 sq.ft.

$1,350,000

Airbnb cash on cash: 0.29%

Traditional cash on cash: 0.97%

Airbnb Rental Income: $3110

Traditional Rental Income: $3257

Airbnb ROI: 0.29%

Traditional ROI: 0.97%

50 Lantern Lane

Vineyard Haven, MA

3 beds | 2 baths | 1,040 sq.ft.

$1,193,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $3110

Traditional Rental Income: $2812

Airbnb ROI: 0.5%

Traditional ROI: 0.87%

36 Ferro Way

Vineyard Haven, MA

5 beds | N/A baths | 4,032 sq.ft.

$1,630,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $3929

Traditional Rental Income: $4454

Airbnb ROI: 0.23%

Traditional ROI: 1.13%

5 Pine Tree Lane

Vineyard Haven, MA

4 beds | 3 baths | 2,730 sq.ft.

$1,999,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $3124

Traditional Rental Income: $4403

Airbnb ROI: -0.14%

Traditional ROI: 0.93%

36 Tashmoo Avenue

Vineyard Haven, MA

4 beds | 3 baths | 2,770 sq.ft.

$2,995,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $3124

Traditional Rental Income: $3875

Airbnb ROI: -0.43%

Traditional ROI: 0.1%

26 Union Court unit: 7 #7

Vineyard Haven, MA

2 beds | N/A baths | 1,532 sq.ft.

$1,625,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 0.94%

Airbnb Rental Income: $3213

Traditional Rental Income: $3894

Airbnb ROI: 0.01%

Traditional ROI: 0.94%

345 Franklin Street

Vineyard Haven, MA

3 beds | 2 baths | 1,012 sq.ft.

$949,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $3110

Traditional Rental Income: $2812

Airbnb ROI: 1.27%

Traditional ROI: 1.73%

124 Skiff Avenue unit: A-11 #A-11

Vineyard Haven, MA

2 beds | 1 baths | 725 sq.ft.

$599,000

Airbnb cash on cash: 2.7%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $3213

Traditional Rental Income: $2111

Airbnb ROI: 2.7%