Real Estate Investment Properties for Sale in Winchester, MA

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

Explore a variety of short-term homes & houses in Winchester, MA. Invest wisely with VRBO & Winchester, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Winchester, MA

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

Showing 10 Condo 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
200 Swanton St #T35 Winchester, MA Just in time for the warm weather. Move right into this 2 bedroom, terrace level condo at...	2 beds \| 1 baths \| 810 sq.ft.	$400,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.46% Airbnb Rental Income: $2124 Traditional Rental Income: $2329 Airbnb ROI: 0.46% Traditional ROI: 2.46%
666 Main St #315 Winchester, MA Location is everything! Located in Winchester Center, on Wedge Pond and walking distance t...	2 beds \| 2 baths \| 1,025 sq.ft.	$649,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.28% Airbnb Rental Income: $2124 Traditional Rental Income: $2709 Airbnb ROI: -0.58% Traditional ROI: 1.28%
666 Main #211 Winchester, MA 666 Main #211, Winchester, MA 01890 \| Condo/Coop	2 beds \| 2 baths \| 1,170 sq.ft.	$700,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.52% Airbnb Rental Income: $2124 Traditional Rental Income: $2522 Airbnb ROI: -0.92% Traditional ROI: 0.52%
200 Swanton #L8 Winchester, MA 200 Swanton #L8, Winchester, MA 01890 \| Condo/Coop	1 beds \| 1 baths \| 388 sq.ft.	$288,750	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.76% Airbnb Rental Income: $1525 Traditional Rental Income: $2013 Airbnb ROI: 0.34% Traditional ROI: 3.76%
83 Church St #15 Winchester, MA 83 Church St #15, Winchester, MA 01890 \| Condo/Coop	2 beds \| 1 baths \| 1,365 sq.ft.	$999,000	Airbnb cash on cash: -1.76% Traditional cash on cash: -0.62% Airbnb Rental Income: $2124 Traditional Rental Income: $2642 Airbnb ROI: -1.76% Traditional ROI: -0.62%
200 Swanton St #228 Winchester, MA Welcome to Parkview Condos! This one bed one bath, bright unit features an open layout wit...	1 beds \| 1 baths \| 606 sq.ft.	$375,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.95% Airbnb Rental Income: $1525 Traditional Rental Income: $1956 Airbnb ROI: -0.53% Traditional ROI: 1.95%
14 Bradford Rd #14 Winchester, MA An affordable, 3 bedroom, 1.5 bath townhome at the Residences at Winchester is ready for n...	3 beds \| 2 baths \| 1,168 sq.ft.	$624,900	Airbnb cash on cash: 1.07% Traditional cash on cash: 2.92% Airbnb Rental Income: $2486 Traditional Rental Income: $2961 Airbnb ROI: 1.07% Traditional ROI: 2.92%

Your search for investment property begins and ends here

Condos for Sale in Winchester, MA

200 Swanton St #T35

Winchester, MA

2 beds | 1 baths | 810 sq.ft.

$400,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $2124

Traditional Rental Income: $2329

Airbnb ROI: 0.46%

Traditional ROI: 2.46%

666 Main St #315

Winchester, MA

2 beds | 2 baths | 1,025 sq.ft.

$649,900

Airbnb cash on cash: -0.58%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $2124

Traditional Rental Income: $2709

Airbnb ROI: -0.58%

Traditional ROI: 1.28%

666 Main #211

Winchester, MA

2 beds | 2 baths | 1,170 sq.ft.

$700,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $2124

Traditional Rental Income: $2522

Airbnb ROI: -0.92%

Traditional ROI: 0.52%

200 Swanton #L8

Winchester, MA

1 beds | 1 baths | 388 sq.ft.

$288,750

Airbnb cash on cash: 0.34%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $1525

Traditional Rental Income: $2013

Airbnb ROI: 0.34%

Traditional ROI: 3.76%

83 Church St #15

Winchester, MA

2 beds | 1 baths | 1,365 sq.ft.

$999,000

Airbnb cash on cash: -1.76%

Traditional cash on cash: -0.62%

Airbnb Rental Income: $2124

Traditional Rental Income: $2642

Airbnb ROI: -1.76%

Traditional ROI: -0.62%

200 Swanton St #228

Winchester, MA

1 beds | 1 baths | 606 sq.ft.

$375,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $1525

Traditional Rental Income: $1956

Airbnb ROI: -0.53%

Traditional ROI: 1.95%

14 Bradford Rd #14

Winchester, MA

3 beds | 2 baths | 1,168 sq.ft.

$624,900

Airbnb cash on cash: 1.07%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $2486

Traditional Rental Income: $2961

Airbnb ROI: 1.07%

Traditional ROI: 2.92%

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