Real Estate Investment Properties for Sale in Westport, MA

Looking for investment property in Westport, MA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
219-R Tickle Rd Westport, MA Discover unparalleled tranquility at your breathtaking, lakefront retreat. Custom-built an...	3 beds \| 2 baths \| 1,200 sq.ft.	$599,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.45% Airbnb Rental Income: $1710 Traditional Rental Income: $2881 Airbnb ROI: 0.51% Traditional ROI: 3.45%
27 Dias Ave Westport, MA PRICE IMPROVEMENT! Set on a peaceful, expansive lot at the end of a quiet street, this bea...	3 beds \| 2 baths \| 1,421 sq.ft.	$775,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 2.65% Airbnb Rental Income: $1710 Traditional Rental Income: $3084 Airbnb ROI: 0.09% Traditional ROI: 2.65%
128 Old Bedford Rd Westport, MA This spacious 5-bedroom, 2.5-bath home offers an updated interior and a layout designed fo...	5 beds \| 2 baths \| 2,683 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $4196 Airbnb ROI: N/A Traditional ROI: 4.78%
9 Kyle Jacob Road Westport, MA Nestled in beautiful Westport, MA, this stunning executive ranch presents an exceptional o...	3 beds \| 2 baths \| 3,208 sq.ft.	$1,195,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.92% Airbnb Rental Income: $1710 Traditional Rental Income: $3953 Airbnb ROI: -0.53% Traditional ROI: 1.92%
2 Winterberry Ln Westport, MA Tucked away at 2 Winterberry Ln in Westport's established Trout Pond Acres community, this...	4 beds \| 2 baths \| 3,442 sq.ft.	$974,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 2.49% Airbnb Rental Income: $2663 Traditional Rental Income: $3797 Airbnb ROI: 0.54% Traditional ROI: 2.49%
1702 Drift Road Westport, MA CLASSIC WITH A CONTEMPORARY TWIST Welcome to 1702 J Drift Road. Located in a waterfront en...	3 beds \| 2 baths \| 4,097 sq.ft.	$2,475,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 0.3% Airbnb Rental Income: $1710 Traditional Rental Income: $3905 Airbnb ROI: -0.87% Traditional ROI: 0.3%
41 RIVERVIEW Drive Westport, MA Step into this charming contemporary home where classic design elements blend seamlessly w...	3 beds \| 2 baths \| 1,900 sq.ft.	$819,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.8% Airbnb Rental Income: $1710 Traditional Rental Income: $3348 Airbnb ROI: 0.03% Traditional ROI: 2.8%

Real Estate investment in Westport, MA

There are 9 properties for sale in the city of Westport . The median list price in Westport is $2,792,500 and the average price per square foot is $574. In March 2026, the average monthly cash on cash return in Westport is 2.00%. The average monthly rental income in Westport is $3,545.

Westport, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 9 investment properties available for sale in Westport.

In 2026, the best neighborhood to buy investment property is Westport.

The ROI for Short-Term is higher than the Long-Term in Westport with average rental income of $1,710.

Your search for investment property begins and ends here

Investment Property for Sale in Westport, MA

219-R Tickle Rd

Westport, MA

3 beds | 2 baths | 1,200 sq.ft.

$599,900

Airbnb cash on cash: 0.51%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $1710

Traditional Rental Income: $2881

Airbnb ROI: 0.51%

Traditional ROI: 3.45%

27 Dias Ave

Westport, MA

3 beds | 2 baths | 1,421 sq.ft.

$775,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $1710

Traditional Rental Income: $3084

Airbnb ROI: 0.09%

Traditional ROI: 2.65%

128 Old Bedford Rd

Westport, MA

5 beds | 2 baths | 2,683 sq.ft.

$699,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.78%

Airbnb Rental Income: $null

Traditional Rental Income: $4196

Airbnb ROI: N/A

Traditional ROI: 4.78%

9 Kyle Jacob Road

Westport, MA

3 beds | 2 baths | 3,208 sq.ft.

$1,195,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $1710

Traditional Rental Income: $3953

Airbnb ROI: -0.53%

Traditional ROI: 1.92%

2 Winterberry Ln

Westport, MA

4 beds | 2 baths | 3,442 sq.ft.

$974,900

Airbnb cash on cash: 0.54%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $2663

Traditional Rental Income: $3797

Airbnb ROI: 0.54%

Traditional ROI: 2.49%

1702 Drift Road

Westport, MA

3 beds | 2 baths | 4,097 sq.ft.

$2,475,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1710

Traditional Rental Income: $3905

Airbnb ROI: -0.87%

Traditional ROI: 0.3%

41 RIVERVIEW Drive

Westport, MA

3 beds | 2 baths | 1,900 sq.ft.

$819,900

Airbnb cash on cash: 0.03%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $1710

Traditional Rental Income: $3348

Airbnb ROI: 0.03%

Traditional ROI: 2.8%

Real Estate investment in Westport, MA

Westport, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

How many investment properties are available for sale in Westport?

Which neighborhoods in Westport to invest in 2026?

Long-Term vs. Short-Term Rentals in Westport, Massachusetts: Which will earn the best returns?

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