About 5293 Highway 66
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.
Features of 5293 Highway 66
| MLS® # | 220219782 |
|---|---|
| Price | $2,195,000 |
| Bedrooms | 4 |
| Bathrooms | 4.00 |
| Full Baths | 3 |
| Half Baths | 1 |
| Square Footage | 4,977 |
| Acres | 29.82 |
| Year Built | 2006 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Northwest |
| Status | Active |
Community Information
| Address | 5293 Highway 66 |
|---|---|
| Subdivision | N/A |
| City | Ashland |
| County | Jackson |
| State | OR |
| Zip Code | 97520 |
Amenities
| Parking | Attached, Driveway, Garage Door Opener, Gated, Gravel, RV Access/Parking, Storage |
|---|---|
| # of Garages | 2 |
| View | Creek/Stream, Mountain(s), Panoramic, Territorial |
| Is Waterfront | Yes |
| Waterfront | Pond, Creek |
Interior
| Interior Features | Built-in Features, Granite Counters, Kitchen Island, Linen Closet, Pantry, Shower/Tub Combo, Soaking Tub, Tile Shower |
|---|---|
| Appliances | Dishwasher, Disposal, Dryer, Microwave, Oven, Refrigerator, Washer, Water Heater |
| Heating | Fireplace(s), Electric, Heat Pump, Propane, Radiant, Zoned |
| Cooling | Heat Pump, Zoned |
| Fireplace | No |
| Fireplaces | Living Room, Propane |
| Stories | Two |
| Basement | Daylight, Finished |
Exterior
| Exterior Features | Spa/Hot Tub |
|---|---|
| Lot Description | Fenced, Landscaped, Pasture, Water Feature |
| Windows | Double Pane Windows, Skylight(s), Wood Frames |
| Roof | Composition |
| Construction | Frame |
| Foundation | Block |
School Information
| Elementary | Bellview Elem |
|---|---|
| Middle | Ashland Middle |
| High | Ashland High |
Additional Information
| Date Listed | April 21st, 2026 |
|---|---|
| Days on Market | 92 |
| Zoning | EFU |
Listing Details
| Office | John L. Scott Medford |
|---|