Real Estate Investment Properties for Sale in Windham, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4 Jerusalem Road Windham, CT Welcome to this Classic Cape styled home in Windham, CT-where timeless charm meets everyda...	3 beds \| 2 baths \| 1,938 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $2185 Airbnb ROI: N/A Traditional ROI: 3.28%
359 Plains Road Windham, CT Welcome to this charming and spacious 3-bedroom, 2-bath Colonial nestled in a peaceful Win...	3 beds \| 2 baths \| 1,900 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.16% Airbnb Rental Income: $null Traditional Rental Income: $3191 Airbnb ROI: N/A Traditional ROI: 9.16%
337 South Windham Road Windham, CT This charming four-bedroom, two-and-a-half-bathroom home offers 2,905 square feet of comfo...	4 beds \| 3 baths \| 2,905 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.16% Airbnb Rental Income: $null Traditional Rental Income: $4164 Airbnb ROI: N/A Traditional ROI: 6.16%
366 Ash Street #APT 2 Windham, CT Move right in to this seldom available townhouse style condo in Windham Oaks with open eff...	2 beds \| 2 baths \| 1,210 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.92% Airbnb Rental Income: $null Traditional Rental Income: $2375 Airbnb ROI: N/A Traditional ROI: 5.92%
84 Machine Shop Hill Road Windham, CT Take a look at this large ranch loaded with all the right features for a great price. Ther...	2 beds \| 2 baths \| 2,396 sq.ft.	$229,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.69% Airbnb Rental Income: $null Traditional Rental Income: $2876 Airbnb ROI: N/A Traditional ROI: 9.69%
29 Kathleen Drive #APT 5E Windham, CT Step inside this immaculate townhouse-style condo and immediately feel the care and attent...	2 beds \| 2 baths \| 998 sq.ft.	$199,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.26% Airbnb Rental Income: $null Traditional Rental Income: $2198 Airbnb ROI: N/A Traditional ROI: 6.26%
378 Mansfield Avenue Windham, CT Welcome to this charming and meticulously maintained ranch-style home nestled in a quiet, ...	3 beds \| 2 baths \| 1,308 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 6% Airbnb Rental Income: $null Traditional Rental Income: $2666 Airbnb ROI: N/A Traditional ROI: 6%
231 Back Road Windham, CT The fraise, "They don't make'em like this anymore" comes to mind as you walk into this cla...	3 beds \| 2 baths \| 2,144 sq.ft.	$329,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $3186 Airbnb ROI: N/A Traditional ROI: 6.86%

Real Estate investment in Windham, CT

There are 10 properties for sale in the city of Windham . The median list price in Windham is $299,900 and the average price per square foot is $138. In November 2025, the average monthly cash on cash return in Windham is 6.00%. The average monthly rental income in Windham is $3,186.

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

There are 10 investment properties available for sale in Windham.

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

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

Your search for investment property begins and ends here

Investment Property for Sale in Windham, CT

4 Jerusalem Road

Windham, CT

3 beds | 2 baths | 1,938 sq.ft.

$399,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.28%

Airbnb Rental Income: $null

Traditional Rental Income: $2185

Airbnb ROI: N/A

Traditional ROI: 3.28%

359 Plains Road

Windham, CT

3 beds | 2 baths | 1,900 sq.ft.

$289,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3191

Airbnb ROI: N/A

Traditional ROI: 9.16%

337 South Windham Road

Windham, CT

4 beds | 3 baths | 2,905 sq.ft.

$469,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.16%

Airbnb Rental Income: $null

Traditional Rental Income: $4164

Airbnb ROI: N/A

Traditional ROI: 6.16%

366 Ash Street #APT 2

Windham, CT

2 beds | 2 baths | 1,210 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2375

Airbnb ROI: N/A

Traditional ROI: 5.92%

84 Machine Shop Hill Road

Windham, CT

2 beds | 2 baths | 2,396 sq.ft.

$229,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2876

Airbnb ROI: N/A

Traditional ROI: 9.69%

29 Kathleen Drive #APT 5E

Windham, CT

2 beds | 2 baths | 998 sq.ft.

$199,500

Airbnb cash on cash: N/A

Traditional cash on cash: 6.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2198

Airbnb ROI: N/A

Traditional ROI: 6.26%

378 Mansfield Avenue

Windham, CT

3 beds | 2 baths | 1,308 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6%

Airbnb Rental Income: $null

Traditional Rental Income: $2666

Airbnb ROI: N/A

Traditional ROI: 6%

231 Back Road

Windham, CT

3 beds | 2 baths | 2,144 sq.ft.

$329,999

Airbnb cash on cash: N/A

Traditional cash on cash: 6.86%

Airbnb Rental Income: $null

Traditional Rental Income: $3186

Airbnb ROI: N/A