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
703 W Benton St Windsor, MO 703 W Benton St, Windsor, MO 64360 \| Single Family Residential	2 beds \| 1 baths \| 1,344 sq.ft.	$135,500	Airbnb cash on cash: N/A Traditional cash on cash: 8.19% Airbnb Rental Income: $null Traditional Rental Income: $1414 Airbnb ROI: N/A Traditional ROI: 8.19%
709 S Windsor St 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.	$131,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.19% Airbnb Rental Income: $null Traditional Rental Income: $1014 Airbnb ROI: N/A Traditional ROI: 6.19%
709 W Benton St 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 Rd 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.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.31% Airbnb Rental Income: $null Traditional Rental Income: $1603 Airbnb ROI: N/A Traditional ROI: 8.31%
709 W Jackson Windsor, MO Storage outbuilding. Handicap ramp not included. Potential RV hookup area and parking, Roo...	3 beds \| 1 baths \| 1,125 sq.ft.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.71% Airbnb Rental Income: $null Traditional Rental Income: $1651 Airbnb ROI: N/A Traditional ROI: 6.71%
1193 SE 23 Hwy Windsor, MO Welcome to this beautifully custom built, partial earth contact home with 3-bedrooms, 3.5-...	3 beds \| 3 baths \| 2,140 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.99% Airbnb Rental Income: $null Traditional Rental Income: $2797 Airbnb ROI: N/A Traditional ROI: 3.99%
609 S Tebo St 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%
106 W Lake Shore Dr Windsor, MO 106 W Lake Shore Dr, Windsor, MO 65360 \| Single Family Residential	3 beds \| 2 baths \| 1,800 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $2197 Airbnb ROI: N/A Traditional ROI: 4.92%
204 W Colt St Windsor, MO 204 W Colt St, Windsor, MO 65360 \| Single Family Residential	2 beds \| 1 baths \| 1,650 sq.ft.	$104,990	Airbnb cash on cash: N/A Traditional cash on cash: 10.75% Airbnb Rental Income: $null Traditional Rental Income: $1387 Airbnb ROI: N/A Traditional ROI: 10.75%
TBD 42.23+/- SE 1151st Rd Windsor, MO TBD 42.23+/- SE 1151st Rd, Windsor, MO 65360 \| Other	N/A beds \| N/A baths \| N/A	$316,725	Airbnb cash on cash: -2.35% Traditional cash on cash: 0.35% Airbnb Rental Income: $201 Traditional Rental Income: $781 Airbnb ROI: -2.35% Traditional ROI: 0.35%
200 N Mill St Windsor, MO 200 N Mill St, Windsor, MO 65360 \| Other	N/A beds \| N/A baths \| N/A	$55,000	Airbnb cash on cash: -4% Traditional cash on cash: 10.45% Airbnb Rental Income: $201 Traditional Rental Income: $781 Airbnb ROI: -4% Traditional ROI: 10.45%
1002 SE 750th Rd Windsor, MO 1002 SE 750th Rd, Windsor, MO 65360 \| Other	N/A beds \| N/A baths \| N/A	$130,000	Airbnb cash on cash: -2.87% Traditional cash on cash: 3.63% Airbnb Rental Income: $201 Traditional Rental Income: $791 Airbnb ROI: -2.87% Traditional ROI: 3.63%
300 E Florence St 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.	$142,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.81% Airbnb Rental Income: $null Traditional Rental Income: $1342 Airbnb ROI: N/A Traditional ROI: 7.81%
603 W Florence N/A Windsor, MO 603 W Florence N/A, Windsor, MO 65360 \| Single Family Residential	2 beds \| 1 baths \| 1,175 sq.ft.	$155,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.74% Airbnb Rental Income: $null Traditional Rental Income: $1382 Airbnb ROI: N/A Traditional ROI: 6.74%
401 E Jackson St Windsor, MO 401 E Jackson St, Windsor, MO 65360 \| Single Family Residential	3 beds \| 2 baths \| 1,981 sq.ft.	$160,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.85% Airbnb Rental Income: $null Traditional Rental Income: $2202 Airbnb ROI: N/A Traditional ROI: 11.85%
10496 Soles Rd Windsor, MO Spacious 5-bedroom, 1 bath Amish-built home on attractive acreage with multiple outbuildin...	5 beds \| 1 baths \| 1,280 sq.ft.	$339,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.47% Airbnb Rental Income: $null Traditional Rental Income: $1745 Airbnb ROI: N/A Traditional ROI: 3.47%
TBD SE 750th Rd Windsor, MO TBD SE 750th Rd, Windsor, MO 65360 \| Other	N/A beds \| N/A baths \| N/A	$70,000	Airbnb cash on cash: -3.6% Traditional cash on cash: 9.89% Airbnb Rental Income: $201 Traditional Rental Income: $916 Airbnb ROI: -3.6% Traditional ROI: 9.89%
106 Westwood Ave Windsor, MO Welcome home to Westwood Hills Subdivision! This charming 4-bedroom, 2-bath home offers sp...	4 beds \| 2 baths \| 1,746 sq.ft.	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.48% Airbnb Rental Income: $null Traditional Rental Income: $2196 Airbnb ROI: N/A Traditional ROI: 9.48%
406 E Florence St Windsor, MO 406 E Florence St, Windsor, MO 65360 \| Single Family Residential	2 beds \| 1 baths \| 1,196 sq.ft.	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.97% Airbnb Rental Income: $null Traditional Rental Income: $1509 Airbnb ROI: N/A Traditional ROI: 8.97%
605 Poplar Drive 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: 7.24% Airbnb Rental Income: $null Traditional Rental Income: $1510 Airbnb ROI: N/A Traditional ROI: 7.24%
424 Hillcrest Drive 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: 8.39% Airbnb Rental Income: $null Traditional Rental Income: $2536 Airbnb ROI: N/A Traditional ROI: 8.39%
10400 52 Highway Windsor, MO Beautiful 19.7 +/- acre property with endless possibilities! This impressive 5,200 sq. ft....	2 beds \| 1 baths \| 1,200 sq.ft.	$468,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $1829 Airbnb ROI: N/A Traditional ROI: 1.91%
1316 965P Road Windsor, MO Seller has received Multiple Offers and requested Final and Best Offers by this evening (6...	3 beds \| 2 baths \| 1,472 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.3% Airbnb Rental Income: $null Traditional Rental Income: $2405 Airbnb ROI: N/A Traditional ROI: 8.3%
706 W Benton St Windsor, MO 706 W Benton St, Windsor, MO 65370 \| Single Family Residential	1 beds \| 2 baths \| 1,200 sq.ft.	$205,000	Airbnb cash on cash: -2.65% Traditional cash on cash: 4.75% Airbnb Rental Income: $177 Traditional Rental Income: $1398 Airbnb ROI: -2.65% Traditional ROI: 4.75%

