Real Estate Investment Properties for Sale in Winchendon, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20 Harvard St Winchendon, MA 20 Harvard St, Winchendon, MA 01475 \| Single Family Residential	4 beds \| 1 baths \| 1,203 sq.ft.	$339,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 6.92% Airbnb Rental Income: $2038 Traditional Rental Income: $3012 Airbnb ROI: 2.22% Traditional ROI: 6.92%
170 Glenallen St Winchendon, MA Price Improvement - Now Offered at $389,900! ??Don't miss this opportunity to own a home t...	3 beds \| 1 baths \| 1,080 sq.ft.	$389,900	Airbnb cash on cash: 2.9% Traditional cash on cash: 5.28% Airbnb Rental Income: $2365 Traditional Rental Income: $2652 Airbnb ROI: 2.9% Traditional ROI: 5.28%
34 Emerald St Winchendon, MA OPEN HOUSE SUNDAY 5/24 12-1:30..Priced to sell.. This property has the space you been look...	4 beds \| 2 baths \| 2,390 sq.ft.	$399,900	Airbnb cash on cash: 1.77% Traditional cash on cash: 7.51% Airbnb Rental Income: $2038 Traditional Rental Income: $3664 Airbnb ROI: 1.77% Traditional ROI: 7.51%
365 Benjamin St Winchendon, MA This beautifully maintained 5 bedroom, 2 1/2 bath colonial boasts over 3400 sq ft. of livi...	5 beds \| 3 baths \| 3,400 sq.ft.	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.6% Airbnb Rental Income: $null Traditional Rental Income: $4884 Airbnb ROI: N/A Traditional ROI: 6.6%
506 Central St Winchendon, MA 506 Central St, Winchendon, MA 01475 \| Single Family Residential	5 beds \| 1 baths \| 2,072 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.8% Airbnb Rental Income: $null Traditional Rental Income: $3134 Airbnb ROI: N/A Traditional ROI: 6.8%
32 Ash St Winchendon, MA 32 Ash St, Winchendon, MA 01475 \| Single Family Residential	3 beds \| 1 baths \| 2,151 sq.ft.	$390,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 5.1% Airbnb Rental Income: $2365 Traditional Rental Income: $2770 Airbnb ROI: 2.4% Traditional ROI: 5.1%
118 Spring St Winchendon, MA 118 Spring St, Winchendon, MA 01475 \| Single Family Residential	4 beds \| 1 baths \| 1,393 sq.ft.	$200,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 11.47% Airbnb Rental Income: $2038 Traditional Rental Income: $2691 Airbnb ROI: 5.25% Traditional ROI: 11.47%
10-12 School Sq Winchendon, MA 10-12 School Sq, Winchendon, MA 01368 \| Multi Family	10 beds \| 4 baths \| 3,818 sq.ft.	$659,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.28% Airbnb Rental Income: $2038 Traditional Rental Income: $2246 Airbnb ROI: 0.08% Traditional ROI: 1.28%
M-2 L-94 School St Winchendon, MA M-2 L-94 School St, Winchendon, MA 01475 \| Other	N/A beds \| N/A baths \| N/A	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $1227 Airbnb ROI: N/A Traditional ROI: 4.41%
Map 2 94 School St Lot 94 Winchendon, MA Map 2 94 School St Lot 94, Winchendon, MA 01475 \| Other	N/A beds \| N/A baths \| N/A	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $1662 Airbnb ROI: N/A Traditional ROI: 6.94%

Real Estate investment in Winchendon, MA

There are 12 properties for sale in the city of Winchendon . The median list price in Winchendon is $314,812 and the average price per square foot is $146. In September 2026, the average monthly cash on cash return in Winchendon is 7.00%. The average monthly rental income in Winchendon is $2,745.

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

There are 12 investment properties available for sale in Winchendon.

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

The ROI for Long-Term is higher than the Short-Term in Winchendon with average rental income of $2,745.

Your search for investment property begins and ends here

Investment Property for Sale in Winchendon, MA

20 Harvard St

Winchendon, MA

4 beds | 1 baths | 1,203 sq.ft.

$339,900

Airbnb cash on cash: 2.22%

Traditional cash on cash: 6.92%

Airbnb Rental Income: $2038

Traditional Rental Income: $3012

Airbnb ROI: 2.22%

Traditional ROI: 6.92%

170 Glenallen St

Winchendon, MA

3 beds | 1 baths | 1,080 sq.ft.

$389,900

Airbnb cash on cash: 2.9%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $2365

Traditional Rental Income: $2652

Airbnb ROI: 2.9%

Traditional ROI: 5.28%

34 Emerald St

Winchendon, MA

4 beds | 2 baths | 2,390 sq.ft.

$399,900

Airbnb cash on cash: 1.77%

Traditional cash on cash: 7.51%

Airbnb Rental Income: $2038

Traditional Rental Income: $3664

Airbnb ROI: 1.77%

Traditional ROI: 7.51%

365 Benjamin St

Winchendon, MA

5 beds | 3 baths | 3,400 sq.ft.

$590,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.6%

Airbnb Rental Income: $null

Traditional Rental Income: $4884

Airbnb ROI: N/A

Traditional ROI: 6.6%

506 Central St

Winchendon, MA

5 beds | 1 baths | 2,072 sq.ft.

$359,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.8%

Airbnb Rental Income: $null

Traditional Rental Income: $3134

Airbnb ROI: N/A

Traditional ROI: 6.8%

32 Ash St

Winchendon, MA

3 beds | 1 baths | 2,151 sq.ft.

$390,000

Airbnb cash on cash: 2.4%

Traditional cash on cash: 5.1%

Airbnb Rental Income: $2365

Traditional Rental Income: $2770

Airbnb ROI: 2.4%

Traditional ROI: 5.1%

118 Spring St

Winchendon, MA

4 beds | 1 baths | 1,393 sq.ft.

$200,000

Airbnb cash on cash: 5.25%

Traditional cash on cash: 11.47%

Airbnb Rental Income: $2038

Traditional Rental Income: $2691

Airbnb ROI: 5.25%

Traditional ROI: 11.47%

10-12 School Sq

Winchendon, MA

10 beds | 4 baths | 3,818 sq.ft.

$659,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $2038

Traditional Rental Income: $2246

Airbnb ROI: 0.08%