3 BD · 3 BA · 2,934 SF · 5.75 AC
5597 Highway 66
Ashland, OR 97520
$880,000
Ashland, OR 97520 · N/A
MLS# 220227806 · Active
Just steps from historic Lithia Park, this special property sits in one of Ashland's most desirable neighborhoods. Offering over 3,000 sq ft on .63 acres, this private home blends timeless character, mid-century charm and flexibility. The main level features two bedrooms, a full bath, an oversized living room with wood-burning fireplace, kitchen and dining area. The lower level offers a den with adjoining bonus room-ideal as an office, gym, media room or studio-plus laundry and a brand-new full bath with tile floors and shower. A separate, self-contained living space has its own living room, full kitchen, full bath and bedroom-ideal for guests, extended family, or potential ADU use. Recent upgrades include a new roof (2026), ducted HVAC heat-pump system, and a mini-split for the additional living space, all within two years. Outside, enjoy privacy, decks, lawn, water feature, circular driveway and carport with storage, plus easy access to Ashland's world class trail system. Tour today!
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| Date | Event | Price |
|---|---|---|
| Sep 22, 2026 | Price cut−$15,000 (1.7%) | $880,000 |
| Aug 27, 2026 | Listed for sale | $895,000 |
From the MLS: original list price and latest price change. 40 days on market.
Approx. Straight-line distance × 1.3 for roads, at in-town and highway speeds. No traffic, snow, or Hwy 97 construction. Ask Cody about real commute times.
42.1921° N · 122.7210° W
DirectionsAssignments come from the listing broker and boundaries change. Verify with the school district before you count on them.
$5,389/mo
$704,000 loan · 30 yr fixed · 6.5%
Loan term
Estimate only. Taxes use the listing's reported amount when there is one; insurance is approximated. A lender can give you an exact number.
3 BD · 3 BA · 2,934 SF · 5.75 AC
5597 Highway 66
Ashland, OR 97520
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Listing information provided by Oregon Data Share. Data last updated Oct 7, 2026, 10:30 AM.
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