Real Estate Investment Properties for Sale in Winston, OR

Looking for investment property in Winston, OR with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
51 SW BRANTLEY Dr Winston, OR INVESTMENT PROPERTY OPPORTUNITY! Well-maintained 4-unit apartment building located in a qu...	3 beds \| 3 baths \| N/A	$485,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.67% Airbnb Rental Income: $1169 Traditional Rental Income: $3172 Airbnb ROI: -0.59% Traditional ROI: 4.67%
202 NE PLUM RIDGE Dr Winston, OR In the heart of Winston, this easy care, single level rancher is ready for your own person...	3 beds \| 2 baths \| 1,343 sq.ft.	$325,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 5.35% Airbnb Rental Income: $1169 Traditional Rental Income: $2324 Airbnb ROI: 0.32% Traditional ROI: 5.35%
71 SE RONALD St Winston, OR Charming remodeled cottage-style home situated on a large quarter acre lot offering comfor...	2 beds \| 1 baths \| 939 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.61% Airbnb Rental Income: $null Traditional Rental Income: $2153 Airbnb ROI: N/A Traditional ROI: 6.61%
263 WIL Way Winston, OR Welcome to Your Like-New Custom Home in Winston, Oregon!Step inside this beautifully craft...	3 beds \| 2 baths \| 1,928 sq.ft.	$489,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 4.89% Airbnb Rental Income: $1169 Traditional Rental Income: $3272 Airbnb ROI: -0.54% Traditional ROI: 4.89%
340 SE DARRELL Ave Winston, OR Solid 3-bedroom, single-level home with a functional layout, attached garage, and fully fe...	3 beds \| 1 baths \| 1,000 sq.ft.	$318,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.74% Airbnb Rental Income: $1169 Traditional Rental Income: $1723 Airbnb ROI: 0.61% Traditional ROI: 3.74%
102 SARAH BEAR Ln Winston, OR Meticulous quality 4 br 3 bath 2660 sq ft home, with real hard wood floors, 2 gas fireplac...	4 beds \| 3 baths \| 2,660 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $4150 Airbnb ROI: N/A Traditional ROI: 6.18%
66 NW CARY St Winston, OR Beautifully maintained 2BD/1BA residence on a generous corner lot in a convenient location...	2 beds \| 1 baths \| 1,224 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $1999 Airbnb ROI: N/A Traditional ROI: 6.41%
1068 RICE CREEK Rd Winston, OR Security gated 8.52-acre property! This beautiful ranch-style home features, updates, pave...	4 beds \| 3 baths \| 2,362 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $3489 Airbnb ROI: N/A Traditional ROI: 3.37%
150 WIL Way Winston, OR Open House 5/30 2-5 pm New Home by JW Construction Inc. This beautifully crafted 2,143 sq ...	3 beds \| 3 baths \| 1,999 sq.ft.	$499,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 6.62% Airbnb Rental Income: $1169 Traditional Rental Income: $4025 Airbnb ROI: -0.31% Traditional ROI: 6.62%
160 WIL Way Winston, OR New Home by JW Construction Inc. This beautiful one-level home offers just over 2,000 squa...	3 beds \| 3 baths \| 2,089 sq.ft.	$499,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 6.01% Airbnb Rental Income: $1169 Traditional Rental Income: $3688 Airbnb ROI: -0.2% Traditional ROI: 6.01%
90 SE DARRELL Ave Winston, OR This charming 2-bedroom, 2-bathroom manufactured home in Winston, Oregon offers comfortabl...	2 beds \| 2 baths \| 924 sq.ft.	$229,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.92% Airbnb Rental Income: $null Traditional Rental Income: $2129 Airbnb ROI: N/A Traditional ROI: 7.92%
411 WOODLAND Dr Winston, OR What if your favorite getaway was home?Set above Lookingglass Creek with stunning views of...	4 beds \| 2 baths \| 2,240 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $3477 Airbnb ROI: N/A Traditional ROI: 3.94%
624 WILLIS CREEK Rd Winston, OR This rare riverfront horse property on the South Umpqua River is not to be missed! The hom...	3 beds \| 2 baths \| 1,782 sq.ft.	$495,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 4.51% Airbnb Rental Income: $1169 Traditional Rental Income: $2817 Airbnb ROI: 0.12% Traditional ROI: 4.51%
605 DEERWOOD Ct Winston, OR This custom-built Passive Solar home, constructed in 1979, offers a rare blend of timeless...	3 beds \| 2 baths \| 2,431 sq.ft.	$524,900	Airbnb cash on cash: -0.47% Traditional cash on cash: 3.75% Airbnb Rental Income: $1169 Traditional Rental Income: $2856 Airbnb ROI: -0.47% Traditional ROI: 3.75%
1580 WINSTON SECTION Rd Winston, OR This 3-bedroom, 2-bathroom "fixer upper" sits on a peaceful 0.18-acre corner lot, offering...	3 beds \| 2 baths \| 1,188 sq.ft.	$179,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 10.73% Airbnb Rental Income: $1169 Traditional Rental Income: $2278 Airbnb ROI: 1.97% Traditional ROI: 10.73%
6700 UPPER OLALLA Rd Winston, OR Stunning custom cedar home on 5 level acres offering the perfect blend of luxury, function...	3 beds \| 3 baths \| 2,720 sq.ft.	$1,100,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 1.8% Airbnb Rental Income: $1169 Traditional Rental Income: $3535 Airbnb ROI: -0.89% Traditional ROI: 1.8%
260 SE Logan St Winston, OR *** Lower Payments Available on this House! Seller offering flexible buyer incentives with...	3 beds \| 2 baths \| 1,629 sq.ft.	$439,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.59% Airbnb Rental Income: $1169 Traditional Rental Income: $2787 Airbnb ROI: -0.27% Traditional ROI: 4.59%
311 SE GRAPE Ave Winston, OR Great investment opportunity on a spacious 0.74-acre lot! This property features a 3-bedro...	3 beds \| 1 baths \| 1,250 sq.ft.	$459,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.2% Airbnb Rental Income: $1169 Traditional Rental Income: $2333 Airbnb ROI: -0.4% Traditional ROI: 3.2%
186 WOODDUCK St Winston, OR Well-maintained home in a quiet neighborhood in the heart of Winston. Move-in ready with b...	3 beds \| 2 baths \| 1,613 sq.ft.	$375,000	Airbnb cash on cash: 0% Traditional cash on cash: 5.31% Airbnb Rental Income: $1169 Traditional Rental Income: $2656 Airbnb ROI: 0% Traditional ROI: 5.31%
2581 BROCKWAY Rd Winston, OR Open House 5/30 2-5pm New listing! This beautifully crafted new construction home offers 2...	3 beds \| 3 baths \| 2,576 sq.ft.	$499,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 6.35% Airbnb Rental Income: $1169 Traditional Rental Income: $3684 Airbnb ROI: 0.15% Traditional ROI: 6.35%

