Real Estate Investment Properties for Sale in Winona, MS

Looking for investment property in Winona, MS with high ROI ?

Explore a variety of short-term homes & houses in Winona, MS. Invest wisely with VRBO & Winona, MS 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, MS

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
621 Middleton Rd Winona, MS Move-in ready and loaded with updates! This spacious 3-bedroom, 2-bath home offers approxi...	3 beds \| 2 baths \| 1,716 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.39% Airbnb Rental Income: $null Traditional Rental Income: $2459 Airbnb ROI: N/A Traditional ROI: 10.39%
810 Michelle Drive Winona, MS	3 beds \| 2 baths \| 1,600 sq.ft.	$174,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.8% Airbnb Rental Income: $null Traditional Rental Income: $2258 Airbnb ROI: N/A Traditional ROI: 10.8%
11 Rolling Green Circle Winona, MS Welcome to 11 Rolling Green Circle - this expertly crafted and well planned 3-bedroom, 2-b...	3 beds \| 2 baths \| 2,100 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.3% Airbnb Rental Income: $null Traditional Rental Income: $2341 Airbnb ROI: N/A Traditional ROI: 5.3%
322 Sawyer Road Winona, MS	4 beds \| 3 baths \| 2,900 sq.ft.	$379,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.28% Airbnb Rental Income: $null Traditional Rental Income: $3339 Airbnb ROI: N/A Traditional ROI: 7.28%
106 Hampton St Winona, MS	3 beds \| 2 baths \| 2,600 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.96% Airbnb Rental Income: $null Traditional Rental Income: $2625 Airbnb ROI: N/A Traditional ROI: 7.96%
13 fisher rd Winona, MS Country setting, acreage, and a complete 2024 renovation - 13 Fisher Road is ready for its...	3 beds \| 2 baths \| 2,388 sq.ft.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.55% Airbnb Rental Income: $null Traditional Rental Income: $2490 Airbnb ROI: N/A Traditional ROI: 6.55%
412 Church St Winona, MS Welcome to Magnolia Manor, one of Winona's premier Queen Anne Victorian homes, beautifully...	4 beds \| 3 baths \| 3,445 sq.ft.	$374,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.5% Airbnb Rental Income: $null Traditional Rental Income: $2868 Airbnb ROI: N/A Traditional ROI: 6.5%
711 Lynn Dr Winona, MS Beautifully renovated 3-bedroom, 21/2-bath home ideally located on the third hole of the W...	3 beds \| 3 baths \| 2,304 sq.ft.	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.97% Airbnb Rental Income: $null Traditional Rental Income: $2756 Airbnb ROI: N/A Traditional ROI: 5.97%
203 Fairground St Winona, MS	3 beds \| N/A baths \| 3,068 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.03% Airbnb Rental Income: $null Traditional Rental Income: $2088 Airbnb ROI: N/A Traditional ROI: 7.03%
400 church street Winona, MS Step back in time with this beautiful Victorian-style home on Church Street in Winona! Dat...	3 beds \| 3 baths \| 2,705 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.93% Airbnb Rental Income: $null Traditional Rental Income: $2852 Airbnb ROI: N/A Traditional ROI: 9.93%
94 County Road 210 Winona, MS Country Dream! This 2 bedroom/2 bathroom home is located on 21 acres with 2 ponds and 2 de...	2 beds \| 2 baths \| 1,056 sq.ft.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.41% Airbnb Rental Income: $null Traditional Rental Income: $1710 Airbnb ROI: N/A Traditional ROI: 9.41%
816 Summit Street Winona, MS 816 Summit is over an acre of serene country living smack dab in the middle of town. Tucke...	2 beds \| 1 baths \| 884 sq.ft.	$99,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.68% Airbnb Rental Income: $null Traditional Rental Income: $1356 Airbnb ROI: N/A Traditional ROI: 11.68%
104 Church Street Winona, MS Own a piece of Winona history with this beautifully maintained 1908 home located in the he...	3 beds \| 3 baths \| 3,000 sq.ft.	$319,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.53% Airbnb Rental Income: $null Traditional Rental Income: $3192 Airbnb ROI: N/A Traditional ROI: 8.53%

Real Estate investment in Winona, MS

There are 13 properties for sale in the city of Winona . The median list price in Winona is $37,000 and the average price per square foot is $16. In November 2026, the average monthly cash on cash return in Winona is 11.00%. The average monthly rental income in Winona is $2,400.

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

There are 13 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, MS

621 Middleton Rd

Winona, MS

3 beds | 2 baths | 1,716 sq.ft.

$199,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.39%

Airbnb Rental Income: $null

Traditional Rental Income: $2459

Airbnb ROI: N/A

Traditional ROI: 10.39%

810 Michelle Drive

Winona, MS

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

$174,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.8%

Airbnb Rental Income: $null

Traditional Rental Income: $2258

Airbnb ROI: N/A

Traditional ROI: 10.8%

11 Rolling Green Circle

Winona, MS

3 beds | 2 baths | 2,100 sq.ft.

$340,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2341

Airbnb ROI: N/A

Traditional ROI: 5.3%

322 Sawyer Road

Winona, MS

4 beds | 3 baths | 2,900 sq.ft.

$379,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.28%

Airbnb Rental Income: $null

Traditional Rental Income: $3339

Airbnb ROI: N/A

Traditional ROI: 7.28%

106 Hampton St

Winona, MS

3 beds | 2 baths | 2,600 sq.ft.

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2625

Airbnb ROI: N/A

Traditional ROI: 7.96%

13 fisher rd

Winona, MS

3 beds | 2 baths | 2,388 sq.ft.

$305,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2490

Airbnb ROI: N/A

Traditional ROI: 6.55%

412 Church St

Winona, MS

4 beds | 3 baths | 3,445 sq.ft.

$374,500

Airbnb cash on cash: N/A

Traditional cash on cash: 6.5%

Airbnb Rental Income: $null

Traditional Rental Income: $2868

Airbnb ROI: N/A

Traditional ROI: 6.5%

711 Lynn Dr

Winona, MS

3 beds | 3 baths | 2,304 sq.ft.

$364,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.97%

Airbnb Rental Income: $null

Traditional Rental Income: $2756

Airbnb ROI: N/A