Real Estate Investment Properties for Sale in Winchester, OR
Looking for investment property in Winchester, OR with high ROI ?
Explore a variety of short-term homes & houses in Winchester, OR. Invest wisely with VRBO & Winchester, 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 Winchester, OR
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
251 MARTHA DrWinchester, ORThis beautiful custom home is located in one of Douglas County's premier neighborhoods and... |
4 beds | 2 baths | 2,964 sq.ft. |
$615,000 |
Airbnb cash on cash: N/A
|
280 VILLAGE DrWinchester, OR**For Sale: Charming 3 Bedroom, 2 Bath Home in Winchester, Oregon**Welcome home to this in... |
3 beds | 2 baths | 1,462 sq.ft. |
$399,900 |
Airbnb cash on cash: N/A
|
335 PAGE RdWinchester, ORBeautifully updated Winchester home with approximately $80K in recent upgrades, offering f... |
3 beds | 3 baths | 1,716 sq.ft. |
$489,000 |
Airbnb cash on cash: N/A
|
539 WILD FERN DrWinchester, ORTucked away in one of Douglas County's most desirable neighborhoods, this stunning 19th ce... |
4 beds | 3 baths | 3,774 sq.ft. |
$999,000 |
Airbnb cash on cash: N/A
|
411 OAK VALLEY LoopWinchester, ORWelcome to 411 Oak Valley Loop, a meticulously maintained custom home offering single-leve... |
3 beds | 3 baths | 2,361 sq.ft. |
$625,000 |
Airbnb cash on cash: N/A
|
147 WINGFOOT CtWinchester, ORLower taxes in the Winchester area, outside the city limits! Home is all on one level! Thi... |
3 beds | 2 baths | 1,820 sq.ft. |
$529,900 |
Airbnb cash on cash: N/A
|
260 VILLAGE DrWinchester, ORTop location in subdivision for view of the pond and greenbelt. Fenced with back deck. Com... |
3 beds | 2 baths | 1,427 sq.ft. |
$415,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winchester, OR
There are 7 properties for sale in the city of Winchester . The median list price in Winchester is $430,000 and the average price per square foot is $189. In September 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $3,451.