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
153 E Main St Sheffield, MA TITLE V PASSED. Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family h...	3 beds \| 2 baths \| 1,482 sq.ft.	$365,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 7.1% Airbnb Rental Income: $2624 Traditional Rental Income: $3222 Airbnb ROI: 3.53% Traditional ROI: 7.1%
856 Barnum Street Sheffield, MA Modernist retreat in a pastoral Berkshire setting-an artful sanctuary where design, landsc...	2 beds \| 3 baths \| 1,753 sq.ft.	$885,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.28% Airbnb Rental Income: $1116 Traditional Rental Income: $3153 Airbnb ROI: -0.65% Traditional ROI: 2.28%
481 Shunpike Rd Sheffield, MA A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own ho...	1 beds \| 2 baths \| 1,296 sq.ft.	$1,475,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.78% Airbnb Rental Income: $646 Traditional Rental Income: $2984 Airbnb ROI: -1.14% Traditional ROI: 0.78%
689 N Main St Sheffield, MA OPEN HOUSE: Friday, May 22nd 2:00pm-3:30pm Completely renovated and exceptionally versatil...	3 beds \| 2 baths \| 2,258 sq.ft.	$459,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 6.36% Airbnb Rental Income: $2624 Traditional Rental Income: $3552 Airbnb ROI: 2.74% 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.	$1,475,000	Airbnb cash on cash: -1.18% Traditional cash on cash: -0.63% Airbnb Rental Income: $2609 Traditional Rental Income: $2738 Airbnb ROI: -1.18% Traditional ROI: -0.63%
40 Traveler St #507 Boston , MA Welcome to Siena Condominium, where modern city living meets elevated comfort. This south-...	1 beds \| 1 baths \| 741 sq.ft.	$760,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.21% Airbnb Rental Income: $2437 Traditional Rental Income: $2633 Airbnb ROI: -0.91% Traditional ROI: 0.21%
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.	$414,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.16% Airbnb Rental Income: $2148 Traditional Rental Income: $2121 Airbnb ROI: 0.82% Traditional ROI: 2.16%
180 Commonwealth Ave #7 Boston , MA 180 Commonwealth Ave #7, Boston, MA 02116 \| Condo/Coop	3 beds \| 2 baths \| 1,070 sq.ft.	$1,450,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.7% Airbnb Rental Income: $null Traditional Rental Income: $2954 Airbnb ROI: N/A Traditional ROI: -0.7%
74 Appleton St #4 Boston , MA 74 Appleton St #4, Boston, MA 02116 \| Condo/Coop	2 beds \| 1 baths \| 1,315 sq.ft.	$1,890,000	Airbnb cash on cash: -1.05% Traditional cash on cash: -1% Airbnb Rental Income: $3238 Traditional Rental Income: $2598 Airbnb ROI: -1.05% Traditional ROI: -1%
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: -1.07% Traditional cash on cash: -0.5% Airbnb Rental Income: $2408 Traditional Rental Income: $2228 Airbnb ROI: -1.07% Traditional ROI: -0.5%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$8,450,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.39% Airbnb Rental Income: $null Traditional Rental Income: $6608 Airbnb ROI: N/A Traditional ROI: -1.39%
319 Forest Hills St #2 Boston , MA 319 Forest Hills St #2, Boston, MA 02130 \| Condo/Coop	2 beds \| 2 baths \| 1,070 sq.ft.	$769,500	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.89% Airbnb Rental Income: $3022 Traditional Rental Income: $3352 Airbnb ROI: 0.46% Traditional ROI: 1.89%
11 Wayne St Boston , MA 11 Wayne St, Boston, MA 02121 \| Multi Family	6 beds \| 4 baths \| 4,819 sq.ft.	$1,295,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 2.41% Airbnb Rental Income: $3611 Traditional Rental Income: $5664 Airbnb ROI: 0.04% Traditional ROI: 2.41%
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: -0.11% Traditional cash on cash: 0.22% Airbnb Rental Income: $3055 Traditional Rental Income: $2708 Airbnb ROI: -0.11% Traditional ROI: 0.22%
13 Wellington St Boston , MA Beautiful townhouse on quiet, tree-lined street minutes from T, Prudential Center, Symphon...	4 beds \| 3 baths \| 3,110 sq.ft.	$3,590,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.38% Airbnb Rental Income: $2921 Traditional Rental Income: $4312 Airbnb ROI: -1% Traditional ROI: -0.38%
1 Franklin St #1205 Boston , MA Move in and see why Millennium Tower Boston is the evolution of luxury residential living!...	2 beds \| 2 baths \| 1,161 sq.ft.	$1,675,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 0.19% Airbnb Rental Income: $4025 Traditional Rental Income: $5552 Airbnb ROI: -1.35% Traditional ROI: 0.19%
14 Avondale St Boston , MA 14 Avondale St, Boston, MA 02124 \| Single Family Residential	4 beds \| 2 baths \| 1,768 sq.ft.	$639,900	Airbnb cash on cash: 2.3% Traditional cash on cash: 3.65% Airbnb Rental Income: $3575 Traditional Rental Income: $3600 Airbnb ROI: 2.3% Traditional ROI: 3.65%
588 S Orleans Road Orleans , MA Lush lawns and hydrangeas flanking a winding seashell driveway create a storybook entrance...	3 beds \| 3 baths \| 2,841 sq.ft.	$1,595,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.04% Airbnb Rental Income: $1623 Traditional Rental Income: $3944 Airbnb ROI: -0.84% Traditional ROI: 1.04%
43 S Highland Road Truro , MA Unique, architecturally designed contemporary cape home set on 1.54 private wooded acres a...	2 beds \| 1 baths \| 1,317 sq.ft.	$925,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 1.13% Airbnb Rental Income: $1545 Traditional Rental Income: $2441 Airbnb ROI: -0.43% Traditional ROI: 1.13%

