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
205 Whitten Street Winona, MN Charming ranch-style home on a desirable corner lot! This well-maintained property feature...	3 beds \| 2 baths \| 1,548 sq.ft.	$249,900	Airbnb cash on cash: 2.01% Traditional cash on cash: 7.02% Airbnb Rental Income: $1454 Traditional Rental Income: $2206 Airbnb ROI: 2.01% Traditional ROI: 7.02%
52 Mount Vernon Court Winona, MN Charming 3-bedroom, 3-bath home located on a quiet cul-de-sac at 52 Mount Vernon Ct in Win...	3 beds \| 3 baths \| 1,832 sq.ft.	$339,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 5.76% Airbnb Rental Income: $1454 Traditional Rental Income: $2534 Airbnb ROI: 1.03% Traditional ROI: 5.76%
659 W 4th Street Winona, MN Affordable homeownership opportunity in the heart of Winona! This 2-bedroom, 1-bath home f...	2 beds \| 1 baths \| 827 sq.ft.	$168,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 6.09% Airbnb Rental Income: $812 Traditional Rental Income: $1361 Airbnb ROI: 0.64% Traditional ROI: 6.09%
552 Hamilton Street Winona, MN This 2-bedroom, 1-bathroom home offers an easy, comfortable layout with a surprisingly ope...	2 beds \| 1 baths \| 1,048 sq.ft.	$170,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.67% Airbnb Rental Income: $812 Traditional Rental Income: $1120 Airbnb ROI: 0.77% Traditional ROI: 4.67%
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.	$635,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.56% Airbnb Rental Income: $1454 Traditional Rental Income: $3091 Airbnb ROI: 0.07% Traditional ROI: 3.56%
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.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.4% Airbnb Rental Income: $null Traditional Rental Income: $3687 Airbnb ROI: N/A Traditional ROI: 3.4%
907 E 4th Street Winona, MN Welcome to this beautiful 4-bedroom, 2 full bath home featuring a gorgeously renovated kit...	4 beds \| 2 baths \| 1,804 sq.ft.	$274,990	Airbnb cash on cash: N/A Traditional cash on cash: 6.81% Airbnb Rental Income: $null Traditional Rental Income: $2320 Airbnb ROI: N/A Traditional ROI: 6.81%
476 Main Street Winona, MN LOCATION, LOCATION, LOCATION! Long time investment property for sale right across the str...	5 beds \| N/A baths \| 1,744 sq.ft.	$255,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.79% Airbnb Rental Income: $null Traditional Rental Income: $2071 Airbnb ROI: N/A Traditional ROI: 5.79%
1308 Parkview Avenue Winona, MN This turnkey home is Cute and waiting for you to move right in -this 3-bedroom, 2-bath hom...	3 beds \| 2 baths \| 2,510 sq.ft.	$319,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 6.3% Airbnb Rental Income: $1454 Traditional Rental Income: $2544 Airbnb ROI: 1.23% Traditional ROI: 6.3%
719 Jimmy Carter Place Winona, MN Welcome to your newly renovated 3 bed, 2 full bath home with updates throughout. Improveme...	3 beds \| 2 baths \| 1,196 sq.ft.	$229,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 6.37% Airbnb Rental Income: $1454 Traditional Rental Income: $1819 Airbnb ROI: 2.69% Traditional ROI: 6.37%
1172 W 4th Street Winona, MN Move right in and enjoy this fully updated 4-bedroom, 2-bathroom home offers modern comfor...	4 beds \| 2 baths \| 1,790 sq.ft.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.03% Airbnb Rental Income: $null Traditional Rental Income: $2353 Airbnb ROI: N/A Traditional ROI: 6.03%
1319 Lakeview Avenue Winona, MN Offer accepted prior to processing	3 beds \| 2 baths \| 1,091 sq.ft.	$259,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.33% Airbnb Rental Income: $1454 Traditional Rental Income: $1893 Airbnb ROI: 1.77% Traditional ROI: 5.33%
959 W 2nd Street Winona, MN Charming and cozy 2-bedroom home offering comfortable main-level living! This well-maintai...	2 beds \| 1 baths \| 772 sq.ft.	$125,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 7.6% Airbnb Rental Income: $812 Traditional Rental Income: $1228 Airbnb ROI: 1.45% Traditional ROI: 7.6%
406 Chestnut Street Winona, MN Welcome to this cozy, move-in-ready home featuring two main-level bedrooms and a full bath...	2 beds \| 2 baths \| 780 sq.ft.	$219,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.46% Airbnb Rental Income: $812 Traditional Rental Income: $1556 Airbnb ROI: 0.31% Traditional ROI: 5.46%
24141 Homer Valley Road Winona, MN Escape to your own private retreat in the scenic bluff country of Winona, MN. This charmin...	2 beds \| 1 baths \| 2,272 sq.ft.	$499,900	Airbnb cash on cash: -0.96% Traditional cash on cash: 1.51% Airbnb Rental Income: $812 Traditional Rental Income: $1642 Airbnb ROI: -0.96% Traditional ROI: 1.51%
708 W Broadway Street Winona, MN This beautiful two-story Winona home offers a rare blend of timeless character and thought...	4 beds \| 2 baths \| 2,298 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $null Traditional Rental Income: $2576 Airbnb ROI: N/A Traditional ROI: 5.91%
78 Shady Oak Court Winona, MN GORGEOUS, SPECTACULAR, EXTRAORDINARY! Welcome to 78 Shady Oak Court. Situated in popular...	5 beds \| 4 baths \| 5,327 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.33% Airbnb Rental Income: $null Traditional Rental Income: $3897 Airbnb ROI: N/A Traditional ROI: 3.33%
398 Pleasant Hill Drive Winona, MN Welcome to this beautifully updated multi-level home in the highly desirable Knopp Valley....	4 beds \| 2 baths \| 2,453 sq.ft.	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 4% Airbnb Rental Income: $null Traditional Rental Income: $2698 Airbnb ROI: N/A Traditional ROI: 4%
407 Hiawatha Boulevard Winona, MN Comfortable one-level living with 3 bedrooms, 1 full bathroom, and a convenient main-level...	3 beds \| 1 baths \| 1,320 sq.ft.	$185,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 7.44% Airbnb Rental Income: $1454 Traditional Rental Income: $1773 Airbnb ROI: 3.17% Traditional ROI: 7.44%
258 Huff Street Winona, MN First time this unit has been offered for sale since it was built in 1984. 55+ HOA communi...	3 beds \| 2 baths \| 1,784 sq.ft.	$259,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 6.07% Airbnb Rental Income: $1454 Traditional Rental Income: $2273 Airbnb ROI: 0.97% Traditional ROI: 6.07%

