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 |
|---|---|---|---|
263 WIL WAYWinston, ORWelcome to Your Like-New Custom Home in Winston, OR!Step inside this beautifully crafted h... |
3 beds | 2 baths | 1,928 sq.ft. |
$489,900 |
Airbnb cash on cash: N/A
|
631 SE ROSE RIDGE DRWinston, ORThis is a gem! Single-level upgraded home built in 2020. This custom property combines qua... |
3 beds | 2 baths | 1,512 sq.ft. |
$429,000 |
Airbnb cash on cash: N/A
|
1470 E WILLIS CREEK RDWinston, ORBuild a second home? 3 tax lots. 80+5+5 acres each & one of the 5-acre lots is buildable! ... |
3 beds | 3 baths | 1,845 sq.ft. |
$749,000 |
Airbnb cash on cash: N/A
|
411 NW WOODLAND DRWinston, OREnd of road privacy in a quiet setting, this great two-story ranch-style home offers an un... |
4 beds | 2 baths | 2,240 sq.ft. |
$725,000 |
Airbnb cash on cash: N/A
|
751 SE MEADOWOOD DRWinston, OR1995 Double-wide manufactured home on a good sized lot in Winston. Not perfect but a lot o... |
2 beds | 2 baths | 1,120 sq.ft. |
$230,000 |
Airbnb cash on cash: 6.09%
|
185 SE LEBLEU LNWinston, OROPEN HOUSE: Sunday, 8/24 from 1:30-4pm. Solid 3 bed, 2 bath in Winston with a newer roof. ... |
3 beds | 2 baths | 1,257 sq.ft. |
$349,900 |
Airbnb cash on cash: N/A
|
231 NE DARRELL AVEWinston, ORGreat location with a custom built one level home located on .39 of an acre at the end of ... |
3 beds | 2 baths | 1,374 sq.ft. |
$325,000 |
Airbnb cash on cash: N/A
|
1068 RICE CREEK RDWinston, ORGated 8.5 acres country living, fenced X Fenced, beautiful ranch style updated home. Newer... |
4 beds | 3 baths | 2,362 sq.ft. |
$739,000 |
Airbnb cash on cash: N/A
|
1090 E WILLIS CREEK RDWinston, ORSecluded 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. |
$695,000 |
Airbnb cash on cash: N/A
|
13224 SE LOOKINGGLASS RDWinston, ORExperience the unique allure of this beautifully updated, original homestead farmhouse nes... |
4 beds | 2 baths | 2,534 sq.ft. |
$479,900 |
Airbnb cash on cash: N/A
|
431 NE DARLENE STWinston, ORThis 3-bedroom, 2-bathroom manufactured home on real property offers 1,620 sq. ft. of comf... |
3 beds | 2 baths | 1,620 sq.ft. |
$225,000 |
Airbnb cash on cash: N/A
|
128 WATUSI CTWinston, ORVery desirable single level home in Lookingglass Estates. Built in 2008 with great curb ap... |
3 beds | 2 baths | 1,832 sq.ft. |
$424,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winston, OR
There are 12 properties for sale in the city of Winston . The median list price in Winston is $429,000 and the average price per square foot is $251. In September 2025, the average monthly cash on cash return in Winston is 5.00%. The average monthly rental income in Winston is $3,257.