Real Estate Investment Properties for Sale in Winslow, AR

Looking for investment property in Winslow, AR with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
21701 Mount Gaylor Winslow, AR Timeless charm and modern ease. This remarkable 69-acre, two-home property, just 30 mins f...	3 beds \| 3 baths \| 4,447 sq.ft.	$1,255,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.05% Airbnb Rental Income: $null Traditional Rental Income: $2561 Airbnb ROI: N/A Traditional ROI: 1.05%
22647 N Highway 71 Winslow, AR Beautiful historic fully remodeled cottage, nestled in the middle of the Boston Mountains....	3 beds \| 2 baths \| 1,920 sq.ft.	$344,800	Airbnb cash on cash: N/A Traditional cash on cash: 4.57% Airbnb Rental Income: $null Traditional Rental Income: $1985 Airbnb ROI: N/A Traditional ROI: 4.57%
21588 S Highway 71 Winslow, AR Turnkey mountain retreat just 24 miles from Fayetteville! Fully renovated and beautifully ...	3 beds \| 2 baths \| 2,920 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $2291 Airbnb ROI: N/A Traditional ROI: 3.43%
10347 Devils Den Road Winslow, AR Experience the perfect blend of privacy and convenience on these 2 parcels totaling 46.5 a...	2 beds \| 1 baths \| 896 sq.ft.	$375,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 2.17% Airbnb Rental Income: $1274 Traditional Rental Income: $1223 Airbnb ROI: 1.18% Traditional ROI: 2.17%
16712 S Highway 71 Winslow, AR Flexible-use fixer on 2.38 acres in Brentwood on the Boston Mountain Scenic Loop. Bones ar...	3 beds \| 2 baths \| 1,856 sq.ft.	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.84% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 5.84%
610 Blueberry Hill Road Winslow, AR This fixer-upper offers an opportunity for your ideal retreat on 4 peaceful acres with eas...	3 beds \| 2 baths \| 1,624 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $1701 Airbnb ROI: N/A Traditional ROI: 4.72%
20845 S Highway 71 Winslow, AR Welcome to this charming 817 sqft home that offers a warm rustic feel with all the comfort...	1 beds \| 1 baths \| 817 sq.ft.	$165,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 7.56% Airbnb Rental Income: $447 Traditional Rental Income: $1455 Airbnb ROI: -0.52% Traditional ROI: 7.56%
17300 Bethlehem Road Winslow, AR Cozy 1586 SF home on 40.66 acres with awesome views! The home sits well back off the road ...	3 beds \| 1 baths \| 1,586 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.41% Airbnb Rental Income: $null Traditional Rental Income: $1459 Airbnb ROI: N/A Traditional ROI: 1.41%
660 Highway 71 Winslow, AR Discover the best of both worlds with this unique 2,034+/- sq ft home on 2.73+/- acres, of...	3 beds \| 2 baths \| 2,034 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.63% Airbnb Rental Income: $null Traditional Rental Income: $2060 Airbnb ROI: N/A Traditional ROI: 6.63%
16902 Bethlehem Road Winslow, AR Your own pond, creek and waterfall with mini-farm country living and the convenience of ev...	5 beds \| 3 baths \| 3,397 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.97% Airbnb Rental Income: $null Traditional Rental Income: $2856 Airbnb ROI: N/A Traditional ROI: 3.97%
10557 Devils Den Winslow, AR Log cabin home situated on 40 beautiful acres with shop and barn. This private property of...	3 beds \| 2 baths \| 1,800 sq.ft.	$667,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $1776 Airbnb ROI: N/A Traditional ROI: 1.4%
11482 Abilene Road Winslow, AR Scenic estate on 21 acres at one of the highest elevations in Washington County at 1920 fe...	4 beds \| 3 baths \| 3,072 sq.ft.	$890,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.44% Airbnb Rental Income: $null Traditional Rental Income: $3055 Airbnb ROI: N/A Traditional ROI: 2.44%
16783 Carpenter Road Winslow, AR Escape to the peace and privacy of country living on just over 10 picturesque acres. As yo...	5 beds \| 4 baths \| 3,089 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $3036 Airbnb ROI: N/A Traditional ROI: 3.85%
21588 (1.50 AC) S Highway 71 Winslow, AR Escape to the beauty of Winslow with gorgeous views! This totally remodeled property featu...	3 beds \| 2 baths \| 2,920 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $2298 Airbnb ROI: N/A Traditional ROI: 4.22%
16940 Highway 71 Winslow, AR Absolutely gorgeous views of the Ozark Mountains, this 21 acre property offers a 2,550 sqf...	3 beds \| 2 baths \| 2,553 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.83% Airbnb Rental Income: $null Traditional Rental Income: $2097 Airbnb ROI: N/A Traditional ROI: 1.83%
14497 Mountain Road Winslow, AR Welcome to your private Ozark retreat in Winslow, nestled in the scenic Boston Mountains j...	3 beds \| 3 baths \| 1,570 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $1626 Airbnb ROI: N/A Traditional ROI: 4.25%
21787 Carter Road Winslow, AR Tucked away in the scenic hills of Winslow, this beautifully maintained home sits on 10 pr...	2 beds \| 2 baths \| 1,982 sq.ft.	$349,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.14% Airbnb Rental Income: $1274 Traditional Rental Income: $1871 Airbnb ROI: 1.11% Traditional ROI: 4.14%

