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
386 Pleasant Hill Dr Winona, MN Tucked into a quiet, country-feel neighborhood just minutes from town amenities, this one-...	3 beds \| 2 baths \| 3,792 sq.ft.	$423,900	Airbnb cash on cash: -0.41% Traditional cash on cash: 5.47% Airbnb Rental Income: $1140 Traditional Rental Income: $3098 Airbnb ROI: -0.41% Traditional ROI: 5.47%
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%
657 Sioux Street Winona, MN Welcome Home to this delightful single-story gem! This charming 2 bedroom 1 bathroom home ...	2 beds \| 1 baths \| 640 sq.ft.	$125,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 8.21% Airbnb Rental Income: $749 Traditional Rental Income: $1298 Airbnb ROI: 1.04% Traditional ROI: 8.21%
215 E 5th St Winona, MN This Unique Triplex has much to offer! A large 3-bedroom unit and 2, 1-bedroom units each ...	5 beds \| 3 baths \| 2,406 sq.ft.	$244,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $2186 Airbnb ROI: N/A Traditional ROI: 6.94%
602 8th St E Winona, MN Step into a beautifully renewed three-bedroom, two-bathroom residence that epitomizes mode...	3 beds \| 2 baths \| 1,500 sq.ft.	$249,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 7.38% Airbnb Rental Income: $1140 Traditional Rental Income: $2178 Airbnb ROI: 1.38% Traditional ROI: 7.38%
8500 W Main St Winona, MN This well maintained spacious 3 bedroom, 2 bathroom home offers comfortable main level liv...	3 beds \| 2 baths \| 1,276 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.43% Airbnb Rental Income: $null Traditional Rental Income: $2013 Airbnb ROI: N/A Traditional ROI: 6.43%
169 Cobblestone Ln Winona, MN Looking for space, privacy, and a top-tier neighborhood? Act fast--this Cobblestone Creek ...	4 beds \| 3 baths \| 2,820 sq.ft.	$587,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $3313 Airbnb ROI: N/A Traditional ROI: 3.88%
384 Valley Oaks Drive Winona, MN Welcome home to this newer twin home in the sought-after Valley Oaks neighborhood, where c...	4 beds \| 3 baths \| 3,104 sq.ft.	$460,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.82% Airbnb Rental Income: $null Traditional Rental Income: $3046 Airbnb ROI: N/A Traditional ROI: 4.82%
714 E Mark St Winona, MN Come and see this remodeled 3 bedroom 2 bath home located just blocks from shopping and Ea...	3 beds \| 2 baths \| 1,680 sq.ft.	$224,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 7.97% Airbnb Rental Income: $1140 Traditional Rental Income: $2207 Airbnb ROI: 1.18% Traditional ROI: 7.97%
922 W Burns Valley Road Winona, MN Listed and Pended	2 beds \| 2 baths \| 1,262 sq.ft.	$265,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 5.53% Airbnb Rental Income: $749 Traditional Rental Income: $1934 Airbnb ROI: -0.47% Traditional ROI: 5.53%

Real Estate investment in Winona, MN

There are 32 properties for sale in the city of Winona . The median list price in Winona is $244,000 and the average price per square foot is $129. In February 2026, the average monthly cash on cash return in Winona is 5.00%. The average monthly rental income in Winona is $1,734.

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

There are 32 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 $749.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, MN

386 Pleasant Hill Dr

Winona, MN

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

$423,900

Airbnb cash on cash: -0.41%

Traditional cash on cash: 5.47%

Airbnb Rental Income: $1140

Traditional Rental Income: $3098

Airbnb ROI: -0.41%

Traditional ROI: 5.47%

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%

657 Sioux Street

Winona, MN

2 beds | 1 baths | 640 sq.ft.

$125,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $749

Traditional Rental Income: $1298

Airbnb ROI: 1.04%

Traditional ROI: 8.21%

215 E 5th St

Winona, MN

5 beds | 3 baths | 2,406 sq.ft.

$244,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.94%

Airbnb Rental Income: $null

Traditional Rental Income: $2186

Airbnb ROI: N/A

Traditional ROI: 6.94%

602 8th St E

Winona, MN

3 beds | 2 baths | 1,500 sq.ft.

$249,900

Airbnb cash on cash: 1.38%

Traditional cash on cash: 7.38%

Airbnb Rental Income: $1140

Traditional Rental Income: $2178

Airbnb ROI: 1.38%

Traditional ROI: 7.38%

8500 W Main St

Winona, MN

3 beds | 2 baths | 1,276 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2013

Airbnb ROI: N/A

Traditional ROI: 6.43%

169 Cobblestone Ln

Winona, MN

4 beds | 3 baths | 2,820 sq.ft.

$587,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.88%

Airbnb Rental Income: $null

Traditional Rental Income: $3313

Airbnb ROI: N/A

Traditional ROI: 3.88%

384 Valley Oaks Drive

Winona, MN

4 beds | 3 baths | 3,104 sq.ft.

$460,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.82%

Airbnb Rental Income: $null

Traditional Rental Income: $3046

Airbnb ROI: N/A