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
122-124 ELM ST Winchendon, MA Invest with success and buy through Auction.com. This bank-owned investment property is a ...	4 beds \| 2 baths \| 2,192 sq.ft.	$263,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.99% Airbnb Rental Income: $null Traditional Rental Income: $3543 Airbnb ROI: N/A Traditional ROI: 11.99%
16 2nd St Winchendon, MA Life Long Memories Await at this Beautiful Waterfront House on Desirable Lake Monomonac! I...	3 beds \| 2 baths \| 2,540 sq.ft.	$899,500	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.42% Airbnb Rental Income: $3257 Traditional Rental Income: $4182 Airbnb ROI: 1.44% Traditional ROI: 3.42%
67 Hill St Winchendon, MA Nestled on a large 6.47 acre lot in the charming town of Winchendon, this new home offers ...	3 beds \| 2 baths \| 2,067 sq.ft.	$575,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 4.88% Airbnb Rental Income: $3257 Traditional Rental Income: $3906 Airbnb ROI: 2.31% Traditional ROI: 4.88%
21 Cottage St Winchendon, MA 21 Cottage St, Winchendon, MA, presents a single-family home, newly built and ready to wel...	3 beds \| 2 baths \| 1,400 sq.ft.	$434,900	Airbnb cash on cash: 4.9% Traditional cash on cash: 7.11% Airbnb Rental Income: $3257 Traditional Rental Income: $3423 Airbnb ROI: 4.9% Traditional ROI: 7.11%
27 Cottage St Winchendon, MA 27 Cottage St, Winchendon, MA, presents a single-family residence, newly built and ready t...	3 beds \| 2 baths \| 1,400 sq.ft.	$424,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 7.22% Airbnb Rental Income: $3257 Traditional Rental Income: $3394 Airbnb ROI: 5.04% Traditional ROI: 7.22%
790 River St Winchendon, MA Showings begin immediately! This 2003-built ranch sits on a secluded 2.25-acre lot surroun...	3 beds \| 2 baths \| 2,044 sq.ft.	$400,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 6.57% Airbnb Rental Income: $3257 Traditional Rental Income: $3470 Airbnb ROI: 4.05% Traditional ROI: 6.57%
33 East St Winchendon, MA ATTENTION CONTRACTORS, FLIPPERS! COME BRING YOUR TOOLS AND IMAGINATION TO BRING THIS GEM B...	3 beds \| 1 baths \| 1,728 sq.ft.	$269,000	Airbnb cash on cash: 7.82% Traditional cash on cash: 8.93% Airbnb Rental Income: $3257 Traditional Rental Income: $2808 Airbnb ROI: 7.82% Traditional ROI: 8.93%
93 High St Winchendon, MA 93 High St, Winchendon, MA 01475 \| Single Family Residential	4 beds \| 1 baths \| 1,868 sq.ft.	$334,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.96% Airbnb Rental Income: $null Traditional Rental Income: $2978 Airbnb ROI: N/A Traditional ROI: 6.96%
34 Prospect St Winchendon, MA 34 Prospect St, Winchendon, MA 01475 \| Multi Family	5 beds \| 3 baths \| 2,498 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $4287 Airbnb ROI: N/A Traditional ROI: 5.94%

Real Estate investment in Winchendon, MA

There are 17 properties for sale in the city of Winchendon . The median list price in Winchendon is $395,000 and the average price per square foot is $218. In March 2026, the average monthly cash on cash return in Winchendon is 7.00%. The average monthly rental income in Winchendon is $3,409.

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

There are 17 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 $3,409.

Your search for investment property begins and ends here

Investment Property for Sale in Winchendon, MA

122-124 ELM ST

Winchendon, MA

4 beds | 2 baths | 2,192 sq.ft.

$263,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.99%

Airbnb Rental Income: $null

Traditional Rental Income: $3543

Airbnb ROI: N/A

Traditional ROI: 11.99%

16 2nd St

Winchendon, MA

3 beds | 2 baths | 2,540 sq.ft.

$899,500

Airbnb cash on cash: 1.44%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $3257

Traditional Rental Income: $4182

Airbnb ROI: 1.44%

Traditional ROI: 3.42%

67 Hill St

Winchendon, MA

3 beds | 2 baths | 2,067 sq.ft.

$575,000

Airbnb cash on cash: 2.31%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $3257

Traditional Rental Income: $3906

Airbnb ROI: 2.31%

Traditional ROI: 4.88%

21 Cottage St

Winchendon, MA

3 beds | 2 baths | 1,400 sq.ft.

$434,900

Airbnb cash on cash: 4.9%

Traditional cash on cash: 7.11%

Airbnb Rental Income: $3257

Traditional Rental Income: $3423

Airbnb ROI: 4.9%

Traditional ROI: 7.11%

27 Cottage St

Winchendon, MA

3 beds | 2 baths | 1,400 sq.ft.

$424,900

Airbnb cash on cash: 5.04%

Traditional cash on cash: 7.22%

Airbnb Rental Income: $3257

Traditional Rental Income: $3394

Airbnb ROI: 5.04%

Traditional ROI: 7.22%

790 River St

Winchendon, MA

3 beds | 2 baths | 2,044 sq.ft.

$400,000

Airbnb cash on cash: 4.05%

Traditional cash on cash: 6.57%

Airbnb Rental Income: $3257

Traditional Rental Income: $3470

Airbnb ROI: 4.05%

Traditional ROI: 6.57%

33 East St

Winchendon, MA

3 beds | 1 baths | 1,728 sq.ft.

$269,000

Airbnb cash on cash: 7.82%

Traditional cash on cash: 8.93%

Airbnb Rental Income: $3257

Traditional Rental Income: $2808

Airbnb ROI: 7.82%

Traditional ROI: 8.93%

93 High St

Winchendon, MA

4 beds | 1 baths | 1,868 sq.ft.

$334,500

Airbnb cash on cash: N/A

Traditional cash on cash: 6.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2978

Airbnb ROI: N/A