Real Estate investment in Winslow, AR

There are 17 properties for sale in the city of Winslow . The median list price in Winslow is $199,999 and the average price per square foot is $133. In May 2026, the average monthly cash on cash return in Winslow is 4.00%. The average monthly rental income in Winslow is $2,002.

Winslow, AR Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 17 investment properties available for sale in Winslow.

In 2026, the best neighborhood to buy investment property is Winslow.

The ROI for Long-Term is higher than the Short-Term in Winslow with average rental income of $2,002.

Your search for investment property begins and ends here

Investment Property for Sale in Winslow, AR

21701 Mount Gaylor

Winslow, AR

3 beds | 3 baths | 4,447 sq.ft.

$1,255,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2561

Airbnb ROI: N/A

Traditional ROI: 1.05%

22647 N Highway 71

Winslow, AR

3 beds | 2 baths | 1,920 sq.ft.

$344,800

Airbnb cash on cash: N/A

Traditional cash on cash: 4.57%

Airbnb Rental Income: $null

Traditional Rental Income: $1985

Airbnb ROI: N/A

Traditional ROI: 4.57%

21588 S Highway 71

Winslow, AR

3 beds | 2 baths | 2,920 sq.ft.

$469,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2291

Airbnb ROI: N/A

Traditional ROI: 3.43%

10347 Devils Den Road

Winslow, AR

2 beds | 1 baths | 896 sq.ft.

$375,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1274

Traditional Rental Income: $1223

Airbnb ROI: 1.18%

Traditional ROI: 2.17%

16712 S Highway 71

Winslow, AR

3 beds | 2 baths | 1,856 sq.ft.

$280,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2002

Airbnb ROI: N/A

Traditional ROI: 5.84%

610 Blueberry Hill Road

Winslow, AR

3 beds | 2 baths | 1,624 sq.ft.

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.72%

Airbnb Rental Income: $null

Traditional Rental Income: $1701

Airbnb ROI: N/A

Traditional ROI: 4.72%

20845 S Highway 71

Winslow, AR

1 beds | 1 baths | 817 sq.ft.

$165,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 7.56%

Airbnb Rental Income: $447

Traditional Rental Income: $1455

Airbnb ROI: -0.52%

Traditional ROI: 7.56%

17300 Bethlehem Road

Winslow, AR

3 beds | 1 baths | 1,586 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.41%

Airbnb Rental Income: $null

Traditional Rental Income: $1459

Airbnb ROI: N/A