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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
375 Porter Creek RdWinston, OREver 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
|
51 SW BRANTLEY DrWinston, ORINVESTMENT PROPERTY OPPORTUNITY! Well-maintained 4-unit apartment building located in a qu... |
3 beds | 3 baths | N/A |
$485,000 |
Airbnb cash on cash: -0.95%
|
0 Rice Creek RdWinston, ORIf 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%
|
71 SE RONALD StWinston, ORCharming 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
|
263 WIL WayWinston, ORWelcome 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%
|
340 NW ELIZABETH AveWinston, ORThis 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%
|
340 SE DARRELL AveWinston, ORSolid 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%
|
600 SE Edgewood StWinston, ORThis 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
|
1068 RICE CREEK RdWinston, ORSecurity 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
|
150 WIL WayWinston, OROpen 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%
|
160 WIL WayWinston, ORNew 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%
|
90 SE DARRELL AveWinston, ORThis 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
|
411 WOODLAND DrWinston, ORWhat 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
|
624 WILLIS CREEK RdWinston, ORThis 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: -0.23%
|
635 Wil WayWinston, OR635 Wil Way, Winston, OR 97496 | Single Family Residential |
4 beds | 3 baths | 3,072 sq.ft. |
$634,900 |
Airbnb cash on cash: N/A
|
1941 Byron Creek RdWinston, OR1941 Byron Creek Rd, Winston, OR 97496 | Manufactured Home |
2 beds | 2 baths | 1,764 sq.ft. |
$469,900 |
Airbnb cash on cash: N/A
|
80 NW Lost LnWinston, OR80 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
|
740 Ireland RdWinston, OR740 Ireland Rd, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$199,000 |
Airbnb cash on cash: N/A
|
0 SW Main StWinston, OR0 SW Main St, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$224,900 |
Airbnb cash on cash: N/A
|
0 Wil WayWinston, OR0 Wil Way, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$185,000 |
Airbnb cash on cash: N/A
|
0 Willis Creek RdWinston, OR0 Willis Creek Rd, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$99,000 |
Airbnb cash on cash: N/A
|
0 E Willis Creek RdWinston, OR0 E Willis Creek Rd, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$249,000 |
Airbnb cash on cash: N/A
|
350 View Point TerWinston, OR350 View Point Ter, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$590,000 |
Airbnb cash on cash: N/A
|
381 SE Gregory DrWinston, ORSeize 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
|
1580 WINSTON SECTION RdWinston, ORThis 3-bedroom, 2-bathroom "fixer upper" sits on a peaceful 0.18-acre corner lot, offering... |
3 beds | 2 baths | 1,188 sq.ft. |
$179,000 |
Airbnb cash on cash: 1.02%
|
101 NE Darrell AveWinston, OR101 NE Darrell Ave, Winston, OR 97496 | Manufactured Home |
2 beds | 1 baths | 784 sq.ft. |
$165,000 |
Airbnb cash on cash: N/A
|
6700 UPPER OLALLA RdWinston, ORStunning 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%
|
101 SW PEACH LnWinston, ORThis 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%
|
311 SE GRAPE AveWinston, ORGreat 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%
|
1349 Willis Creek RdWinston, OR1349 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%
|
380 NW Cary StWinston, OR380 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
|
Willis Creek RdWinston, ORWillis Creek Rd, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$220,000 |
Airbnb cash on cash: N/A
|
186 WOODDUCK StWinston, ORWell-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%
|
2581 BROCKWAY RdWinston, OROpen 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%
|
9114 Old Highway 99 SWinston, OR9114 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%
|
3707 Willis Creek RdWinston, OR3707 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
|
572 Dillard Gardens RdWinston, OR572 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
|
Berry Creek RdWinston, ORBerry Creek Rd, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$125,000 |
Airbnb cash on cash: N/A
|
10 SW Peach LnWinston, OR10 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%
|
330 WIL WayWinston, ORCustom-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
|
Real Estate investment in Winston, OR
There are 43 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 $186. In July 2026, the average monthly cash on cash return in Winston is 5.00%. The average monthly rental income in Winston is $2,216.