Real Estate Investment Properties for Sale in Hopkinton, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 N Pond Way #28 Hopkinton, MA Welcome to Maspenock Woods! The Barrett Model features 2 Bdrms on the 2nd Floor. Located j...	2 beds \| 2 baths \| 2,000 sq.ft.	$874,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 1.17% Airbnb Rental Income: $2807 Traditional Rental Income: $3497 Airbnb ROI: -0.48% Traditional ROI: 1.17%
2 Emerald Drive Hopkinton, MA Welcome to Emerald Drive, an exclusive enclave of 8 exquisite modern farmhouse-style homes...	5 beds \| 6 baths \| 5,248 sq.ft.	$2,199,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.85% Airbnb Rental Income: $3996 Traditional Rental Income: $8400 Airbnb ROI: -0.73% Traditional ROI: 1.85%
13 Summer St Hopkinton, MA Welcome Home to this immaculately renovated Colonial nestled in sought after Downtown Hopk...	3 beds \| 2 baths \| 1,460 sq.ft.	$719,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 2.63% Airbnb Rental Income: $1619 Traditional Rental Income: $3216 Airbnb ROI: -0.43% Traditional ROI: 2.63%
1 Emerald Drive Hopkinton, MA Welcome to 1 Emerald Drive, an exceptional new luxury home on Hopkinton's premier cul-de-s...	5 beds \| 6 baths \| 5,357 sq.ft.	$2,275,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.65% Airbnb Rental Income: $3996 Traditional Rental Income: $8267 Airbnb ROI: -0.78% Traditional ROI: 1.65%
5 Singletary Way Hopkinton, MA Set in Hopkinton's desirable Highland Park neighborhood, this beautifully crafted home off...	4 beds \| 6 baths \| 6,107 sq.ft.	$2,499,900	Airbnb cash on cash: -1.5% Traditional cash on cash: 1.29% Airbnb Rental Income: $2354 Traditional Rental Income: $8254 Airbnb ROI: -1.5% Traditional ROI: 1.29%
4 Lowell Dr unit: 4 Hopkinton, MA This beautifully updated 2-bedroom, 2.5-bath condo featuring a two-story foyer is complete...	2 beds \| 2 baths \| 1,750 sq.ft.	$515,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.51% Airbnb Rental Income: $2807 Traditional Rental Income: $3007 Airbnb ROI: 1.73% Traditional ROI: 3.51%
19 Stoney Brook Rd Hopkinton, MA Magnificent custom home in prestigious Highland Park, set in the highly sought-after commu...	4 beds \| 6 baths \| 6,616 sq.ft.	$2,450,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 1.5% Airbnb Rental Income: $2354 Traditional Rental Income: $8500 Airbnb ROI: -1.46% Traditional ROI: 1.5%
4 Emerald Drive Hopkinton, MA Welcome to 4 Emerald Drive, a remarkable new luxury residence set on Hopkinton's most soug...	5 beds \| 5 baths \| 4,167 sq.ft.	$1,999,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.76% Airbnb Rental Income: $3996 Traditional Rental Income: $5624 Airbnb ROI: -0.58% Traditional ROI: 0.76%
1 Whisper Way Hopkinton, MA STUNNING 4+ bedroom Colonial on over an acre of land in one of Hopkinton's premier neighbo...	4 beds \| 6 baths \| 4,232 sq.ft.	$2,100,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 1.98% Airbnb Rental Income: $2354 Traditional Rental Income: $8518 Airbnb ROI: -1.48% Traditional ROI: 1.98%
4 Lowell Dr #4 Hopkinton, MA 4 Lowell Dr #4, Hopkinton, MA 01748 \| Townhouse	2 beds \| 2 baths \| 1,750 sq.ft.	$515,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.94% Airbnb Rental Income: $2807 Traditional Rental Income: $3007 Airbnb ROI: 0.16% Traditional ROI: 1.94%
12 Highcroft Way #12 Hopkinton, MA 12 Highcroft Way #12, Hopkinton, MA 01748 \| Townhouse	2 beds \| 3 baths \| 3,125 sq.ft.	$775,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.52% Airbnb Rental Income: $2807 Traditional Rental Income: $3007 Airbnb ROI: -0.67% Traditional ROI: 0.52%
10 Queen Anne Rd Hopkinton, MA 10 Queen Anne Rd, Hopkinton, MA 01748 \| Single Family Residential	6 beds \| 5 baths \| 6,472 sq.ft.	$2,895,000	Airbnb cash on cash: -1.09% Traditional cash on cash: N/A Airbnb Rental Income: $3996 Traditional Rental Income: $0 Airbnb ROI: -1.09% Traditional ROI: N/A
5 Weybridge Ln #5 Hopkinton, MA 5 Weybridge Ln #5, Hopkinton, MA 01748 \| Townhouse	2 beds \| 2 baths \| 1,815 sq.ft.	$579,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.95% Airbnb Rental Income: $2807 Traditional Rental Income: $3007 Airbnb ROI: 0.37% Traditional ROI: 1.95%
75 Wilson St Hopkinton, MA 75 Wilson St, Hopkinton, MA 01748 \| Other	N/A beds \| N/A baths \| N/A	$929,000	Airbnb cash on cash: -0.65% Traditional cash on cash: -0.49% Airbnb Rental Income: $1965 Traditional Rental Income: $1590 Airbnb ROI: -0.65% Traditional ROI: -0.49%
220 Pond St Hopkinton, MA 220 Pond St, Hopkinton, MA 01748 \| Single Family Residential	4 beds \| 2 baths \| 2,146 sq.ft.	$925,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.77% Airbnb Rental Income: $2354 Traditional Rental Income: $4392 Airbnb ROI: -0.27% Traditional ROI: 2.77%
2 Country Way Hopkinton, MA 2 Country Way, Hopkinton, MA 01748 \| Single Family Residential	5 beds \| 4 baths \| 5,991 sq.ft.	$1,850,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 1.05% Airbnb Rental Income: $3996 Traditional Rental Income: $5724 Airbnb ROI: -0.45% Traditional ROI: 1.05%
19 Wood St Hopkinton, MA 19 Wood St, Hopkinton, MA 01748 \| Single Family Residential	5 beds \| 3 baths \| 4,226 sq.ft.	$1,475,000	Airbnb cash on cash: 0% Traditional cash on cash: N/A Airbnb Rental Income: $3996 Traditional Rental Income: $0 Airbnb ROI: 0% Traditional ROI: N/A
17 Highcroft Way #17 Hopkinton, MA 17 Highcroft Way #17, Hopkinton, MA 01748 \| Townhouse	2 beds \| 3 baths \| 3,004 sq.ft.	$800,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.44% Airbnb Rental Income: $2807 Traditional Rental Income: $3007 Airbnb ROI: -0.71% Traditional ROI: 0.44%
5 C St Hopkinton, MA 5 C St, Hopkinton, MA 01748 \| Single Family Residential	3 beds \| 1 baths \| 1,413 sq.ft.	$450,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.73% Airbnb Rental Income: $1619 Traditional Rental Income: $3443 Airbnb ROI: 0.31% Traditional ROI: 5.73%
5 Victory Ln Hopkinton, MA Experience a home as unique as its setting, where contemporary architecture meets a serene...	3 beds \| 2 baths \| 1,316 sq.ft.	$685,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.02% Airbnb Rental Income: $1619 Traditional Rental Income: $3443 Airbnb ROI: -0.55% Traditional ROI: 3.02%
2 Grandview Dr Hopkinton, MA 2 Grandview Dr, Hopkinton, MA 01748 \| Single Family Residential	3 beds \| 3 baths \| 3,770 sq.ft.	$1,299,900	Airbnb cash on cash: -1.59% Traditional cash on cash: 0.3% Airbnb Rental Income: $1619 Traditional Rental Income: $3443 Airbnb ROI: -1.59% Traditional ROI: 0.3%
300 West Main St Hopkinton, MA 300 West Main St, Hopkinton, MA 01748 \| Single Family Residential	4 beds \| 1 baths \| 1,531 sq.ft.	$674,900	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.72% Airbnb Rental Income: $2354 Traditional Rental Income: $3207 Airbnb ROI: 0.45% Traditional ROI: 2.72%

