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
15459 Whitehouse Rd Winslow, AR New Roof. Located in the Boston mountains of the Ozarks, Heart Stone Castle has been an in...	4 beds \| 2 baths \| 3,774 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $2604 Airbnb ROI: N/A Traditional ROI: 2.67%
21701 Mount Gaylor Winslow, AR Panoramic mountaintop views! This remarkable 69-acre, two-home property, just 30 mins from...	3 beds \| 3 baths \| 4,447 sq.ft.	$1,375,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.87% Airbnb Rental Income: $null Traditional Rental Income: $2561 Airbnb ROI: N/A Traditional ROI: 0.87%
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.	$364,800	Airbnb cash on cash: N/A Traditional cash on cash: 3.91% Airbnb Rental Income: $null Traditional Rental Income: $1985 Airbnb ROI: N/A Traditional ROI: 3.91%
16325 Sunset (wc 38) Rd Winslow, AR AMAZING RARE OPPORTUNITY! 2 houses+private inground saltwater pool+20x50 Metal Shop+ponds+...	4 beds \| 3 baths \| 4,385 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $3447 Airbnb ROI: N/A Traditional ROI: 2.16%
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.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2291 Airbnb ROI: N/A Traditional ROI: 3.38%
10347 Devils Den Rd 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: 0.18% Traditional cash on cash: 1.59% Airbnb Rental Income: $1099 Traditional Rental Income: $1223 Airbnb ROI: 0.18% Traditional ROI: 1.59%
16712 S Highway 71 Winslow, AR Flexible-use fixer on 2.38 acres in Brentwood. Bones are good on this all-brick ranch, one...	3 beds \| 1 baths \| 1,856 sq.ft.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.96% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 5.96%
610 Blueberry Hill Rd Winslow, AR Fixer Upper home offers potential for investors or DIY buyers. Older house, some newer fea...	3 beds \| 1 baths \| 1,624 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.88% Airbnb Rental Income: $null Traditional Rental Income: $1701 Airbnb ROI: N/A Traditional ROI: 4.88%
17300 Bethlehem Rd Winslow, AR This beautifully updated 3 bedroom, 1 bathroom home sits on an expansive 40-acre dream pro...	3 beds \| 1 baths \| 1,586 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.35% Airbnb Rental Income: $null Traditional Rental Income: $1459 Airbnb ROI: N/A Traditional ROI: 1.35%
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: 6.11% Airbnb Rental Income: $null Traditional Rental Income: $2060 Airbnb ROI: N/A Traditional ROI: 6.11%
22439 Carter (wc 147) Ln Winslow, AR If you like the warm glow of Brazilian wood floors, hand crafted doors and wood work, a sl...	2 beds \| 1 baths \| 1,887 sq.ft.	$288,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 5.2% Airbnb Rental Income: $1099 Traditional Rental Income: $1943 Airbnb ROI: 0.72% Traditional ROI: 5.2%

Real Estate investment in Winslow, AR

There are 16 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 $132. In February 2026, the average monthly cash on cash return in Winslow is 3.00%. The average monthly rental income in Winslow is $2,002.

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

There are 16 investment properties available for sale in Winslow.

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

The ROI for Short-Term is higher than the Long-Term in Winslow with average rental income of $1,099.

Your search for investment property begins and ends here

Investment Property for Sale in Winslow, AR

15459 Whitehouse Rd

Winslow, AR

4 beds | 2 baths | 3,774 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2604

Airbnb ROI: N/A

Traditional ROI: 2.67%

21701 Mount Gaylor

Winslow, AR

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

$1,375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2561

Airbnb ROI: N/A

Traditional ROI: 0.87%

22647 N Highway 71

Winslow, AR

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

$364,800

Airbnb cash on cash: N/A

Traditional cash on cash: 3.91%

Airbnb Rental Income: $null

Traditional Rental Income: $1985

Airbnb ROI: N/A

Traditional ROI: 3.91%

16325 Sunset (wc 38) Rd

Winslow, AR

4 beds | 3 baths | 4,385 sq.ft.

$1,100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3447

Airbnb ROI: N/A

Traditional ROI: 2.16%

21588 S Highway 71

Winslow, AR

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

$475,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2291

Airbnb ROI: N/A

Traditional ROI: 3.38%

10347 Devils Den Rd

Winslow, AR

2 beds | 1 baths | 896 sq.ft.

$375,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 1.59%

Airbnb Rental Income: $1099

Traditional Rental Income: $1223

Airbnb ROI: 0.18%

Traditional ROI: 1.59%

16712 S Highway 71

Winslow, AR

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

$290,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2002

Airbnb ROI: N/A

Traditional ROI: 5.96%

610 Blueberry Hill Rd

Winslow, AR

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

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.88%

Airbnb Rental Income: $null

Traditional Rental Income: $1701

Airbnb ROI: N/A