Real Estate Investment Properties for Sale in Sheffield, MA

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
397 Clayton Rd Sheffield, MA Spacious 4 bedroom Cape with several useful storage buildings for anyone with a business a...	4 beds \| 2 baths \| 1,340 sq.ft.	$379,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 6.29% Airbnb Rental Income: $2433 Traditional Rental Income: $2972 Airbnb ROI: 3.1% Traditional ROI: 6.29%
254 Main St Sheffield, MA Step into a canvas of timeless character in this Historic Colonial, originally built and o...	3 beds \| 2 baths \| 2,485 sq.ft.	$329,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 9.55% Airbnb Rental Income: $2432 Traditional Rental Income: $3768 Airbnb ROI: 3.31% Traditional ROI: 9.55%
689 N Main St Sheffield, MA Completely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located...	3 beds \| 2 baths \| 2,258 sq.ft.	$459,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 6.36% Airbnb Rental Income: $2432 Traditional Rental Income: $3552 Airbnb ROI: 2.37% Traditional ROI: 6.36%
Investment Properties for Sale in Other Cities of Massachusetts
12 Hereford St #2 Boston , MA 12 Hereford St #2, Boston, MA 02115 \| Condo/Coop	1 beds \| 2 baths \| 1,195 sq.ft.	$1,440,000	Airbnb cash on cash: -1.53% Traditional cash on cash: -0.6% Airbnb Rental Income: $2018 Traditional Rental Income: $2738 Airbnb ROI: -1.53% Traditional ROI: -0.6%
1 Franklin St #5102 Boston , MA 1 Franklin St #5102, Boston, MA 02110 \| Condo/Coop	3 beds \| 4 baths \| 3,172 sq.ft.	$6,750,000	Airbnb cash on cash: -2.81% Traditional cash on cash: -2.44% Airbnb Rental Income: $3943 Traditional Rental Income: $5400 Airbnb ROI: -2.81% Traditional ROI: -2.44%
699 Hyde Park Ave #6 Boston , MA Sunny and well-maintained 2-bedroom condo in a convenient Roslindale location near Forest ...	2 beds \| 1 baths \| 746 sq.ft.	$409,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 2.2% Airbnb Rental Income: $2549 Traditional Rental Income: $2121 Airbnb ROI: 1.71% Traditional ROI: 2.2%
11 Whipple Ave #1 Boston , MA 11 Whipple Ave #1, Boston, MA 02131 \| Condo/Coop	2 beds \| 2 baths \| 1,275 sq.ft.	$535,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.27% Airbnb Rental Income: $2549 Traditional Rental Income: $2970 Airbnb ROI: 0.2% Traditional ROI: 2.27%
12 Stoneholm St #418 Boston , MA	1 beds \| 1 baths \| 400 sq.ft.	$469,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 0.7% Airbnb Rental Income: $1512 Traditional Rental Income: $1892 Airbnb ROI: -1.17% Traditional ROI: 0.7%
35 Fay St #202 Boston , MA 35 Fay St #202, Boston, MA 02118 \| Condo/Coop	1 beds \| 1 baths \| 1,004 sq.ft.	$775,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.5% Airbnb Rental Income: $1966 Traditional Rental Income: $2228 Airbnb ROI: -1.58% Traditional ROI: -0.5%
4 Mount Vernon Ave #3 Charlestown , MA 4 Mount Vernon Ave #3, Charlestown, MA 02129 \| Condo/Coop	2 beds \| 2 baths \| 1,332 sq.ft.	$1,350,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.44% Airbnb Rental Income: $2899 Traditional Rental Income: $2662 Airbnb ROI: -0.79% Traditional ROI: -0.44%
198 Byron St Boston , MA 198 Byron St, Boston, MA 02128 \| Single Family Residential	3 beds \| 1 baths \| 2,385 sq.ft.	$1,150,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.22% Airbnb Rental Income: $2448 Traditional Rental Income: $2708 Airbnb ROI: -0.58% Traditional ROI: 0.22%
19 Salem St #2 Charlestown , MA 19 Salem St #2, Charlestown, MA 02129 \| Condo/Coop	1 beds \| 1 baths \| 745 sq.ft.	$649,999	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.29% Airbnb Rental Income: $1867 Traditional Rental Income: $1630 Airbnb ROI: -0.72% Traditional ROI: -0.29%
580 Washington St #1414 Boston , MA	1 beds \| 1 baths \| 799 sq.ft.	$849,000	Airbnb cash on cash: -1.68% Traditional cash on cash: -0.87% Airbnb Rental Income: $2150 Traditional Rental Income: $2242 Airbnb ROI: -1.68% Traditional ROI: -0.87%
15 Spinney Street #1 Boston , MA Beautiful two-bedroom condo in a thoughtfully restored brick two-family home in desirable ...	2 beds \| 2 baths \| 1,059 sq.ft.	$665,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 2.4% Airbnb Rental Income: $2762 Traditional Rental Income: $2748 Airbnb ROI: 1.38% Traditional ROI: 2.4%
58 High St #5 Charlestown , MA 58 High St #5, Charlestown, MA 02129 \| Condo/Coop	2 beds \| 2 baths \| 1,293 sq.ft.	$1,270,000	Airbnb cash on cash: -0.61% Traditional cash on cash: -0.3% Airbnb Rental Income: $2899 Traditional Rental Income: $2594 Airbnb ROI: -0.61% Traditional ROI: -0.3%
3 Avery St #604 Boston , MA 3 Avery St #604, Boston, MA 02111 \| Condo/Coop	2 beds \| 3 baths \| 1,748 sq.ft.	$1,095,000	Airbnb cash on cash: -3.07% Traditional cash on cash: -2.74% Airbnb Rental Income: $3781 Traditional Rental Income: $3294 Airbnb ROI: -3.07% Traditional ROI: -2.74%

