Real Estate Investment Properties for Sale in Holliston, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20 Constitution Cir Holliston, MA Step into your dream home! This stunning 4 bed, 3 bath colonial is nestled on a 2 acre lot...	4 beds \| 3 baths \| 3,872 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.54% Airbnb Rental Income: $null Traditional Rental Income: $4342 Airbnb ROI: N/A Traditional ROI: 1.54%
15 Whispering Lane Holliston, MA Meticulous craftsmanship defines this exceptional home in the coveted Deer Creek community...	5 beds \| 4 baths \| 6,498 sq.ft.	$1,650,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 1.89% Airbnb Rental Income: $2860 Traditional Rental Income: $6446 Airbnb ROI: -0.88% Traditional ROI: 1.89%
66 Lakeshore Dr Holliston, MA Property is available for online auction only. See Realty Bid for property, auction, showi...	2 beds \| 1 baths \| 1,060 sq.ft.	$420,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 5% Airbnb Rental Income: $1197 Traditional Rental Income: $2483 Airbnb ROI: 0.74% Traditional ROI: 5%
615 Mayflower Landing Holliston, MA LUXE New Construction! Exceptional 4BR, 5BA custom home offering 4,600+ SF of STUNNING liv...	4 beds \| 5 baths \| 4,600 sq.ft.	$1,600,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.2% Airbnb Rental Income: $null Traditional Rental Income: $6674 Airbnb ROI: N/A Traditional ROI: 2.2%
48 N Mill St Holliston, MA GREAT OPPORTUNITY TO OWN OR HAVE AS AN INVESTMENT, THIS FOUR FAMILY HOME IS WELL MANTAINED...	7 beds \| 4 baths \| 2,900 sq.ft.	$1,100,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.9% Airbnb Rental Income: $2860 Traditional Rental Income: $5051 Airbnb ROI: 0.11% Traditional ROI: 2.9%
107 Dorset Rd Holliston, MA Impeccably updated ranch in one of Holliston's most desirable neighborhoods, ready for its...	3 beds \| 1 baths \| 1,432 sq.ft.	$595,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.61% Airbnb Rental Income: $2492 Traditional Rental Income: $2807 Airbnb ROI: 0.96% Traditional ROI: 2.61%
49 Stonybrook Dr Holliston, MA Welcome to this well-maintained three-bedroom 2.5 bath home ideally located in a desirable...	3 beds \| 3 baths \| 2,027 sq.ft.	$699,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.45% Airbnb Rental Income: $2492 Traditional Rental Income: $3920 Airbnb ROI: 0.33% Traditional ROI: 3.45%
11 Regal St Holliston, MA A wonderful opportunity to make Holliston your home. This 3-bedroom property is full of po...	3 beds \| 1 baths \| 1,176 sq.ft.	$495,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 3.34% Airbnb Rental Income: $2492 Traditional Rental Income: $2663 Airbnb ROI: 1.67% Traditional ROI: 3.34%
19 Orchard Ln Holliston, MA Tucked away in one of Holliston's most idyllic neighborhoods, this contemporary colonial o...	4 beds \| 3 baths \| 1,728 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $3660 Airbnb ROI: N/A Traditional ROI: 3.1%

Real Estate investment in Holliston, MA

There are 11 properties for sale in the city of Holliston . The median list price in Holliston is $724,900 and the average price per square foot is $270. In May 2026, the average monthly cash on cash return in Holliston is 3.00%. The average monthly rental income in Holliston is $3,821.

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

There are 11 investment properties available for sale in Holliston.

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

The ROI for Long-Term is higher than the Short-Term in Holliston with average rental income of $3,821.

Your search for investment property begins and ends here

Investment Property for Sale in Holliston, MA

20 Constitution Cir

Holliston, MA

4 beds | 3 baths | 3,872 sq.ft.

$1,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.54%

Airbnb Rental Income: $null

Traditional Rental Income: $4342

Airbnb ROI: N/A

Traditional ROI: 1.54%

15 Whispering Lane

Holliston, MA

5 beds | 4 baths | 6,498 sq.ft.

$1,650,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $2860

Traditional Rental Income: $6446

Airbnb ROI: -0.88%

Traditional ROI: 1.89%

66 Lakeshore Dr

Holliston, MA

2 beds | 1 baths | 1,060 sq.ft.

$420,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 5%

Airbnb Rental Income: $1197

Traditional Rental Income: $2483

Airbnb ROI: 0.74%

Traditional ROI: 5%

615 Mayflower Landing

Holliston, MA

4 beds | 5 baths | 4,600 sq.ft.

$1,600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.2%

Airbnb Rental Income: $null

Traditional Rental Income: $6674

Airbnb ROI: N/A

Traditional ROI: 2.2%

48 N Mill St

Holliston, MA

7 beds | 4 baths | 2,900 sq.ft.

$1,100,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $2860

Traditional Rental Income: $5051

Airbnb ROI: 0.11%

Traditional ROI: 2.9%

107 Dorset Rd

Holliston, MA

3 beds | 1 baths | 1,432 sq.ft.

$595,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $2492

Traditional Rental Income: $2807

Airbnb ROI: 0.96%

Traditional ROI: 2.61%

49 Stonybrook Dr

Holliston, MA

3 beds | 3 baths | 2,027 sq.ft.

$699,900

Airbnb cash on cash: 0.33%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2492

Traditional Rental Income: $3920

Airbnb ROI: 0.33%

Traditional ROI: 3.45%

11 Regal St

Holliston, MA

3 beds | 1 baths | 1,176 sq.ft.

$495,000

Airbnb cash on cash: 1.67%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $2492

Traditional Rental Income: $2663

Airbnb ROI: 1.67%