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Winston, OR Houses for Rent

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  • 120 Winston Section Rd, Winston, OR 97496
    120 Winston Section Rd, Winston, OR 97496
    120 Winston Section Rd, Winston, OR 97496
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    $2,495 Per Month

    • 5 Beds
    • 2 Baths
    • 2,560 Sq Ft
    • 6+ Bdrm Home Built 1895. Close In. With Pastures.

    120 Winston Section Rd, Winston, OR 97496

    A house with a history. 1895 Home with 5+ bedrooms and lots of charm. This home has been in the family for 50+ years. 5+ Bdrm home. Built in 1895. On the River. Close In. Bedrooms/Bonus: 2 Small bedrooms are in attic, three are on 2nd floor. There are three "extra" rooms on first floor that have been used in the past as an office, music room, master bedroom, playroom,

    120 Winston Section Rd, Winston, OR 97496
  • 184 SE Gregory Dr, Winston, OR 97496
    184 SE Gregory Dr, Winston, OR 97496
    184 SE Gregory Dr, Winston, OR 97496
    /12

    $1,100 Per Month

    • 2 Beds
    • 1 Bath
    • 927 Sq Ft
    • 2 Bd 1 bath remodeled duplex w/Garage in Winston

    184 SE Gregory Dr, Winston, OR 97496

    Centrally located, and tucked away in a cul-de-sac, this 2 bd 1 bath duplex has a garage and a small private partially fenced back yard. Electric baseboard heat, FS range, and fridge included. Built in microwave above range. Laundry room with washer/dryer hook ups. Newer carpet throughout. Sewer & Garbage paid.Rental Terms:• 6 month lease required• No pets • Renter’s

    184 SE Gregory Dr, Winston, OR 97496
  • 8741 Old Hwy 99 S, Winston, OR 97496
    8741 Old Hwy 99 S, Winston, OR 97496
    8741 Old Hwy 99 S, Winston, OR 97496
    /27

    $2,095 Per Month

    • 3 Beds
    • 2 Baths
    • 1,839 Sq Ft
    • House for Rent

    8741 Old Hwy 99 S, Winston, OR 97496

    Beautiful 3 bedroom, 2 bathroom home offering 1,839 sq ft of living space with gorgeous field and mountain views. Conveniently located right off Old Highway 99 with easy access to Winston and surrounding areas.This spacious home features hardwood floors, a large living room, cozy wood stove/fireplace, and abundant built-in storage throughout. The kitchen offers extensive cabinet space and

    8741 Old Hwy 99 S, Winston, OR 97496
Oregon Douglas County Winston

Houses for Rent in Winston, OR

Frequently Asked Questions

How much does it cost to rent a single-family home in Winston, OR?
The median rent for a single-family home in Winston, OR is $1,798 per month, though prices vary by neighborhood, size, and property type. As of June 2026, single-family homes tend to be the most affordable option while condos are currently more expensive.
How much do you need to make to afford rent in Winston, OR?
To comfortably afford the median rent in Winston, OR, a household needs to earn roughly $83,800 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,095 per month in Winston, OR, renters typically need to show $6,285 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winston, OR?
In Winston, OR, the price-to-rent ratio is 12.7, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Home Trends in Winston, OR

There are currently 3 single-family homes available for rent in Winston, OR. The median rent is $1,798 per month, with 5-bedroom houses at $2,495.

Rental Home Trends

Number of Houses for Rent
3
Median Single Family Home Rent
$1,798
Median 5 Bedroom Single Family Home Rent
$2,495
How to Rent a Home

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