Real Estate investment in Sheffield, MA

There are 3 properties for sale in the city of Sheffield . The median list price in Sheffield is $379,000 and the average price per square foot is $187. In August 2026, the average monthly cash on cash return in Sheffield is 6.00%. The average monthly rental income in Sheffield is $3,552.

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

There are 3 investment properties available for sale in Sheffield.

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

The ROI for Long-Term is higher than the Short-Term in Sheffield with average rental income of $3,552.

Your search for investment property begins and ends here

Investment Property for Sale in Sheffield, MA

397 Clayton Rd

Sheffield, MA

4 beds | 2 baths | 1,340 sq.ft.

$379,000

Airbnb cash on cash: 3.1%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $2433

Traditional Rental Income: $2972

Airbnb ROI: 3.1%

Traditional ROI: 6.29%

254 Main St

Sheffield, MA

3 beds | 2 baths | 2,485 sq.ft.

$329,000

Airbnb cash on cash: 3.31%

Traditional cash on cash: 9.55%

Airbnb Rental Income: $2432

Traditional Rental Income: $3768

Airbnb ROI: 3.31%

Traditional ROI: 9.55%

689 N Main St

Sheffield, MA

3 beds | 2 baths | 2,258 sq.ft.

$459,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 6.36%

Airbnb Rental Income: $2432

Traditional Rental Income: $3552

Airbnb ROI: 2.37%

Traditional ROI: 6.36%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

1 beds | 2 baths | 1,195 sq.ft.

$1,440,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: -0.6%

Airbnb Rental Income: $2018

Traditional Rental Income: $2738

Airbnb ROI: -1.53%

Traditional ROI: -0.6%

Boston , MA

3 beds | 4 baths | 3,172 sq.ft.

$6,750,000

Airbnb cash on cash: -2.81%

Traditional cash on cash: -2.44%

Airbnb Rental Income: $3943

Traditional Rental Income: $5400

Airbnb ROI: -2.81%

Traditional ROI: -2.44%

Boston , MA

2 beds | 1 baths | 746 sq.ft.

$409,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $2549

Traditional Rental Income: $2121

Airbnb ROI: 1.71%

Traditional ROI: 2.2%

Boston , MA

2 beds | 2 baths | 1,275 sq.ft.

$535,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $2549

Traditional Rental Income: $2970

Airbnb ROI: 0.2%

Traditional ROI: 2.27%

Boston , MA

1 beds | 1 baths | 400 sq.ft.

$469,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: 0.7%

Airbnb Rental Income: $1512

Traditional Rental Income: $1892

Airbnb ROI: -1.17%

Traditional ROI: 0.7%

Boston , MA

1 beds | 1 baths | 1,004 sq.ft.

$775,000