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 27 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
375 Porter Creek Rd Winston, OR Ever dreamed of owning your own vineyard and winery? Make your dream a reality! Own a tast...	4 beds \| 3 baths \| 3,000 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $4115 Airbnb ROI: N/A Traditional ROI: 4.3%
0 Rice Creek Rd Winston, OR If you seek seclusion, passive solar design, & a quiet setting: LOOK here! Seller construc...	1 beds \| 1 baths \| 1,000 sq.ft.	$190,000	Airbnb cash on cash: -1.98% Traditional cash on cash: 8.91% Airbnb Rental Income: $163 Traditional Rental Income: $1913 Airbnb ROI: -1.98% Traditional ROI: 8.91%
71 SE RONALD St Winston, OR Charming remodeled cottage-style home situated on a large quarter acre lot offering comfor...	2 beds \| 1 baths \| 939 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.91% Airbnb Rental Income: $null Traditional Rental Income: $2153 Airbnb ROI: N/A Traditional ROI: 6.91%
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.	$489,900	Airbnb cash on cash: -0.89% Traditional cash on cash: 4.89% Airbnb Rental Income: $975 Traditional Rental Income: $3272 Airbnb ROI: -0.89% Traditional ROI: 4.89%
340 NW ELIZABETH Ave Winston, OR This 3-bedroom, 2-bath home offers a functional layout with plenty of potential for its ne...	3 beds \| 2 baths \| 1,594 sq.ft.	$315,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 6.3% Airbnb Rental Income: $975 Traditional Rental Income: $2708 Airbnb ROI: -0.74% Traditional ROI: 6.3%
340 SE DARRELL Ave Winston, OR Solid 3-bedroom, single-level home with a functional layout, attached garage, and fully fe...	3 beds \| 1 baths \| 1,000 sq.ft.	$318,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.74% Airbnb Rental Income: $975 Traditional Rental Income: $1723 Airbnb ROI: 0.07% Traditional ROI: 3.74%
1068 RICE CREEK Rd Winston, OR Security gated 8.52-acre property! This beautiful ranch-style home features, updates, pave...	4 beds \| 3 baths \| 2,362 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.53% Airbnb Rental Income: $null Traditional Rental Income: $3489 Airbnb ROI: N/A Traditional ROI: 3.53%
150 WIL Way Winston, OR Open House 5/30 2-5 pm New Home by JW Construction Inc. This beautifully crafted 2,143 sq ...	3 beds \| 3 baths \| 1,999 sq.ft.	$499,900	Airbnb cash on cash: -0.66% Traditional cash on cash: 6.62% Airbnb Rental Income: $975 Traditional Rental Income: $4025 Airbnb ROI: -0.66% 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 squa...	3 beds \| 3 baths \| 2,089 sq.ft.	$499,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 6.01% Airbnb Rental Income: $975 Traditional Rental Income: $3688 Airbnb ROI: -0.55% Traditional ROI: 6.01%
411 WOODLAND Dr Winston, OR What if your favorite getaway was home?Set above Lookingglass Creek with stunning views of...	4 beds \| 2 baths \| 2,240 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $3477 Airbnb ROI: N/A Traditional ROI: 3.94%
635 Wil Way Winston, OR 635 Wil Way, Winston, OR 97496 \| Single Family Residential	4 beds \| 3 baths \| 3,072 sq.ft.	$634,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $3704 Airbnb ROI: N/A Traditional ROI: 4.13%
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.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.98% Airbnb Rental Income: $null Traditional Rental Income: $2128 Airbnb ROI: N/A Traditional ROI: 7.98%
6700 UPPER OLALLA Rd Winston, OR Stunning custom cedar home on 5 level acres offering the perfect blend of luxury, function...	3 beds \| 3 baths \| 2,720 sq.ft.	$1,100,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 1.8% Airbnb Rental Income: $975 Traditional Rental Income: $3535 Airbnb ROI: -1.05% Traditional ROI: 1.8%
101 SW PEACH Ln Winston, OR This single-level home features 3 bedrooms and 1 bathroom, offering comfortable and conven...	3 beds \| 1 baths \| 1,348 sq.ft.	$315,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.59% Airbnb Rental Income: $975 Traditional Rental Income: $1952 Airbnb ROI: 0.11% Traditional ROI: 4.59%
311 SE GRAPE Ave Winston, OR Great investment opportunity on a spacious 0.74-acre lot! This property features a 3-bedro...	3 beds \| 1 baths \| 1,250 sq.ft.	$459,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.2% Airbnb Rental Income: $975 Traditional Rental Income: $2333 Airbnb ROI: -0.78% Traditional ROI: 3.2%
1349 Willis Creek Rd Winston, OR 1349 Willis Creek Rd, Winston, OR 97496 \| Single Family Residential	3 beds \| 2 baths \| 2,856 sq.ft.	$1,199,900	Airbnb cash on cash: -1.49% Traditional cash on cash: 0.67% Airbnb Rental Income: $975 Traditional Rental Income: $3037 Airbnb ROI: -1.49% Traditional ROI: 0.67%
380 NW Cary St Winston, OR 380 NW Cary St, Winston, OR 97496 \| Single Family Residential	4 beds \| 2 baths \| 1,710 sq.ft.	$355,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.13% Airbnb Rental Income: $null Traditional Rental Income: $2791 Airbnb ROI: N/A Traditional ROI: 6.13%
186 WOODDUCK St Winston, OR Well-maintained home in a quiet neighborhood in the heart of Winston. Move-in ready with b...	3 beds \| 2 baths \| 1,613 sq.ft.	$375,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 5.31% Airbnb Rental Income: $975 Traditional Rental Income: $2656 Airbnb ROI: -0.46% Traditional ROI: 5.31%
2581 BROCKWAY Rd Winston, OR Open House 5/30 2-5pm New listing! This beautifully crafted new construction home offers 2...	3 beds \| 3 baths \| 2,576 sq.ft.	$499,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 6.35% Airbnb Rental Income: $975 Traditional Rental Income: $3684 Airbnb ROI: -0.2% Traditional ROI: 6.35%
9114 Old Highway 99 S Winston, OR 9114 Old Highway 99 S, Winston, OR 97496 \| Single Family Residential	3 beds \| 3 baths \| 2,722 sq.ft.	$735,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 3.24% Airbnb Rental Income: $975 Traditional Rental Income: $3656 Airbnb ROI: -1.19% Traditional ROI: 3.24%
3707 Willis Creek Rd Winston, OR 3707 Willis Creek Rd, Winston, OR 97496 \| Single Family Residential	2 beds \| 1 baths \| 1,070 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $1806 Airbnb ROI: N/A Traditional ROI: 5.05%
572 Dillard Gardens Rd Winston, OR 572 Dillard Gardens Rd, Winston, OR 97496 \| Single Family Residential	2 beds \| 2 baths \| 1,440 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $2120 Airbnb ROI: N/A Traditional ROI: 2.17%
10 SW Peach Ln Winston, OR 10 SW Peach Ln, Winston, OR 97496 \| Single Family Residential	3 beds \| 1 baths \| 1,440 sq.ft.	$389,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.91% Airbnb Rental Income: $975 Traditional Rental Income: $1869 Airbnb ROI: -0.51% Traditional ROI: 2.91%
330 WIL Way Winston, OR Custom-built in 2014 and thoughtfully designed by the owner, this 2,091 SF ranch style hom...	4 beds \| 2 baths \| 2,091 sq.ft.	$509,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $3199 Airbnb ROI: N/A Traditional ROI: 4.56%
2620 NW Brockway Rd Winston, OR Beautiful Craftsman-style home with fantastic curb appeal and a slate-tile covered front p...	3 beds \| 2 baths \| 4,024 sq.ft.	$525,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 2.56% Airbnb Rental Income: $975 Traditional Rental Income: $2292 Airbnb ROI: -0.84% Traditional ROI: 2.56%
509 NW Elwood Dr Winston, OR 509 NW Elwood Dr, Winston, OR 97496 \| Single Family Residential	3 beds \| 1 baths \| 960 sq.ft.	$280,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.89% Airbnb Rental Income: $975 Traditional Rental Income: $1900 Airbnb ROI: 0.05% Traditional ROI: 4.89%
150 SW Brantley Dr Winston, OR 150 SW Brantley Dr, Winston, OR 97496 \| Single Family Residential	4 beds \| 3 baths \| 2,270 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.47% Airbnb Rental Income: $null Traditional Rental Income: $3456 Airbnb ROI: N/A Traditional ROI: 7.47%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winston, OR

