Real Estate Investment Properties for Sale in Winona, TX

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
17410 County Road 366 Winona, TX Priced Below Market Value! Fixer Uppers. Bring Your Horses and Enjoy Country Living on Alm...	4 beds \| 3 baths \| 4,544 sq.ft.	$309,900	Airbnb cash on cash: 5.99% Traditional cash on cash: 5.72% Airbnb Rental Income: $3445 Traditional Rental Income: $2603 Airbnb ROI: 5.99% Traditional ROI: 5.72%
429 GARRETT CIR Winona, TX LIKE-NEW HOME IN GARRETT ESTATES â LESS THAN 3 YRS YEAR OLD! Experience the best of smal...	3 beds \| 2 baths \| 1,468 sq.ft.	$243,900	Airbnb cash on cash: 6.36% Traditional cash on cash: 5.79% Airbnb Rental Income: $2776 Traditional Rental Income: $1992 Airbnb ROI: 6.36% Traditional ROI: 5.79%
113 Hay Meadow Winona, TX Stunning home in highly desirable Nolan Farms neighborhood. Walk into this beautiful home ...	4 beds \| 2 baths \| 1,840 sq.ft.	$295,500	Airbnb cash on cash: 7.37% Traditional cash on cash: 5.95% Airbnb Rental Income: $3445 Traditional Rental Income: $2289 Airbnb ROI: 7.37% Traditional ROI: 5.95%
20009 SOUTHSIDE CIR Winona, TX Escape to Your Private Retreat on Howell Lake! ???? Situated on the shores of the serene ...	2 beds \| 2 baths \| 1,491 sq.ft.	$250,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 8.03% Airbnb Rental Income: $2065 Traditional Rental Income: $2245 Airbnb ROI: 5.01% Traditional ROI: 8.03%
20009 Southside Winona, TX Welcome to your own private retreat on the shores of Howell Lake in Winona, Texas. This st...	2 beds \| 2 baths \| 1,491 sq.ft.	$250,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 8.1% Airbnb Rental Income: $2065 Traditional Rental Income: $2261 Airbnb ROI: 5.01% Traditional ROI: 8.1%
107 Rose Row Winona, TX This like-new construction by J.K. Thompson is in tip-top condition. One occupant and mos...	4 beds \| 2 baths \| 1,715 sq.ft.	$299,500	Airbnb cash on cash: 7.17% Traditional cash on cash: 5.55% Airbnb Rental Income: $3445 Traditional Rental Income: $2225 Airbnb ROI: 7.17% Traditional ROI: 5.55%
203 Toro Dr. Winona, TX Brand New Construction in Nolan Farms! Built in 2024 and never lived in, this stunning 3-...	3 beds \| 2 baths \| 1,628 sq.ft.	$284,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 1.87% Airbnb Rental Income: $2776 Traditional Rental Income: $2050 Airbnb ROI: 2.15% Traditional ROI: 1.87%
18454 County Road 3186 Winona, TX Welcome to a blend of comfort and elegance in this beautifully built 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 1,855 sq.ft.	$345,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.07% Airbnb Rental Income: $2776 Traditional Rental Income: $2251 Airbnb ROI: 1.68% Traditional ROI: 2.07%
14266 Timberidge Lane Winona, TX Come see this peaceful 1918 sf, 3 bedroom, 2 bath home sitting on 36.261 acres in Winona, ...	3 beds \| 2 baths \| 1,918 sq.ft.	$649,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 2.65% Airbnb Rental Income: $2776 Traditional Rental Income: $2376 Airbnb ROI: 2.23% Traditional ROI: 2.65%
16713 Creek Bottom Court Winona, TX Super cozy barndominium on 4.89 acres. Single-story 2BR + 2BA home with attached 2-car gar...	2 beds \| 2 baths \| 1,200 sq.ft.	$439,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 2.48% Airbnb Rental Income: $2065 Traditional Rental Income: $1741 Airbnb ROI: 1.97% Traditional ROI: 2.48%
109 Hay Meadow Winona, TX Welcome to Nolan Farmsâa postcard-worthy community where East Texas charm meets modern c...	3 beds \| 2 baths \| 1,704 sq.ft.	$268,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 4.78% Airbnb Rental Income: $2776 Traditional Rental Income: $2186 Airbnb ROI: 4.54% Traditional ROI: 4.78%
114 Hay Meadow Winona, TX Welcome to Nolan Farms, where East Texas country charm meets elevated craftsmanship just 1...	3 beds \| 2 baths \| 1,730 sq.ft.	$275,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 4.72% Airbnb Rental Income: $2776 Traditional Rental Income: $2199 Airbnb ROI: 4.44% Traditional ROI: 4.72%
19899 Southside Cir Winona, TX All furnishings convey. Escape to your own lakeside retreat with this charming 728 sq. ft....	1 beds \| 1 baths \| 728 sq.ft.	$175,000	Airbnb cash on cash: -2.21% Traditional cash on cash: 5.59% Airbnb Rental Income: $208 Traditional Rental Income: $1285 Airbnb ROI: -2.21% Traditional ROI: 5.59%
18478 CR 3186 Winona, TX This 4-bedroom, 2-bath, 2-car garage home is currently under construction and offers the p...	4 beds \| 2 baths \| 2,080 sq.ft.	$380,000	Airbnb cash on cash: 3% Traditional cash on cash: 2.04% Airbnb Rental Income: $3445 Traditional Rental Income: $2341 Airbnb ROI: 3% Traditional ROI: 2.04%
108 HAY MEADOW Winona, TX Welcome to this beautiful 4 bedroom, 2 bath home with 2-car garage, built in 2023 and thou...	4 beds \| 2 baths \| 1,606 sq.ft.	$299,900	Airbnb cash on cash: 6.29% Traditional cash on cash: 5.11% Airbnb Rental Income: $3445 Traditional Rental Income: $2350 Airbnb ROI: 6.29% Traditional ROI: 5.11%
18484 County Road 3186 Winona, TX Welcome to your brand-new home nestled just outside the city limits. This thoughtfully des...	3 beds \| 2 baths \| 1,855 sq.ft.	$345,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.11% Airbnb Rental Income: $2776 Traditional Rental Income: $2264 Airbnb ROI: 1.68% Traditional ROI: 2.11%
13240 CR 353 Winona, TX Discover this one-of-a-kind 3-bedroom, 2-bath home with a 3-car carport, perfectly set on ...	3 beds \| 2 baths \| 3,672 sq.ft.	$473,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 1.92% Airbnb Rental Income: $2776 Traditional Rental Income: $1905 Airbnb ROI: 2.41% Traditional ROI: 1.92%
11154 County Road 3116 Winona, TX Discover peace, privacy, and possibility on this beautiful 12.2 acre property. A 1988 manu...	3 beds \| 2 baths \| 1,330 sq.ft.	$239,900	Airbnb cash on cash: 6.18% Traditional cash on cash: 4.29% Airbnb Rental Income: $2776 Traditional Rental Income: $1695 Airbnb ROI: 6.18% Traditional ROI: 4.29%
7440 CR 374 Winona, TX Welcome home to Winona, TX! This 3 bedroom, 2 bath mobile home sits nestled on approximate...	3 beds \| 2 baths \| 1,568 sq.ft.	$239,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 5.43% Airbnb Rental Income: $2776 Traditional Rental Income: $1947 Airbnb ROI: 6.22% Traditional ROI: 5.43%
TBD Ridgeway Ct #3 Winona, TX TBD Ridgeway Ct #3, Winona, TX 75792 \| Other	N/A beds \| N/A baths \| N/A	$119,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 0.62% Airbnb Rental Income: $1415 Traditional Rental Income: $481 Airbnb ROI: 5.06% Traditional ROI: 0.62%
16643 Ridgeline Loop Winona, TX 16643 Ridgeline Loop, Winona, TX 75792 \| Other	N/A beds \| N/A baths \| N/A	$140,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 0.13% Airbnb Rental Income: $1415 Traditional Rental Income: $481 Airbnb ROI: 3.92% Traditional ROI: 0.13%
16416 Ridgeline Loop Winona, TX 16416 Ridgeline Loop, Winona, TX 75792 \| Other	N/A beds \| N/A baths \| N/A	$120,000	Airbnb cash on cash: 5% Traditional cash on cash: 0.6% Airbnb Rental Income: $1415 Traditional Rental Income: $481 Airbnb ROI: 5% Traditional ROI: 0.6%

