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.

Single Family Homes for Sale in Holliston, MA

Search for Single Family Residential for Sale in Holliston, Massachusetts. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 20 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
423 South St Holliston, MA Step Back in time w/this Storybook Charming Antique home filled w/Todays Renovations & you...	3 beds \| 1 baths \| 1,896 sq.ft.	$725,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.31% Airbnb Rental Income: $2870 Traditional Rental Income: $3163 Airbnb ROI: 0.89% Traditional ROI: 2.31%
14 Fiske Pond Rd Holliston, MA 14 Fiske Pond Rd, Holliston, MA 01746 \| Single Family Residential	5 beds \| 5 baths \| 5,740 sq.ft.	$2,350,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 0.7% Airbnb Rental Income: $3129 Traditional Rental Income: $7011 Airbnb ROI: -1.41% Traditional ROI: 0.7%
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%
Lot 8 Pond Vw Holliston, MA Lot 8 Pond Vw, Holliston, MA 01746 \| Single Family Residential	5 beds \| 4 baths \| 4,959 sq.ft.	$2,375,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 0.44% Airbnb Rental Income: $3129 Traditional Rental Income: $5961 Airbnb ROI: -1.17% Traditional ROI: 0.44%
109 Jerrold St Holliston, MA Offer accepted, OH cancelled!!! Expanded contemporary on 1/2 an acre in Holliston's desi...	3 beds \| 3 baths \| 2,221 sq.ft.	$739,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.24% Airbnb Rental Income: $2870 Traditional Rental Income: $3821 Airbnb ROI: 0.89% Traditional ROI: 3.24%
135 Locust St Holliston, MA Feel instantly at home in this charming Storybook-style 3-bedroom, 2 full bath Cape, where...	3 beds \| 2 baths \| 1,547 sq.ft.	$675,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 3.02% Airbnb Rental Income: $2870 Traditional Rental Income: $3257 Airbnb ROI: 1.34% Traditional ROI: 3.02%
10 Timber Ledge Dr Holliston, MA 10 Timber Ledge Dr, Holliston, MA 01746 \| Single Family Residential	4 beds \| 3 baths \| 4,613 sq.ft.	$1,325,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.51% Airbnb Rental Income: $null Traditional Rental Income: $4748 Airbnb ROI: N/A Traditional ROI: 1.51%
228 Norfolk St #228 Holliston, MA 228 Norfolk St #228, Holliston, MA 01746 \| Single Family Residential	3 beds \| 2 baths \| 1,936 sq.ft.	$750,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.05% Airbnb Rental Income: $2870 Traditional Rental Income: $3777 Airbnb ROI: 0.8% Traditional ROI: 3.05%
615 Norfolk St Holliston, MA 615 Norfolk St, Holliston, MA 01746 \| Single Family Residential	3 beds \| 3 baths \| 2,600 sq.ft.	$875,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 3% Airbnb Rental Income: $2870 Traditional Rental Income: $4348 Airbnb ROI: 0.37% Traditional ROI: 3%
15 Bullard St Holliston, MA 15 Bullard St, Holliston, MA 01746 \| Single Family Residential	4 beds \| 3 baths \| 2,704 sq.ft.	$839,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $4502 Airbnb ROI: N/A Traditional ROI: 3.41%
243 Oak St Holliston, MA 243 Oak St, Holliston, MA 01746 \| Single Family Residential	5 beds \| 2 baths \| 3,686 sq.ft.	$1,199,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.4% Airbnb Rental Income: $3129 Traditional Rental Income: $4132 Airbnb ROI: -0.14% Traditional ROI: 1.4%
10 Winston Rd Holliston, MA 10 Winston Rd, Holliston, MA 01746 \| Single Family Residential	4 beds \| 2 baths \| 3,648 sq.ft.	$1,185,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.32% Airbnb Rental Income: $null Traditional Rental Income: $3992 Airbnb ROI: N/A Traditional ROI: 1.32%
16 Kingsbury Dr Holliston, MA Nestled in sought-after Cedarbrook, this exceptional 5-bed Colonial offers many updates in...	5 beds \| 4 baths \| 7,165 sq.ft.	$1,875,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.01% Airbnb Rental Income: $3129 Traditional Rental Income: $5827 Airbnb ROI: -0.95% Traditional ROI: 1.01%
45 Johnson Dr Holliston, MA 45 Johnson Dr, Holliston, MA 01746 \| Single Family Residential	4 beds \| 3 baths \| 4,198 sq.ft.	$1,325,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.57% Airbnb Rental Income: $null Traditional Rental Income: $4762 Airbnb ROI: N/A Traditional ROI: 1.57%
120 Mohawk Path Holliston, MA 120 Mohawk Path, Holliston, MA 01746 \| Single Family Residential	4 beds \| 3 baths \| 4,035 sq.ft.	$1,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.51% Airbnb Rental Income: $null Traditional Rental Income: $4957 Airbnb ROI: N/A Traditional ROI: 1.51%
53 Louis St Holliston, MA 53 Louis St, Holliston, MA 01746 \| Single Family Residential	3 beds \| 2 baths \| 1,812 sq.ft.	$950,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.91% Airbnb Rental Income: $2870 Traditional Rental Income: $3751 Airbnb ROI: 0.16% Traditional ROI: 1.91%
58 Wedgewood Dr Holliston, MA 58 Wedgewood, Holliston, MA 01746 \| Single Family Residential	3 beds \| 2 baths \| 2,089 sq.ft.	$649,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 3.03% Airbnb Rental Income: $2870 Traditional Rental Income: $3275 Airbnb ROI: 1.26% Traditional ROI: 3.03%
40 Maple St Holliston, MA Investors, Contractors & Visionaries - Don't Miss This Opportunity! Bring your imagination...	3 beds \| 2 baths \| 1,152 sq.ft.	$375,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 6.21% Airbnb Rental Income: $2870 Traditional Rental Income: $3073 Airbnb ROI: 3.73% Traditional ROI: 6.21%