375 Porter Creek Rd

Winston, OR

4 beds | 3 baths | 3,000 sq.ft.

$775,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.3%

Airbnb Rental Income: $null

Traditional Rental Income: $4115

Airbnb ROI: N/A

Traditional ROI: 4.3%

0 Rice Creek Rd

Winston, OR

1 beds | 1 baths | 1,000 sq.ft.

$190,000

Airbnb cash on cash: -1.98%

Traditional cash on cash: 8.91%

Airbnb Rental Income: $163

Traditional Rental Income: $1913

Airbnb ROI: -1.98%

Traditional ROI: 8.91%

71 SE RONALD St

Winston, OR

2 beds | 1 baths | 939 sq.ft.

$249,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2153

Airbnb ROI: N/A

Traditional ROI: 6.91%

263 WIL Way

Winston, OR

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

$489,900

Airbnb cash on cash: -0.89%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $975

Traditional Rental Income: $3272

Airbnb ROI: -0.89%

Traditional ROI: 4.89%

340 NW ELIZABETH Ave

Winston, OR

3 beds | 2 baths | 1,594 sq.ft.

$315,000

Airbnb cash on cash: -0.74%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $975

Traditional Rental Income: $2708

Airbnb ROI: -0.74%

Traditional ROI: 6.3%

340 SE DARRELL Ave

Winston, OR

3 beds | 1 baths | 1,000 sq.ft.

$318,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $975

Traditional Rental Income: $1723

Airbnb ROI: 0.07%

Traditional ROI: 3.74%

1068 RICE CREEK Rd

Winston, OR

4 beds | 3 baths | 2,362 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3489

Airbnb ROI: N/A

Traditional ROI: 3.53%

150 WIL Way

Winston, OR

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

$499,900

Airbnb cash on cash: -0.66%

Traditional cash on cash: 6.62%

Airbnb Rental Income: $975

Traditional Rental Income: $4025

Airbnb ROI: -0.66%