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
16021 FM 2015 Winona, TX Nestled amidst serene surroundings, this exceptional property offers a harmonious blend of...	3 beds \| 2 baths \| 2,113 sq.ft.	$589,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 2.85% Airbnb Rental Income: $2776 Traditional Rental Income: $2673 Airbnb ROI: 1.85% Traditional ROI: 2.85%
204 Nolan Farms Winona, TX Discover this stunning 3-bedroom, 2-bathroom home, perfectly situated near Winona schools....	3 beds \| 2 baths \| 1,584 sq.ft.	$265,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 6.35% Airbnb Rental Income: $2776 Traditional Rental Income: $1995 Airbnb ROI: 6.87% Traditional ROI: 6.35%
17466 Hwy 271 Winona, TX What an incredible opportunity! This is your chance to acquire this stunning 14.242-acre e...	3 beds \| 2 baths \| 1,760 sq.ft.	$494,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.72% Airbnb Rental Income: $2776 Traditional Rental Income: $1658 Airbnb ROI: 2.72% Traditional ROI: 1.72%
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.	$244,900	Airbnb cash on cash: 6.33% Traditional cash on cash: 5.76% Airbnb Rental Income: $2776 Traditional Rental Income: $1992 Airbnb ROI: 6.33% Traditional ROI: 5.76%
210 Nolan Farms Blvd Winona, TX Welcome to this stunning 4-bedroom, 2-bathroom home, with a sleek contemporary design and ...	4 beds \| 2 baths \| 1,901 sq.ft.	$319,900	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.56% Airbnb Rental Income: $3445 Traditional Rental Income: $2418 Airbnb ROI: 5.44% Traditional ROI: 4.56%
120 Hay Meadow Winona, TX Bring all offers! New construction home! Introducing the epitome of modern living nestled ...	4 beds \| 2 baths \| 1,850 sq.ft.	$307,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 4.57% Airbnb Rental Income: $3445 Traditional Rental Income: $2279 Airbnb ROI: 5.96% Traditional ROI: 4.57%
113 Hay Meadow Winona, TX Bring all offers! New construction home! Welcome to the epitome of contemporary living in ...	4 beds \| 2 baths \| 1,840 sq.ft.	$305,500	Airbnb cash on cash: 7.1% Traditional cash on cash: 5.73% Airbnb Rental Income: $3445 Traditional Rental Income: $2289 Airbnb ROI: 7.1% Traditional ROI: 5.73%
5664 FM 757 Winona, TX OLD HOUSE TO BE SOLD AS IS CONDITION, SELLER WILL NOT FIX ANYTHING AGENTS BRING YOUR INVES...	3 beds \| 2 baths \| 1,591 sq.ft.	$330,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 4.8% Airbnb Rental Income: $2776 Traditional Rental Income: $2036 Airbnb ROI: 5.09% Traditional ROI: 4.8%
20009 SOUTHSIDE CIR Winona, TX Escape to Your Private Retreat on Howell Lake! ???? Nestled on the shores of the serene H...	2 beds \| 2 baths \| 1,491 sq.ft.	$299,995	Airbnb cash on cash: 4.03% Traditional cash on cash: 6.55% Airbnb Rental Income: $2065 Traditional Rental Income: $2245 Airbnb ROI: 4.03% Traditional ROI: 6.55%
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 Yes you can afford a brand new home! Seller offering up to $5000 in closing costs! Constru...	3 beds \| 2 baths \| 1,629 sq.ft.	$289,900	Airbnb cash on cash: 2.18% Traditional cash on cash: 1.9% Airbnb Rental Income: $2776 Traditional Rental Income: $2050 Airbnb ROI: 2.18% Traditional ROI: 1.9%
222 Nolan Farms Rd Winona, TX Bring all offers! New construction home! Welcome to your brand-new dream home in the highl...	3 beds \| 2 baths \| 1,605 sq.ft.	$280,875	Airbnb cash on cash: 6.41% Traditional cash on cash: 6.14% Airbnb Rental Income: $2776 Traditional Rental Income: $2051 Airbnb ROI: 6.41% Traditional ROI: 6.14%
16928 CR 358 Winona, TX Price improvement! Motivated Seller! Welcome to this charming 2.4-acre property that offer...	3 beds \| 2 baths \| 2,400 sq.ft.	$405,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 4.49% Airbnb Rental Income: $2776 Traditional Rental Income: $2278 Airbnb ROI: 4.09% Traditional ROI: 4.49%
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.	$365,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 1.9% Airbnb Rental Income: $2776 Traditional Rental Income: $2251 Airbnb ROI: 1.53% Traditional ROI: 1.9%
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.	$675,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.51% Airbnb Rental Income: $2776 Traditional Rental Income: $2376 Airbnb ROI: 2.11% Traditional ROI: 2.51%
16652 Caeli Heights Ct Winona, TX Nestled on 1.681 acres, this stunning Modern Farmhouse-style home offers the serenity of c...	5 beds \| 4 baths \| 3,208 sq.ft.	$689,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.55% Airbnb Rental Income: $null Traditional Rental Income: $3685 Airbnb ROI: N/A Traditional ROI: 3.55%
22732 INTERSTATE 20E Winona, TX COUNTRY LIVING AT IT'S FINEST!!! 21 ACRES (FENCED & CROSS FENCED) IS THE PERFECT SETTING F...	3 beds \| 3 baths \| 2,300 sq.ft.	$860,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.79% Airbnb Rental Income: $2776 Traditional Rental Income: $2686 Airbnb ROI: 0.09% Traditional ROI: 0.79%
308 N Kay St Winona, TX Charming Duplex with Great Potential in Winona, TX â 2/1 Per Unit This modest yet promi...	N/A beds \| 2 baths \| 1,800 sq.ft.	$239,900	Airbnb cash on cash: 6.72% Traditional cash on cash: 5.33% Airbnb Rental Income: $2776 Traditional Rental Income: $1809 Airbnb ROI: 6.72% Traditional ROI: 5.33%
19316 Spillway Rd Winona, TX SPECIAL FINANCING AVAILABLE! Stunning turnkey ranch on 40 acres with a 1 Bed 1 Bath moder...	1 beds \| 1 baths \| 1,054 sq.ft.	$875,000	Airbnb cash on cash: -2% Traditional cash on cash: -1.3% Airbnb Rental Income: $1115 Traditional Rental Income: $1304 Airbnb ROI: -2% Traditional ROI: -1.3%
14049 FM 757 Winona, TX Enjoy peaceful country living on just under 10 acres with this well-maintained 3-bedroom, ...	3 beds \| 2 baths \| 2,576 sq.ft.	$499,900	Airbnb cash on cash: 2.94% Traditional cash on cash: 3.51% Airbnb Rental Income: $2776 Traditional Rental Income: $2390 Airbnb ROI: 2.94% Traditional ROI: 3.51%
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.	$299,500	Airbnb cash on cash: 3.96% Traditional cash on cash: 4.18% Airbnb Rental Income: $2776 Traditional Rental Income: $2186 Airbnb ROI: 3.96% Traditional ROI: 4.18%
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.	$295,500	Airbnb cash on cash: 4.07% Traditional cash on cash: 4.33% Airbnb Rental Income: $2776 Traditional Rental Income: $2199 Airbnb ROI: 4.07% Traditional ROI: 4.33%
19525 FM 2767 Winona, TX Charming 2025 Modular Home on 1.15 Secluded Acres!! Located in Chapel Hill ISD, this brand...	2 beds \| 2 baths \| 832 sq.ft.	$180,000	Airbnb cash on cash: 7.18% Traditional cash on cash: 6.67% Airbnb Rental Income: $2065 Traditional Rental Income: $1445 Airbnb ROI: 7.18% Traditional ROI: 6.67%
19899 Southside Cir Winona, TX Escape to your own lakeside retreat with this charming 728 sq. ft. rustic home nestled rig...	1 beds \| 1 baths \| 728 sq.ft.	$175,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 5.59% Airbnb Rental Income: $1115 Traditional Rental Income: $1285 Airbnb ROI: 2.32% 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%

