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 10 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...	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%
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%
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%
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%
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%

Your search for investment property begins and ends here

Single Family Homes 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%

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%

Traditional ROI: 6.62%

160 WIL Way

Winston, OR

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%

411 WOODLAND Dr

Winston, OR

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%

605 DEERWOOD Ct

Winston, OR

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%