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.

Single Family Homes for Sale in Winchester, MA

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

Showing 5 Single Family Residential 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
571 Washington St Winchester, MA Best valued single family in Winchester with incredible fenced backyard and expansive pati...	3 beds \| 1 baths \| 1,425 sq.ft.	$898,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.95% Airbnb Rental Income: $2123 Traditional Rental Income: $2674 Airbnb ROI: -0.36% Traditional ROI: 0.95%
20 Grove Pl Winchester, MA From the moment you enter this European-style Victorian, you'll be charmed. The first leve...	5 beds \| 4 baths \| 3,294 sq.ft.	$1,869,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.35% Airbnb Rental Income: $3379 Traditional Rental Income: $5861 Airbnb ROI: -0.52% Traditional ROI: 1.35%
446 Highland Ave Winchester, MA Charming Spanish-style home in desirable Winchester! This unique property features a beaut...	2 beds \| 2 baths \| 2,033 sq.ft.	$999,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.87% Airbnb Rental Income: $2243 Traditional Rental Income: $3084 Airbnb ROI: -0.64% Traditional ROI: 0.87%
32 Oak St. Winchester, MA Prime location near town center! This renovated 4-bed, 3-bath home is nestled in a private...	4 beds \| 3 baths \| 2,652 sq.ft.	$1,350,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.38% Airbnb Rental Income: $3351 Traditional Rental Income: $4108 Airbnb ROI: 0.18% Traditional ROI: 1.38%
35 Glen Grn Winchester, MA Welcome to this beautifully maintained Colonial in a highly desirable family neighborhood ...	4 beds \| 2 baths \| 3,509 sq.ft.	$1,999,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.07% Airbnb Rental Income: $3351 Traditional Rental Income: $3828 Airbnb ROI: -0.59% Traditional ROI: 0.07%

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Single Family Homes for Sale in Winchester, MA

571 Washington St

Winchester, MA

3 beds | 1 baths | 1,425 sq.ft.

$898,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $2123

Traditional Rental Income: $2674

Airbnb ROI: -0.36%

Traditional ROI: 0.95%

20 Grove Pl

Winchester, MA

5 beds | 4 baths | 3,294 sq.ft.

$1,869,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $3379

Traditional Rental Income: $5861

Airbnb ROI: -0.52%

Traditional ROI: 1.35%

446 Highland Ave

Winchester, MA

2 beds | 2 baths | 2,033 sq.ft.

$999,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $2243

Traditional Rental Income: $3084

Airbnb ROI: -0.64%

Traditional ROI: 0.87%

32 Oak St.

Winchester, MA

4 beds | 3 baths | 2,652 sq.ft.

$1,350,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $3351

Traditional Rental Income: $4108

Airbnb ROI: 0.18%

Traditional ROI: 1.38%

35 Glen Grn

Winchester, MA

4 beds | 2 baths | 3,509 sq.ft.

$1,999,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 0.07%

Airbnb Rental Income: $3351

Traditional Rental Income: $3828

Airbnb ROI: -0.59%

Traditional ROI: 0.07%

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