Real Estate investment in Winona, MN

There are 22 properties for sale in the city of Winona . The median list price in Winona is $259,900 and the average price per square foot is $130. In May 2026, the average monthly cash on cash return in Winona is 5.00%. The average monthly rental income in Winona is $1,754.

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

There are 22 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 $1,754.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, MN

205 Whitten Street

Winona, MN

3 beds | 2 baths | 1,548 sq.ft.

$249,900

Airbnb cash on cash: 2.01%

Traditional cash on cash: 7.02%

Airbnb Rental Income: $1454

Traditional Rental Income: $2206

Airbnb ROI: 2.01%

Traditional ROI: 7.02%

52 Mount Vernon Court

Winona, MN

3 beds | 3 baths | 1,832 sq.ft.

$339,900

Airbnb cash on cash: 1.03%

Traditional cash on cash: 5.76%

Airbnb Rental Income: $1454

Traditional Rental Income: $2534

Airbnb ROI: 1.03%

Traditional ROI: 5.76%

659 W 4th Street

Winona, MN

2 beds | 1 baths | 827 sq.ft.

$168,000

Airbnb cash on cash: 0.64%

Traditional cash on cash: 6.09%

Airbnb Rental Income: $812

Traditional Rental Income: $1361

Airbnb ROI: 0.64%

Traditional ROI: 6.09%

552 Hamilton Street

Winona, MN

2 beds | 1 baths | 1,048 sq.ft.

$170,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $812

Traditional Rental Income: $1120

Airbnb ROI: 0.77%

Traditional ROI: 4.67%

24555 Highway 61

Winona, MN

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

$635,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $1454

Traditional Rental Income: $3091

Airbnb ROI: 0.07%

Traditional ROI: 3.56%

104 Forest Oaks Court

Winona, MN

4 beds | 4 baths | 4,785 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.4%

Airbnb Rental Income: $null

Traditional Rental Income: $3687

Airbnb ROI: N/A

Traditional ROI: 3.4%

907 E 4th Street

Winona, MN

4 beds | 2 baths | 1,804 sq.ft.

$274,990

Airbnb cash on cash: N/A

Traditional cash on cash: 6.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2320

Airbnb ROI: N/A

Traditional ROI: 6.81%

476 Main Street

Winona, MN

5 beds | N/A baths | 1,744 sq.ft.

$255,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.79%

Airbnb Rental Income: $null

Traditional Rental Income: $2071

Airbnb ROI: N/A