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
23 Webster St Winchendon, MA Welcome to 23 Webster Street in Winchendon, MA. This Colonial-style home offers a practica...	2 beds \| 2 baths \| 996 sq.ft.	$307,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 7.75% Airbnb Rental Income: $1966 Traditional Rental Income: $2814 Airbnb ROI: 3.03% Traditional ROI: 7.75%
25 Fairbank Street Winchendon, MA Looking to be away from it all, yet still convenient enough for commuting--just 4 miles fr...	4 beds \| 4 baths \| 3,400 sq.ft.	$599,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 5.4% Airbnb Rental Income: $2565 Traditional Rental Income: $4302 Airbnb ROI: 1.2% Traditional ROI: 5.4%
263 Front St. Winchendon, MA UPDATE: All electrical has been updated and brought up to code. 263 Front St. is a well-ma...	6 beds \| 2 baths \| 2,289 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.53% Airbnb Rental Income: $null Traditional Rental Income: $3726 Airbnb ROI: N/A Traditional ROI: 8.53%
173 Baldwinville Rd Winchendon, MA Come on out and be the first to see this new to market 3 bedroom ranch with more than 5 pr...	3 beds \| 1 baths \| 1,092 sq.ft.	$309,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 6.53% Airbnb Rental Income: $2611 Traditional Rental Income: $2590 Airbnb ROI: 4.46% Traditional ROI: 6.53%
374 Front Street Winchendon, MA There's something special about a Village Colonial: the character, the generous rooms and ...	4 beds \| 2 baths \| 1,686 sq.ft.	$385,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 7.8% Airbnb Rental Income: $2565 Traditional Rental Income: $3550 Airbnb ROI: 3.37% Traditional ROI: 7.8%
River St lot: 1 Winchendon, MA Newly built and ready to welcome its first residents. This new home offers the promise of ...	3 beds \| 3 baths \| 1,400 sq.ft.	$464,900	Airbnb cash on cash: 2.13% Traditional cash on cash: 5.47% Airbnb Rental Income: $2611 Traditional Rental Income: $3441 Airbnb ROI: 2.13% Traditional ROI: 5.47%
River St lot: 2 Winchendon, MA Newly built and ready to welcome its first residents. This new home offers the promise of ...	3 beds \| 3 baths \| 1,400 sq.ft.	$489,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 2.57% Airbnb Rental Income: $2611 Traditional Rental Income: $2289 Airbnb ROI: 1.91% Traditional ROI: 2.57%
202 Ash St Winchendon, MA Historic character meets country living at "The Corners," a distinctive Federal-style resi...	4 beds \| 3 baths \| 2,940 sq.ft.	$739,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 4.44% Airbnb Rental Income: $2565 Traditional Rental Income: $4340 Airbnb ROI: 0.97% Traditional ROI: 4.44%
179 Glenallen St Winchendon, MA Welcome to 179 Glenallen Street! This spacious 3-bedroom home offers plenty of room to spr...	3 beds \| 2 baths \| 1,596 sq.ft.	$329,900	Airbnb cash on cash: 4.19% Traditional cash on cash: 8.54% Airbnb Rental Income: $2611 Traditional Rental Income: $3334 Airbnb ROI: 4.19% Traditional ROI: 8.54%
103 High St Winchendon, MA Newly built and ready to welcome its first homeowner. This new home offers the promise of ...	3 beds \| 3 baths \| 1,500 sq.ft.	$484,900	Airbnb cash on cash: 3.11% Traditional cash on cash: 6.51% Airbnb Rental Income: $2611 Traditional Rental Income: $3529 Airbnb ROI: 3.11% Traditional ROI: 6.51%

Real Estate investment in Winchendon, MA

There are 10 properties for sale in the city of Winchendon . The median list price in Winchendon is $369,824 and the average price per square foot is $187. In November 2026, the average monthly cash on cash return in Winchendon is 7.00%. The average monthly rental income in Winchendon is $3,485.

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

There are 10 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 $3,485.

Your search for investment property begins and ends here

Investment Property for Sale in Winchendon, MA

23 Webster St

Winchendon, MA

2 beds | 2 baths | 996 sq.ft.

$307,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 7.75%

Airbnb Rental Income: $1966

Traditional Rental Income: $2814

Airbnb ROI: 3.03%

Traditional ROI: 7.75%

25 Fairbank Street

Winchendon, MA

4 beds | 4 baths | 3,400 sq.ft.

$599,900

Airbnb cash on cash: 1.2%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $2565

Traditional Rental Income: $4302

Airbnb ROI: 1.2%

Traditional ROI: 5.4%

263 Front St.

Winchendon, MA

6 beds | 2 baths | 2,289 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3726

Airbnb ROI: N/A

Traditional ROI: 8.53%

173 Baldwinville Rd

Winchendon, MA

3 beds | 1 baths | 1,092 sq.ft.

$309,900

Airbnb cash on cash: 4.46%

Traditional cash on cash: 6.53%

Airbnb Rental Income: $2611

Traditional Rental Income: $2590

Airbnb ROI: 4.46%

Traditional ROI: 6.53%

374 Front Street

Winchendon, MA

4 beds | 2 baths | 1,686 sq.ft.

$385,000

Airbnb cash on cash: 3.37%

Traditional cash on cash: 7.8%

Airbnb Rental Income: $2565

Traditional Rental Income: $3550

Airbnb ROI: 3.37%

Traditional ROI: 7.8%

River St lot: 1

Winchendon, MA

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

$464,900

Airbnb cash on cash: 2.13%

Traditional cash on cash: 5.47%

Airbnb Rental Income: $2611

Traditional Rental Income: $3441

Airbnb ROI: 2.13%

Traditional ROI: 5.47%

River St lot: 2

Winchendon, MA

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

$489,900

Airbnb cash on cash: 1.91%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $2611

Traditional Rental Income: $2289

Airbnb ROI: 1.91%

Traditional ROI: 2.57%

202 Ash St

Winchendon, MA

4 beds | 3 baths | 2,940 sq.ft.

$739,900

Airbnb cash on cash: 0.97%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $2565

Traditional Rental Income: $4340

Airbnb ROI: 0.97%