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.

Investment Property for Sale in Winchester, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
711 West Wakefield Boulevard Winchester, CT Build your DREAM home! Largest lot available on the lake with great views and parking! Wil...	3 beds \| 3 baths \| 2,664 sq.ft.	$1,500,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.55% Airbnb Rental Income: $4795 Traditional Rental Income: $3932 Airbnb ROI: 1.46% Traditional ROI: 1.55%
115 Moore Avenue Winchester, CT If you are looking for a mini estate look no further. This completely remodeled home has e...	3 beds \| 3 baths \| 2,240 sq.ft.	$449,900	Airbnb cash on cash: 6.83% Traditional cash on cash: 6.44% Airbnb Rental Income: $4795 Traditional Rental Income: $3642 Airbnb ROI: 6.83% Traditional ROI: 6.44%
25 Hillside Avenue Winchester, CT Wow, this handsome Historic Manson is a rare beauty. It was coverted into 5 units and has ...	6 beds \| 5 baths \| 5,001 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.65% Airbnb Rental Income: $null Traditional Rental Income: $6277 Airbnb ROI: N/A Traditional ROI: 9.65%
111 Riverton Road #53 Winchester, CT Welcome to 111 Riverton Road, Unit 53-your perfect home just in time for the holidays! Thi...	2 beds \| 2 baths \| 1,204 sq.ft.	$190,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 10.18% Airbnb Rental Income: $1785 Traditional Rental Income: $2744 Airbnb ROI: 2.18% Traditional ROI: 10.18%
39 South Main Street Winchester, CT THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totali...	9 beds \| 5 baths \| 4,446 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.01% Airbnb Rental Income: $null Traditional Rental Income: $6023 Airbnb ROI: N/A Traditional ROI: 8.01%
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: 3% Traditional cash on cash: 3.03% Airbnb Rental Income: $4795 Traditional Rental Income: $3827 Airbnb ROI: 3% Traditional ROI: 3.03%
522 West Wakefield Boulevard Winchester, CT LOCATION! LOCATION! LOCATION! Direct Waterfront Lake Property on a VERY RARE 1 ACRE level ...	2 beds \| 1 baths \| 1,134 sq.ft.	$650,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 0.88% Airbnb Rental Income: $1785 Traditional Rental Income: $2289 Airbnb ROI: -0.75% Traditional ROI: 0.88%
247 North Main Street Winchester, CT Architectural wonder and great investment opportunity. You will love the entrancing detail...	8 beds \| 5 baths \| 5,093 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.72% Airbnb Rental Income: $null Traditional Rental Income: $6097 Airbnb ROI: N/A Traditional ROI: 9.72%
110 South Road Winchester, CT Your private oasis nestled in historic Winchester Center, offering serenity, lakes, trails...	4 beds \| 3 baths \| 3,870 sq.ft.	$694,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.35% Airbnb Rental Income: $3619 Traditional Rental Income: $4284 Airbnb ROI: 1.1% Traditional ROI: 3.35%
19 Cottage Street Winchester, CT Welcome to 19 Cottage Street, a stunning turnkey Colonial in the heart of Winsted that bea...	4 beds \| 4 baths \| 2,674 sq.ft.	$399,999	Airbnb cash on cash: 4.17% Traditional cash on cash: 8.3% Airbnb Rental Income: $3619 Traditional Rental Income: $4373 Airbnb ROI: 4.17% Traditional ROI: 8.3%
161 Marshall Street Winchester, CT Lovely Country home located on the outskirts of town features 8 rooms 3-4 bedrooms and 2 f...	4 beds \| 2 baths \| 2,216 sq.ft.	$359,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 7.11% Airbnb Rental Income: $3619 Traditional Rental Income: $3548 Airbnb ROI: 4.98% Traditional ROI: 7.11%
220 Gilbert Avenue Winchester, CT WOW - Welcome to 220 Gilbert Ave! Stop by for a visit and view the amazing transformation ...	4 beds \| 2 baths \| 2,176 sq.ft.	$379,900	Airbnb cash on cash: 4.56% Traditional cash on cash: 5.87% Airbnb Rental Income: $3619 Traditional Rental Income: $3295 Airbnb ROI: 4.56% Traditional ROI: 5.87%
111 Riverton Road #APT 83 Winchester, CT Rarely Available End Unit at Riverwalk Condos! This pristine 2-bedroom, 1.5-bath condo off...	2 beds \| 2 baths \| 1,204 sq.ft.	$195,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 7.89% Airbnb Rental Income: $1785 Traditional Rental Income: $2608 Airbnb ROI: 0.82% Traditional ROI: 7.89%
111 Torringford Street #APT 19 Winchester, CT Welcome to this nicely maintained 2-3 bedroom condo, offering a perfect blend of comfort a...	2 beds \| 2 baths \| 1,626 sq.ft.	$199,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 8.72% Airbnb Rental Income: $1785 Traditional Rental Income: $2637 Airbnb ROI: 1.63% Traditional ROI: 8.72%
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%
129 Skinner Road Winchester, CT Explore 129 Skinner, a captivating retreat offering abundant charm and privacy. Spanning n...	4 beds \| 2 baths \| 2,177 sq.ft.	$369,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 6.72% Airbnb Rental Income: $3619 Traditional Rental Income: $3499 Airbnb ROI: 4.78% Traditional ROI: 6.72%

Real Estate investment in Winchester, CT

There are 17 properties for sale in the city of Winchester . The median list price in Winchester is $374,450 and the average price per square foot is $155. In December 2024, the average monthly cash on cash return in Winchester is 7.00%. The average monthly rental income in Winchester is $3,551.

Winchester, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 17 investment properties available for sale in Winchester.

In 2024, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $3,551.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CT

711 West Wakefield Boulevard

Winchester, CT

3 beds | 3 baths | 2,664 sq.ft.

$1,500,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $4795

Traditional Rental Income: $3932

Airbnb ROI: 1.46%

Traditional ROI: 1.55%

115 Moore Avenue

Winchester, CT

3 beds | 3 baths | 2,240 sq.ft.

$449,900

Airbnb cash on cash: 6.83%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $4795

Traditional Rental Income: $3642

Airbnb ROI: 6.83%

Traditional ROI: 6.44%

25 Hillside Avenue

Winchester, CT

6 beds | 5 baths | 5,001 sq.ft.

$575,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.65%

Airbnb Rental Income: $null

Traditional Rental Income: $6277

Airbnb ROI: N/A

Traditional ROI: 9.65%

111 Riverton Road #53

Winchester, CT

2 beds | 2 baths | 1,204 sq.ft.

$190,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 10.18%

Airbnb Rental Income: $1785

Traditional Rental Income: $2744

Airbnb ROI: 2.18%

Traditional ROI: 10.18%

39 South Main Street

Winchester, CT

9 beds | 5 baths | 4,446 sq.ft.

$649,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.01%

Airbnb Rental Income: $null

Traditional Rental Income: $6023

Airbnb ROI: N/A

Traditional ROI: 8.01%

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: 3%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $4795

Traditional Rental Income: $3827

Airbnb ROI: 3%

Traditional ROI: 3.03%

522 West Wakefield Boulevard

Winchester, CT

2 beds | 1 baths | 1,134 sq.ft.

$650,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 0.88%

Airbnb Rental Income: $1785

Traditional Rental Income: $2289

Airbnb ROI: -0.75%