Real Estate Investment Properties for Sale in Windsor, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20 Last Leaf Circle #20 Windsor, CT Welcome to Walden Woods and this well maintained 2 bedroom, 2.5 bath townhouse. The comple...	2 beds \| 3 baths \| 1,536 sq.ft.	$329,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 5.94% Airbnb Rental Income: $2443 Traditional Rental Income: $3114 Airbnb ROI: 1.86% Traditional ROI: 5.94%
26 Darwyn Drive Windsor, CT Unique well maintained 4 bedroom house with in-law suite on the main level. The kitchen ha...	4 beds \| 3 baths \| 1,975 sq.ft.	$499,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.79% Airbnb Rental Income: $null Traditional Rental Income: $3794 Airbnb ROI: N/A Traditional ROI: 4.79%
113 Maple Avenue Windsor, CT Come inside to view this astonishingly remodeled home full of character, updated for moder...	3 beds \| 2 baths \| 1,287 sq.ft.	$319,900	Airbnb cash on cash: 7.84% Traditional cash on cash: 5.93% Airbnb Rental Income: $4293 Traditional Rental Income: $2813 Airbnb ROI: 7.84% Traditional ROI: 5.93%
76 Allen Street Windsor, CT Beatifully finished home. Hardwood floors, 3 beds, 1 and 1/2 baths, Open concept the kitch...	3 beds \| 2 baths \| 1,478 sq.ft.	$319,000	Airbnb cash on cash: 7.87% Traditional cash on cash: 5.85% Airbnb Rental Income: $4293 Traditional Rental Income: $2783 Airbnb ROI: 7.87% Traditional ROI: 5.85%
418 River Street Windsor, CT Craving a home that is close to all local amenities but feels like your own private retrea...	3 beds \| 3 baths \| 1,965 sq.ft.	$459,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 4.69% Airbnb Rental Income: $4293 Traditional Rental Income: $3459 Airbnb ROI: 4.52% Traditional ROI: 4.69%
181 Willowcrest Drive Windsor, CT Introducing Style and Comfort at 181 Willowcrest Drive! This revitalized, rejuvenated, ren...	3 beds \| 3 baths \| 1,800 sq.ft.	$399,900	Airbnb cash on cash: 5.67% Traditional cash on cash: 6.03% Airbnb Rental Income: $4293 Traditional Rental Income: $3524 Airbnb ROI: 5.67% Traditional ROI: 6.03%
25 Sunnyside Circle Windsor, CT Cozy 6 room Cape, with new pressured treated front entry; JUST MOVE IN- home is painted ne...	3 beds \| 2 baths \| 1,075 sq.ft.	$269,000	Airbnb cash on cash: 9.88% Traditional cash on cash: 6.56% Airbnb Rental Income: $4293 Traditional Rental Income: $2547 Airbnb ROI: 9.88% Traditional ROI: 6.56%
110 Belmont Avenue Windsor, CT Beautiful home in great Windsor location. Fully refinished. Oversize 2 car garage. New sep...	4 beds \| 1 baths \| 1,138 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.95% Airbnb Rental Income: $null Traditional Rental Income: $2482 Airbnb ROI: N/A Traditional ROI: 4.95%
925 Matianuck Avenue Windsor, CT Move-in ready 3 Bedroom Cape features a spacious 12'x24' insulated 3 season room with vaul...	3 beds \| 1 baths \| 1,256 sq.ft.	$285,000	Airbnb cash on cash: 9.16% Traditional cash on cash: 5.51% Airbnb Rental Income: $4293 Traditional Rental Income: $2409 Airbnb ROI: 9.16% Traditional ROI: 5.51%
16 Hobson Avenue Windsor, CT Don't miss this charming 1,715 sq. ft. Cape Cod home featuring 4 bedrooms and 2 baths, set...	4 beds \| 3 baths \| 1,715 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.47% Airbnb Rental Income: $null Traditional Rental Income: $3793 Airbnb ROI: N/A Traditional ROI: 8.47%
3 Sarah Anne Lane Windsor, CT Welcome to your dream 55+ PUD! This beautifully designed 3-bedroom, 2.5-bath residence fea...	3 beds \| 3 baths \| 1,743 sq.ft.	$389,900	Airbnb cash on cash: 5.49% Traditional cash on cash: 4.66% Airbnb Rental Income: $4293 Traditional Rental Income: $3086 Airbnb ROI: 5.49% Traditional ROI: 4.66%
1056 Windsor Avenue Windsor, CT Welcome to this charming reproduction Victorian that beautifully combines timeless charact...	4 beds \| 4 baths \| 2,347 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.61% Airbnb Rental Income: $null Traditional Rental Income: $5110 Airbnb ROI: N/A Traditional ROI: 7.61%
650 Pigeon Hill Road Windsor, CT This charming 3-bedroom, 1.5-bathroom home is nestled on over 2 acres of land, offering pr...	3 beds \| 2 baths \| 1,504 sq.ft.	$485,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.27% Airbnb Rental Income: $4293 Traditional Rental Income: $2992 Airbnb ROI: 4.14% Traditional ROI: 3.27%
957 Palisado Avenue Windsor, CT Welcome to this charming 1773 center chimney colonial in the highly desirable town of Wind...	4 beds \| 3 baths \| 2,738 sq.ft.	$429,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $4144 Airbnb ROI: N/A Traditional ROI: 6.94%

