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...	2 beds \| 3 baths \| 2,304 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.04% Airbnb Rental Income: $null Traditional Rental Income: $2899 Airbnb ROI: N/A Traditional ROI: 3.04%
263 WIL Way Winston, OR Welcome to Your Like-New Custom Home in Winston, Oregon!Step inside this beautifully craft...	3 beds \| 2 baths \| 1,928 sq.ft.	$499,900	Airbnb cash on cash: -2.29% Traditional cash on cash: 4.77% Airbnb Rental Income: $190 Traditional Rental Income: $3272 Airbnb ROI: -2.29% Traditional ROI: 4.77%
380 SUNNYSIDE Dr Winston, OR Welcome to 380 Sunnyside! This move-in-ready 3-bedroom, 2-bath home offers comfort, qualit...	3 beds \| 2 baths \| 1,433 sq.ft.	$357,900	Airbnb cash on cash: -2.24% Traditional cash on cash: 5.49% Airbnb Rental Income: $190 Traditional Rental Income: $2565 Airbnb ROI: -2.24% Traditional ROI: 5.49%
2414 BROCKWAY Rd Winston, OR Opportunity awaits! Whether you're a savvy investor seeking passive income, a large family...	7 beds \| 5 baths \| N/A	$409,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.12% Airbnb Rental Income: $null Traditional Rental Income: $1318 Airbnb ROI: N/A Traditional ROI: 1.12%
751 SE MEADOWOOD Dr Winston, OR 1995 Double-wide manufactured home on a good sized lot in Winston. Not perfect but a lot o...	2 beds \| 2 baths \| 1,120 sq.ft.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.32% Airbnb Rental Income: $null Traditional Rental Income: $2286 Airbnb ROI: N/A Traditional ROI: 10.32%
102 SARAH BEAR Ln Winston, OR Meticulous quality 4 br 3 bath 2660 sq ft home, with real wood floors, 2 gas fireplaces, c...	4 beds \| 3 baths \| 2,660 sq.ft.	$555,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $4150 Airbnb ROI: N/A Traditional ROI: 5.86%
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.	$475,000	Airbnb cash on cash: -1.72% Traditional cash on cash: 4.33% Airbnb Rental Income: $190 Traditional Rental Income: $2659 Airbnb ROI: -1.72% Traditional ROI: 4.33%
150 WIL Way Winston, OR OPEN HOUSE! Sunday 1-4 pm 4/12 New Home by JW Construction Inc.This beautifully crafted 2,...	3 beds \| 3 baths \| 1,999 sq.ft.	$499,900	Airbnb cash on cash: -2.06% Traditional cash on cash: 6.62% Airbnb Rental Income: $190 Traditional Rental Income: $4025 Airbnb ROI: -2.06% Traditional ROI: 6.62%
160 WIL Way Winston, OR OPEN HOUSE! Sunday 4/12 1-4pm New Home by JW Construction Inc. This beautiful one-level ho...	3 beds \| 3 baths \| 2,089 sq.ft.	$499,900	Airbnb cash on cash: -1.95% Traditional cash on cash: 6.01% Airbnb Rental Income: $190 Traditional Rental Income: $3688 Airbnb ROI: -1.95% Traditional ROI: 6.01%
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: N/A Traditional cash on cash: 7.92% Airbnb Rental Income: $null Traditional Rental Income: $2129 Airbnb ROI: N/A 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.	$699,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $3477 Airbnb ROI: N/A Traditional ROI: 3.84%
210 NW TIMOTHY Ave Winston, OR Welcome to this beautifully maintained triple-wide manufactured home offering 1,848 sq ft ...	3 beds \| 2 baths \| 1,848 sq.ft.	$349,900	Airbnb cash on cash: -1.98% Traditional cash on cash: 6.71% Airbnb Rental Income: $190 Traditional Rental Income: $2825 Airbnb ROI: -1.98% Traditional ROI: 6.71%
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: -1.58% Traditional cash on cash: 3.96% Airbnb Rental Income: $190 Traditional Rental Income: $2817 Airbnb ROI: -1.58% Traditional ROI: 3.96%
605 DEERWOOD Ct Winston, OR This custom-built Passive Solar home, constructed in 1979, offers a rare blend of timeless...	3 beds \| 2 baths \| 2,431 sq.ft.	$599,000	Airbnb cash on cash: -2% Traditional cash on cash: 3.17% Airbnb Rental Income: $190 Traditional Rental Income: $2856 Airbnb ROI: -2% Traditional ROI: 3.17%
381 SE GREGORY Dr Winston, OR Seize this opportunity with this charming single-story 1948 ranch style home boasting 2 be...	2 beds \| 1 baths \| 1,323 sq.ft.	$230,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.03% Airbnb Rental Income: $null Traditional Rental Income: $2128 Airbnb ROI: N/A Traditional ROI: 7.03%
1580 WINSTON SECTION Rd Winston, OR This 3-bedroom, 2-bathroom "fixer upper" sits on a peaceful 0.18-acre corner lot, offering...	3 beds \| 2 baths \| 1,188 sq.ft.	$199,900	Airbnb cash on cash: -2.64% Traditional cash on cash: 9.53% Airbnb Rental Income: $190 Traditional Rental Income: $2278 Airbnb ROI: -2.64% Traditional ROI: 9.53%
771 SE HALL St Winston, OR Welcome to 771 SE Hall St in Winston where comfort meets convenience in this spacious 3 be...	3 beds \| 2 baths \| 1,650 sq.ft.	$265,000	Airbnb cash on cash: -2.25% Traditional cash on cash: 8.66% Airbnb Rental Income: $190 Traditional Rental Income: $2698 Airbnb ROI: -2.25% Traditional ROI: 8.66%
6700 UPPER OLALLA Rd Winston, OR Exquisite Lindal Custom Cedar home on 5 flat acres featuring a 2,400 sq ft shop with full ...	3 beds \| 3 baths \| 2,720 sq.ft.	$1,200,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 1.57% Airbnb Rental Income: $190 Traditional Rental Income: $3535 Airbnb ROI: -1.63% Traditional ROI: 1.57%