Real Estate investment in Sheffield, MA

There are 4 properties for sale in the city of Sheffield . The median list price in Sheffield is $672,000 and the average price per square foot is $396. In June 2026, the average monthly cash on cash return in Sheffield is 4.00%. The average monthly rental income in Sheffield is $3,188.

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

There are 4 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 $3,188.

Your search for investment property begins and ends here

Investment Property for Sale in Sheffield, MA

153 E Main St

Sheffield, MA

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

$365,000

Airbnb cash on cash: 3.53%

Traditional cash on cash: 7.1%

Airbnb Rental Income: $2624

Traditional Rental Income: $3222

Airbnb ROI: 3.53%

Traditional ROI: 7.1%

856 Barnum Street

Sheffield, MA

2 beds | 3 baths | 1,753 sq.ft.

$885,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $1116

Traditional Rental Income: $3153

Airbnb ROI: -0.65%

Traditional ROI: 2.28%

481 Shunpike Rd

Sheffield, MA

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

$1,475,000

Airbnb cash on cash: -1.14%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $646

Traditional Rental Income: $2984

Airbnb ROI: -1.14%

Traditional ROI: 0.78%

689 N Main St

Sheffield, MA

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

$459,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 6.36%

Airbnb Rental Income: $2624

Traditional Rental Income: $3552

Airbnb ROI: 2.74%

Traditional ROI: 6.36%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

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

$1,475,000

Airbnb cash on cash: -1.18%

Traditional cash on cash: -0.63%

Airbnb Rental Income: $2609

Traditional Rental Income: $2738

Airbnb ROI: -1.18%

Traditional ROI: -0.63%

Boston , MA

1 beds | 1 baths | 741 sq.ft.

$760,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: 0.21%

Airbnb Rental Income: $2437

Traditional Rental Income: $2633

Airbnb ROI: -0.91%

Traditional ROI: 0.21%

Boston , MA

2 beds | 1 baths | 746 sq.ft.

$414,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $2148

Traditional Rental Income: $2121

Airbnb ROI: 0.82%

Traditional ROI: 2.16%

Boston , MA

3 beds | 2 baths | 1,070 sq.ft.

$1,450,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.7%

Airbnb Rental Income: $null

Traditional Rental Income: $2954

Airbnb ROI: N/A

Traditional ROI: -0.7%

Boston , MA

2 beds | 1 baths | 1,315 sq.ft.