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 |
|---|---|---|---|
621 SE ROSE RIDGE DRWinston, ORWelcome to 621 SE Rose Ridge Dr in Winstonâs desirable Orchard View neighborhoodâa bea... |
3 beds | 2 baths | 1,620 sq.ft. |
$399,900 |
Airbnb cash on cash: N/A
|
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
|
310 NW LOST LNWinston, ORFreshly updated and move-in ready, this Winston home combines comfort, convenience, and ch... |
4 beds | 2 baths | 1,769 sq.ft. |
$319,900 |
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. |
$748,700 |
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. |
$220,000 |
Airbnb cash on cash: 1.91%
|
185 SE LEBLEU LNWinston, ORPrice Improved! Solid home in Winston with a newer roof. Welcome home to this well maintai... |
3 beds | 2 baths | 1,257 sq.ft. |
$339,000 |
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, ORThis gated, 8.52-acre property is fenced and cross-fenced, offering plenty of country livi... |
4 beds | 3 baths | 2,362 sq.ft. |
$734,000 |
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
|
700 SE TOKAY STWinston, ORWelcome to this inviting 3-bedroom, 2-bathroom home offering comfort, convenience, and mod... |
3 beds | 2 baths | 1,404 sq.ft. |
$375,000 |
Airbnb cash on cash: N/A
|
800 BYRON CREEK RDWinston, ORWelcome to this charming country home set on over 5 acres of flat, usable land with Firewi... |
3 beds | 3 baths | 1,320 sq.ft. |
$495,000 |
Airbnb cash on cash: N/A
|
180 TWIN OAKS LOOPWinston, ORProperty Listing: 180 Twin Oaks Loop, Winston, ORRenovated 3-Bedroom, 2-Bathroom Double Wi... |
3 beds | 2 baths | 1,404 sq.ft. |
$137,000 |
Airbnb cash on cash: N/A
|
150 WIL WAYWinston, ORNew Home by JW Construction Inc.This beautifully crafted 2,143 sq ft home offers 3 bedroom... |
3 beds | 3 baths | 1,999 sq.ft. |
$525,000 |
Airbnb cash on cash: N/A
|
160 WIL WAYWinston, ORNew Home by JW Construction Inc.This beautiful one-level home offers just over 2,000 squar... |
3 beds | 3 baths | 2,089 sq.ft. |
$525,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winston, OR
There are 16 properties for sale in the city of Winston . The median list price in Winston is $454,450 and the average price per square foot is $262. In October 2025, the average monthly cash on cash return in Winston is 5.00%. The average monthly rental income in Winston is $2,941.