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
65 Valley Trail Drive Winona, MN This well-designed 3-level split townhouse offers a comfortable layout with great function...	2 beds \| 2 baths \| 1,258 sq.ft.	$220,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $1865 Airbnb ROI: N/A Traditional ROI: 5.45%
386 Pleasant Hill Drive Winona, MN Tucked into a quiet, country-feel neighborhood just minutes from town amenities, this one-...	3 beds \| 4 baths \| 3,792 sq.ft.	$423,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.47% Airbnb Rental Income: $null Traditional Rental Income: $3098 Airbnb ROI: N/A Traditional ROI: 5.47%
552 E 4th St Winona, MN Move-in ready and beautifully updated from top to bottom, this charming 3-bedroom, 1-bath ...	3 beds \| 1 baths \| 1,137 sq.ft.	$198,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.43% Airbnb Rental Income: $null Traditional Rental Income: $1546 Airbnb ROI: N/A Traditional ROI: 6.43%
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.	$219,700	Airbnb cash on cash: N/A Traditional cash on cash: 8.57% Airbnb Rental Income: $null Traditional Rental Income: $2228 Airbnb ROI: N/A Traditional ROI: 8.57%
24555 Highway 61 Winona, MN Absolutely unique and stunning, this 3-bedroom, 3-bathroom home with a 2-stall garage offe...	3 beds \| 3 baths \| 2,700 sq.ft.	$599,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $3091 Airbnb ROI: N/A Traditional ROI: 3.83%
1178 W Broadway Street Winona, MN Charming 5 Bedroom Home with Great Rental Potential in Central Winona. This spacious prope...	5 beds \| 2 baths \| 1,600 sq.ft.	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.38% Airbnb Rental Income: $null Traditional Rental Income: $2343 Airbnb ROI: N/A Traditional ROI: 9.38%
75 Debi Lei Drive Winona, MN Welcome to this beautifully maintained 5-bedroom, 3-bath home set in a desired neighborhoo...	5 beds \| 3 baths \| 3,414 sq.ft.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.72% Airbnb Rental Income: $null Traditional Rental Income: $3223 Airbnb ROI: N/A Traditional ROI: 5.72%
616 E Sarnia Street Winona, MN Discover this inviting 1.5 story home on E. Sarina St., offering scenic views of Winona Bl...	5 beds \| 2 baths \| 2,534 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.07% Airbnb Rental Income: $null Traditional Rental Income: $2646 Airbnb ROI: N/A Traditional ROI: 8.07%
953 W Burns Valley Road Winona, MN Nestled on a serene .75-acre lot tucked behind Sugar Loaf, this charming 4-bedroom, 2-bath...	4 beds \| 2 baths \| 1,888 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.5% Airbnb Rental Income: $null Traditional Rental Income: $2453 Airbnb ROI: N/A Traditional ROI: 5.5%
215 E 5th Street Winona, MN This Unique Triplex has much to offer! A large 3-bedroom unit and 2, 1-bedroom units each ...	5 beds \| N/A baths \| 2,406 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.78% Airbnb Rental Income: $null Traditional Rental Income: $2186 Airbnb ROI: N/A Traditional ROI: 6.78%
602 8th Street E Winona, MN Step into a beautifully renewed three-bedroom, two-bathroom residence that epitomizes mode...	3 beds \| 2 baths \| 1,500 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.07% Airbnb Rental Income: $null Traditional Rental Income: $2178 Airbnb ROI: N/A Traditional ROI: 7.07%
1610 Gilmore Valley Road Winona, MN Spacious one-level home situated on a generous 1+ acre lot at the edge of town. Opportuni...	2 beds \| 2 baths \| 1,008 sq.ft.	$234,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.89% Airbnb Rental Income: $null Traditional Rental Income: $1791 Airbnb ROI: N/A Traditional ROI: 5.89%

Real Estate investment in Winona, MN

There are 15 properties for sale in the city of Winona . The median list price in Winona is $249,000 and the average price per square foot is $132. In December 2025, the average monthly cash on cash return in Winona is 6.00%. The average monthly rental income in Winona is $2,228.

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

There are 15 investment properties available for sale in Winona.

In 2025, 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, MN

65 Valley Trail Drive

Winona, MN

2 beds | 2 baths | 1,258 sq.ft.

$220,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.45%

Airbnb Rental Income: $null

Traditional Rental Income: $1865

Airbnb ROI: N/A

Traditional ROI: 5.45%

386 Pleasant Hill Drive

Winona, MN

3 beds | 4 baths | 3,792 sq.ft.

$423,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.47%

Airbnb Rental Income: $null

Traditional Rental Income: $3098

Airbnb ROI: N/A

Traditional ROI: 5.47%

552 E 4th St

Winona, MN

3 beds | 1 baths | 1,137 sq.ft.

$198,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.43%

Airbnb Rental Income: $null

Traditional Rental Income: $1546

Airbnb ROI: N/A

Traditional ROI: 6.43%

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

Traditional ROI: 6.19%

749 W 4th Street

Winona, MN

3 beds | 2 baths | 1,599 sq.ft.

$219,700

Airbnb cash on cash: N/A

Traditional cash on cash: 8.57%

Airbnb Rental Income: $null

Traditional Rental Income: $2228

Airbnb ROI: N/A

Traditional ROI: 8.57%

24555 Highway 61

Winona, MN

3 beds | 3 baths | 2,700 sq.ft.

$599,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.83%

Airbnb Rental Income: $null

Traditional Rental Income: $3091

Airbnb ROI: N/A

Traditional ROI: 3.83%

1178 W Broadway Street

Winona, MN

5 beds | 2 baths | 1,600 sq.ft.

$209,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2343

Airbnb ROI: N/A

Traditional ROI: 9.38%

75 Debi Lei Drive

Winona, MN

5 beds | 3 baths | 3,414 sq.ft.

$430,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.72%

Airbnb Rental Income: $null

Traditional Rental Income: $3223

Airbnb ROI: N/A