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 12 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
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.	$179,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 9.77% Airbnb Rental Income: $1289 Traditional Rental Income: $2105 Airbnb ROI: 2.65% Traditional ROI: 9.77%
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%
118 Meadow Street Winchester, CT This charming historic home, built in 1860, blends timeless character with thoughtful upda...	3 beds \| 2 baths \| 1,652 sq.ft.	$290,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.17% Airbnb Rental Income: $1611 Traditional Rental Income: $1808 Airbnb ROI: 0.77% Traditional ROI: 3.17%
55 Walnut Street Winchester, CT Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunn...	5 beds \| 4 baths \| 5,016 sq.ft.	$499,999	Airbnb cash on cash: N/A Traditional cash on cash: 9.3% Airbnb Rental Income: $null Traditional Rental Income: $5903 Airbnb ROI: N/A Traditional ROI: 9.3%
722 Lake Drive Winchester, CT Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccab...	3 beds \| 3 baths \| 2,420 sq.ft.	$1,270,000	Airbnb cash on cash: -2.23% Traditional cash on cash: 0.4% Airbnb Rental Income: $1611 Traditional Rental Income: $4265 Airbnb ROI: -2.23% Traditional ROI: 0.4%
440 Platt Hill Road Winchester, CT Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque c...	4 beds \| 3 baths \| 3,416 sq.ft.	$500,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 7.28% Airbnb Rental Income: $3395 Traditional Rental Income: $4956 Airbnb ROI: 2.33% Traditional ROI: 7.28%
197 Spencer Hill Road Winchester, CT Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a...	3 beds \| 2 baths \| 2,167 sq.ft.	$499,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 3.78% Airbnb Rental Income: $1611 Traditional Rental Income: $3312 Airbnb ROI: -0.85% Traditional ROI: 3.78%
156 Lincoln Avenue Winchester, CT Welcome to your cozy cottage retreat in beautiful Highland Lake Community. Views of the la...	2 beds \| 1 baths \| 702 sq.ft.	$299,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.25% Airbnb Rental Income: $1289 Traditional Rental Income: $1890 Airbnb ROI: -0.31% Traditional ROI: 3.25%
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.	$339,900	Airbnb cash on cash: 4.86% Traditional cash on cash: 7.13% Airbnb Rental Income: $3395 Traditional Rental Income: $3365 Airbnb ROI: 4.86% Traditional ROI: 7.13%
95 Nalette Drive Winchester, CT Stunning Contemporary Home on a Quiet Corner Lot. This unique home offers a beautifully u...	3 beds \| 3 baths \| 2,356 sq.ft.	$365,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 7.98% Airbnb Rental Income: $1611 Traditional Rental Income: $3893 Airbnb ROI: -0.02% Traditional ROI: 7.98%
208 Spencer Hill Road Winchester, CT Discover this beautifully maintained 3-bedroom, 1.5-bath Colonial set on a level one-acre ...	3 beds \| 2 baths \| 1,969 sq.ft.	$399,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 5.55% Airbnb Rental Income: $1611 Traditional Rental Income: $3337 Airbnb ROI: -0.28% Traditional ROI: 5.55%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, CT

8 Oak Street

Winchester, CT

2 beds | 2 baths | 832 sq.ft.

$179,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 9.77%

Airbnb Rental Income: $1289

Traditional Rental Income: $2105

Airbnb ROI: 2.65%

Traditional ROI: 9.77%

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%

118 Meadow Street

Winchester, CT

3 beds | 2 baths | 1,652 sq.ft.

$290,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $1611

Traditional Rental Income: $1808

Airbnb ROI: 0.77%

Traditional ROI: 3.17%

55 Walnut Street

Winchester, CT

5 beds | 4 baths | 5,016 sq.ft.

$499,999

Airbnb cash on cash: N/A

Traditional cash on cash: 9.3%

Airbnb Rental Income: $null

Traditional Rental Income: $5903

Airbnb ROI: N/A

Traditional ROI: 9.3%

722 Lake Drive

Winchester, CT

3 beds | 3 baths | 2,420 sq.ft.

$1,270,000

Airbnb cash on cash: -2.23%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $1611

Traditional Rental Income: $4265

Airbnb ROI: -2.23%

Traditional ROI: 0.4%

440 Platt Hill Road

Winchester, CT

4 beds | 3 baths | 3,416 sq.ft.

$500,000

Airbnb cash on cash: 2.33%

Traditional cash on cash: 7.28%

Airbnb Rental Income: $3395

Traditional Rental Income: $4956

Airbnb ROI: 2.33%

Traditional ROI: 7.28%

197 Spencer Hill Road

Winchester, CT

3 beds | 2 baths | 2,167 sq.ft.

$499,000

Airbnb cash on cash: -0.85%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $1611

Traditional Rental Income: $3312

Airbnb ROI: -0.85%

Traditional ROI: 3.78%

156 Lincoln Avenue

Winchester, CT

2 beds | 1 baths | 702 sq.ft.

$299,900

Airbnb cash on cash: -0.31%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $1289

Traditional Rental Income: $1890

Airbnb ROI: -0.31%