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
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%
51 SW Brantley Dr Winston, OR INVESTMENT PROPERTY OPPORTUNITY! Well-maintained 4-unit apartment building located in a qu...	6 beds \| N/A baths \| N/A	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 4.67%
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%
600 SE Edgewood St Winston, OR This 1970 manufactured home sits on a spacious 0.43-acre lot, offering plenty of room to e...	2 beds \| 1 baths \| 800 sq.ft.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.98% Airbnb Rental Income: $null Traditional Rental Income: $1810 Airbnb ROI: N/A Traditional ROI: 8.98%
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%
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.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.49% Airbnb Rental Income: $null Traditional Rental Income: $2129 Airbnb ROI: N/A Traditional ROI: 8.49%
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%
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.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.51% Airbnb Rental Income: $null Traditional Rental Income: $2817 Airbnb ROI: N/A Traditional ROI: 4.51%
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%
1941 Byron Creek Rd Winston, OR 1941 Byron Creek Rd, Winston, OR 97496 \| Manufactured Home	2 beds \| 2 baths \| 1,764 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.52% Airbnb Rental Income: $null Traditional Rental Income: $2074 Airbnb ROI: N/A Traditional ROI: 2.52%
80 NW Lost Ln Winston, OR 80 NW Lost Ln, Winston, OR 97496 \| Manufactured Home	4 beds \| 2 baths \| 1,992 sq.ft.	$2,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.63% Airbnb Rental Income: $null Traditional Rental Income: $2568 Airbnb ROI: N/A Traditional ROI: -0.63%
740 Ireland Rd Winston, OR 740 Ireland Rd, Winston, OR 97496 \| Other	N/A beds \| N/A baths \| N/A	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.17% Airbnb Rental Income: $null Traditional Rental Income: $685 Airbnb ROI: N/A Traditional ROI: 1.17%
0 SW Main St Winston, OR 0 SW Main St, Winston, OR 97496 \| Other	N/A beds \| N/A baths \| N/A	$224,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.7% Airbnb Rental Income: $null Traditional Rental Income: $659 Airbnb ROI: N/A Traditional ROI: 0.7%
0 Wil Way Winston, OR 0 Wil Way, Winston, OR 97496 \| Other	N/A beds \| N/A baths \| N/A	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $685 Airbnb ROI: N/A Traditional ROI: 1.4%
0 Willis Creek Rd Winston, OR 0 Willis Creek Rd, Winston, OR 97496 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.19% Airbnb Rental Income: $null Traditional Rental Income: $685 Airbnb ROI: N/A Traditional ROI: 4.19%
0 E Willis Creek Rd Winston, OR 0 E Willis Creek Rd, Winston, OR 97496 \| Other	N/A beds \| N/A baths \| N/A	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.56% Airbnb Rental Income: $null Traditional Rental Income: $685 Airbnb ROI: N/A Traditional ROI: 0.56%
350 View Point Ter Winston, OR 350 View Point Ter, Winston, OR 97496 \| Other	N/A beds \| N/A baths \| N/A	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.89% Airbnb Rental Income: $null Traditional Rental Income: $685 Airbnb ROI: N/A Traditional ROI: -0.89%
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%
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.	$174,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.05% Airbnb Rental Income: $null Traditional Rental Income: $2278 Airbnb ROI: N/A Traditional ROI: 11.05%
101 NE Darrell Ave Winston, OR 101 NE Darrell Ave, Winston, OR 97496 \| Manufactured Home	2 beds \| 1 baths \| 784 sq.ft.	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.59% Airbnb Rental Income: $null Traditional Rental Income: $1439 Airbnb ROI: N/A Traditional ROI: 6.59%
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%
Willis Creek Rd Winston, OR Willis Creek Rd, Winston, OR 97496 \| Other	N/A beds \| N/A baths \| N/A	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.51% Airbnb Rental Income: $null Traditional Rental Income: $783 Airbnb ROI: N/A Traditional ROI: 1.51%
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%

Real Estate investment in Winston, OR

There are 55 properties for sale in the city of Winston . The median list price in Winston is $320,808 and the average price per square foot is $191. In September 2026, the average monthly cash on cash return in Winston is 5.00%. The average monthly rental income in Winston is $2,221.

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

There are 55 investment properties available for sale in Winston.

The ROI for Short-Term is higher than the Long-Term in Winston with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property 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%

51 SW Brantley Dr

Winston, OR

6 beds | N/A baths | N/A

$485,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.67%

Airbnb Rental Income: $null

Traditional Rental Income: $3172

Airbnb ROI: N/A

Traditional ROI: 4.67%

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