Real Estate Investment Properties for Sale in Winsted, CT

Looking for investment property in Winsted, CT with high ROI ?

Explore a variety of short-term homes & houses in Winsted, CT. Invest wisely with VRBO & Winsted, 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 Winsted, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Winsted, Connecticut at the moment.
Other Investment Properties for Sale in Connecticut
2 Elmwood Drive #2 Fairfield , CT Rare offering in the coveted Southport Green complex, just steps from Southport Village an...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,495,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.29% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.53% Traditional ROI: 0.29%
175 Ferry Road #3 Old Saybrook , CT Welcome to Eden Harbour, an elegant and vibrant 55+ Condominium Community in Old Saybrook!...	2 beds \| 2 baths \| 1,670 sq.ft.	$599,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.71% Airbnb Rental Income: $2716 Traditional Rental Income: $2824 Airbnb ROI: 0.37% Traditional ROI: 1.71%
360 North Society Road Canterbury , CT INSTANT EQUITY when you finish this SPRAWLING Cape it COMPS out $525,000 to $550,000! OVER...	3 beds \| 2 baths \| 2,236 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.16% Airbnb Rental Income: $null Traditional Rental Income: $3171 Airbnb ROI: N/A Traditional ROI: 8.16%
15 Capewell Drive Bloomfield , CT NEW PRICE! Stop scrolling! This is the part where every buyer gasps and every agent double...	3 beds \| 1 baths \| 1,279 sq.ft.	$299,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 6.33% Airbnb Rental Income: $886 Traditional Rental Income: $2420 Airbnb ROI: -0.3% Traditional ROI: 6.33%
32 WILLINGTON AVENUE Stafford Springs , CT Completely renovated old-style Colonial that sits on1.72 private acres. Nestled in the woo...	3 beds \| 2 baths \| 1,047 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2593 Airbnb ROI: N/A Traditional ROI: 5.4%
125 Warner Hill Road #85 Stratford , CT Welcome to Tudor Ridge conveniently located in Stratford's NE adjacent to Shelton with gre...	1 beds \| 1 baths \| 748 sq.ft.	$259,900	Airbnb cash on cash: -1.09% Traditional cash on cash: 4.38% Airbnb Rental Income: $1114 Traditional Rental Income: $2081 Airbnb ROI: -1.09% Traditional ROI: 4.38%
2 Currier Court #2 Cheshire , CT Currier Woods is located in a 160-unit community known for its mature trees, private windi...	2 beds \| 2 baths \| 1,362 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.57% Airbnb Rental Income: $null Traditional Rental Income: $2572 Airbnb ROI: N/A Traditional ROI: 5.57%
153 THOMPSON HILL RD Portland , CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,704 sq.ft.	$451,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.54% Airbnb Rental Income: $1388 Traditional Rental Income: $2560 Airbnb ROI: -0.23% Traditional ROI: 3.54%
180 East Rocks Road Norwalk , CT Welcome to 180 East Rocks Road in the desirable Cranbury neighborhood. Experience comfort ...	4 beds \| 3 baths \| 3,332 sq.ft.	$1,050,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.48% Airbnb Rental Income: $4407 Traditional Rental Income: $5637 Airbnb ROI: 1.28% Traditional ROI: 3.48%
114 Terrill Road Stratford , CT Welcome to this charming Paradise Green Ranch, perfectly situated within walking distance ...	3 beds \| 2 baths \| 1,922 sq.ft.	$424,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 5.92% Airbnb Rental Income: $2065 Traditional Rental Income: $3394 Airbnb ROI: 1.24% Traditional ROI: 5.92%
23 Pemberwick Road Greenwich , CT This storybook Pemberwick Colonial is an ideal condo alternative and oodles of character f...	2 beds \| 2 baths \| 1,169 sq.ft.	$695,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.22% Airbnb Rental Income: $1933 Traditional Rental Income: $3272 Airbnb ROI: 0.36% Traditional ROI: 3.22%
109 Timber Trail Tolland , CT Welcome to 109 Timber Trail in Tolland! This beautiful 4-bedroom, 3-bath home combines tho...	4 beds \| 3 baths \| 2,884 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.89% Airbnb Rental Income: $null Traditional Rental Income: $4437 Airbnb ROI: N/A Traditional ROI: 8.89%
273 Derby Avenue #213 Derby , CT Wonderful move-in ready Birmingham townhouse. This well maintained unit has two private en...	2 beds \| 2 baths \| 1,022 sq.ft.	$260,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 5.9% Airbnb Rental Income: $1016 Traditional Rental Income: $2288 Airbnb ROI: -0.74% Traditional ROI: 5.9%

Real Estate investment in Winsted, CT

There are 0 properties for sale in the city of Winsted . The median list price in Winsted is $460,000 and the average price per square foot is $152. In November 2025, the average monthly cash on cash return in Winsted is 7.00%. The average monthly rental income in Winsted is $4,126.

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

There are 0 investment properties available for sale in Winsted.

In 2025, the best neighborhood to buy investment property is Winsted.

The ROI for Long-Term is higher than the Short-Term in Winsted with average rental income of $4,126.

Your search for investment property begins and ends here

Investment Property for Sale in Winsted, CT

Other Investment Properties for Sale in Connecticut

Fairfield , CT

3 beds | 4 baths | 3,328 sq.ft.

$2,495,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.53%

Traditional ROI: 0.29%

Old Saybrook , CT

2 beds | 2 baths | 1,670 sq.ft.

$599,000

Airbnb cash on cash: 0.37%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $2716

Traditional Rental Income: $2824

Airbnb ROI: 0.37%

Traditional ROI: 1.71%

Canterbury , CT

3 beds | 2 baths | 2,236 sq.ft.

$289,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3171

Airbnb ROI: N/A

Traditional ROI: 8.16%

Bloomfield , CT

3 beds | 1 baths | 1,279 sq.ft.

$299,900

Airbnb cash on cash: -0.3%

Traditional cash on cash: 6.33%

Airbnb Rental Income: $886

Traditional Rental Income: $2420

Airbnb ROI: -0.3%

Traditional ROI: 6.33%

Stafford Springs , CT

3 beds | 2 baths | 1,047 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.4%

Airbnb Rental Income: $null

Traditional Rental Income: $2593

Airbnb ROI: N/A

Traditional ROI: 5.4%

Stratford , CT

1 beds | 1 baths | 748 sq.ft.

$259,900

Airbnb cash on cash: -1.09%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $1114

Traditional Rental Income: $2081

Airbnb ROI: -1.09%

Traditional ROI: 4.38%

Cheshire , CT

2 beds | 2 baths | 1,362 sq.ft.

$319,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.57%

Airbnb Rental Income: $null

Traditional Rental Income: $2572

Airbnb ROI: N/A

Traditional ROI: 5.57%

Portland , CT

3 beds | 2 baths | 1,704 sq.ft.

$451,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $1388

Traditional Rental Income: $2560

Airbnb ROI: -0.23%

Traditional ROI: 3.54%

Norwalk , CT

4 beds | 3 baths | 3,332 sq.ft.

$1,050,000

Airbnb cash on cash: 1.28%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $4407