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
60 Nod Road Windsor, CT This spacious 3 bedroom/2 full bath colonial is located in a quiet neighborhood at the end...	3 beds \| 2 baths \| 2,128 sq.ft.	$345,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 6.95% Airbnb Rental Income: $1296 Traditional Rental Income: $3194 Airbnb ROI: -0.14% Traditional ROI: 6.95%
47 Wilson Avenue Windsor, CT This fantastic colonial on a dead end street, is located in a desirable section of windsor...	3 beds \| 2 baths \| 1,415 sq.ft.	$314,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 6.05% Airbnb Rental Income: $1296 Traditional Rental Income: $2694 Airbnb ROI: -0.05% Traditional ROI: 6.05%
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.	$421,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.46% Airbnb Rental Income: $null Traditional Rental Income: $4144 Airbnb ROI: N/A Traditional ROI: 7.46%
58 Amanda Circle Windsor, CT PRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and w...	3 beds \| 3 baths \| 1,952 sq.ft.	$449,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 5.5% Airbnb Rental Income: $1296 Traditional Rental Income: $3493 Airbnb ROI: -0.69% Traditional ROI: 5.5%
39 Loren Circle Windsor, CT Spacious 4-bedroom, 2-bathroom Contemporary home on a cul-de-sac. The open floor plan incl...	4 beds \| 2 baths \| 2,402 sq.ft.	$344,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.18% Airbnb Rental Income: $null Traditional Rental Income: $3666 Airbnb ROI: N/A Traditional ROI: 8.18%
118 High Path Road unit: 118 Windsor, CT Welcome to this well-maintained and move-in ready, lovely unit in the desirable Chateau Wo...	2 beds \| 3 baths \| 1,148 sq.ft.	$229,999	Airbnb cash on cash: 0.42% Traditional cash on cash: 6.01% Airbnb Rental Income: $1688 Traditional Rental Income: $2434 Airbnb ROI: 0.42% Traditional ROI: 6.01%
211 Macktown Road Windsor, CT Spacious 4-bedroom, 2.5-bath Raised Ranch offering over 1,800 sq ft of living space, set o...	4 beds \| 3 baths \| 1,194 sq.ft.	$299,999	Airbnb cash on cash: N/A Traditional cash on cash: 9.61% Airbnb Rental Income: $null Traditional Rental Income: $3659 Airbnb ROI: N/A Traditional ROI: 9.61%
105 Trent Drive Windsor, CT 4-bedroom colonial on cul de sac across from Trent Park. Formal dining room and 1st-floor ...	4 beds \| 3 baths \| 1,960 sq.ft.	$424,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.77% Airbnb Rental Income: $null Traditional Rental Income: $3821 Airbnb ROI: N/A Traditional ROI: 6.77%
1946 Poquonock Avenue Windsor, CT Attention investors! Don't miss this rare opportunity to own a well-maintained two-family ...	4 beds \| 2 baths \| 2,036 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.5% Airbnb Rental Income: $null Traditional Rental Income: $3394 Airbnb ROI: N/A Traditional ROI: 5.5%
943 High Path Road unit: 943 Windsor, CT Renovated in 2022. Combo LR/DR. Kitchen appliances new in 2022. Primary bedroom with walk-...	2 beds \| 2 baths \| 972 sq.ft.	$199,999	Airbnb cash on cash: 1.07% Traditional cash on cash: 6.66% Airbnb Rental Income: $1688 Traditional Rental Income: $2280 Airbnb ROI: 1.07% Traditional ROI: 6.66%
109 Old Village Circle Windsor, CT Absolutely beautiful turn-key townhome at The Villages at Poquonock! The sought-after 64 a...	3 beds \| 3 baths \| 1,800 sq.ft.	$399,900	Airbnb cash on cash: -1.58% Traditional cash on cash: 3.64% Airbnb Rental Income: $1296 Traditional Rental Income: $2850 Airbnb ROI: -1.58% Traditional ROI: 3.64%
121 Woodland Street Windsor, CT Welcome to this fantastic opportunity to own a 3BD 1BA cape style home. Home features a Up...	3 beds \| 1 baths \| 1,075 sq.ft.	$280,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 4.7% Airbnb Rental Income: $1296 Traditional Rental Income: $2040 Airbnb ROI: 0.34% Traditional ROI: 4.7%
66 Maple Avenue Windsor, CT Welcome to a truly unique residential opportunity offering the perfect blend of living and...	1 beds \| 2 baths \| 1,868 sq.ft.	$385,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 4.57% Airbnb Rental Income: $837 Traditional Rental Income: $2567 Airbnb ROI: -1.13% Traditional ROI: 4.57%
485 River Street Windsor, CT Available now is this well maintained 3 bedroom colonial set back on a 1 acre lot in Winds...	3 beds \| 3 baths \| 2,494 sq.ft.	$499,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 4.93% Airbnb Rental Income: $1296 Traditional Rental Income: $3738 Airbnb ROI: -1.16% Traditional ROI: 4.93%
28 Sycamore Street Windsor, CT Beautiful colonial with exquisite Custom Woodwork and Built ins! Beautiful Wood Floors Thr...	4 beds \| 3 baths \| 2,600 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.82% Airbnb Rental Income: $null Traditional Rental Income: $4473 Airbnb ROI: N/A Traditional ROI: 7.82%

