Real Estate Investment Properties for Sale in Winona, MO

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
16428 Mo-19 Winona, MO One-of-a-kind business & residential opportunity on 46 acres!Interior pictures coming soon...	4 beds \| 3 baths \| 1,753 sq.ft.	$879,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 1.6%
7922 Old Alton Road Winona, MO Peaceful country living with convenience! This 2 bedroom, 2 bathroom, laundry room the hom...	2 beds \| 2 baths \| 1,305 sq.ft.	$219,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.43% Airbnb Rental Income: $null Traditional Rental Income: $2309 Airbnb ROI: N/A Traditional ROI: 9.43%
8969 County Road 445 Winona, MO FARMING - HUNTING - PRIVACY - COUNTRY HOME!This property is well-suited for horse and equi...	4 beds \| 2 baths \| 1,880 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $1923 Airbnb ROI: N/A Traditional ROI: 3.95%
19033 County Road 579 Winona, MO Secluded 5-Bedroom Home on 22 Acres - Outdoor Lover's Dream Near Government LandWelcome to...	5 beds \| 3 baths \| 2,792 sq.ft.	$529,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $2961 Airbnb ROI: N/A Traditional ROI: 4.65%
8612 Sapper Street Winona, MO Welcome to a home that truly has it all. This move-in-ready 4-bedroom townhouse stands out...	4 beds \| 2 baths \| 1,237 sq.ft.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.84% Airbnb Rental Income: $null Traditional Rental Income: $1775 Airbnb ROI: N/A Traditional ROI: 9.84%
18197 7th Street Winona, MO Spacious and modern 3-bedroom, 2-bath townhome situated on a desirable corner lot and a ha...	3 beds \| 2 baths \| 1,352 sq.ft.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.25% Airbnb Rental Income: $null Traditional Rental Income: $1640 Airbnb ROI: N/A Traditional ROI: 8.25%
8643 Sapper Street Winona, MO Charming in-town home situated on a desirable corner lot! This 4-bedroom, 1-bath property ...	4 beds \| 1 baths \| 1,114 sq.ft.	$129,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.37% Airbnb Rental Income: $null Traditional Rental Income: $1660 Airbnb ROI: N/A Traditional ROI: 11.37%
8737 Sapper Street Winona, MO Very nice brick home on a corner lot. New roof on home and storage building this year!This...	3 beds \| 2 baths \| 1,629 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.28% Airbnb Rental Income: $null Traditional Rental Income: $2280 Airbnb ROI: N/A Traditional ROI: 10.28%

Real Estate investment in Winona, MO

There are 9 properties for sale in the city of Winona . The median list price in Winona is $94,943 and the average price per square foot is $37. In July 2026, the average monthly cash on cash return in Winona is 10.00%. The average monthly rental income in Winona is $2,295.

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

There are 9 investment properties available for sale in Winona.

The ROI for Short-Term is higher than the Long-Term in Winona with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, MO

16428 Mo-19

Winona, MO

4 beds | 3 baths | 1,753 sq.ft.

$879,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2371

Airbnb ROI: N/A

Traditional ROI: 1.6%

7922 Old Alton Road

Winona, MO

2 beds | 2 baths | 1,305 sq.ft.

$219,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2309

Airbnb ROI: N/A

Traditional ROI: 9.43%

8969 County Road 445

Winona, MO

4 beds | 2 baths | 1,880 sq.ft.

$379,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.95%

Airbnb Rental Income: $null

Traditional Rental Income: $1923

Airbnb ROI: N/A

Traditional ROI: 3.95%

19033 County Road 579

Winona, MO

5 beds | 3 baths | 2,792 sq.ft.

$529,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.65%

Airbnb Rental Income: $null

Traditional Rental Income: $2961

Airbnb ROI: N/A

Traditional ROI: 4.65%

8612 Sapper Street

Winona, MO

4 beds | 2 baths | 1,237 sq.ft.

$159,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.84%

Airbnb Rental Income: $null

Traditional Rental Income: $1775

Airbnb ROI: N/A

Traditional ROI: 9.84%

18197 7th Street

Winona, MO

3 beds | 2 baths | 1,352 sq.ft.

$169,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.25%

Airbnb Rental Income: $null

Traditional Rental Income: $1640

Airbnb ROI: N/A

Traditional ROI: 8.25%

8643 Sapper Street

Winona, MO

4 beds | 1 baths | 1,114 sq.ft.

$129,900

Airbnb cash on cash: N/A

Traditional cash on cash: 11.37%

Airbnb Rental Income: $null

Traditional Rental Income: $1660

Airbnb ROI: N/A

Traditional ROI: 11.37%

8737 Sapper Street

Winona, MO

3 beds | 2 baths | 1,629 sq.ft.

$199,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.28%

Airbnb Rental Income: $null

Traditional Rental Income: $2280

Airbnb ROI: N/A