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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1180 Ashley Falls Rd Sheffield, MA	3 beds \| 6 baths \| 4,044 sq.ft.	$695,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 9.03% Airbnb Rental Income: $2734 Traditional Rental Income: $7284 Airbnb ROI: 1.02% Traditional ROI: 9.03%
153 East Main St Sheffield, MA Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle do...	3 beds \| 2 baths \| 1,482 sq.ft.	$399,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 6.42% Airbnb Rental Income: $2734 Traditional Rental Income: $3222 Airbnb ROI: 3.39% Traditional ROI: 6.42%
1592 County Rd Sheffield, MA Michael Harrigan [email protected] 413-429-7788 BERKSHIRE HATHAWAY HOMESERVICES ...	4 beds \| 3 baths \| 1,360 sq.ft.	$425,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 6.57% Airbnb Rental Income: $2815 Traditional Rental Income: $3567 Airbnb ROI: 3.03% Traditional ROI: 6.57%
483 Home Rd Sheffield, MA Suzann Laverack Ward [email protected] 413-329-3031 HOUSATONIC REAL ESTATE	3 beds \| 3 baths \| 1,991 sq.ft.	$695,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 2.76% Airbnb Rental Income: $2734 Traditional Rental Income: $3318 Airbnb ROI: 0.87% Traditional ROI: 2.76%
481 Shunpike Rd Sheffield, MA Suzann Laverack Ward, Suzann l Ward [email protected] 413-329-3031 HOUSATONIC REAL ESTA...	1 beds \| 2 baths \| 1,296 sq.ft.	$1,475,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.78% Airbnb Rental Income: $1371 Traditional Rental Income: $2984 Airbnb ROI: -0.7% Traditional ROI: 0.78%
60 Parsley Ln Sheffield, MA Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath hom...	5 beds \| 5 baths \| 3,100 sq.ft.	$995,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 5.91% Airbnb Rental Income: $5497 Traditional Rental Income: $6519 Airbnb ROI: 3.62% Traditional ROI: 5.91%
168 Main St Sheffield, MA	5 beds \| 3 baths \| 2,750 sq.ft.	$649,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 5.45% Airbnb Rental Income: $5497 Traditional Rental Income: $4505 Airbnb ROI: 5.26% Traditional ROI: 5.45%
1427 Hewins St Sheffield, MA Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a...	3 beds \| 2 baths \| 1,730 sq.ft.	$775,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.69% Airbnb Rental Income: $2734 Traditional Rental Income: $3507 Airbnb ROI: 1.73% Traditional ROI: 3.69%
95 Water Farm Rd Sheffield, MA Open House 10-11-25 @ 11:00-1:00. Inside photo's to follow. Experience the perfect blend o...	4 beds \| 2 baths \| 1,531 sq.ft.	$495,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 5.64% Airbnb Rental Income: $2815 Traditional Rental Income: $3471 Airbnb ROI: 2.81% Traditional ROI: 5.64%
2049 South Undermountain Rd Sheffield, MA	9 beds \| 5 baths \| 8,406 sq.ft.	$1,200,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 3.89% Airbnb Rental Income: $5497 Traditional Rental Income: $6619 Airbnb ROI: 1.9% Traditional ROI: 3.89%
604 Sheffield Plain Rd Sheffield, MA	6 beds \| 5 baths \| 4,572 sq.ft.	$695,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 8.34% Airbnb Rental Income: $5497 Traditional Rental Income: $6869 Airbnb ROI: 4.52% Traditional ROI: 8.34%
2105 South Undermountain Rd Sheffield, MA Dan Alden [email protected] 413-335-9300 ALDEN COUNTRY REAL ESTATE SERVICES	3 beds \| 3 baths \| 3,217 sq.ft.	$395,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 8.95% Airbnb Rental Income: $2734 Traditional Rental Income: $4154 Airbnb ROI: 3.38% Traditional ROI: 8.95%
1786 South Undermountain Road Sheffield, MA Classic 3-Bedroom Cape with Pool Perfectly positioned between NW Connecticut and Sheffiel...	3 beds \| 3 baths \| 2,408 sq.ft.	$795,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.01% Airbnb Rental Income: $2734 Traditional Rental Income: $3971 Airbnb ROI: 0.47% Traditional ROI: 3.01%

Real Estate investment in Sheffield, MA

There are 13 properties for sale in the city of Sheffield . The median list price in Sheffield is $695,000 and the average price per square foot is $251. In December 2025, the average monthly cash on cash return in Sheffield is 6.00%. The average monthly rental income in Sheffield is $3,768.

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

There are 13 investment properties available for sale in Sheffield.

In 2025, 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 $3,768.

Your search for investment property begins and ends here

Investment Property for Sale in Sheffield, MA

1180 Ashley Falls Rd

Sheffield, MA

3 beds | 6 baths | 4,044 sq.ft.

$695,000

Airbnb cash on cash: 1.02%

Traditional cash on cash: 9.03%

Airbnb Rental Income: $2734

Traditional Rental Income: $7284

Airbnb ROI: 1.02%

Traditional ROI: 9.03%

153 East Main St

Sheffield, MA

3 beds | 2 baths | 1,482 sq.ft.

$399,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 6.42%

Airbnb Rental Income: $2734

Traditional Rental Income: $3222

Airbnb ROI: 3.39%

Traditional ROI: 6.42%

1592 County Rd

Sheffield, MA

4 beds | 3 baths | 1,360 sq.ft.

$425,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 6.57%

Airbnb Rental Income: $2815

Traditional Rental Income: $3567

Airbnb ROI: 3.03%

Traditional ROI: 6.57%

483 Home Rd

Sheffield, MA

3 beds | 3 baths | 1,991 sq.ft.

$695,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2734

Traditional Rental Income: $3318

Airbnb ROI: 0.87%

Traditional ROI: 2.76%

481 Shunpike Rd

Sheffield, MA

1 beds | 2 baths | 1,296 sq.ft.

$1,475,000

Airbnb cash on cash: -0.7%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $1371

Traditional Rental Income: $2984

Airbnb ROI: -0.7%

Traditional ROI: 0.78%

60 Parsley Ln

Sheffield, MA

5 beds | 5 baths | 3,100 sq.ft.

$995,000

Airbnb cash on cash: 3.62%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $5497

Traditional Rental Income: $6519

Airbnb ROI: 3.62%

Traditional ROI: 5.91%

168 Main St

Sheffield, MA

5 beds | 3 baths | 2,750 sq.ft.

$649,000

Airbnb cash on cash: 5.26%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $5497

Traditional Rental Income: $4505

Airbnb ROI: 5.26%

Traditional ROI: 5.45%

1427 Hewins St

Sheffield, MA

3 beds | 2 baths | 1,730 sq.ft.

$775,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2734

Traditional Rental Income: $3507

Airbnb ROI: 1.73%