Real Estate investment in Winona, TX

There are 22 properties for sale in the city of Winona . The median list price in Winona is $259,000 and the average price per square foot is $101. In January 2026, the average monthly cash on cash return in Winona is 5.00%. The average monthly rental income in Winona is $2,186.

Winona, TX 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 Short-Term is higher than the Long-Term in Winona with average rental income of $2,776.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, TX

17410 County Road 366

Winona, TX

4 beds | 3 baths | 4,544 sq.ft.

$309,900

Airbnb cash on cash: 5.99%

Traditional cash on cash: 5.72%

Airbnb Rental Income: $3445

Traditional Rental Income: $2603

Airbnb ROI: 5.99%

Traditional ROI: 5.72%

429 GARRETT CIR

Winona, TX

3 beds | 2 baths | 1,468 sq.ft.

$243,900

Airbnb cash on cash: 6.36%

Traditional cash on cash: 5.79%

Airbnb Rental Income: $2776

Traditional Rental Income: $1992

Airbnb ROI: 6.36%

Traditional ROI: 5.79%

113 Hay Meadow

Winona, TX

4 beds | 2 baths | 1,840 sq.ft.

$295,500

Airbnb cash on cash: 7.37%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $3445

Traditional Rental Income: $2289

Airbnb ROI: 7.37%

Traditional ROI: 5.95%

20009 SOUTHSIDE CIR

Winona, TX

2 beds | 2 baths | 1,491 sq.ft.

$250,000

Airbnb cash on cash: 5.01%

Traditional cash on cash: 8.03%

Airbnb Rental Income: $2065

Traditional Rental Income: $2245

Airbnb ROI: 5.01%

Traditional ROI: 8.03%

20009 Southside

Winona, TX

2 beds | 2 baths | 1,491 sq.ft.

$250,000

Airbnb cash on cash: 5.01%

Traditional cash on cash: 8.1%

Airbnb Rental Income: $2065

Traditional Rental Income: $2261

Airbnb ROI: 5.01%

Traditional ROI: 8.1%

107 Rose Row

Winona, TX

4 beds | 2 baths | 1,715 sq.ft.

$299,500

Airbnb cash on cash: 7.17%

Traditional cash on cash: 5.55%

Airbnb Rental Income: $3445

Traditional Rental Income: $2225

Airbnb ROI: 7.17%

Traditional ROI: 5.55%

203 Toro Dr.

Winona, TX

3 beds | 2 baths | 1,628 sq.ft.

$284,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $2776

Traditional Rental Income: $2050

Airbnb ROI: 2.15%

Traditional ROI: 1.87%

18454 County Road 3186

Winona, TX

3 beds | 2 baths | 1,855 sq.ft.

$345,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2776

Traditional Rental Income: $2251

Airbnb ROI: 1.68%