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
9740 Upper Olalla Rd Winston, OR Country setting 29.80 acres, A-frame Cedar home with vaulted ceilings. Master on main leve...	2 beds \| 2 baths \| 2,304 sq.ft.	$675,000	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%
110 Teresa Ln Winston, OR Welcome home to this beautifully maintained single-level residence in the sought-after Cre...	3 beds \| 2 baths \| 1,290 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $2297 Airbnb ROI: N/A Traditional ROI: 4.61%
645 SE Garden Way Dr Winston, OR Built in 2019, this well-maintained single-level home offers 3 bedrooms, 2 baths, and an o...	3 beds \| 2 baths \| 1,447 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.58% Airbnb Rental Income: $null Traditional Rental Income: $2929 Airbnb ROI: N/A Traditional ROI: 5.58%
1470 E WILLIS CREEK Rd Winston, OR Nestled on 90 acres of private land, this stunning 3-bedroom, 2.5-bath log home offers the...	3 beds \| 2 baths \| 1,845 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $3379 Airbnb ROI: N/A Traditional ROI: 3.75%
2414 Brockway Rd Winston, OR Opportunity awaits! Whether you're a savvy investor seeking passive income, a large family...	7 beds \| 4 baths \| 3,861 sq.ft.	$409,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.07% Airbnb Rental Income: $null Traditional Rental Income: $1318 Airbnb ROI: N/A Traditional ROI: 1.07%
102 Sarah Bear Ln Winston, OR Stately quality 4 br 3 bath home, real wood floors, 2 gas fireplaces, central vac, top qua...	4 beds \| 3 baths \| 2,660 sq.ft.	$555,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.65% Airbnb Rental Income: $null Traditional Rental Income: $4150 Airbnb ROI: N/A Traditional ROI: 5.65%
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.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.11% Airbnb Rental Income: $null Traditional Rental Income: $2440 Airbnb ROI: N/A Traditional ROI: 6.11%
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.	$370,000	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.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.62% Airbnb Rental Income: $null Traditional Rental Income: $4025 Airbnb ROI: N/A 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 squar...	3 beds \| 2 baths \| 2,089 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.01% Airbnb Rental Income: $null Traditional Rental Income: $3688 Airbnb ROI: N/A Traditional ROI: 6.01%
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.	$229,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 7.92% Airbnb Rental Income: $1071 Traditional Rental Income: $2129 Airbnb ROI: 1.34% Traditional ROI: 7.92%
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.	$709,000	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%
308 NW Civil Bend Ave Winston, OR Welcome home to this 3-bedroom, 2-bath manufactured home on your own property in a quiet W...	3 beds \| 2 baths \| 1,296 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.46% Airbnb Rental Income: $null Traditional Rental Income: $2319 Airbnb ROI: N/A Traditional ROI: 7.46%
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.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $2817 Airbnb ROI: N/A Traditional ROI: 3.37%
605 Deerwood Ct Winston, OR 605 Deerwood Ct, Winston, OR 97496 \| Single Family Residential	3 beds \| 2 baths \| 2,431 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.6% Airbnb Rental Income: $null Traditional Rental Income: $2856 Airbnb ROI: N/A Traditional ROI: 2.6%

Real Estate investment in Winston, OR

There are 45 properties for sale in the city of Winston . The median list price in Winston is $400,000 and the average price per square foot is $263. In March 2026, the average monthly cash on cash return in Winston is 6.00%. The average monthly rental income in Winston is $2,580.

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

There are 45 investment properties available for sale in Winston.

In 2026, 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 $2,580.

Your search for investment property begins and ends here

Investment Property for Sale in Winston, OR

9740 Upper Olalla Rd

Winston, OR

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

$675,000

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%

110 Teresa Ln

Winston, OR

3 beds | 2 baths | 1,290 sq.ft.

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2297

Airbnb ROI: N/A

Traditional ROI: 4.61%

645 SE Garden Way Dr

Winston, OR

3 beds | 2 baths | 1,447 sq.ft.

$385,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.58%

Airbnb Rental Income: $null

Traditional Rental Income: $2929

Airbnb ROI: N/A

Traditional ROI: 5.58%

1470 E WILLIS CREEK Rd

Winston, OR

3 beds | 2 baths | 1,845 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.75%

Airbnb Rental Income: $null

Traditional Rental Income: $3379

Airbnb ROI: N/A

Traditional ROI: 3.75%

2414 Brockway Rd

Winston, OR

7 beds | 4 baths | 3,861 sq.ft.

$409,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.07%

Airbnb Rental Income: $null

Traditional Rental Income: $1318

Airbnb ROI: N/A

Traditional ROI: 1.07%

102 Sarah Bear Ln

Winston, OR

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

$555,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.65%

Airbnb Rental Income: $null

Traditional Rental Income: $4150

Airbnb ROI: N/A

Traditional ROI: 5.65%

231 NE Darrell Ave

Winston, OR

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

$315,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.11%

Airbnb Rental Income: $null

Traditional Rental Income: $2440

Airbnb ROI: N/A

Traditional ROI: 6.11%

700 SE Tokay St

Winston, OR

3 beds | 2 baths | 1,404 sq.ft.

$370,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2500

Airbnb ROI: N/A