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
9740 UPPER OLALLA Rd Winston, OR Country setting 29.80 acres, A-frame Cedar home with vaulted ceilings. Master on main leve...	3 beds \| 2 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%
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 \| 2 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 you're a savvy investor seeking passive income, a large family...	7 beds \| N/A baths \| N/A	$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%
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: 6.44% Airbnb Rental Income: $null Traditional Rental Income: $3728 Airbnb ROI: N/A Traditional ROI: 6.44%
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 \| 2 baths \| 1,320 sq.ft.	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A Traditional ROI: 4.22%
180 TWIN OAKS Loop Winston, OR application and park requirements, No other fees to HOA except basic space rent 604$+121$ ...	3 beds \| 2 baths \| 1,404 sq.ft.	$137,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.99% Airbnb Rental Income: $null Traditional Rental Income: $2461 Airbnb ROI: N/A Traditional ROI: 11.99%
150 WIL Way Winston, OR New Home by JW Construction Inc.This beautifully crafted 2,143 sq ft home offers 3 bedroom...	3 beds \| 2 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 \| 2 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%
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.	$239,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 7.55% Airbnb Rental Income: $1071 Traditional Rental Income: $2129 Airbnb ROI: 1.24% Traditional ROI: 7.55%
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%
210 NW TIMOTHY Ave Winston, OR Extremely nice 1999 triple-wide on a beautiful corner lot. Features 3 bedrooms, 2 baths wi...	3 beds \| 2 baths \| 1,848 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.71% Airbnb Rental Income: $null Traditional Rental Income: $2825 Airbnb ROI: N/A Traditional ROI: 6.71%
301 NW MIDWAY St Winston, OR AMAZING INVESTMENT OPPORTUNITY!!! Cosmetic fixer upper features 3 Bedrooms, 2 baths, 2 car...	3 beds \| 2 baths \| 1,156 sq.ft.	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.68% Airbnb Rental Income: $null Traditional Rental Income: $2528 Airbnb ROI: N/A Traditional ROI: 10.68%
291 SE SHIGLEY St Winston, OR Contemporary custom 2014 sq ft. tri level home on .21 acre level lot. Has 8x24 green house...	3 beds \| 2 baths \| 2,014 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.48% Airbnb Rental Income: $null Traditional Rental Income: $3380 Airbnb ROI: N/A Traditional ROI: 7.48%

Real Estate investment in Winston, OR

There are 17 properties for sale in the city of Winston . The median list price in Winston is $407,000 and the average price per square foot is $242. In December 2025, the average monthly cash on cash return in Winston is 6.00%. The average monthly rental income in Winston is $2,742.

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

There are 17 investment properties available for sale in Winston.

In 2025, the best neighborhood to buy investment property is Winston.

The ROI for Long-Term is higher than the Short-Term in Winston with average rental income of $2,742.

Your search for investment property begins and ends here

Investment Property for Sale in Winston, OR

9740 UPPER OLALLA Rd

Winston, OR

3 beds | 2 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%

1470 E WILLIS CREEK Rd

Winston, OR

3 beds | 2 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 | N/A baths | N/A

$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%

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: 6.44%

Airbnb Rental Income: $null

Traditional Rental Income: $3728

Airbnb ROI: N/A

Traditional ROI: 6.44%

700 SE TOKAY St

Winston, OR

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

3 beds | 2 baths | 1,320 sq.ft.

$485,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.22%

Airbnb Rental Income: $null

Traditional Rental Income: $2659

Airbnb ROI: N/A