Real Estate Investment Properties for Sale in Winona, MN

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24425 County Road 17 Winona, MN Bathed in natural light and surrounded by breathtaking views of Winonaâs bluffs and roll...	3 beds \| 2 baths \| 2,176 sq.ft.	$400,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.56% Airbnb Rental Income: $1765 Traditional Rental Income: $2461 Airbnb ROI: 1.41% Traditional ROI: 4.56%
830 Prairie Island Road N Winona, MN This remarkable 5-bedroom, 4-bath riverfront home seamlessly blends timeless design, thoug...	5 beds \| 4 baths \| 5,938 sq.ft.	$1,700,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.8% Airbnb Rental Income: $null Traditional Rental Income: $4159 Airbnb ROI: N/A Traditional ROI: 0.8%
609 E 2nd Street Winona, MN Welcome to your cozy retreat! This 1 bed, 1 bath smaller home boasts a nice sized 2-car ga...	1 beds \| 1 baths \| 810 sq.ft.	$134,500	Airbnb cash on cash: 5.6% Traditional cash on cash: 6.8% Airbnb Rental Income: $1442 Traditional Rental Income: $1168 Airbnb ROI: 5.6% Traditional ROI: 6.8%
8830 E 8th Street Winona, MN Welcome to your dream home nestled just outside Winona, a residence that seamlessly blends...	4 beds \| 3 baths \| 3,835 sq.ft.	$462,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $2956 Airbnb ROI: N/A Traditional ROI: 5.02%
1008 W 2nd Street Winona, MN Come check out this charming two bedroom on main level, with one bedroom apartment upstair...	3 beds \| 2 baths \| 1,224 sq.ft.	$204,900	Airbnb cash on cash: 4.21% Traditional cash on cash: 7.64% Airbnb Rental Income: $1765 Traditional Rental Income: $1950 Airbnb ROI: 4.21% Traditional ROI: 7.64%
611 Clarks Lane Winona, MN CHARM AND CHARACTER GALORE! This 5 Bedroom, 2.5 Bath, 2-story home offers tons of space, ...	5 beds \| 3 baths \| 2,066 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.76% Airbnb Rental Income: $null Traditional Rental Income: $3005 Airbnb ROI: N/A Traditional ROI: 6.76%
366 Kansas Street Winona, MN Unique opportunity near parks, campus, and downtown! This 4 bed, 2 bath home offers main f...	4 beds \| 2 baths \| 1,877 sq.ft.	$214,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.85% Airbnb Rental Income: $null Traditional Rental Income: $2361 Airbnb ROI: N/A Traditional ROI: 8.85%
1252 W Broadway Street Winona, MN This enchanting home Showcases both Quality and Character with it's Distinctive Features a...	4 beds \| 2 baths \| 2,071 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.19% Airbnb Rental Income: $null Traditional Rental Income: $2582 Airbnb ROI: N/A Traditional ROI: 6.19%
749 W 4th Street Winona, MN This 3 bedroom, 2 bathroom home with a 1 car garage is move in ready with some fresh paint...	3 beds \| 2 baths \| 1,599 sq.ft.	$227,600	Airbnb cash on cash: 3.85% Traditional cash on cash: 8.24% Airbnb Rental Income: $1765 Traditional Rental Income: $2228 Airbnb ROI: 3.85% Traditional ROI: 8.24%
1702 Edgewood Road Winona, MN Rare opportunity! Homes on this street donât come up for sale often. This 4-bedroom, 2-b...	4 beds \| 2 baths \| 2,060 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.79% Airbnb Rental Income: $null Traditional Rental Income: $2569 Airbnb ROI: N/A Traditional ROI: 6.79%
220 Janet Marie Lane Winona, MN WELCOME TO 220 JANET MARIE LANE! Built in 2008, this well maintained, one-story townhome o...	2 beds \| 2 baths \| 1,270 sq.ft.	$299,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 4.7% Airbnb Rental Income: $1610 Traditional Rental Income: $2037 Airbnb ROI: 1.57% Traditional ROI: 4.7%
706 W Broadway Street Winona, MN This beautifully maintained 4-bedroom, 3-bathroom home offers a perfect blend of character...	4 beds \| 3 baths \| 2,175 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.17% Airbnb Rental Income: $null Traditional Rental Income: $2812 Airbnb ROI: N/A Traditional ROI: 7.17%
317 E 2nd Street Winona, MN Come and see this 4-bedroom, 1-bathroom home with just over 1600 square feet of living sp...	4 beds \| 1 baths \| 1,640 sq.ft.	$230,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $1817 Airbnb ROI: N/A Traditional ROI: 6.12%
616 Lafayette Street Winona, MN One-Level Living in the Heart of Winona! Enjoy the ease of single-level living just minut...	1 beds \| 1 baths \| 732 sq.ft.	$120,000	Airbnb cash on cash: 6.23% Traditional cash on cash: 8.43% Airbnb Rental Income: $1442 Traditional Rental Income: $1267 Airbnb ROI: 6.23% Traditional ROI: 8.43%

Real Estate investment in Winona, MN

There are 20 properties for sale in the city of Winona . The median list price in Winona is $244,500 and the average price per square foot is $120. In September 2025, the average monthly cash on cash return in Winona is 7.00%. The average monthly rental income in Winona is $2,326.

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

There are 20 investment properties available for sale in Winona.

In 2025, the best neighborhood to buy investment property is Winona.

The ROI for Long-Term is higher than the Short-Term in Winona with average rental income of $2,326.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, MN

24425 County Road 17

Winona, MN

3 beds | 2 baths | 2,176 sq.ft.

$400,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $1765

Traditional Rental Income: $2461

Airbnb ROI: 1.41%

Traditional ROI: 4.56%

830 Prairie Island Road N

Winona, MN

5 beds | 4 baths | 5,938 sq.ft.

$1,700,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.8%

Airbnb Rental Income: $null

Traditional Rental Income: $4159

Airbnb ROI: N/A

Traditional ROI: 0.8%

609 E 2nd Street

Winona, MN

1 beds | 1 baths | 810 sq.ft.

$134,500

Airbnb cash on cash: 5.6%

Traditional cash on cash: 6.8%

Airbnb Rental Income: $1442

Traditional Rental Income: $1168

Airbnb ROI: 5.6%

Traditional ROI: 6.8%

8830 E 8th Street

Winona, MN

4 beds | 3 baths | 3,835 sq.ft.

$462,500

Airbnb cash on cash: N/A

Traditional cash on cash: 5.02%

Airbnb Rental Income: $null

Traditional Rental Income: $2956

Airbnb ROI: N/A

Traditional ROI: 5.02%

1008 W 2nd Street

Winona, MN

3 beds | 2 baths | 1,224 sq.ft.

$204,900

Airbnb cash on cash: 4.21%

Traditional cash on cash: 7.64%

Airbnb Rental Income: $1765

Traditional Rental Income: $1950

Airbnb ROI: 4.21%

Traditional ROI: 7.64%

611 Clarks Lane

Winona, MN

5 beds | 3 baths | 2,066 sq.ft.

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.76%

Airbnb Rental Income: $null

Traditional Rental Income: $3005

Airbnb ROI: N/A

Traditional ROI: 6.76%

366 Kansas Street

Winona, MN

4 beds | 2 baths | 1,877 sq.ft.

$214,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.85%

Airbnb Rental Income: $null

Traditional Rental Income: $2361

Airbnb ROI: N/A

Traditional ROI: 8.85%

1252 W Broadway Street

Winona, MN

4 beds | 2 baths | 2,071 sq.ft.

$329,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2582

Airbnb ROI: N/A