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 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.	$430,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 5.38% Airbnb Rental Income: $1746 Traditional Rental Income: $3098 Airbnb ROI: 0.83% Traditional ROI: 5.38%
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.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2956 Airbnb ROI: N/A Traditional ROI: 5.4%
628 Main St Winona, MN Charming Character Meets Modern Living â Steps from Winonaâs Best! Welcome to this be...	4 beds \| 4 baths \| 2,562 sq.ft.	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.78% Airbnb Rental Income: $null Traditional Rental Income: $2937 Airbnb ROI: N/A Traditional ROI: 6.78%
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: 4.13% Traditional cash on cash: 7.64% Airbnb Rental Income: $1746 Traditional Rental Income: $1950 Airbnb ROI: 4.13% Traditional ROI: 7.64%
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: 3.94% Traditional cash on cash: 8.57% Airbnb Rental Income: $1746 Traditional Rental Income: $2228 Airbnb ROI: 3.94% Traditional ROI: 8.57%
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.	$179,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.09% Airbnb Rental Income: $null Traditional Rental Income: $1817 Airbnb ROI: N/A Traditional ROI: 8.09%
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: 0.57% Traditional cash on cash: 3.83% Airbnb Rental Income: $1746 Traditional Rental Income: $3091 Airbnb ROI: 0.57% Traditional ROI: 3.83%
826 E 5th Street Winona, MN Welcome to this cute & cozy two-bedroom, two-bath home that that is completely move in rea...	2 beds \| 2 baths \| 1,564 sq.ft.	$189,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 8.9% Airbnb Rental Income: $2025 Traditional Rental Income: $1998 Airbnb ROI: 6.12% Traditional ROI: 8.9%
1376 Skyline Drive Winona, MN Welcome to this spacious 4-bedroom, 3-bath home that offers both comfort and room to grow....	4 beds \| 3 baths \| 2,175 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $2791 Airbnb ROI: N/A Traditional ROI: 5.29%
519 Chestnut Street Winona, MN Donât miss your opportunity to own a piece of timeless beauty with this charming 3 bedro...	3 beds \| 1 baths \| 1,872 sq.ft.	$209,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 6.34% Airbnb Rental Income: $1746 Traditional Rental Income: $1719 Airbnb ROI: 4.05% Traditional ROI: 6.34%
204 Harvester Avenue Winona, MN This beautifully renovated home offers comfortable main floor living with a host of modern...	2 beds \| 1 baths \| 788 sq.ft.	$194,900	Airbnb cash on cash: 5.87% Traditional cash on cash: 5.1% Airbnb Rental Income: $2025 Traditional Rental Income: $1355 Airbnb ROI: 5.87% Traditional ROI: 5.1%
1176 W 4th Street Winona, MN Discover comfort and convenience in this beautifully renovated 3-bedroom, 1-bathroom home,...	3 beds \| 1 baths \| 1,304 sq.ft.	$220,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 6.37% Airbnb Rental Income: $1746 Traditional Rental Income: $1694 Airbnb ROI: 4.32% Traditional ROI: 6.37%
207 E Sanborn Street Winona, MN Welcome to 207 E 8th St, a well-maintained 5-bedroom, 2-bath certified rental situated in ...	5 beds \| 2 baths \| 2,028 sq.ft.	$220,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.94% Airbnb Rental Income: $null Traditional Rental Income: $2611 Airbnb ROI: N/A Traditional ROI: 9.94%
473 Chatfield Street Winona, MN This charming five-bedroom, one-bath home is rich with character, boasting original woodwo...	5 beds \| 1 baths \| 1,827 sq.ft.	$219,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.63% Airbnb Rental Income: $null Traditional Rental Income: $1857 Airbnb ROI: N/A Traditional ROI: 6.63%

Real Estate investment in Winona, MN

There are 24 properties for sale in the city of Winona . The median list price in Winona is $220,000 and the average price per square foot is $107. In October 2025, the average monthly cash on cash return in Winona is 7.00%. The average monthly rental income in Winona is $2,228.

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

There are 24 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 $2,228.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, MN

386 Pleasant Hill Drive

Winona, MN

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

$430,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $1746

Traditional Rental Income: $3098

Airbnb ROI: 0.83%

Traditional ROI: 5.38%

8830 E 8th Street

Winona, MN

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

$435,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.4%

Airbnb Rental Income: $null

Traditional Rental Income: $2956

Airbnb ROI: N/A

Traditional ROI: 5.4%

628 Main St

Winona, MN

4 beds | 4 baths | 2,562 sq.ft.

$364,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.78%

Airbnb Rental Income: $null

Traditional Rental Income: $2937

Airbnb ROI: N/A

Traditional ROI: 6.78%

1008 W 2nd Street

Winona, MN

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

$204,900

Airbnb cash on cash: 4.13%

Traditional cash on cash: 7.64%

Airbnb Rental Income: $1746

Traditional Rental Income: $1950

Airbnb ROI: 4.13%

Traditional ROI: 7.64%

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: 3.94%

Traditional cash on cash: 8.57%

Airbnb Rental Income: $1746

Traditional Rental Income: $2228

Airbnb ROI: 3.94%

Traditional ROI: 8.57%

706 W Broadway Street

Winona, MN

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

4 beds | 1 baths | 1,640 sq.ft.

$179,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.09%

Airbnb Rental Income: $null

Traditional Rental Income: $1817

Airbnb ROI: N/A