Real Estate investment in Winston, OR

There are 18 properties for sale in the city of Winston . The median list price in Winston is $357,900 and the average price per square foot is $215. In April 2026, the average monthly cash on cash return in Winston is 6.00%. The average monthly rental income in Winston is $2,679.

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

There are 18 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 $2,679.

Your search for investment property begins and ends here

Investment Property for Sale in Winston, OR

9740 UPPER OLALLA Rd

Winston, OR

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

$675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.04%

Airbnb Rental Income: $null

Traditional Rental Income: $2899

Airbnb ROI: N/A

Traditional ROI: 3.04%

263 WIL Way

Winston, OR

3 beds | 2 baths | 1,928 sq.ft.

$499,900

Airbnb cash on cash: -2.29%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $190

Traditional Rental Income: $3272

Airbnb ROI: -2.29%

Traditional ROI: 4.77%

380 SUNNYSIDE Dr

Winston, OR

3 beds | 2 baths | 1,433 sq.ft.

$357,900

Airbnb cash on cash: -2.24%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $190

Traditional Rental Income: $2565

Airbnb ROI: -2.24%

Traditional ROI: 5.49%

2414 BROCKWAY Rd

Winston, OR

7 beds | 5 baths | N/A

$409,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.12%

Airbnb Rental Income: $null

Traditional Rental Income: $1318

Airbnb ROI: N/A

Traditional ROI: 1.12%

751 SE MEADOWOOD Dr

Winston, OR

2 beds | 2 baths | 1,120 sq.ft.

$195,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2286

Airbnb ROI: N/A

Traditional ROI: 10.32%

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: 5.86%

Airbnb Rental Income: $null

Traditional Rental Income: $4150

Airbnb ROI: N/A

Traditional ROI: 5.86%

800 BYRON CREEK Rd

Winston, OR

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

$475,000

Airbnb cash on cash: -1.72%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $190

Traditional Rental Income: $2659

Airbnb ROI: -1.72%

Traditional ROI: 4.33%

150 WIL Way

Winston, OR

3 beds | 3 baths | 1,999 sq.ft.

$499,900

Airbnb cash on cash: -2.06%

Traditional cash on cash: 6.62%

Airbnb Rental Income: $190

Traditional Rental Income: $4025

Airbnb ROI: -2.06%