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.

Boro Investment Property for Sale in Winchendon, MA

Search for Boro Investment Property for Sale in Winchendon, Massachusetts. Browse all of Mashvisor’s Boro Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 8 Boro Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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.	$480,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 5.99% Airbnb Rental Income: $3257 Traditional Rental Income: $3673 Airbnb ROI: 3.44% Traditional ROI: 5.99%
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%

Your search for investment property begins and ends here

Boro Investment Property for Sale in Winchendon, MA

80 Elmwood Rd

Winchendon, MA

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

$480,000

Airbnb cash on cash: 3.44%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $3257

Traditional Rental Income: $3673

Airbnb ROI: 3.44%

Traditional ROI: 5.99%

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%