Real Estate Investment Properties for Sale in Winona, MS

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
205 Shirley Ave Winona, MS Step into timeless charm and modern comfort with this beautifully updated 4-bedroom, 3-bat...	4 beds \| 3 baths \| 2,600 sq.ft.	$279,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.04% Airbnb Rental Income: $null Traditional Rental Income: $3284 Airbnb ROI: N/A Traditional ROI: 10.04%
308 Jones Winona, MS Wonderful opportunity to own a historic home located in the city limits of Winona with an ...	3 beds \| 2 baths \| 2,734 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.59% Airbnb Rental Income: $null Traditional Rental Income: $2720 Airbnb ROI: N/A Traditional ROI: 10.59%
1509 Highway 407 Winona, MS	3 beds \| 2 baths \| 1,269 sq.ft.	$160,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.3% Airbnb Rental Income: $null Traditional Rental Income: $1942 Airbnb ROI: N/A Traditional ROI: 10.3%
109 Mission Road Winona, MS What to love about 109 Mission Road: 2 living spaces-your front porch leads into a spaciou...	3 beds \| 1 baths \| 1,694 sq.ft.	$149,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.58% Airbnb Rental Income: $null Traditional Rental Income: $1870 Airbnb ROI: N/A Traditional ROI: 10.58%
621 Middleton Road Winona, MS Welcome home to comfort and convenience in a prime location! This well-maintained property...	3 beds \| 2 baths \| 1,716 sq.ft.	$220,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $1217 Airbnb ROI: N/A Traditional ROI: 3.41%
599 Highway 51 Winona, MS Perched on 5 beautiful acres, this stunning 4-bedroom, 3.5-bath home offers the perfect bl...	4 beds \| 4 baths \| N/A	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.67% Airbnb Rental Income: $null Traditional Rental Income: $4086 Airbnb ROI: N/A Traditional ROI: 11.67%
810 Michelle Drive Winona, MS	3 beds \| 2 baths \| N/A	$179,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.48% Airbnb Rental Income: $null Traditional Rental Income: $2258 Airbnb ROI: N/A Traditional ROI: 10.48%
59 Redell Drive Winona, MS Prime location on the outskirts of Winona, MS in a wonderful, established neighborhood! ...	3 beds \| 3 baths \| N/A	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.86% Airbnb Rental Income: $null Traditional Rental Income: $2647 Airbnb ROI: N/A Traditional ROI: 8.86%

Real Estate investment in Winona, MS

There are 8 properties for sale in the city of Winona . The median list price in Winona is $229,500 and the average price per square foot is $97. In March 2026, the average monthly cash on cash return in Winona is 13.00%. The average monthly rental income in Winona is $2,647.

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

There are 8 investment properties available for sale in Winona.

In 2026, the best neighborhood to buy investment property is 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, MS

205 Shirley Ave

Winona, MS

4 beds | 3 baths | 2,600 sq.ft.

$279,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.04%

Airbnb Rental Income: $null

Traditional Rental Income: $3284

Airbnb ROI: N/A

Traditional ROI: 10.04%

308 Jones

Winona, MS

3 beds | 2 baths | 2,734 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.59%

Airbnb Rental Income: $null

Traditional Rental Income: $2720

Airbnb ROI: N/A

Traditional ROI: 10.59%

1509 Highway 407

Winona, MS

3 beds | 2 baths | 1,269 sq.ft.

$160,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.3%

Airbnb Rental Income: $null

Traditional Rental Income: $1942

Airbnb ROI: N/A

Traditional ROI: 10.3%

109 Mission Road

Winona, MS

3 beds | 1 baths | 1,694 sq.ft.

$149,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.58%

Airbnb Rental Income: $null

Traditional Rental Income: $1870

Airbnb ROI: N/A

Traditional ROI: 10.58%

621 Middleton Road

Winona, MS

3 beds | 2 baths | 1,716 sq.ft.

$220,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.41%

Airbnb Rental Income: $null

Traditional Rental Income: $1217

Airbnb ROI: N/A

Traditional ROI: 3.41%

599 Highway 51

Winona, MS

4 beds | 4 baths | N/A

$315,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.67%

Airbnb Rental Income: $null

Traditional Rental Income: $4086

Airbnb ROI: N/A

Traditional ROI: 11.67%

810 Michelle Drive

Winona, MS

3 beds | 2 baths | N/A

$179,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2258

Airbnb ROI: N/A

Traditional ROI: 10.48%

59 Redell Drive

Winona, MS

3 beds | 3 baths | N/A

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.86%

Airbnb Rental Income: $null

Traditional Rental Income: $2647

Airbnb ROI: N/A