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
235 SE LEBLEU LN Winston, OR Situated in a Winston neighborhood, this welcoming three-bedroom home offers a practical a...	3 beds \| 3 baths \| 1,743 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.39% Airbnb Rental Income: $null Traditional Rental Income: $3447 Airbnb ROI: N/A Traditional ROI: 8.39%
1260 IRELAND RD Winston, OR Exceptional property located in Winston OR. This 10.02 acre is private and tucked back of...	3 beds \| 2 baths \| N/A	$865,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $4018 Airbnb ROI: N/A Traditional ROI: 2.91%
149 TERESA LN Winston, OR Adorable newer home situated on a quiet street in Winston with mountain views. This home f...	3 beds \| 3 baths \| 1,250 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.31% Airbnb Rental Income: $null Traditional Rental Income: $3125 Airbnb ROI: N/A Traditional ROI: 7.31%
1800 E WILLIS CREEK RD Winston, OR Discover your dream retreat on 274 acres of land with this charming 2-bedroom, 1-bath home...	2 beds \| 1 baths \| 1,080 sq.ft.	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.88% Airbnb Rental Income: $null Traditional Rental Income: $1832 Airbnb ROI: N/A Traditional ROI: 0.88%
315 DEGNATH GATEWAY LN Winston, OR Serene and picturesque 6.6 acre parcel with stunning panoramic views of the mountains and ...	2 beds \| 2 baths \| 972 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.24% Airbnb Rental Income: $null Traditional Rental Income: $2525 Airbnb ROI: N/A Traditional ROI: 11.24%
441 NW SUSAN AVE Winston, OR Nice 3 bed home on a corner lot with a picket fence. Separate storage shed, garage convert...	3 beds \| 1 baths \| 1,005 sq.ft.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $1925 Airbnb ROI: N/A Traditional ROI: 4.66%
411 NW WOODLAND DR Winston, OR End of road privacy in a quiet setting, this great two-story ranch-style home offers an un...	4 beds \| 2 baths \| 2,240 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $3485 Airbnb ROI: N/A Traditional ROI: 3.19%
145 SE LEBLEU LN Winston, OR Experience modern elegance in this beautifully designed contemporary home in the sought-af...	4 beds \| 3 baths \| 2,006 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.82% Airbnb Rental Income: $null Traditional Rental Income: $4030 Airbnb ROI: N/A Traditional ROI: 7.82%
127 NW TEAL ST Winston, OR Welcome to Your Dream Home!Nestled in the heart of Winston, Oregon, this stunning 4-bedr...	4 beds \| 2 baths \| 1,830 sq.ft.	$449,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.94% Airbnb Rental Income: $null Traditional Rental Income: $2959 Airbnb ROI: N/A Traditional ROI: 4.94%
241 TIMOTHY AVE Winston, OR Looking for a home that combines space, functionality, and convenience? This generously si...	3 beds \| 2 baths \| 1,728 sq.ft.	$314,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.19% Airbnb Rental Income: $null Traditional Rental Income: $2800 Airbnb ROI: N/A Traditional ROI: 7.19%
2651 NW BROCKWAY RD Winston, OR This lovely home offers breathtaking views of the mountains, valley, and Abacela Vineyard,...	3 beds \| 3 baths \| 1,980 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.05% Airbnb Rental Income: $null Traditional Rental Income: $3729 Airbnb ROI: N/A Traditional ROI: 8.05%

Real Estate investment in Winston, OR

There are 11 properties for sale in the city of Winston . The median list price in Winston is $364,900 and the average price per square foot is $234. In January 2025, the average monthly cash on cash return in Winston is 7.00%. The average monthly rental income in Winston is $3,042.

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

There are 11 investment properties available for sale in Winston.

In 2025, 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Winston, OR

235 SE LEBLEU LN

Winston, OR

3 beds | 3 baths | 1,743 sq.ft.

$349,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.39%

Airbnb Rental Income: $null

Traditional Rental Income: $3447

Airbnb ROI: N/A

Traditional ROI: 8.39%

1260 IRELAND RD

Winston, OR

3 beds | 2 baths | N/A

$865,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.91%

Airbnb Rental Income: $null

Traditional Rental Income: $4018

Airbnb ROI: N/A

Traditional ROI: 2.91%

149 TERESA LN

Winston, OR

3 beds | 3 baths | 1,250 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.31%

Airbnb Rental Income: $null

Traditional Rental Income: $3125

Airbnb ROI: N/A

Traditional ROI: 7.31%

1800 E WILLIS CREEK RD

Winston, OR

2 beds | 1 baths | 1,080 sq.ft.

$895,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.88%

Airbnb Rental Income: $null

Traditional Rental Income: $1832

Airbnb ROI: N/A

Traditional ROI: 0.88%

315 DEGNATH GATEWAY LN

Winston, OR

2 beds | 2 baths | 972 sq.ft.

$199,900

Airbnb cash on cash: N/A

Traditional cash on cash: 11.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2525

Airbnb ROI: N/A

Traditional ROI: 11.24%

441 NW SUSAN AVE

Winston, OR

3 beds | 1 baths | 1,005 sq.ft.

$305,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.66%

Airbnb Rental Income: $null

Traditional Rental Income: $1925

Airbnb ROI: N/A

Traditional ROI: 4.66%

411 NW WOODLAND DR

Winston, OR

4 beds | 2 baths | 2,240 sq.ft.

$825,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.19%

Airbnb Rental Income: $null

Traditional Rental Income: $3485

Airbnb ROI: N/A

Traditional ROI: 3.19%

145 SE LEBLEU LN

Winston, OR

4 beds | 3 baths | 2,006 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.82%

Airbnb Rental Income: $null

Traditional Rental Income: $4030

Airbnb ROI: N/A