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
1 Gem Drive Windham, CT Welcome to 1 Gem Drive. This well cared for 3-bedroom, 2-bath raised ranch offers comfort,...	3 beds \| 2 baths \| 912 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.67% Airbnb Rental Income: $null Traditional Rental Income: $1907 Airbnb ROI: N/A Traditional ROI: 3.67%
100 Bolivia Street Windham, CT Looking for an owner-occupied multi-family? Here it is! Located on a quiet street in the d...	2 beds \| 2 baths \| 2,210 sq.ft.	$275,000	Airbnb cash on cash: -1.85% Traditional cash on cash: 6.95% Airbnb Rental Income: $789 Traditional Rental Income: $2750 Airbnb ROI: -1.85% Traditional ROI: 6.95%
272 Prospect Street Windham, CT Step back in time in this majestic REMODELED 5-Bedroom Queen Anne-style Victorian home com...	5 beds \| 3 baths \| 2,848 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.47% Airbnb Rental Income: $null Traditional Rental Income: $4188 Airbnb ROI: N/A Traditional ROI: 7.47%
257 Walnut Street Windham, CT Historic Hill Colonial with Timeless Charm & Endless Potential Nestled on a desirable corn...	4 beds \| 2 baths \| 1,922 sq.ft.	$235,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 11.25% Airbnb Rental Income: $1588 Traditional Rental Income: $3395 Airbnb ROI: 1.08% Traditional ROI: 11.25%
187 Tuckie Rd Windham, CT 187 Tuckie Rd, Windham, CT 06256 \| Single Family Residential	3 beds \| 2 baths \| 2,158 sq.ft.	$399,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.03% Airbnb Rental Income: $null Traditional Rental Income: $2774 Airbnb ROI: N/A Traditional ROI: 4.03%
254 Beaver Hill Rd Windham, CT 254 Beaver Hill Rd, Windham, CT 06256 \| Single Family Residential	3 beds \| 2 baths \| 1,808 sq.ft.	$874,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.13% Airbnb Rental Income: $null Traditional Rental Income: $2746 Airbnb ROI: N/A Traditional ROI: 0.13%
15 Cracow Ave Windham, CT Welcome to 15 Cracow Ave in Windham, a beautifully updated 3-bedroom, 2-full-bath ranch of...	3 beds \| 2 baths \| 1,228 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.59% Airbnb Rental Income: $null Traditional Rental Income: $2798 Airbnb ROI: N/A Traditional ROI: 5.59%
253 Brick Top Rd Windham, CT 253 Brick Top Rd, Windham, CT 06280 \| Other	N/A beds \| N/A baths \| N/A	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: -1.96% Airbnb Rental Income: $null Traditional Rental Income: $959 Airbnb ROI: N/A Traditional ROI: -1.96%
415 Jerusalem Rd Windham, CT 415 Jerusalem Rd, Windham, CT 06280 \| Single Family Residential	4 beds \| 2 baths \| 2,856 sq.ft.	$499,900	Airbnb cash on cash: -0.89% Traditional cash on cash: 1.56% Airbnb Rental Income: $1588 Traditional Rental Income: $2280 Airbnb ROI: -0.89% Traditional ROI: 1.56%
6 Autumn Rdg Windham, CT 6 Autumn Rdg, Windham, CT 06280 \| Single Family Residential	2 beds \| 1 baths \| 2,428 sq.ft.	$499,900	Airbnb cash on cash: -2.32% Traditional cash on cash: -0.32% Airbnb Rental Income: $789 Traditional Rental Income: $1401 Airbnb ROI: -2.32% Traditional ROI: -0.32%
220 Plains Rd Windham, CT 220 Plains Rd, Windham, CT 06280 \| Other	N/A beds \| N/A baths \| N/A	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.56% Airbnb Rental Income: $null Traditional Rental Income: $959 Airbnb ROI: N/A Traditional ROI: 0.56%
394 Jerusalem Rd Windham, CT Timeless New England charm meets modern-day opportunity in this impressive 5-bedroom, 3.5-...	5 beds \| 3 baths \| 2,836 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.89% Airbnb Rental Income: $null Traditional Rental Income: $5152 Airbnb ROI: N/A Traditional ROI: 10.89%

Real Estate investment in Windham, CT

There are 20 properties for sale in the city of Windham . The median list price in Windham is $462,450 and the average price per square foot is $204. In September 2026, the average monthly cash on cash return in Windham is 8.00%. The average monthly rental income in Windham is $2,495.

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

There are 20 investment properties available for sale in Windham.

In 2026, the best neighborhood to buy investment property is Windham.

The ROI for Long-Term is higher than the Short-Term in Windham with average rental income of $2,495.

Your search for investment property begins and ends here

Investment Property for Sale in Windham, CT

1 Gem Drive

Windham, CT

3 beds | 2 baths | 912 sq.ft.

$289,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.67%

Airbnb Rental Income: $null

Traditional Rental Income: $1907

Airbnb ROI: N/A

Traditional ROI: 3.67%

100 Bolivia Street

Windham, CT

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

$275,000

Airbnb cash on cash: -1.85%

Traditional cash on cash: 6.95%

Airbnb Rental Income: $789

Traditional Rental Income: $2750

Airbnb ROI: -1.85%

Traditional ROI: 6.95%

272 Prospect Street

Windham, CT

5 beds | 3 baths | 2,848 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.47%

Airbnb Rental Income: $null

Traditional Rental Income: $4188

Airbnb ROI: N/A

Traditional ROI: 7.47%

257 Walnut Street

Windham, CT

4 beds | 2 baths | 1,922 sq.ft.

$235,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 11.25%

Airbnb Rental Income: $1588

Traditional Rental Income: $3395

Airbnb ROI: 1.08%

Traditional ROI: 11.25%

187 Tuckie Rd

Windham, CT

3 beds | 2 baths | 2,158 sq.ft.

$399,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.03%

Airbnb Rental Income: $null

Traditional Rental Income: $2774

Airbnb ROI: N/A

Traditional ROI: 4.03%

254 Beaver Hill Rd

Windham, CT

3 beds | 2 baths | 1,808 sq.ft.

$874,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2746

Airbnb ROI: N/A

Traditional ROI: 0.13%

15 Cracow Ave

Windham, CT

3 beds | 2 baths | 1,228 sq.ft.

$360,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.59%

Airbnb Rental Income: $null

Traditional Rental Income: $2798

Airbnb ROI: N/A

Traditional ROI: 5.59%

253 Brick Top Rd

Windham, CT

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

$799,900

Airbnb cash on cash: N/A

Traditional cash on cash: -1.96%

Airbnb Rental Income: $null

Traditional Rental Income: $959

Airbnb ROI: N/A