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
50 Lantern Lane Vineyard Haven, MA Nestled in a quiet enclave on Lantern Lane, this charming 3-bedroom, 2-bath home offers th...	3 beds \| 2 baths \| 1,040 sq.ft.	$1,195,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.87% Airbnb Rental Income: $3258 Traditional Rental Income: $2812 Airbnb ROI: 0.61% 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: 0.08% Traditional cash on cash: 1.13% Airbnb Rental Income: $3665 Traditional Rental Income: $4454 Airbnb ROI: 0.08% 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: 0.1% Traditional cash on cash: 0.93% Airbnb Rental Income: $3656 Traditional Rental Income: $4403 Airbnb ROI: 0.1% Traditional ROI: 0.93%
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: 0.38% Traditional cash on cash: 0.94% Airbnb Rental Income: $3883 Traditional Rental Income: $3894 Airbnb ROI: 0.38% 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: 1.41% Traditional cash on cash: 1.73% Airbnb Rental Income: $3258 Traditional Rental Income: $2812 Airbnb ROI: 1.41% Traditional ROI: 1.73%
124 Skiff Avenue unit: A-11 #A-11 Vineyard Haven, MA Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and ...	2 beds \| 1 baths \| 725 sq.ft.	$650,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 1.79% Airbnb Rental Income: $3883 Traditional Rental Income: $2111 Airbnb ROI: 3.33% Traditional ROI: 1.79%
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: -1.13% Traditional cash on cash: -0.99% Airbnb Rental Income: $3665 Traditional Rental Income: $4394 Airbnb ROI: -1.13% Traditional ROI: -0.99%
124 Skiff Avenue unit: D10 #D10 Vineyard Haven, MA Bright first-floor, three-bedroom, two bath condo in the popular Vineyard Haven Causeway H...	3 beds \| 2 baths \| 1,356 sq.ft.	$799,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 2.46% Airbnb Rental Income: $3258 Traditional Rental Income: $3037 Airbnb ROI: 1.78% Traditional ROI: 2.46%
139 Main Street Vineyard Haven, MA Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly...	5 beds \| 7 baths \| 4,372 sq.ft.	$3,750,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 0.73% Airbnb Rental Income: $3665 Traditional Rental Income: $7989 Airbnb ROI: -0.74% 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: 1.91% Traditional cash on cash: 1.87% Airbnb Rental Income: $3258 Traditional Rental Income: $2498 Airbnb ROI: 1.91% Traditional ROI: 1.87%
16 Frog Hollow Vineyard Haven, MA Timeless Water View Home on Vineyard Haven Harbor. Nestled between historic Main Street an...	3 beds \| 2 baths \| 1,716 sq.ft.	$4,695,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.64% Airbnb Rental Income: $3258 Traditional Rental Income: $3495 Airbnb ROI: -0.86% Traditional ROI: -0.64%
34 Davis Street Vineyard Haven, MA NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this ...	3 beds \| N/A baths \| 2,453 sq.ft.	$2,395,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.16% Airbnb Rental Income: $3258 Traditional Rental Income: $2998 Airbnb ROI: -0.05% Traditional ROI: 0.16%
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: 0.1% Traditional cash on cash: 0.56% Airbnb Rental Income: $3258 Traditional Rental Income: $3454 Airbnb ROI: 0.1% 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: -0.35% Traditional cash on cash: 0.75% Airbnb Rental Income: $3665 Traditional Rental Income: $5519 Airbnb ROI: -0.35% Traditional ROI: 0.75%

Real Estate investment in Vineyard-haven, MA

There are 14 properties for sale in the city of Vineyard Haven . The median list price in Vineyard Haven is $1,814,500 and the average price per square foot is $848. In October 2025, the average monthly cash on cash return in Vineyard Haven is 1.00%. The average monthly rental income in Vineyard Haven is $3,475.

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

There are 14 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 $3,457.

Your search for investment property begins and ends here

Investment Property for Sale in Vineyard Haven, MA

50 Lantern Lane

Vineyard Haven, MA

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

$1,195,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $3258

Traditional Rental Income: $2812

Airbnb ROI: 0.61%

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: 0.08%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $3665

Traditional Rental Income: $4454

Airbnb ROI: 0.08%

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: 0.1%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $3656

Traditional Rental Income: $4403

Airbnb ROI: 0.1%

Traditional ROI: 0.93%

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: 0.38%

Traditional cash on cash: 0.94%

Airbnb Rental Income: $3883

Traditional Rental Income: $3894

Airbnb ROI: 0.38%

Traditional ROI: 0.94%

345 Franklin Street

Vineyard Haven, MA

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

$949,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $3258

Traditional Rental Income: $2812

Airbnb ROI: 1.41%

Traditional ROI: 1.73%

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

Vineyard Haven, MA

2 beds | 1 baths | 725 sq.ft.

$650,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $3883

Traditional Rental Income: $2111

Airbnb ROI: 3.33%

Traditional ROI: 1.79%

33 Goethals Way

Vineyard Haven, MA

5 beds | 3 baths | 2,794 sq.ft.

$12,500,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: -0.99%

Airbnb Rental Income: $3665

Traditional Rental Income: $4394

Airbnb ROI: -1.13%

Traditional ROI: -0.99%

124 Skiff Avenue unit: D10 #D10

Vineyard Haven, MA

3 beds | 2 baths | 1,356 sq.ft.

$799,000

Airbnb cash on cash: 1.78%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $3258

Traditional Rental Income: $3037

Airbnb ROI: 1.78%