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.

Condos for Sale in Winchester, CT

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

Showing 25 Condos 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
538 Wheelers Point Winchester, CT Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with...	4 beds \| 3 baths \| 2,496 sq.ft.	$1,699,500	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.94% Airbnb Rental Income: $2382 Traditional Rental Income: $4813 Airbnb ROI: -0.97% Traditional ROI: 0.94%
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%
18-4A Taylor Brook Road Winchester, CT Beautiful custom built gem situated on a private site with a stream! Bright, sunny open fl...	3 beds \| 3 baths \| 2,135 sq.ft.	$650,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.03% Airbnb Rental Income: $2365 Traditional Rental Income: $3827 Airbnb ROI: -0.34% Traditional ROI: 3.03%
22 Stanton Avenue Winchester, CT Welcome to this well-maintained 3-bedroom, 1-bathroom home located on a quiet street in th...	3 beds \| 1 baths \| 1,058 sq.ft.	$264,900	Airbnb cash on cash: 4.76% Traditional cash on cash: 3.37% Airbnb Rental Income: $2365 Traditional Rental Income: $1435 Airbnb ROI: 4.76% Traditional ROI: 3.37%
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: 9.14% Airbnb Rental Income: $null Traditional Rental Income: $3553 Airbnb ROI: N/A Traditional ROI: 9.14%
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.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.95% Airbnb Rental Income: $null Traditional Rental Income: $5903 Airbnb ROI: N/A Traditional ROI: 8.95%
111 South Road Winchester, CT Perched up higher than the rest with sweeping views up a private driveway in beautiful Win...	3 beds \| 4 baths \| 4,953 sq.ft.	$779,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 4.25% Airbnb Rental Income: $2365 Traditional Rental Income: $5454 Airbnb ROI: -0.8% Traditional ROI: 4.25%
181 Torringford Street Winchester, CT Motivated seller! Charming Colonial on Nearly an Acre! Discover the perfect blend of comfo...	3 beds \| 2 baths \| 2,160 sq.ft.	$345,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 7.15% Airbnb Rental Income: $2365 Traditional Rental Income: $3418 Airbnb ROI: 2.1% Traditional ROI: 7.15%
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.	$1,295,000	Airbnb cash on cash: -1.73% Traditional cash on cash: 0.34% Airbnb Rental Income: $2365 Traditional Rental Income: $4265 Airbnb ROI: -1.73% Traditional ROI: 0.34%
12 Cherry Street Winchester, CT This Home is Modern day updates Meets Old World Charm...The Updated Kitchen offers granite...	4 beds \| 1 baths \| 1,492 sq.ft.	$287,750	Airbnb cash on cash: 3.17% Traditional cash on cash: 5.99% Airbnb Rental Income: $2382 Traditional Rental Income: $2561 Airbnb ROI: 3.17% Traditional ROI: 5.99%
147 Smith Hill Road Winchester, CT Tucked away on a wooded lot, this meticulously maintained Cape features 4 spacious bedroom...	4 beds \| 2 baths \| 1,910 sq.ft.	$365,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 6.81% Airbnb Rental Income: $2382 Traditional Rental Income: $3494 Airbnb ROI: 1.85% Traditional ROI: 6.81%
15 John Street Winchester, CT Feels Like New - Without the New Construction Price! Looking for a move-in ready home that...	3 beds \| 2 baths \| 1,538 sq.ft.	$299,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 7.11% Airbnb Rental Income: $2365 Traditional Rental Income: $2971 Airbnb ROI: 2.89% Traditional ROI: 7.11%
441 Platt Hill Road Winchester, CT Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to ...	5 beds \| 3 baths \| 3,404 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.2% Airbnb Rental Income: $null Traditional Rental Income: $4951 Airbnb ROI: N/A Traditional ROI: 5.2%
174 Wallens Street #APT H1 Winchester, CT Discover effortless living in this inviting home at the sought-after Clockmaker's Hill com...	1 beds \| 2 baths \| 1,334 sq.ft.	$235,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 6.81% Airbnb Rental Income: $1753 Traditional Rental Income: $2770 Airbnb ROI: 0.06% Traditional ROI: 6.81%
166 Torringford Street Winchester, CT Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litch...	3 beds \| 2 baths \| 2,024 sq.ft.	$380,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.49% Airbnb Rental Income: $2365 Traditional Rental Income: $3163 Airbnb ROI: 1.62% Traditional ROI: 5.49%
126 Forest Avenue Winchester, CT Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath C...	3 beds \| 2 baths \| 1,833 sq.ft.	$355,750	Airbnb cash on cash: 1.94% Traditional cash on cash: 6.28% Airbnb Rental Income: $2365 Traditional Rental Income: $3232 Airbnb ROI: 1.94% Traditional ROI: 6.28%
101 Norfolk Road Winchester, CT Beautifully updated Raised- Ranch retreat on 1.33 wooded acres! Nestled in a serene, natur...	2 beds \| 1 baths \| 1,880 sq.ft.	$315,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.43% Airbnb Rental Income: $2117 Traditional Rental Income: $2033 Airbnb ROI: 1.89% Traditional ROI: 3.43%

Your search for investment property begins and ends here

Condos for Sale in Winchester, CT

538 Wheelers Point

Winchester, CT

4 beds | 3 baths | 2,496 sq.ft.

$1,699,500

Airbnb cash on cash: -0.97%

Traditional cash on cash: 0.94%

Airbnb Rental Income: $2382

Traditional Rental Income: $4813

Airbnb ROI: -0.97%

Traditional ROI: 0.94%

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%

18-4A Taylor Brook Road

Winchester, CT

3 beds | 3 baths | 2,135 sq.ft.

$650,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $2365

Traditional Rental Income: $3827

Airbnb ROI: -0.34%

Traditional ROI: 3.03%

22 Stanton Avenue

Winchester, CT

3 beds | 1 baths | 1,058 sq.ft.

$264,900

Airbnb cash on cash: 4.76%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $2365

Traditional Rental Income: $1435

Airbnb ROI: 4.76%

Traditional ROI: 3.37%

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: 9.14%

Airbnb Rental Income: $null

Traditional Rental Income: $3553

Airbnb ROI: N/A

Traditional ROI: 9.14%

55 Walnut Street

Winchester, CT

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

$515,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.95%

Airbnb Rental Income: $null

Traditional Rental Income: $5903

Airbnb ROI: N/A

Traditional ROI: 8.95%

111 South Road

Winchester, CT

3 beds | 4 baths | 4,953 sq.ft.

$779,900

Airbnb cash on cash: -0.8%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $2365

Traditional Rental Income: $5454

Airbnb ROI: -0.8%

Traditional ROI: 4.25%

181 Torringford Street

Winchester, CT

3 beds | 2 baths | 2,160 sq.ft.

$345,000

Airbnb cash on cash: 2.1%

Traditional cash on cash: 7.15%

Airbnb Rental Income: $2365

Traditional Rental Income: $3418

Airbnb ROI: 2.1%