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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winston, OR

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

Showing 19 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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...	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: -2.2% Traditional cash on cash: 4.77% Airbnb Rental Income: $242 Traditional Rental Income: $3272 Airbnb ROI: -2.2% 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: -2.11% Traditional cash on cash: 5.49% Airbnb Rental Income: $242 Traditional Rental Income: $2565 Airbnb ROI: -2.11% 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%
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: -1.63% Traditional cash on cash: 4.33% Airbnb Rental Income: $242 Traditional Rental Income: $2659 Airbnb ROI: -1.63% Traditional ROI: 4.33%
150 WIL Way Winston, OR OPEN HOUSE! Sunday 1-3pm 3/29 New Home by JW Construction Inc.This beautifully crafted 2,1...	3 beds \| 3 baths \| 1,999 sq.ft.	$499,900	Airbnb cash on cash: -1.96% Traditional cash on cash: 6.62% Airbnb Rental Income: $242 Traditional Rental Income: $4025 Airbnb ROI: -1.96% Traditional ROI: 6.62%
160 WIL Way Winston, OR OPEN HOUSE! Sunday 3/29 1-3pm New Home by JW Construction Inc.This beautiful one-level hom...	3 beds \| 3 baths \| 2,089 sq.ft.	$499,900	Airbnb cash on cash: -1.86% Traditional cash on cash: 6.01% Airbnb Rental Income: $242 Traditional Rental Income: $3688 Airbnb ROI: -1.86% 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: -1.26% Traditional cash on cash: 5.59% Airbnb Rental Income: $242 Traditional Rental Income: $3025 Airbnb ROI: -1.26% 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: 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%
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: -1.49% Traditional cash on cash: 3.96% Airbnb Rental Income: $242 Traditional Rental Income: $2817 Airbnb ROI: -1.49% 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: -1.92% Traditional cash on cash: 3.17% Airbnb Rental Income: $242 Traditional Rental Income: $2856 Airbnb ROI: -1.92% 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%
871 SE MEADOWOOD Dr Winston, OR Double-wide home on a great fenced lot with excellent potential. The home is in need of so...	3 beds \| 2 baths \| 1,620 sq.ft.	$200,000	Airbnb cash on cash: -2.16% Traditional cash on cash: 11.94% Airbnb Rental Income: $242 Traditional Rental Income: $2689 Airbnb ROI: -2.16% Traditional ROI: 11.94%
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: -2.41% Traditional cash on cash: 7.45% Airbnb Rental Income: $242 Traditional Rental Income: $1883 Airbnb ROI: -2.41% Traditional ROI: 7.45%
182 WOODDUCK St Winston, OR Quality contemporary 3 bedroom, 2 bath 1452 sq ft home built in 2005 in Hunters Crossing. ...	3 beds \| 2 baths \| 1,452 sq.ft.	$375,000	Airbnb cash on cash: -2.27% Traditional cash on cash: 3.05% Airbnb Rental Income: $242 Traditional Rental Income: $1883 Airbnb ROI: -2.27% Traditional ROI: 3.05%
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: -2.08% Traditional cash on cash: 8.66% Airbnb Rental Income: $242 Traditional Rental Income: $2698 Airbnb ROI: -2.08% 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: -1.59% Traditional cash on cash: 0.09% Airbnb Rental Income: $242 Traditional Rental Income: $1883 Airbnb ROI: -1.59% Traditional ROI: 0.09%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential 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: -2.2%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $242

Traditional Rental Income: $3272

Airbnb ROI: -2.2%

Traditional ROI: 4.77%

380 SUNNYSIDE Dr

Winston, OR

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

$357,900

Airbnb cash on cash: -2.11%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $242

Traditional Rental Income: $2565

Airbnb ROI: -2.11%

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%

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: -1.63%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $242

Traditional Rental Income: $2659

Airbnb ROI: -1.63%

Traditional ROI: 4.33%

150 WIL Way

Winston, OR

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

$499,900

Airbnb cash on cash: -1.96%

Traditional cash on cash: 6.62%

Airbnb Rental Income: $242

Traditional Rental Income: $4025

Airbnb ROI: -1.96%

Traditional ROI: 6.62%

160 WIL Way

Winston, OR

3 beds | 3 baths | 2,089 sq.ft.

$499,900

Airbnb cash on cash: -1.86%

Traditional cash on cash: 6.01%

Airbnb Rental Income: $242

Traditional Rental Income: $3688

Airbnb ROI: -1.86%