Real Estate investment in Hopkinton, MA

There are 26 properties for sale in the city of Hopkinton . The median list price in Hopkinton is $929,000 and the average price per square foot is $272. In March 2026, the average monthly cash on cash return in Hopkinton is 2.00%. The average monthly rental income in Hopkinton is $3,443.

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

There are 26 investment properties available for sale in Hopkinton.

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

The ROI for Long-Term is higher than the Short-Term in Hopkinton with average rental income of $3,443.

Your search for investment property begins and ends here

Investment Property for Sale in Hopkinton, MA

5 N Pond Way #28

Hopkinton, MA

2 beds | 2 baths | 2,000 sq.ft.

$874,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $2807

Traditional Rental Income: $3497

Airbnb ROI: -0.48%

Traditional ROI: 1.17%

2 Emerald Drive

Hopkinton, MA

5 beds | 6 baths | 5,248 sq.ft.

$2,199,000

Airbnb cash on cash: -0.73%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $3996

Traditional Rental Income: $8400

Airbnb ROI: -0.73%

Traditional ROI: 1.85%

13 Summer St

Hopkinton, MA

3 beds | 2 baths | 1,460 sq.ft.

$719,900

Airbnb cash on cash: -0.43%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1619

Traditional Rental Income: $3216

Airbnb ROI: -0.43%

Traditional ROI: 2.63%

1 Emerald Drive

Hopkinton, MA

5 beds | 6 baths | 5,357 sq.ft.

$2,275,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $3996

Traditional Rental Income: $8267

Airbnb ROI: -0.78%

Traditional ROI: 1.65%

5 Singletary Way

Hopkinton, MA

4 beds | 6 baths | 6,107 sq.ft.

$2,499,900

Airbnb cash on cash: -1.5%

Traditional cash on cash: 1.29%

Airbnb Rental Income: $2354

Traditional Rental Income: $8254

Airbnb ROI: -1.5%

Traditional ROI: 1.29%

4 Lowell Dr unit: 4

Hopkinton, MA

2 beds | 2 baths | 1,750 sq.ft.

$515,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $2807

Traditional Rental Income: $3007

Airbnb ROI: 1.73%

Traditional ROI: 3.51%

19 Stoney Brook Rd

Hopkinton, MA

4 beds | 6 baths | 6,616 sq.ft.

$2,450,000

Airbnb cash on cash: -1.46%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $2354

Traditional Rental Income: $8500

Airbnb ROI: -1.46%

Traditional ROI: 1.5%

4 Emerald Drive

Hopkinton, MA

5 beds | 5 baths | 4,167 sq.ft.

$1,999,900

Airbnb cash on cash: -0.58%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $3996

Traditional Rental Income: $5624

Airbnb ROI: -0.58%