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 38 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
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: N/A Traditional cash on cash: 8.91% Airbnb Rental Income: $null Traditional Rental Income: $1913 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $3272 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $2708 Airbnb ROI: N/A 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.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.57% Airbnb Rental Income: $null Traditional Rental Income: $1723 Airbnb ROI: N/A Traditional ROI: 4.57%
623 SE Garden Way Dr Winston, OR Welcome to this stunning home with a plethora of desirable features! Step inside and be gr...	3 beds \| 2 baths \| 1,680 sq.ft.	$409,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.62% Airbnb Rental Income: $null Traditional Rental Income: $2221 Airbnb ROI: N/A Traditional ROI: 3.62%
185 SE Lebleu Ln Winston, OR Solid home in Winston with a newer roof and open concept floorplan. Welcome home to this w...	3 beds \| 2 baths \| 1,257 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2372 Airbnb ROI: N/A Traditional ROI: 5.19%
1068 Rice Creek Rd Winston, OR Security gated 8.52-acre property! This beautiful ranch-style home features, updates, pave...	4 beds \| 2 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%
1090 E Willis Creek Rd Winston, OR Secluded private 2167 sq ft 3 br 2 bath contemporary home on 9.81 acres. Has open beam cei...	3 beds \| 2 baths \| 2,167 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.44% Airbnb Rental Income: $null Traditional Rental Income: $3476 Airbnb ROI: N/A Traditional ROI: 7.44%
128 Watusi Ct Winston, OR Very desirable single level home in Lookingglass Estates. Built in 2008 with great curb ap...	3 beds \| 2 baths \| 1,832 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $null Traditional Rental Income: $3257 Airbnb ROI: N/A Traditional ROI: 5.91%
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 \| 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 squa...	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%
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.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.43% Airbnb Rental Income: $null Traditional Rental Income: $2128 Airbnb ROI: N/A Traditional ROI: 8.43%
6700 Upper Olalla Rd Winston, OR Stunning custom cedar home on 5 level acres offering the perfect blend of luxury, function...	3 beds \| 2 baths \| 2,720 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $3535 Airbnb ROI: N/A 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.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $1952 Airbnb ROI: N/A Traditional ROI: 4.89%
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: N/A Traditional cash on cash: 3.2% Airbnb Rental Income: $null Traditional Rental Income: $2333 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.67% Airbnb Rental Income: $null Traditional Rental Income: $3037 Airbnb ROI: N/A 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.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.25% Airbnb Rental Income: $null Traditional Rental Income: $2791 Airbnb ROI: N/A Traditional ROI: 6.25%
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.	$366,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.47% Airbnb Rental Income: $null Traditional Rental Income: $2656 Airbnb ROI: N/A Traditional ROI: 5.47%
2581 Brockway Rd Winston, OR Open House 5/30 2-5pm New listing! This beautifully crafted new construction home offers 2...	3 beds \| 2 baths \| 2,576 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.35% Airbnb Rental Income: $null Traditional Rental Income: $3684 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $3656 Airbnb ROI: N/A 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.	$255,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.16% Airbnb Rental Income: $null Traditional Rental Income: $1806 Airbnb ROI: N/A Traditional ROI: 5.16%
572 Dillard Gardens Rd Winston, OR 572 Dillard Gardens Rd, Winston, OR 97496 \| Single Family Residential	2 beds \| 2 baths \| 1,440 sq.ft.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.25% Airbnb Rental Income: $null Traditional Rental Income: $2120 Airbnb ROI: N/A Traditional ROI: 2.25%
265 SE Logan St Winston, OR Welcome to Rolling Meadows Estates, Winston's newest neighborhood community where quality ...	3 beds \| 2 baths \| 1,555 sq.ft.	$409,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $2749 Airbnb ROI: N/A Traditional ROI: 5.26%
10 SW Peach Ln Winston, OR 10 SW Peach Ln, Winston, OR 97496 \| Single Family Residential	3 beds \| 1 baths \| 1,440 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $1869 Airbnb ROI: N/A Traditional ROI: 3.22%
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.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.74% Airbnb Rental Income: $null Traditional Rental Income: $2292 Airbnb ROI: N/A Traditional ROI: 2.74%
509 NW Elwood Dr Winston, OR 509 NW Elwood Dr, Winston, OR 97496 \| Single Family Residential	3 beds \| 1 baths \| 960 sq.ft.	$268,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 5.19%
150 SW Brantley Dr Winston, OR 150 SW Brantley Dr, Winston, OR 97496 \| Single Family Residential	4 beds \| 3 baths \| 2,270 sq.ft.	$369,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.75% Airbnb Rental Income: $null Traditional Rental Income: $3456 Airbnb ROI: N/A Traditional ROI: 7.75%
675 SE Brush Ct Winston, OR 675 SE Brush Ct, Winston, OR 97496 \| Single Family Residential	3 beds \| 2 baths \| 1,498 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $2496 Airbnb ROI: N/A Traditional ROI: 4.46%
535 SE Parkway Dr Winston, OR 535 SE Parkway Dr, Winston, OR 97496 \| Single Family Residential	3 beds \| 2 baths \| 1,442 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $2200 Airbnb ROI: N/A Traditional ROI: 3.15%
351 SE Darrell Ave Winston, OR 351 SE Darrell Ave, Winston, OR 97496 \| Single Family Residential	3 beds \| 1 baths \| 960 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $1789 Airbnb ROI: N/A Traditional ROI: 3.85%
261 SE Darrell Ave Winston, OR 261 SE Darrell Ave, Winston, OR 97496 \| Single Family Residential	2 beds \| 1 baths \| 1,080 sq.ft.	$285,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $1767 Airbnb ROI: N/A Traditional ROI: 4.27%
117 NW Romayo Ct Winston, OR 117 NW Romayo Ct, Winston, OR 97496 \| Single Family Residential	3 beds \| 2 baths \| 1,426 sq.ft.	$387,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.65% Airbnb Rental Income: $null Traditional Rental Income: $2133 Airbnb ROI: N/A Traditional ROI: 3.65%
104 Kenya Ct Winston, OR 104 Kenya Ct, Winston, OR 97496 \| Single Family Residential	3 beds \| 2 baths \| 1,800 sq.ft.	$487,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.32% Airbnb Rental Income: $null Traditional Rental Income: $2500 Airbnb ROI: N/A Traditional ROI: 3.32%

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: N/A

Traditional cash on cash: 8.91%

Airbnb Rental Income: $null

Traditional Rental Income: $1913

Airbnb ROI: N/A

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: N/A

Traditional cash on cash: 4.89%

Airbnb Rental Income: $null

Traditional Rental Income: $3272

Airbnb ROI: N/A

Traditional ROI: 4.89%

340 NW Elizabeth Ave

Winston, OR

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

$315,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2708

Airbnb ROI: N/A

Traditional ROI: 6.3%

340 SE Darrell Ave

Winston, OR

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

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.57%

Airbnb Rental Income: $null

Traditional Rental Income: $1723

Airbnb ROI: N/A

Traditional ROI: 4.57%

623 SE Garden Way Dr

Winston, OR

3 beds | 2 baths | 1,680 sq.ft.

$409,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.62%

Airbnb Rental Income: $null

Traditional Rental Income: $2221

Airbnb ROI: N/A

Traditional ROI: 3.62%

185 SE Lebleu Ln

Winston, OR

3 beds | 2 baths | 1,257 sq.ft.

$339,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2372

Airbnb ROI: N/A