Real Estate Investment Properties for Sale in Winchester, CT

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

Explore a variety of short-term homes & houses in Winchester, CT. Invest wisely with VRBO & Winchester, CT 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, CT

Search for Single Family Residential for Sale in Winchester, Connecticut. 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 2 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
146 SPENCER HILL ROAD Winchester, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	5 beds \| 3 baths \| 3,204 sq.ft.	$681,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.7% Airbnb Rental Income: $null Traditional Rental Income: $4428 Airbnb ROI: N/A Traditional ROI: 3.7%
Other Investment Properties for Sale in Winchester
18 Curtice Street Winchester , CT Move-in ready and thoughtfully updated, this inviting home at 18 Curtice Street offers pea...	2 beds \| 2 baths \| 1,252 sq.ft.	$229,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 8.88% Airbnb Rental Income: $1289 Traditional Rental Income: $2546 Airbnb ROI: 1.21% Traditional ROI: 8.88%
8 Oak Street Winchester , CT Discover a low maintenance and hassle-free alternative to condo living with this easy-to-m...	2 beds \| 2 baths \| 832 sq.ft.	$159,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 11.12% Airbnb Rental Income: $1289 Traditional Rental Income: $2105 Airbnb ROI: 3.09% Traditional ROI: 11.12%
77 Hubbard Street Winchester , CT Discover this versatile two-family residence offering a blend of modern updates and timele...	6 beds \| 2 baths \| 2,699 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 10% Airbnb Rental Income: $null Traditional Rental Income: $3553 Airbnb ROI: N/A Traditional ROI: 10%
148 Danbury Quarter Road Winchester , CT Welcome to this Wonderful Historic Colonial Farmhouse.. This home has been lovingly remode...	4 beds \| 2 baths \| 1,999 sq.ft.	$329,900	Airbnb cash on cash: 5.82% Traditional cash on cash: 8.16% Airbnb Rental Income: $3395 Traditional Rental Income: $3365 Airbnb ROI: 5.82% Traditional ROI: 8.16%
106 Rockwell Street Winchester , CT Looking to expand your investment portfolio-or live nearly rent-free while building one? T...	6 beds \| 3 baths \| 1,874 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.12% Airbnb Rental Income: $null Traditional Rental Income: $3574 Airbnb ROI: N/A Traditional ROI: 10.12%
00 Chapel Rd Winchester , CT 00 Chapel Rd, Winchester, CT 06098 \| Other	N/A beds \| N/A baths \| 8,862 sq.ft.	$300,000	Airbnb cash on cash: 2.29% Traditional cash on cash: -0.31% Airbnb Rental Income: $2170 Traditional Rental Income: $884 Airbnb ROI: 2.29% Traditional ROI: -0.31%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, CT

146 SPENCER HILL ROAD

Winchester, CT

5 beds | 3 baths | 3,204 sq.ft.

$681,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.7%

Airbnb Rental Income: $null

Traditional Rental Income: $4428

Airbnb ROI: N/A

Traditional ROI: 3.7%

Other Investment Properties for Sale in Winchester

18 Curtice Street

Winchester , CT

2 beds | 2 baths | 1,252 sq.ft.

$229,000

Airbnb cash on cash: 1.21%

Traditional cash on cash: 8.88%

Airbnb Rental Income: $1289

Traditional Rental Income: $2546

Airbnb ROI: 1.21%

Traditional ROI: 8.88%

8 Oak Street

Winchester , CT

2 beds | 2 baths | 832 sq.ft.

$159,000

Airbnb cash on cash: 3.09%

Traditional cash on cash: 11.12%

Airbnb Rental Income: $1289

Traditional Rental Income: $2105

Airbnb ROI: 3.09%

Traditional ROI: 11.12%

77 Hubbard Street

Winchester , CT

6 beds | 2 baths | 2,699 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10%

Airbnb Rental Income: $null

Traditional Rental Income: $3553

Airbnb ROI: N/A

Traditional ROI: 10%

148 Danbury Quarter Road

Winchester , CT

4 beds | 2 baths | 1,999 sq.ft.

$329,900

Airbnb cash on cash: 5.82%

Traditional cash on cash: 8.16%

Airbnb Rental Income: $3395

Traditional Rental Income: $3365

Airbnb ROI: 5.82%

Traditional ROI: 8.16%

106 Rockwell Street

Winchester , CT

6 beds | 3 baths | 1,874 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.12%

Airbnb Rental Income: $null

Traditional Rental Income: $3574

Airbnb ROI: N/A

Traditional ROI: 10.12%

00 Chapel Rd

Winchester , CT

N/A beds | N/A baths | 8,862 sq.ft.

$300,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: -0.31%

Airbnb Rental Income: $2170

Traditional Rental Income: $884

Airbnb ROI: 2.29%

Traditional ROI: -0.31%

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