Real Estate investment in Winona, TX

There are 25 properties for sale in the city of Winona . The median list price in Winona is $307,000 and the average price per square foot is $172. In September 2025, the average monthly cash on cash return in Winona is 5.00%. The average monthly rental income in Winona is $2,212.

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

There are 25 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 $2,212.

Your search for investment property begins and ends here

Investment Property for Sale in Winona, TX

16021 FM 2015

Winona, TX

3 beds | 2 baths | 2,113 sq.ft.

$589,000

Airbnb cash on cash: 1.85%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $2776

Traditional Rental Income: $2673

Airbnb ROI: 1.85%

Traditional ROI: 2.85%

204 Nolan Farms

Winona, TX

3 beds | 2 baths | 1,584 sq.ft.

$265,000

Airbnb cash on cash: 6.87%

Traditional cash on cash: 6.35%

Airbnb Rental Income: $2776

Traditional Rental Income: $1995

Airbnb ROI: 6.87%

Traditional ROI: 6.35%

17466 Hwy 271

Winona, TX

3 beds | 2 baths | 1,760 sq.ft.

$494,900

Airbnb cash on cash: 2.72%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $2776

Traditional Rental Income: $1658

Airbnb ROI: 2.72%

Traditional ROI: 1.72%

429 GARRETT CIR

Winona, TX

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

$244,900

Airbnb cash on cash: 6.33%

Traditional cash on cash: 5.76%

Airbnb Rental Income: $2776

Traditional Rental Income: $1992

Airbnb ROI: 6.33%

Traditional ROI: 5.76%

210 Nolan Farms Blvd

Winona, TX

4 beds | 2 baths | 1,901 sq.ft.

$319,900

Airbnb cash on cash: 5.44%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $3445

Traditional Rental Income: $2418

Airbnb ROI: 5.44%

Traditional ROI: 4.56%

120 Hay Meadow

Winona, TX

4 beds | 2 baths | 1,850 sq.ft.

$307,000

Airbnb cash on cash: 5.96%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $3445

Traditional Rental Income: $2279

Airbnb ROI: 5.96%

Traditional ROI: 4.57%

113 Hay Meadow

Winona, TX

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

$305,500

Airbnb cash on cash: 7.1%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $3445

Traditional Rental Income: $2289

Airbnb ROI: 7.1%

Traditional ROI: 5.73%

5664 FM 757

Winona, TX

3 beds | 2 baths | 1,591 sq.ft.

$330,000

Airbnb cash on cash: 5.09%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $2776

Traditional Rental Income: $2036

Airbnb ROI: 5.09%