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.

Tment Property for Sale in Winchester, CT

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

Showing 9 Tment Property 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%
25 Center Street Winchester, CT Don't miss this unique opportunity to own a multi family residential property and an offic...	3 beds \| 3 baths \| 2,754 sq.ft.	$359,900	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.3% Airbnb Rental Income: $1611 Traditional Rental Income: $1369 Airbnb ROI: 1.58% Traditional ROI: 2.3%
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%
436 Main Street Winchester, CT One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in th...	4 beds \| 2 baths \| 5,389 sq.ft.	$750,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 3.64% Airbnb Rental Income: $3395 Traditional Rental Income: $3768 Airbnb ROI: 2.02% Traditional ROI: 3.64%
5 Stadler Heights Winchester, CT Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with ple...	4 beds \| 3 baths \| 3,556 sq.ft.	$499,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 0.4% Airbnb Rental Income: $3395 Traditional Rental Income: $1515 Airbnb ROI: 2.81% Traditional ROI: 0.4%
156 Shore Drive Winchester, CT Summer is just around the corner, and this is your opportunity to own a highly sought-afte...	5 beds \| 2 baths \| 1,258 sq.ft.	$789,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.78% Airbnb Rental Income: $null Traditional Rental Income: $3118 Airbnb ROI: N/A Traditional ROI: 1.78%

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Tment Property 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%

25 Center Street

Winchester, CT

3 beds | 3 baths | 2,754 sq.ft.

$359,900

Airbnb cash on cash: 1.58%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $1611

Traditional Rental Income: $1369

Airbnb ROI: 1.58%

Traditional ROI: 2.3%

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%

436 Main Street

Winchester, CT

4 beds | 2 baths | 5,389 sq.ft.

$750,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $3395

Traditional Rental Income: $3768

Airbnb ROI: 2.02%

Traditional ROI: 3.64%

5 Stadler Heights

Winchester, CT

4 beds | 3 baths | 3,556 sq.ft.

$499,000

Airbnb cash on cash: 2.81%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $3395

Traditional Rental Income: $1515

Airbnb ROI: 2.81%

Traditional ROI: 0.4%

156 Shore Drive

Winchester, CT

5 beds | 2 baths | 1,258 sq.ft.

$789,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.78%

Airbnb Rental Income: $null

Traditional Rental Income: $3118

Airbnb ROI: N/A

Traditional ROI: 1.78%

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