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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
103 S St Charles Street Windsor, MO 5 Newer Homes - Built end of 2023 / beginning of 2024. 900 sq ft homes with 2 bedrooms, 1 ...	N/A beds \| N/A baths \| N/A	$748,800	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $1452 Airbnb ROI: N/A Traditional ROI: 0.94%
618 E Benton Street Windsor, MO Three sheds (offering lots of storage capacity) and the Visitor's Lodge/game building and ...	3 beds \| 2 baths \| 997 sq.ft.	$164,997	Airbnb cash on cash: N/A Traditional cash on cash: 9.28% Airbnb Rental Income: $null Traditional Rental Income: $1763 Airbnb ROI: N/A Traditional ROI: 9.28%
305 California Avenue Windsor, MO Discover the perfect blend of comfort, space, and convenience in this 4 bedroom, 2 bath sp...	4 beds \| 2 baths \| 1,512 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.57% Airbnb Rental Income: $null Traditional Rental Income: $2335 Airbnb ROI: N/A Traditional ROI: 8.57%
301 W Benton Street Windsor, MO Step Back in Timeâwith All the Modern Comforts! This stunning 5-bedroom, 3-bath 1870-bu...	5 beds \| 3 baths \| 3,870 sq.ft.	$255,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.86% Airbnb Rental Income: $null Traditional Rental Income: $3100 Airbnb ROI: N/A Traditional ROI: 10.86%
14337 52 Windsor, MO When opportunity knocks...pack up your things and move! What a fantastic property! 3 good ...	3 beds \| 3 baths \| 1,731 sq.ft.	$439,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $2533 Airbnb ROI: N/A Traditional ROI: 4.65%
403 S Olive Windsor, MO This Windsor ranch truly checks all the boxes! Brimming with updates, this homeâs kitche...	2 beds \| 1 baths \| 1,144 sq.ft.	$138,500	Airbnb cash on cash: N/A Traditional cash on cash: 10.53% Airbnb Rental Income: $null Traditional Rental Income: $1698 Airbnb ROI: N/A Traditional ROI: 10.53%
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%

Real Estate investment in Windsor, MO

There are 8 properties for sale in the city of Windsor . The median list price in Windsor is $156,000 and the average price per square foot is $88. In September 2025, the average monthly cash on cash return in Windsor is 11.00%. The average monthly rental income in Windsor is $2,335.

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

There are 8 investment properties available for sale in Windsor.

In 2025, 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

103 S St Charles Street

Windsor, MO

N/A beds | N/A baths | N/A

$748,800

Airbnb cash on cash: N/A

Traditional cash on cash: 0.94%

Airbnb Rental Income: $null

Traditional Rental Income: $1452

Airbnb ROI: N/A

Traditional ROI: 0.94%

618 E Benton Street

Windsor, MO

3 beds | 2 baths | 997 sq.ft.

$164,997

Airbnb cash on cash: N/A

Traditional cash on cash: 9.28%

Airbnb Rental Income: $null

Traditional Rental Income: $1763

Airbnb ROI: N/A

Traditional ROI: 9.28%

305 California Avenue

Windsor, MO

4 beds | 2 baths | 1,512 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.57%

Airbnb Rental Income: $null

Traditional Rental Income: $2335

Airbnb ROI: N/A

Traditional ROI: 8.57%

301 W Benton Street

Windsor, MO

5 beds | 3 baths | 3,870 sq.ft.

$255,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.86%

Airbnb Rental Income: $null

Traditional Rental Income: $3100

Airbnb ROI: N/A

Traditional ROI: 10.86%

14337 52

Windsor, MO

3 beds | 3 baths | 1,731 sq.ft.

$439,500

Airbnb cash on cash: N/A

Traditional cash on cash: 4.65%

Airbnb Rental Income: $null

Traditional Rental Income: $2533

Airbnb ROI: N/A

Traditional ROI: 4.65%

403 S Olive

Windsor, MO

2 beds | 1 baths | 1,144 sq.ft.

$138,500

Airbnb cash on cash: N/A

Traditional cash on cash: 10.53%

Airbnb Rental Income: $null

Traditional Rental Income: $1698

Airbnb ROI: N/A

Traditional ROI: 10.53%

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%

Real Estate investment in Windsor, MO

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

How many investment properties are available for sale in Windsor?

Which neighborhoods in Windsor to invest in 2025?

Long-Term vs. Short-Term Rentals in Windsor, Missouri: Which will earn the best returns?

Use analytics to find lucrative traditional or Airbnb properties in a matter of minutes.

No more spreadsheets, no more searching.