Real Estate investment in Windsor, CT

There are 14 properties for sale in the city of Windsor . The median list price in Windsor is $334,900 and the average price per square foot is $208. In December 2024, the average monthly cash on cash return in Windsor is 6.00%. The average monthly rental income in Windsor is $3,039.

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

There are 14 investment properties available for sale in Windsor.

In 2024, the best neighborhood to buy investment property is Windsor.

The ROI for Short-Term is higher than the Long-Term in Windsor with average rental income of $4,293.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, CT

20 Last Leaf Circle #20

Windsor, CT

2 beds | 3 baths | 1,536 sq.ft.

$329,900

Airbnb cash on cash: 1.86%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $2443

Traditional Rental Income: $3114

Airbnb ROI: 1.86%

Traditional ROI: 5.94%

26 Darwyn Drive

Windsor, CT

4 beds | 3 baths | 1,975 sq.ft.

$499,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.79%

Airbnb Rental Income: $null

Traditional Rental Income: $3794

Airbnb ROI: N/A

Traditional ROI: 4.79%

113 Maple Avenue

Windsor, CT

3 beds | 2 baths | 1,287 sq.ft.

$319,900

Airbnb cash on cash: 7.84%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $4293

Traditional Rental Income: $2813

Airbnb ROI: 7.84%

Traditional ROI: 5.93%

76 Allen Street

Windsor, CT

3 beds | 2 baths | 1,478 sq.ft.

$319,000

Airbnb cash on cash: 7.87%

Traditional cash on cash: 5.85%

Airbnb Rental Income: $4293

Traditional Rental Income: $2783

Airbnb ROI: 7.87%

Traditional ROI: 5.85%

418 River Street

Windsor, CT

3 beds | 3 baths | 1,965 sq.ft.

$459,000

Airbnb cash on cash: 4.52%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $4293

Traditional Rental Income: $3459

Airbnb ROI: 4.52%

Traditional ROI: 4.69%

181 Willowcrest Drive

Windsor, CT

3 beds | 3 baths | 1,800 sq.ft.

$399,900

Airbnb cash on cash: 5.67%

Traditional cash on cash: 6.03%

Airbnb Rental Income: $4293

Traditional Rental Income: $3524

Airbnb ROI: 5.67%

Traditional ROI: 6.03%

25 Sunnyside Circle

Windsor, CT

3 beds | 2 baths | 1,075 sq.ft.

$269,000

Airbnb cash on cash: 9.88%

Traditional cash on cash: 6.56%

Airbnb Rental Income: $4293

Traditional Rental Income: $2547

Airbnb ROI: 9.88%

Traditional ROI: 6.56%

110 Belmont Avenue

Windsor, CT

4 beds | 1 baths | 1,138 sq.ft.

$315,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2482

Airbnb ROI: N/A