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%
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.	$269,999	Airbnb cash on cash: 2.08% Traditional cash on cash: 4.65% Airbnb Rental Income: $1611 Traditional Rental Income: $1808 Airbnb ROI: 2.08% Traditional ROI: 4.65%
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%
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: 9.32% Airbnb Rental Income: $null Traditional Rental Income: $5903 Airbnb ROI: N/A Traditional ROI: 9.32%
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%
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%
720 Main Street Winchester, CT Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building locate...	3 beds \| 2 baths \| 1,909 sq.ft.	$395,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 6.35% Airbnb Rental Income: $1611 Traditional Rental Income: $2945 Airbnb ROI: 1.51% Traditional ROI: 6.35%
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%
21 Riveredge Drive unit: 21 #21 Winchester, CT Updated 2-bedroom, 1.5-bath condo featuring a renovated kitchen with new appliances (2022)...	2 beds \| 2 baths \| 992 sq.ft.	$170,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 7.78% Airbnb Rental Income: $1289 Traditional Rental Income: $2230 Airbnb ROI: -0.52% Traditional ROI: 7.78%
35 Riveredge Drive unit: 35 #35 Winchester, CT Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom...	2 beds \| 2 baths \| 992 sq.ft.	$164,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 7.59% Airbnb Rental Income: $1289 Traditional Rental Income: $2117 Airbnb ROI: -0.28% Traditional ROI: 7.59%
107 Birdsall Street Winchester, CT Spacious colonial with 4 bedrooms, 2 full baths, generous size living room, dining room, s...	4 beds \| 2 baths \| 1,874 sq.ft.	$250,000	Airbnb cash on cash: 8.3% Traditional cash on cash: 11.38% Airbnb Rental Income: $3395 Traditional Rental Income: $3368 Airbnb ROI: 8.3% Traditional ROI: 11.38%

Real Estate investment in Winchester, CT

There are 17 properties for sale in the city of Winchester . The median list price in Winchester is $414,900 and the average price per square foot is $184. In January 2026, the average monthly cash on cash return in Winchester is 7.00%. The average monthly rental income in Winchester is $3,339.

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

There are 17 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 $3,339.

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%

118 Meadow Street

Winchester, CT

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

$269,999

Airbnb cash on cash: 2.08%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $1611

Traditional Rental Income: $1808

Airbnb ROI: 2.08%

Traditional ROI: 4.65%

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%

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: 9.32%

Airbnb Rental Income: $null

Traditional Rental Income: $5903

Airbnb ROI: N/A

Traditional ROI: 9.32%

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%

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%