The median home in Winchester, Oregon is valued at $492,488, up 1.6% year over year. Winchester is part of the Roseburg, OR metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

See the full metro analysis: Roseburg, OR stress score, crash risk, and 12-month forecast →

Home Value$492,488

+1.6%

AFFORDABILITY

Enter your income for Winchester.

Income (annual)

Down Payment

$98,498 on $492,488

Out of reach — 47.8% of income

Need $128,057/yr to afford.

PITI$2,988

P/I47.8%

Afford$288K

Gap-$204K

P&I $2,490Tax $398Ins $100

6.50% 30yr, 20% down, county tax + OR ins. 28% per HUD.

Home Buying Kit For Dummies (2025)Financing, negotiation, closing

Other cities in Oregon

Compare Winchester with other housing markets across Oregon.

Powell Butte$986K Arch Cape$885K Raleigh Hills$882K Cannon Beach$871K Lake Oswego$853K Manzanita$803K Durham$779K Sisters$774K

Full Roseburg, OR analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Roseburg, OR metro.

View Roseburg, OR metro →

WINCHESTER, OR