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
50 Hollow Brook Road Windsor, CT Beautifully maintained with a level of care evident throughout, 50 Hollow Brook Road eleva...	3 beds \| 3 baths \| 1,978 sq.ft.	$398,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 4.78% Airbnb Rental Income: $1859 Traditional Rental Income: $2850 Airbnb ROI: 0.78% Traditional ROI: 4.78%
621 Kennedy Road Windsor, CT Just in time for the holidays, this very special home has been through a lot of work to sh...	3 beds \| 3 baths \| 1,826 sq.ft.	$469,900	Airbnb cash on cash: 0.59% Traditional cash on cash: 5.7% Airbnb Rental Income: $1859 Traditional Rental Income: $3606 Airbnb ROI: 0.59% Traditional ROI: 5.7%
36 Woodybrook Road Windsor, CT Welcome to Windsor! This well-maintained home offers a bright, functional layout with comf...	3 beds \| 2 baths \| 1,229 sq.ft.	$274,995	Airbnb cash on cash: 2.01% Traditional cash on cash: 6.83% Airbnb Rental Income: $1859 Traditional Rental Income: $2611 Airbnb ROI: 2.01% Traditional ROI: 6.83%
625 Palisado Avenue #102 Windsor, CT One bedroom now available on FIRST FLOOR at Delamere Woods - an independent retirement com...	1 beds \| 1 baths \| 683 sq.ft.	$52,000	Airbnb cash on cash: -25.66% Traditional cash on cash: -7.65% Airbnb Rental Income: $1011 Traditional Rental Income: $1604 Airbnb ROI: -25.66% Traditional ROI: -7.65%
20 Center Street Windsor, CT Beautiful Contemporary Colonial on 4.34 acres! Designed like no other, this stunning home ...	4 beds \| 3 baths \| 2,594 sq.ft.	$659,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.18% Airbnb Rental Income: $2231 Traditional Rental Income: $4223 Airbnb ROI: 0.03% Traditional ROI: 4.18%
49 Green Manor Avenue Windsor, CT Welcome to this beautifully updated 3-bedroom, 2-bath ranch offering comfortable one-level...	3 beds \| 3 baths \| 1,691 sq.ft.	$424,900	Airbnb cash on cash: 0.9% Traditional cash on cash: 4.64% Airbnb Rental Income: $1859 Traditional Rental Income: $2850 Airbnb ROI: 0.9% Traditional ROI: 4.64%
40 High Path Road #40 Windsor, CT Beautiful location,well maintained condo,walking distance for grocery store.Highway is ver...	2 beds \| 3 baths \| 1,020 sq.ft.	$249,900	Airbnb cash on cash: -2.48% Traditional cash on cash: 4.92% Airbnb Rental Income: $898 Traditional Rental Income: $2307 Airbnb ROI: -2.48% Traditional ROI: 4.92%
38 Milo Peck Lane Windsor, CT Words can't capture the value packed into this beautiful home in a settled, sought-after n...	4 beds \| 3 baths \| 2,891 sq.ft.	$574,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 5.5% Airbnb Rental Income: $2231 Traditional Rental Income: $4396 Airbnb ROI: 0.43% Traditional ROI: 5.5%
144 Morning Glory Court #144 Windsor, CT Welcome to 144 Morning Glory Court, a bright and beautifully maintained 2BR, 2BA condo off...	2 beds \| 2 baths \| 1,506 sq.ft.	$379,900	Airbnb cash on cash: -2.6% Traditional cash on cash: 2.23% Airbnb Rental Income: $898 Traditional Rental Income: $2280 Airbnb ROI: -2.6% Traditional ROI: 2.23%

Real Estate investment in Windsor, CT

There are 11 properties for sale in the city of Windsor . The median list price in Windsor is $620,000 and the average price per square foot is $194. In November 2026, the average monthly cash on cash return in Windsor is 5.00%. The average monthly rental income in Windsor is $2,719.

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

There are 11 investment properties available for sale in Windsor.

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

The ROI for Long-Term is higher than the Short-Term in Windsor with average rental income of $2,719.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, CT

50 Hollow Brook Road

Windsor, CT

3 beds | 3 baths | 1,978 sq.ft.

$398,000

Airbnb cash on cash: 0.78%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $1859

Traditional Rental Income: $2850

Airbnb ROI: 0.78%

Traditional ROI: 4.78%

621 Kennedy Road

Windsor, CT

3 beds | 3 baths | 1,826 sq.ft.

$469,900

Airbnb cash on cash: 0.59%

Traditional cash on cash: 5.7%

Airbnb Rental Income: $1859

Traditional Rental Income: $3606

Airbnb ROI: 0.59%

Traditional ROI: 5.7%

36 Woodybrook Road

Windsor, CT

3 beds | 2 baths | 1,229 sq.ft.

$274,995

Airbnb cash on cash: 2.01%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $1859

Traditional Rental Income: $2611

Airbnb ROI: 2.01%

Traditional ROI: 6.83%

625 Palisado Avenue #102

Windsor, CT

1 beds | 1 baths | 683 sq.ft.

$52,000

Airbnb cash on cash: -25.66%

Traditional cash on cash: -7.65%

Airbnb Rental Income: $1011

Traditional Rental Income: $1604

Airbnb ROI: -25.66%

Traditional ROI: -7.65%

20 Center Street

Windsor, CT

4 beds | 3 baths | 2,594 sq.ft.

$659,900

Airbnb cash on cash: 0.03%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $2231

Traditional Rental Income: $4223

Airbnb ROI: 0.03%

Traditional ROI: 4.18%

49 Green Manor Avenue

Windsor, CT

3 beds | 3 baths | 1,691 sq.ft.

$424,900

Airbnb cash on cash: 0.9%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1859

Traditional Rental Income: $2850

Airbnb ROI: 0.9%

Traditional ROI: 4.64%

40 High Path Road #40

Windsor, CT

2 beds | 3 baths | 1,020 sq.ft.

$249,900

Airbnb cash on cash: -2.48%

Traditional cash on cash: 4.92%

Airbnb Rental Income: $898

Traditional Rental Income: $2307

Airbnb ROI: -2.48%

Traditional ROI: 4.92%

38 Milo Peck Lane

Windsor, CT

4 beds | 3 baths | 2,891 sq.ft.

$574,900

Airbnb cash on cash: 0.43%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $2231

Traditional Rental Income: $4396

Airbnb ROI: 0.43%