Outside our home market
Ryan Realty works Central Oregon. Our brokers live in Bend and cover the towns around it, from Redmond and Sisters to Sunriver and La Pine. Ashland is outside that area. Our MLS feed is statewide, so this home and its price are live and current — what we cannot tell you is which street in Ashland is the one to buy on.
A broker who works Ashland every day will know it better than we do. Tell us what you need and we will introduce you to one we would use ourselves. No cost, no obligation.
This 4-bed, 3-bath home at 1395 Woodland Drive in Ashland is listed at $899,000. It has 3,127 square feet, sits on 0.3 acres, was built in 1932, and is in N/A. Status is Active, with 15 days on market.
Overview
Interior
Exterior & lot
Systems & utilities
Financial
Listing
There's something special about a home that gives you room to live a little bigger. Your mornings can start with coffee on the large porch with unobstructed views of Grizzly Peak, while evenings offer the same backdrop from the large sitting room on the main level. Built in 1932 and offering 3,127 SF on a .30-acre lot, this is a home with history, personality, and plenty of room for what comes next. The main house has 3 bedrooms and 1.5 baths, while a permitted 1/1 ADU on the lower level creates a separate space for guests, family, or rental income. Beyond the house, the oversized heated two-story garage and shop is a major part of what makes this property unique. There's room for serious projects, hobbies, gear, storage, and vehicles, plus dedicated off-street RV parking. Inside, the home hasn't been updated to look like every other house on the market--and that's part of the opportunity.
A rough estimate, not a quote. Loan amount $719,200 · $179,800 down · 30 year term.
Insurance starts at 0.35% of price each year. Type your quote to replace it.
sold in the last 90 days
Every active and pending listing of every property type on the regional MLS through Oregon Data Share in Ashland. The wash is sales density of closes in the last 90 days; homes for sale and pending stay as marks. Pulses and the sold count are the closes of the last 30 days. Counts and medians cover every listing read for this map. 14 of the 353 sit beyond the frame's edges: counted in every figure, not drawn.
| Date | Event | Price |
|---|---|---|
| Sep 30, 2026 | Listed | $899,000 |
| Year | Tax |
|---|---|
| 2025 | $8,552 |
Tax as filed on the listing. Jackson County. Parcel 10087907.
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Tour requests usually get a same-day reply.
Listing courtesy of John L Scott Ashland
Data last updated October 15, 2026
Based on information from Oregon Data Share. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listing information is for consumers personal, non-commercial use only.
