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
80 Elmwood Rd Winchendon, MA Welcome to 80 Elmwood Rd! A beautifully maintained 3-bedroom, 2.5-bath young colonial buil...	3 beds \| 3 baths \| 1,768 sq.ft.	$470,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 6.14% Airbnb Rental Income: $3257 Traditional Rental Income: $3673 Airbnb ROI: 3.53% Traditional ROI: 6.14%
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: 7.89% Traditional cash on cash: 11.99% Airbnb Rental Income: $3257 Traditional Rental Income: $3543 Airbnb ROI: 7.89% Traditional ROI: 11.99%
16 2nd St Winchendon, MA Life Long Memories Await at this Beautiful Waterfront House on Desirable Lake Monomonac! Y...	3 beds \| 3 baths \| 2,540 sq.ft.	$939,900	Airbnb cash on cash: 1.34% Traditional cash on cash: 3.23% Airbnb Rental Income: $3257 Traditional Rental Income: $4182 Airbnb ROI: 1.34% Traditional ROI: 3.23%
241 Mill Glen Road Winchendon, MA Cherished by its original owner, this Cape blends classic charm with decades of thoughtful...	3 beds \| 2 baths \| 1,428 sq.ft.	$379,900	Airbnb cash on cash: 4.88% Traditional cash on cash: 6.61% Airbnb Rental Income: $3257 Traditional Rental Income: $3142 Airbnb ROI: 4.88% Traditional ROI: 6.61%
150 Lakeshore Drive Winchendon, MA Wow, just wow. This home has everything you need and more. Nestled on this large lot, s...	4 beds \| 2 baths \| 2,184 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.06% Airbnb Rental Income: $null Traditional Rental Income: $3844 Airbnb ROI: N/A Traditional ROI: 6.06%
32 Old County Rd Winchendon, MA Tucked back from the road for full privacy, this beautifully maintained 3-bedroom, 1.5-bat...	3 beds \| 2 baths \| 1,568 sq.ft.	$489,900	Airbnb cash on cash: 3.34% Traditional cash on cash: 4.99% Airbnb Rental Income: $3257 Traditional Rental Income: $3283 Airbnb ROI: 3.34% Traditional ROI: 4.99%
15 Cottage St Winchendon, MA Sun filled colonial in quiet Winchendon location. This home has been rehabbed from top to ...	4 beds \| 2 baths \| 1,668 sq.ft.	$459,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.53% Airbnb Rental Income: $null Traditional Rental Income: $3579 Airbnb ROI: N/A Traditional ROI: 6.53%
Lot 1 Cottage St Winchendon, MA Lot 1 Cottage St, Winchendon, MA, presents a single-family residence, constructed in 2025 ...	3 beds \| 3 baths \| 1,400 sq.ft.	$479,900	Airbnb cash on cash: 3.2% Traditional cash on cash: 5.16% Airbnb Rental Income: $3257 Traditional Rental Income: $3408 Airbnb ROI: 3.2% Traditional ROI: 5.16%

Real Estate investment in Winchendon, MA

There are 8 properties for sale in the city of Winchendon . The median list price in Winchendon is $474,950 and the average price per square foot is $258. In September 2025, the average monthly cash on cash return in Winchendon is 6.00%. The average monthly rental income in Winchendon is $3,561.

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

There are 8 investment properties available for sale in Winchendon.

In 2025, 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 $3,561.

Your search for investment property begins and ends here

Investment Property for Sale in Winchendon, MA

80 Elmwood Rd

Winchendon, MA

3 beds | 3 baths | 1,768 sq.ft.

$470,000

Airbnb cash on cash: 3.53%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $3257

Traditional Rental Income: $3673

Airbnb ROI: 3.53%

Traditional ROI: 6.14%

122-124 ELM ST

Winchendon, MA

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

$263,000

Airbnb cash on cash: 7.89%

Traditional cash on cash: 11.99%

Airbnb Rental Income: $3257

Traditional Rental Income: $3543

Airbnb ROI: 7.89%

Traditional ROI: 11.99%

16 2nd St

Winchendon, MA

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

$939,900

Airbnb cash on cash: 1.34%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $3257

Traditional Rental Income: $4182

Airbnb ROI: 1.34%

Traditional ROI: 3.23%

241 Mill Glen Road

Winchendon, MA

3 beds | 2 baths | 1,428 sq.ft.

$379,900

Airbnb cash on cash: 4.88%

Traditional cash on cash: 6.61%

Airbnb Rental Income: $3257

Traditional Rental Income: $3142

Airbnb ROI: 4.88%

Traditional ROI: 6.61%

150 Lakeshore Drive

Winchendon, MA

4 beds | 2 baths | 2,184 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.06%

Airbnb Rental Income: $null

Traditional Rental Income: $3844

Airbnb ROI: N/A

Traditional ROI: 6.06%

32 Old County Rd

Winchendon, MA

3 beds | 2 baths | 1,568 sq.ft.

$489,900

Airbnb cash on cash: 3.34%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $3257

Traditional Rental Income: $3283

Airbnb ROI: 3.34%

Traditional ROI: 4.99%

15 Cottage St

Winchendon, MA

4 beds | 2 baths | 1,668 sq.ft.

$459,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3579

Airbnb ROI: N/A

Traditional ROI: 6.53%

Lot 1 Cottage St

Winchendon, MA

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

$479,900

Airbnb cash on cash: 3.2%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $3257

Traditional Rental Income: $3408

Airbnb ROI: 3.2%