Real Estate investment in Winston, OR

There are 20 properties for sale in the city of Winston . The median list price in Winston is $317,836 and the average price per square foot is $180. In June 2026, the average monthly cash on cash return in Winston is 5.00%. The average monthly rental income in Winston is $2,817.

Winston, OR Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 20 investment properties available for sale in Winston.

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

The ROI for Short-Term is higher than the Long-Term in Winston with average rental income of $1,169.

Your search for investment property begins and ends here

Investment Property for Sale in Winston, OR

51 SW BRANTLEY Dr

Winston, OR

3 beds | 3 baths | N/A

$485,000

Airbnb cash on cash: -0.59%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $1169

Traditional Rental Income: $3172

Airbnb ROI: -0.59%

Traditional ROI: 4.67%

202 NE PLUM RIDGE Dr

Winston, OR

3 beds | 2 baths | 1,343 sq.ft.

$325,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $1169

Traditional Rental Income: $2324

Airbnb ROI: 0.32%

Traditional ROI: 5.35%

71 SE RONALD St

Winston, OR

2 beds | 1 baths | 939 sq.ft.

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2153

Airbnb ROI: N/A

Traditional ROI: 6.61%

263 WIL Way

Winston, OR

3 beds | 2 baths | 1,928 sq.ft.

$489,900

Airbnb cash on cash: -0.54%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $1169

Traditional Rental Income: $3272

Airbnb ROI: -0.54%

Traditional ROI: 4.89%

340 SE DARRELL Ave

Winston, OR

3 beds | 1 baths | 1,000 sq.ft.

$318,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $1169

Traditional Rental Income: $1723

Airbnb ROI: 0.61%

Traditional ROI: 3.74%

102 SARAH BEAR Ln

Winston, OR

4 beds | 3 baths | 2,660 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.18%

Airbnb Rental Income: $null

Traditional Rental Income: $4150

Airbnb ROI: N/A

Traditional ROI: 6.18%

66 NW CARY St

Winston, OR

2 beds | 1 baths | 1,224 sq.ft.

$245,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.41%

Airbnb Rental Income: $null

Traditional Rental Income: $1999

Airbnb ROI: N/A

Traditional ROI: 6.41%

1068 RICE CREEK Rd

Winston, OR

4 beds | 3 baths | 2,362 sq.ft.

$725,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.37%

Airbnb Rental Income: $null

Traditional Rental Income: $3489

Airbnb ROI: N/A