Real Estate Investment Properties for Sale in South Windham, CT

Looking for investment property in South Windham, CT with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
59 MACHINE SHOP HILL RD SOUTH WINDHAM, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	N/A beds \| N/A baths \| N/A	$267,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $1526 Airbnb ROI: N/A Traditional ROI: 2.58%
Investment Properties for Sale in Other Cities of Connecticut
23 Heaton Street Waterbury , CT Welcome to this inviting 3-bedroom, 3-bathroom home offering 1,716 sq ft of living space i...	3 beds \| 3 baths \| 1,716 sq.ft.	$399,995	Airbnb cash on cash: 0.1% Traditional cash on cash: 4.12% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: 0.1% Traditional ROI: 4.12%
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%
360 North Society Road Canterbury , CT INSTANT EQUITY when you finish this SPRAWLING Cape it COMPS out at $499,900!! OVERSIZED 2 ...	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 Tucked away on a quiet tree-lined street, this beautifully reimagined ranch feels like a f...	3 beds \| 1 baths \| 1,279 sq.ft.	$329,990	Airbnb cash on cash: -0.46% Traditional cash on cash: 5.67% Airbnb Rental Income: $850 Traditional Rental Income: $2420 Airbnb ROI: -0.46% Traditional ROI: 5.67%
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%
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: 1.62% Traditional cash on cash: 5.57% Airbnb Rental Income: $1889 Traditional Rental Income: $2572 Airbnb ROI: 1.62% 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: 0.79% Traditional cash on cash: 3.54% Airbnb Rental Income: $1906 Traditional Rental Income: $2560 Airbnb ROI: 0.79% 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: 1.68% Traditional cash on cash: 5.92% Airbnb Rental Income: $2272 Traditional Rental Income: $3394 Airbnb ROI: 1.68% 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: 0.65% Traditional cash on cash: 3.22% Airbnb Rental Income: $2158 Traditional Rental Income: $3272 Airbnb ROI: 0.65% 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.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.66% Airbnb Rental Income: $null Traditional Rental Income: $4437 Airbnb ROI: N/A Traditional ROI: 8.66%

Real Estate investment in South-windham, CT

There are 1 properties for sale in the city of South Windham . The median list price in South Windham is $267,000 and the average price per square foot is $NaN. In October 2025, the average monthly cash on cash return in South Windham is 3.00%. The average monthly rental income in South Windham is $1,526.

South-windham, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 1 investment properties available for sale in South-windham.

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

The ROI for Short-Term is higher than the Long-Term in South-windham with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in South Windham, CT

59 MACHINE SHOP HILL RD

SOUTH WINDHAM, CT

N/A beds | N/A baths | N/A

$267,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.58%

Airbnb Rental Income: $null

Traditional Rental Income: $1526

Airbnb ROI: N/A

Traditional ROI: 2.58%

Investment Properties for Sale in Other Cities of Connecticut

Waterbury , CT

3 beds | 3 baths | 1,716 sq.ft.

$399,995

Airbnb cash on cash: 0.1%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: 0.1%

Traditional ROI: 4.12%

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%

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.

$329,990

Airbnb cash on cash: -0.46%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $850

Traditional Rental Income: $2420

Airbnb ROI: -0.46%

Traditional ROI: 5.67%

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%

Cheshire , CT

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

$319,900

Airbnb cash on cash: 1.62%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $1889

Traditional Rental Income: $2572

Airbnb ROI: 1.62%

Traditional ROI: 5.57%

Portland , CT

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

$451,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $1906

Traditional Rental Income: $2560

Airbnb ROI: 0.79%

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%