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

separator

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.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.15% Airbnb Rental Income: $null Traditional Rental Income: $3447 Airbnb ROI: N/A Traditional ROI: 8.15%
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 \| 2,600 sq.ft.	$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%
1470 E WILLIS CREEK RD Winston, OR CITY WATER CONNECTED. True paradise! Peaceful enjoyment on this private, secluded acreage....	3 beds \| 3 baths \| 1,845 sq.ft.	$784,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $3379 Airbnb ROI: N/A Traditional ROI: 3.25%
1220 DEGNATH GATEWAY LN Winston, OR This is a stunning 80-acre rural property boasting unparalleled privacy and breathtaking v...	3 beds \| 2 baths \| 1,188 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.08% Airbnb Rental Income: $null Traditional Rental Income: $2769 Airbnb ROI: N/A Traditional ROI: 4.08%
211 NW PLUM AVE Winston, OR One level 3 bedroom 2 bath Winston home, slightly oversized lot at the end of a cul-de-sac...	3 beds \| 2 baths \| 1,704 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.02% Airbnb Rental Income: $null Traditional Rental Income: $3504 Airbnb ROI: N/A Traditional ROI: 8.02%
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%
149 WOODDUCK ST Winston, OR Beautiful one level 3B/2BA 1684 SF Home w/Bonus Room in desirable neighborhood. Updated St...	3 beds \| 2 baths \| 1,684 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.78% Airbnb Rental Income: $null Traditional Rental Income: $3387 Airbnb ROI: N/A Traditional ROI: 7.78%
780 BUSHNELL DR Winston, OR State of property is a "fixer upper". There is plenty of space, has 2 stories with loft. H...	1 beds \| 1 baths \| 2,000 sq.ft.	$194,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $1915 Airbnb ROI: N/A Traditional ROI: 8.1%
271 NW Sherry St Winston, OR Welcome to 271 NW Sherry St., a delightful home located in the charming town of Winston, O...	3 beds \| 1 baths \| 1,260 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.85% Airbnb Rental Income: $null Traditional Rental Income: $2458 Airbnb ROI: N/A Traditional ROI: 6.85%
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: 8.71% Airbnb Rental Income: $null Traditional Rental Income: $4030 Airbnb ROI: N/A Traditional ROI: 8.71%

Real Estate investment in Winston, OR

There are 14 properties for sale in the city of Winston . The median list price in Winston is $360,000 and the average price per square foot is $226. In November 2024, the average monthly cash on cash return in Winston is 7.00%. The average monthly rental income in Winston is $3,125.

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

There are 14 investment properties available for sale in Winston.

In 2024, 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.

$359,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.15%

Airbnb Rental Income: $null

Traditional Rental Income: $3447

Airbnb ROI: N/A

Traditional ROI: 8.15%

1260 IRELAND RD

Winston, OR

3 beds | 2 baths | 2,600 sq.ft.

$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%

1470 E WILLIS CREEK RD

Winston, OR

3 beds | 3 baths | 1,845 sq.ft.

$784,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.25%

Airbnb Rental Income: $null

Traditional Rental Income: $3379

Airbnb ROI: N/A

Traditional ROI: 3.25%

1220 DEGNATH GATEWAY LN

Winston, OR

3 beds | 2 baths | 1,188 sq.ft.

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.08%

Airbnb Rental Income: $null

Traditional Rental Income: $2769

Airbnb ROI: N/A

Traditional ROI: 4.08%

211 NW PLUM AVE

Winston, OR

3 beds | 2 baths | 1,704 sq.ft.

$370,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.02%

Airbnb Rental Income: $null

Traditional Rental Income: $3504

Airbnb ROI: N/A

Traditional ROI: 8.02%

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