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
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%
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%
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%

Real Estate investment in Winchester, CT

There are 8 properties for sale in the city of Winchester . The median list price in Winchester is $415,000 and the average price per square foot is $186. In March 2026, the average monthly cash on cash return in Winchester is 9.00%. The average monthly rental income in Winchester is $3,459.

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

There are 8 investment properties available for sale in Winchester.

In 2026, 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 $3,459.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CT

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%

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%

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%

Real Estate investment in Winchester, CT

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

How many investment properties are available for sale in Winchester?

Which neighborhoods in Winchester to invest in 2026?

Long-Term vs. Short-Term Rentals in Winchester, Connecticut: Which will earn the best returns?

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