Real Estate Investment Properties for Sale in Windsor, MO

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
207 WINCHELL Windsor, MO Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 1 baths \| 1,622 sq.ft.	$187,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.93% Airbnb Rental Income: $null Traditional Rental Income: $2123 Airbnb ROI: N/A Traditional ROI: 9.93%
207 Phelps Street Windsor, MO This could be it!! Updated Windsor home packed with value and ready for it's new owner. Ne...	3 beds \| 1 baths \| 1,719 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.55% Airbnb Rental Income: $null Traditional Rental Income: $1913 Airbnb ROI: N/A Traditional ROI: 8.55%
709 W Benton Street Windsor, MO Charming and well-maintained home situated on a spacious corner lot, offering a fantastic ...	3 beds \| 1 baths \| 1,278 sq.ft.	$138,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.47% Airbnb Rental Income: $null Traditional Rental Income: $1407 Airbnb ROI: N/A Traditional ROI: 8.47%
232 S County Line Road Windsor, MO Cleaner-upper!!! Bring a little sweat equity and make this your storybook ranch on half an...	3 beds \| 2 baths \| 849 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.53% Airbnb Rental Income: $null Traditional Rental Income: $1603 Airbnb ROI: N/A Traditional ROI: 7.53%
609 S tebo Windsor, MO Here is a nice 2 bedroom 1 bath brick home with a detached garage a roof thats just a few ...	2 beds \| 1 baths \| 1,300 sq.ft.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.41% Airbnb Rental Income: $null Traditional Rental Income: $1790 Airbnb ROI: N/A Traditional ROI: 10.41%
709 S Windsor Windsor, MO Find your Forever Home in Windsor! This home which sits on a spacious corner lot within ci...	2 beds \| 1 baths \| 882 sq.ft.	$128,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.75% Airbnb Rental Income: $null Traditional Rental Income: $1464 Airbnb ROI: N/A Traditional ROI: 9.75%
300 E Florence Street Windsor, MO Welcome to 300 E Florence St, Windsor! This beautifully renovated 2-bedroom, 1-bath bungal...	2 beds \| 1 baths \| 1,124 sq.ft.	$148,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.51% Airbnb Rental Income: $null Traditional Rental Income: $1342 Airbnb ROI: N/A Traditional ROI: 7.51%
605 Poplar Windsor, MO Charming and move-in ready 3-bedroom, 1-bath home located on a quiet street! This well-mai...	3 beds \| 1 baths \| 1,056 sq.ft.	$169,950	Airbnb cash on cash: N/A Traditional cash on cash: 6.79% Airbnb Rental Income: $null Traditional Rental Income: $1510 Airbnb ROI: N/A Traditional ROI: 6.79%
104 W Birch Drive Windsor, MO Charming home with great updates and plenty of space to enjoy both inside and out! This pr...	3 beds \| 1 baths \| 1,268 sq.ft.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.56% Airbnb Rental Income: $null Traditional Rental Income: $1728 Airbnb ROI: N/A Traditional ROI: 7.56%
424 Hillcrest Windsor, MO Welcome to this spacious, well-maintained home offering 4 bedrooms and 2 full bathrooms on...	4 beds \| 2 baths \| 2,341 sq.ft.	$255,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.52% Airbnb Rental Income: $null Traditional Rental Income: $2536 Airbnb ROI: N/A Traditional ROI: 8.52%
218 Century Street Windsor, MO Charming 4-bedroom home offering space, convenience, and a large lot with room to spread o...	4 beds \| 2 baths \| 1,792 sq.ft.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.82% Airbnb Rental Income: $null Traditional Rental Income: $2521 Airbnb ROI: N/A Traditional ROI: 11.82%
406 E Washington Street Windsor, MO Welcome Home! This true ranch-style property offers the ease of single-level living, with ...	3 beds \| 1 baths \| 1,400 sq.ft.	$159,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $1077 Airbnb ROI: N/A Traditional ROI: 4.78%

Real Estate investment in Windsor, MO

There are 13 properties for sale in the city of Windsor . The median list price in Windsor is $602,475 and the average price per square foot is $199. In May 2026, the average monthly cash on cash return in Windsor is 9.00%. The average monthly rental income in Windsor is $1,737.

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

There are 13 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, MO

207 WINCHELL

Windsor, MO

3 beds | 1 baths | 1,622 sq.ft.

$187,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.93%

Airbnb Rental Income: $null

Traditional Rental Income: $2123

Airbnb ROI: N/A

Traditional ROI: 9.93%

207 Phelps Street

Windsor, MO

3 beds | 1 baths | 1,719 sq.ft.

$189,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.55%

Airbnb Rental Income: $null

Traditional Rental Income: $1913

Airbnb ROI: N/A

Traditional ROI: 8.55%

709 W Benton Street

Windsor, MO

3 beds | 1 baths | 1,278 sq.ft.

$138,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.47%

Airbnb Rental Income: $null

Traditional Rental Income: $1407

Airbnb ROI: N/A

Traditional ROI: 8.47%

232 S County Line Road

Windsor, MO

3 beds | 2 baths | 849 sq.ft.

$175,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.53%

Airbnb Rental Income: $null

Traditional Rental Income: $1603

Airbnb ROI: N/A

Traditional ROI: 7.53%

609 S tebo

Windsor, MO

2 beds | 1 baths | 1,300 sq.ft.

$149,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.41%

Airbnb Rental Income: $null

Traditional Rental Income: $1790

Airbnb ROI: N/A

Traditional ROI: 10.41%

709 S Windsor

Windsor, MO

2 beds | 1 baths | 882 sq.ft.

$128,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.75%

Airbnb Rental Income: $null

Traditional Rental Income: $1464

Airbnb ROI: N/A

Traditional ROI: 9.75%

300 E Florence Street

Windsor, MO

2 beds | 1 baths | 1,124 sq.ft.

$148,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.51%

Airbnb Rental Income: $null

Traditional Rental Income: $1342

Airbnb ROI: N/A

Traditional ROI: 7.51%

605 Poplar

Windsor, MO

3 beds | 1 baths | 1,056 sq.ft.

$169,950

Airbnb cash on cash: N/A

Traditional cash on cash: 6.79%

Airbnb Rental Income: $null

Traditional Rental Income: $1510

Airbnb ROI: N/A