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
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: 7.15% Airbnb Rental Income: $null Traditional Rental Income: $4144 Airbnb ROI: N/A Traditional ROI: 7.15%
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.	$436,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 5.21% Airbnb Rental Income: $1296 Traditional Rental Income: $3493 Airbnb ROI: -1.17% Traditional ROI: 5.21%
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.	$344,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.91% Airbnb Rental Income: $null Traditional Rental Income: $3666 Airbnb ROI: N/A Traditional ROI: 7.91%
39 Old Kennedy Road Windsor, CT Opportunity knocks! This 3-bedroom, 1-bath home with a 1-car garage offers great potential...	3 beds \| 2 baths \| 1,168 sq.ft.	$235,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 8.72% Airbnb Rental Income: $1296 Traditional Rental Income: $2731 Airbnb ROI: 0.47% Traditional ROI: 8.72%
101 Seymour Street Windsor, CT Turnkey Ranch with Solar & Smart Savings - Just $249,000! Welcome to this sun-soaked, ene...	2 beds \| 1 baths \| 960 sq.ft.	$235,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 4.29% Airbnb Rental Income: $1688 Traditional Rental Income: $1736 Airbnb ROI: 1.96% Traditional ROI: 4.29%
175 East Pershing Street Windsor, CT Welcome to 175 E Pershing Street-a beautifully renovated home nestled on a dead end street...	3 beds \| 1 baths \| 1,128 sq.ft.	$335,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.86% Airbnb Rental Income: $1296 Traditional Rental Income: $2288 Airbnb ROI: -0.58% Traditional ROI: 3.86%
2200 Dover Court Windsor, CT Welcome to 2200 Dover Court, a well-maintained 2-bedroom, 1.5-bath townhouse-style condo o...	2 beds \| 2 baths \| 1,276 sq.ft.	$289,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 4.39% Airbnb Rental Income: $1688 Traditional Rental Income: $2552 Airbnb ROI: -0.51% Traditional ROI: 4.39%
140 Portman Street Windsor, CT H&B Due 10/02/2025 12pm This adorable ranch-style home offers the perfect blend of com...	3 beds \| 1 baths \| 950 sq.ft.	$244,999	Airbnb cash on cash: 0.34% Traditional cash on cash: 5.58% Airbnb Rental Income: $1296 Traditional Rental Income: $2104 Airbnb ROI: 0.34% Traditional ROI: 5.58%
145 Carriage Way Windsor, CT Wow! Spectacular, stylish & gorgeous, this delicious home sits on a desirable cul-de-sac. ...	4 beds \| 3 baths \| 2,236 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $3934 Airbnb ROI: N/A Traditional ROI: 4.35%
99 Pepperbush Way Windsor, CT 3-bedroom, 2.5-bath raised ranch offering comfort and convenience in a desirable setting. ...	3 beds \| 3 baths \| 1,194 sq.ft.	$259,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 7.4% Airbnb Rental Income: $1296 Traditional Rental Income: $2671 Airbnb ROI: 0.15% Traditional ROI: 7.4%
107 Sunnyfield Drive Windsor, CT Scenic setting for this 7 room, 3 bedroom, 2.5-bath raised ranch with lower-level rec room...	3 beds \| 3 baths \| 1,352 sq.ft.	$329,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 5.57% Airbnb Rental Income: $1296 Traditional Rental Income: $2786 Airbnb ROI: -0.54% Traditional ROI: 5.57%
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 \| 1,800 sq.ft.	$314,999	Airbnb cash on cash: N/A Traditional cash on cash: 8.92% Airbnb Rental Income: $null Traditional Rental Income: $3659 Airbnb ROI: N/A Traditional ROI: 8.92%
1492 Poquonock Avenue Windsor, CT Welcome to a rare and exceptional opportunity to own a ranch-style home that combines time...	3 beds \| 2 baths \| 1,533 sq.ft.	$409,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 4.32% Airbnb Rental Income: $1296 Traditional Rental Income: $2945 Airbnb ROI: -1.04% Traditional ROI: 4.32%
14 Loren Circle Windsor, CT Tucked at the end of a quiet cul-de-sac, this beautifully maintained raised ranch offers a...	3 beds \| 3 baths \| 1,942 sq.ft.	$405,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 5.99% Airbnb Rental Income: $1296 Traditional Rental Income: $3549 Airbnb ROI: -1.02% Traditional ROI: 5.99%

Real Estate investment in Windsor, CT

There are 16 properties for sale in the city of Windsor . The median list price in Windsor is $332,450 and the average price per square foot is $202. In October 2025, the average monthly cash on cash return in Windsor is 6.00%. The average monthly rental income in Windsor is $2,866.

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

There are 16 investment properties available for sale in Windsor.

In 2025, 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 $2,866.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, CT

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: 7.15%

Airbnb Rental Income: $null

Traditional Rental Income: $4144

Airbnb ROI: N/A

Traditional ROI: 7.15%

58 Amanda Circle

Windsor, CT

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

$436,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $1296

Traditional Rental Income: $3493

Airbnb ROI: -1.17%

Traditional ROI: 5.21%

39 Loren Circle

Windsor, CT

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

$344,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.91%

Airbnb Rental Income: $null

Traditional Rental Income: $3666

Airbnb ROI: N/A

Traditional ROI: 7.91%

39 Old Kennedy Road

Windsor, CT

3 beds | 2 baths | 1,168 sq.ft.

$235,900

Airbnb cash on cash: 0.47%

Traditional cash on cash: 8.72%

Airbnb Rental Income: $1296

Traditional Rental Income: $2731

Airbnb ROI: 0.47%

Traditional ROI: 8.72%

101 Seymour Street

Windsor, CT

2 beds | 1 baths | 960 sq.ft.

$235,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $1688

Traditional Rental Income: $1736

Airbnb ROI: 1.96%

Traditional ROI: 4.29%

175 East Pershing Street

Windsor, CT

3 beds | 1 baths | 1,128 sq.ft.

$335,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 3.86%

Airbnb Rental Income: $1296

Traditional Rental Income: $2288

Airbnb ROI: -0.58%

Traditional ROI: 3.86%

2200 Dover Court

Windsor, CT

2 beds | 2 baths | 1,276 sq.ft.

$289,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $1688

Traditional Rental Income: $2552

Airbnb ROI: -0.51%

Traditional ROI: 4.39%

140 Portman Street

Windsor, CT

3 beds | 1 baths | 950 sq.ft.

$244,999

Airbnb cash on cash: 0.34%

Traditional cash on cash: 5.58%

Airbnb Rental Income: $1296

Traditional Rental Income: $2104

Airbnb ROI: 0.34%