Real Estate investment in Windsor, CT

There are 19 properties for sale in the city of Windsor . The median list price in Windsor is $617,000 and the average price per square foot is $195. In March 2026, the average monthly cash on cash return in Windsor is 6.00%. The average monthly rental income in Windsor is $3,014.

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

There are 19 investment properties available for sale in Windsor.

In 2026, 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 $1,296.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, CT

60 Nod Road

Windsor, CT

3 beds | 2 baths | 2,128 sq.ft.

$345,900

Airbnb cash on cash: -0.14%

Traditional cash on cash: 6.95%

Airbnb Rental Income: $1296

Traditional Rental Income: $3194

Airbnb ROI: -0.14%

Traditional ROI: 6.95%

47 Wilson Avenue

Windsor, CT

3 beds | 2 baths | 1,415 sq.ft.

$314,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 6.05%

Airbnb Rental Income: $1296

Traditional Rental Income: $2694

Airbnb ROI: -0.05%

Traditional ROI: 6.05%

957 Palisado Avenue

Windsor, CT

4 beds | 3 baths | 2,738 sq.ft.

$421,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.46%

Airbnb Rental Income: $null

Traditional Rental Income: $4144

Airbnb ROI: N/A

Traditional ROI: 7.46%

58 Amanda Circle

Windsor, CT

3 beds | 3 baths | 1,952 sq.ft.

$449,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1296

Traditional Rental Income: $3493

Airbnb ROI: -0.69%

Traditional ROI: 5.5%

39 Loren Circle

Windsor, CT

4 beds | 2 baths | 2,402 sq.ft.

$344,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.18%

Airbnb Rental Income: $null

Traditional Rental Income: $3666

Airbnb ROI: N/A

Traditional ROI: 8.18%

118 High Path Road unit: 118

Windsor, CT

2 beds | 3 baths | 1,148 sq.ft.

$229,999

Airbnb cash on cash: 0.42%

Traditional cash on cash: 6.01%

Airbnb Rental Income: $1688

Traditional Rental Income: $2434

Airbnb ROI: 0.42%

Traditional ROI: 6.01%

211 Macktown Road

Windsor, CT

4 beds | 3 baths | 1,194 sq.ft.

$299,999

Airbnb cash on cash: N/A

Traditional cash on cash: 9.61%

Airbnb Rental Income: $null

Traditional Rental Income: $3659

Airbnb ROI: N/A

Traditional ROI: 9.61%

105 Trent Drive

Windsor, CT

4 beds | 3 baths | 1,960 sq.ft.

$424,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.77%

Airbnb Rental Income: $null

Traditional Rental Income: $3821

Airbnb ROI: N/A