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.

Single Family Homes for Sale in Winston, OR

Search for Single Family Residential for Sale in Winston, Oregon. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 14 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9740 UPPER OLALLA RD Winston, OR Country setting 29.80 acres, A-frame Cedar home with vaulted ceilings. Master on main leve...	3 beds \| 3 baths \| 2,304 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $2899 Airbnb ROI: N/A Traditional ROI: 2.89%
310 NW LOST LN Winston, OR Freshly updated and move-in ready, this Winston home combines comfort, convenience, and ch...	4 beds \| 2 baths \| 1,769 sq.ft.	$304,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.01% Airbnb Rental Income: $null Traditional Rental Income: $2976 Airbnb ROI: N/A Traditional ROI: 8.01%
1470 E WILLIS CREEK RD Winston, OR Build a second home? 3 tax lots. 80+5+5 acres each & one of the 5-acre lots is buildable! ...	3 beds \| 3 baths \| 1,845 sq.ft.	$748,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $3379 Airbnb ROI: N/A Traditional ROI: 3.45%
2414 BROCKWAY RD Winston, OR Opportunity awaits! Whether youâre a savvy investor seeking passive income, a large fami...	7 beds \| 5 baths \| 3,861 sq.ft.	$439,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.98% Airbnb Rental Income: $null Traditional Rental Income: $1318 Airbnb ROI: N/A Traditional ROI: 0.98%
185 SE LEBLEU LN Winston, OR Solid home in Winston with a newer roof and open concept floorplan. Welcome home to this w...	3 beds \| 2 baths \| 1,257 sq.ft.	$335,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $2372 Airbnb ROI: N/A Traditional ROI: 5.26%
231 NE DARRELL AVE Winston, OR Great location with a custom built one level home located on .39 of an acre at the end of ...	3 beds \| 2 baths \| 1,374 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.89% Airbnb Rental Income: $null Traditional Rental Income: $2440 Airbnb ROI: N/A Traditional ROI: 5.89%
1068 RICE CREEK RD Winston, OR This gated, 8.52-acre property is fenced and cross-fenced, offering plenty of country livi...	4 beds \| 3 baths \| 2,362 sq.ft.	$734,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $3489 Airbnb ROI: N/A Traditional ROI: 3.34%
13224 SE LOOKINGGLASS RD Winston, OR Experience this beautifully updated, original homestead farmhouse nestled in Safari Estate...	4 beds \| 2 baths \| 2,534 sq.ft.	$474,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.46% Airbnb Rental Income: $null Traditional Rental Income: $3728 Airbnb ROI: N/A Traditional ROI: 6.46%
700 SE TOKAY ST Winston, OR Welcome to this inviting one level 3-bedroom, 2-bathroom home offering comfort, convenienc...	3 beds \| 2 baths \| 1,404 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $2500 Airbnb ROI: N/A Traditional ROI: 5.05%
800 BYRON CREEK RD Winston, OR Welcome to this charming country home set on over 5 acres of flat, usable land with Firewi...	3 beds \| 3 baths \| 1,320 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A Traditional ROI: 4.12%
150 WIL WAY Winston, OR New Home by JW Construction Inc.This beautifully crafted 2,143 sq ft home offers 3 bedroom...	3 beds \| 3 baths \| 1,999 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.4% Airbnb Rental Income: $null Traditional Rental Income: $4025 Airbnb ROI: N/A Traditional ROI: 6.4%
160 WIL WAY Winston, OR New Home by JW Construction Inc.This beautiful one-level home offers just over 2,000 squar...	3 beds \| 3 baths \| 2,089 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.98% Airbnb Rental Income: $null Traditional Rental Income: $3688 Airbnb ROI: N/A Traditional ROI: 5.98%
109 CITATION CT Winston, OR Welcome to 109 Citation Ct, a brand-new single-level home nestled in the highly sought-aft...	3 beds \| 2 baths \| 1,770 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.59% Airbnb Rental Income: $null Traditional Rental Income: $3025 Airbnb ROI: N/A Traditional ROI: 5.59%
411 WOODLAND DR Winston, OR Discover a lifestyle rooted in fresh air, room to roam, and time spent outside. This two-s...	4 beds \| 2 baths \| 2,240 sq.ft.	$719,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.71% Airbnb Rental Income: $null Traditional Rental Income: $3477 Airbnb ROI: N/A Traditional ROI: 3.71%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winston, OR

9740 UPPER OLALLA RD

Winston, OR

3 beds | 3 baths | 2,304 sq.ft.

$700,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.89%

Airbnb Rental Income: $null

Traditional Rental Income: $2899

Airbnb ROI: N/A

Traditional ROI: 2.89%

310 NW LOST LN

Winston, OR

4 beds | 2 baths | 1,769 sq.ft.

$304,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2976

Airbnb ROI: N/A

Traditional ROI: 8.01%

1470 E WILLIS CREEK RD

Winston, OR

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

$748,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3379

Airbnb ROI: N/A

Traditional ROI: 3.45%

2414 BROCKWAY RD

Winston, OR

7 beds | 5 baths | 3,861 sq.ft.

$439,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.98%

Airbnb Rental Income: $null

Traditional Rental Income: $1318

Airbnb ROI: N/A

Traditional ROI: 0.98%

185 SE LEBLEU LN

Winston, OR

3 beds | 2 baths | 1,257 sq.ft.

$335,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2372

Airbnb ROI: N/A

Traditional ROI: 5.26%

231 NE DARRELL AVE

Winston, OR

3 beds | 2 baths | 1,374 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.89%

Airbnb Rental Income: $null

Traditional Rental Income: $2440

Airbnb ROI: N/A

Traditional ROI: 5.89%

1068 RICE CREEK RD

Winston, OR

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

$734,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.34%

Airbnb Rental Income: $null

Traditional Rental Income: $3489

Airbnb ROI: N/A

Traditional ROI: 3.34%

13224 SE LOOKINGGLASS RD

Winston, OR

4 beds | 2 baths | 2,534 sq.ft.

$474,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.46%

Airbnb Rental Income: $null

Traditional Rental Income: $3728

Airbnb ROI: N/A