Your search for investment property begins and ends here

Single Family Homes for Sale in Holliston, MA

423 South St

Holliston, MA

3 beds | 1 baths | 1,896 sq.ft.

$725,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $2870

Traditional Rental Income: $3163

Airbnb ROI: 0.89%

Traditional ROI: 2.31%

14 Fiske Pond Rd

Holliston, MA

5 beds | 5 baths | 5,740 sq.ft.

$2,350,000

Airbnb cash on cash: -1.41%

Traditional cash on cash: 0.7%

Airbnb Rental Income: $3129

Traditional Rental Income: $7011

Airbnb ROI: -1.41%

Traditional ROI: 0.7%

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%

Lot 8 Pond Vw

Holliston, MA

5 beds | 4 baths | 4,959 sq.ft.

$2,375,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: 0.44%

Airbnb Rental Income: $3129

Traditional Rental Income: $5961

Airbnb ROI: -1.17%

Traditional ROI: 0.44%

109 Jerrold St

Holliston, MA

3 beds | 3 baths | 2,221 sq.ft.

$739,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $2870

Traditional Rental Income: $3821

Airbnb ROI: 0.89%

Traditional ROI: 3.24%

135 Locust St

Holliston, MA

3 beds | 2 baths | 1,547 sq.ft.

$675,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $2870

Traditional Rental Income: $3257

Airbnb ROI: 1.34%

Traditional ROI: 3.02%

10 Timber Ledge Dr

Holliston, MA

4 beds | 3 baths | 4,613 sq.ft.

$1,325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.51%

Airbnb Rental Income: $null

Traditional Rental Income: $4748

Airbnb ROI: N/A

Traditional ROI: 1.51%

228 Norfolk St #228

Holliston, MA

3 beds | 2 baths | 1,936 sq.ft.

$750,000

Airbnb cash on cash: 0.8%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $2870

Traditional Rental Income: $3777

Airbnb ROI: 0.8%