Real Estate investment in Windsor, MO

There are 25 properties for sale in the city of Windsor . The median list price in Windsor is $164,801 and the average price per square foot is $56. In August 2026, the average monthly cash on cash return in Windsor is 9.00%. The average monthly rental income in Windsor is $1,510.

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

There are 25 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 $1,510.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, MO

703 W Benton St

Windsor, MO

2 beds | 1 baths | 1,344 sq.ft.

$135,500

Airbnb cash on cash: N/A

Traditional cash on cash: 8.19%

Airbnb Rental Income: $null

Traditional Rental Income: $1414

Airbnb ROI: N/A

Traditional ROI: 8.19%

709 S Windsor St

Windsor, MO

2 beds | 1 baths | 882 sq.ft.

$131,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.19%

Airbnb Rental Income: $null

Traditional Rental Income: $1014

Airbnb ROI: N/A

Traditional ROI: 6.19%

709 W Benton St

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 Rd

Windsor, MO

3 beds | 2 baths | 849 sq.ft.

$159,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.31%

Airbnb Rental Income: $null

Traditional Rental Income: $1603

Airbnb ROI: N/A

Traditional ROI: 8.31%

709 W Jackson

Windsor, MO

3 beds | 1 baths | 1,125 sq.ft.

$189,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.71%

Airbnb Rental Income: $null

Traditional Rental Income: $1651

Airbnb ROI: N/A

Traditional ROI: 6.71%

1193 SE 23 Hwy

Windsor, MO

3 beds | 3 baths | 2,140 sq.ft.

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.99%

Airbnb Rental Income: $null

Traditional Rental Income: $2797

Airbnb ROI: N/A

Traditional ROI: 3.99%

609 S Tebo St

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%

106 W Lake Shore Dr

Windsor, MO

3 beds | 2 baths | 1,800 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2197

Airbnb ROI: N/A