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
607 E 2nd Street Winona, MN Updated 3 bed 1 bath home with newer flooring, paint, large kitchen, fenced in yard, detac...	3 beds \| 1 baths \| 992 sq.ft.	$159,900	Airbnb cash on cash: 5.2% Traditional cash on cash: 7.62% Airbnb Rental Income: $1572 Traditional Rental Income: $1490 Airbnb ROI: 5.2% Traditional ROI: 7.62%
263 Cummings Street Winona, MN Great 4 bedroom, 2 bathroom home beautiful hardwood floors throughout. The kitchen and bat...	4 beds \| 2 baths \| 1,465 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $2318 Airbnb ROI: N/A Traditional ROI: 8.1%
716 E 4th Street Winona, MN Start building your rental portfolio or settle in and make this your own. This inviting tw...	3 beds \| 2 baths \| 1,320 sq.ft.	$199,999	Airbnb cash on cash: 3.67% Traditional cash on cash: 6.81% Airbnb Rental Income: $1572 Traditional Rental Income: $1717 Airbnb ROI: 3.67% Traditional ROI: 6.81%
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: 0.49% Traditional cash on cash: 5.47% Airbnb Rental Income: $1572 Traditional Rental Income: $3098 Airbnb ROI: 0.49% Traditional ROI: 5.47%
463 Liberty Street Winona, MN Welcome to a 2-bedroom, 2-bath home offering convenient main-level living. Features includ...	2 beds \| 2 baths \| 1,238 sq.ft.	$195,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 8.9% Airbnb Rental Income: $1004 Traditional Rental Income: $2074 Airbnb ROI: 1.2% Traditional ROI: 8.9%
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%
701 Wilson Street Winona, MN Welcome to 701 Wilson Street...an architecturally-striking 3 bedroom home which features t...	3 beds \| 3 baths \| 1,561 sq.ft.	$295,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 4.41% Airbnb Rental Income: $1572 Traditional Rental Income: $1834 Airbnb ROI: 1.84% Traditional ROI: 4.41%
714 E Mark Street 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.	$218,900	Airbnb cash on cash: 2.97% Traditional cash on cash: 8.21% Airbnb Rental Income: $1572 Traditional Rental Income: $2207 Airbnb ROI: 2.97% Traditional ROI: 8.21%
358 E Wabasha (7th) Street Winona, MN STEPS TO SINCLAIR PARK and a short walking distance to downtown Winona! This charming 3+ b...	3 beds \| 2 baths \| 1,386 sq.ft.	$249,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 4.09% Airbnb Rental Income: $1572 Traditional Rental Income: $1430 Airbnb ROI: 2.79% Traditional ROI: 4.09%
1073 W King Street Winona, MN Well-planned split-level home featuring 4+ bedrooms, including 3 on the main level, plus a...	4 beds \| 2 baths \| 2,035 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $1395 Airbnb ROI: N/A Traditional ROI: 3.45%
257 Market Street Winona, MN This charming 3 bedroom, 1 bathroom home with a 1 car garage is as cute on the inside as i...	3 beds \| 1 baths \| 2,326 sq.ft.	$250,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 3.81% Airbnb Rental Income: $1572 Traditional Rental Income: $1430 Airbnb ROI: 2.5% Traditional ROI: 3.81%
104 Forest Oaks Court Winona, MN Set on 1.5 private acres at the end of a cul-de-sac across a rare double lot, this cedar-c...	4 beds \| 4 baths \| 4,785 sq.ft.	$729,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3687 Airbnb ROI: N/A Traditional ROI: 3.22%
152 E Mark Street Winona, MN Opportunity awaits with this investor special! This property is ready for your vision and ...	3 beds \| 1 baths \| 960 sq.ft.	$99,900	Airbnb cash on cash: 8.09% Traditional cash on cash: 11.27% Airbnb Rental Income: $1572 Traditional Rental Income: $1430 Airbnb ROI: 8.09% Traditional ROI: 11.27%
71 Stone Street Winona, MN Why rent when you can own your own home? 2 bedroom 1 bath with fenced in yard with some re...	3 beds \| 1 baths \| 850 sq.ft.	$114,900	Airbnb cash on cash: 7.6% Traditional cash on cash: 10.39% Airbnb Rental Income: $1572 Traditional Rental Income: $1430 Airbnb ROI: 7.6% Traditional ROI: 10.39%
1565 W King Street Winona, MN Beautifully remodeled 3-bedroom, 2-bath home thatâs truly move-in ready! This inviting p...	3 beds \| 2 baths \| 1,560 sq.ft.	$245,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 4.02% Airbnb Rental Income: $1572 Traditional Rental Income: $1430 Airbnb ROI: 2.68% Traditional ROI: 4.02%
1333 Ridgewood Dr Winona, MN Nestled in a desirable Winona neighborhood, this well-maintained 4-bedroom, 3.5-bath home ...	4 beds \| 4 baths \| 3,500 sq.ft.	$449,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.99% Airbnb Rental Income: $null Traditional Rental Income: $1395 Airbnb ROI: N/A Traditional ROI: 0.99%

Real Estate investment in Winona, MN

There are 19 properties for sale in the city of Winona . The median list price in Winona is $245,000 and the average price per square foot is $118. In April 2026, the average monthly cash on cash return in Winona is 4.00%. The average monthly rental income in Winona is $1,395.

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

There are 19 investment properties available for sale in Winona.

In 2026, 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 $1,395.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, MN

607 E 2nd Street

Winona, MN

3 beds | 1 baths | 992 sq.ft.

$159,900

Airbnb cash on cash: 5.2%

Traditional cash on cash: 7.62%

Airbnb Rental Income: $1572

Traditional Rental Income: $1490

Airbnb ROI: 5.2%

Traditional ROI: 7.62%

263 Cummings Street

Winona, MN

4 beds | 2 baths | 1,465 sq.ft.

$249,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2318

Airbnb ROI: N/A

Traditional ROI: 8.1%

716 E 4th Street

Winona, MN

3 beds | 2 baths | 1,320 sq.ft.

$199,999

Airbnb cash on cash: 3.67%

Traditional cash on cash: 6.81%

Airbnb Rental Income: $1572

Traditional Rental Income: $1717

Airbnb ROI: 3.67%

Traditional ROI: 6.81%

386 Pleasant Hill Drive

Winona, MN

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

$423,900

Airbnb cash on cash: 0.49%

Traditional cash on cash: 5.47%

Airbnb Rental Income: $1572

Traditional Rental Income: $3098

Airbnb ROI: 0.49%

Traditional ROI: 5.47%

463 Liberty Street

Winona, MN

2 beds | 2 baths | 1,238 sq.ft.

$195,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 8.9%

Airbnb Rental Income: $1004

Traditional Rental Income: $2074

Airbnb ROI: 1.2%

Traditional ROI: 8.9%

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%

701 Wilson Street

Winona, MN

3 beds | 3 baths | 1,561 sq.ft.

$295,000

Airbnb cash on cash: 1.84%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1572

Traditional Rental Income: $1834

Airbnb ROI: 1.84%

Traditional ROI: 4.41%

714 E Mark Street

Winona, MN

3 beds | 2 baths | 1,680 sq.ft.

$218,900

Airbnb cash on cash: 2.97%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $1572

Traditional Rental Income: $2207

Airbnb ROI: 2.97%