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
117 Shirley Avenue Winona, MS	3 beds \| 2 baths \| 1,542 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.19% Airbnb Rental Income: $null Traditional Rental Income: $2440 Airbnb ROI: N/A Traditional ROI: 11.19%
113 Shirley Avenue Winona, MS	3 beds \| 2 baths \| 1,193 sq.ft.	$147,500	Airbnb cash on cash: N/A Traditional cash on cash: 11.65% Airbnb Rental Income: $null Traditional Rental Income: $1966 Airbnb ROI: N/A Traditional ROI: 11.65%
205 Shirley Ave Winona, MS Step into timeless charm and modern comfort with this beautifully updated 4-bedroom, 3-bat...	4 beds \| 3 baths \| 2,600 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.67% Airbnb Rental Income: $null Traditional Rental Income: $3284 Airbnb ROI: N/A Traditional ROI: 9.67%
Investment Properties for Sale in Other Cities of Mississippi
299 Wood Dale Drive Jackson , MS This updated, move-in ready charmer is a must-see! Located in the heart of the city on a g...	4 beds \| 3 baths \| 3,291 sq.ft.	$445,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.79% Airbnb Rental Income: $1500 Traditional Rental Income: $2830 Airbnb ROI: 0.55% Traditional ROI: 4.79%
4650 Manila Drive Jackson , MS Welcome to this beautiful home with the perfect mix of original character and modern updat...	4 beds \| 2 baths \| 1,732 sq.ft.	$169,000	Airbnb cash on cash: 5.58% Traditional cash on cash: 10.1% Airbnb Rental Income: $1718 Traditional Rental Income: $1972 Airbnb ROI: 5.58% Traditional ROI: 10.1%
214 River Place Jackson , MS FRESHLY PAINTED 3 BR/2 BA Condo in Northeast Jackson offers a flexible split floor plan wi...	3 beds \| 2 baths \| 1,400 sq.ft.	$151,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 8.17% Airbnb Rental Income: $1838 Traditional Rental Income: $1692 Airbnb ROI: 5.75% Traditional ROI: 8.17%
2230 Ridgewood Drive Laurel , MS Nestled near the heart of charming downtown Laurel, MS, this exquisite 5-bedroom, 3-full b...	5 beds \| 6 baths \| 4,748 sq.ft.	$673,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 7.36% Airbnb Rental Income: $2365 Traditional Rental Income: $5848 Airbnb ROI: 0.89% Traditional ROI: 7.36%
159 Acadian Cr. Tupelo , MS 4/3 in Acadian Village with brand new roof!All brick exterior, with beautiful landscaping....	4 beds \| 3 baths \| 3,510 sq.ft.	$440,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.33% Airbnb Rental Income: $1565 Traditional Rental Income: $2192 Airbnb ROI: 0.72% Traditional ROI: 3.33%
109 Hampton Chase Madison , MS Lake Caroline beauty!!Beautifully maintained 3BR/2BA home with NEW flooring, whole-house g...	3 beds \| 2 baths \| 2,079 sq.ft.	$325,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 4.82% Airbnb Rental Income: $1024 Traditional Rental Income: $2089 Airbnb ROI: 0.16% Traditional ROI: 4.82%
2001 Claudette Court Biloxi , MS This stunning 4-bedroom, 4.5-bathroom home in the desirable Bent Oaks subdivision offers a...	4 beds \| 5 baths \| 4,929 sq.ft.	$1,100,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.43% Airbnb Rental Income: $1608 Traditional Rental Income: $5235 Airbnb ROI: -0.56% Traditional ROI: 3.43%
203 Nash Circle Oxford , MS This spacious upgraded home at The Villages of Oxford features 4 bedrooms and 2.5 bathroom...	4 beds \| 3 baths \| 2,519 sq.ft.	$459,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.89% Airbnb Rental Income: $1605 Traditional Rental Income: $2539 Airbnb ROI: 0.65% Traditional ROI: 3.89%
1300 Beanland Oxford , MS Take a look at this location and consider the potential. This mid century house is locate...	4 beds \| 4 baths \| 3,409 sq.ft.	$1,250,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.35% Airbnb Rental Income: $1605 Traditional Rental Income: $3762 Airbnb ROI: -0.9% Traditional ROI: 1.35%

Real Estate investment in Winona, MS

There are 3 properties for sale in the city of Winona . The median list price in Winona is $140,000 and the average price per square foot is $82. In October 2025, the average monthly cash on cash return in Winona is 15.00%. The average monthly rental income in Winona is $2,371.

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

There are 3 investment properties available for sale in 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

117 Shirley Avenue

Winona, MS

3 beds | 2 baths | 1,542 sq.ft.

$185,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2440

Airbnb ROI: N/A

Traditional ROI: 11.19%

113 Shirley Avenue

Winona, MS

3 beds | 2 baths | 1,193 sq.ft.

$147,500

Airbnb cash on cash: N/A

Traditional cash on cash: 11.65%

Airbnb Rental Income: $null

Traditional Rental Income: $1966

Airbnb ROI: N/A

Traditional ROI: 11.65%

205 Shirley Ave

Winona, MS

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

$289,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.67%

Airbnb Rental Income: $null

Traditional Rental Income: $3284

Airbnb ROI: N/A

Traditional ROI: 9.67%

Investment Properties for Sale in Other Cities of Mississippi

Jackson , MS

4 beds | 3 baths | 3,291 sq.ft.

$445,000

Airbnb cash on cash: 0.55%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $1500

Traditional Rental Income: $2830

Airbnb ROI: 0.55%

Traditional ROI: 4.79%

Jackson , MS

4 beds | 2 baths | 1,732 sq.ft.

$169,000

Airbnb cash on cash: 5.58%

Traditional cash on cash: 10.1%

Airbnb Rental Income: $1718

Traditional Rental Income: $1972

Airbnb ROI: 5.58%

Traditional ROI: 10.1%

Jackson , MS

3 beds | 2 baths | 1,400 sq.ft.

$151,000

Airbnb cash on cash: 5.75%

Traditional cash on cash: 8.17%

Airbnb Rental Income: $1838

Traditional Rental Income: $1692

Airbnb ROI: 5.75%

Traditional ROI: 8.17%

Laurel , MS

5 beds | 6 baths | 4,748 sq.ft.

$673,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 7.36%

Airbnb Rental Income: $2365

Traditional Rental Income: $5848

Airbnb ROI: 0.89%

Traditional ROI: 7.36%

Tupelo , MS

4 beds | 3 baths | 3,510 sq.ft.

$440,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $1565

Traditional Rental Income: $2192

Airbnb ROI: 0.72%

Traditional ROI: 3.33%

Madison , MS

3 beds | 2 baths | 2,079 sq.ft.

$325,000