# 5366 Pioneer Road, Medford, OR 97501 > **TL;DR:** 4bd/3ba single family, $535,000 ($258/sqft), built 1990, 2,071 sqft. > Fireplace, View, A/C, 2-car garage. Est. $2,861/mo. Listed 181 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $535,000 | | Price/sqft | $258 | | Bedrooms | 4 | | Bathrooms | 3 full | | Square Feet | 2,071 | | Year Built | 1990 | | Lot Size | 64,469 sqft (1.48 acres) | | Stories | 2 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 181 | ## Why This Home Stands Out - **Views** - Valley ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,705 | | Estimated Insurance | $156 | | **Total** | **$2,861** | ## Nearby Schools - **Elementary:** Phoenix Elem - **Middle:** Talent Middle - **High:** Phoenix High ## Key Amenities - Fireplace - View - A/C - 2-car garage ## Property Highlights - Built in 1990 - 1.48 acre lot - 2 stories - Fireplace ## Description ### Agent Description A little piece of country paradise in the heart of Southern Oregon! The main home offers 3 bedrooms, 2 full baths all on one level, with an upgraded kitchen and guest bath. But! Here's what makes this property extra special....A PRIVATE 1 BEDROOM, 1 FULL BATH APARTMENT sits above the oversized garage and has its OWN ENTRANCE! Possibilities: Rental Income Airbnb/short term rental potential Private Space for guests Multigenerational living Private home office or studio The county has lumped the square footage and # of bedrooms and baths combined together with the main house and the ADU(apartment) . Come take a look. You may just fall in love with the view! ## Location - **Address:** 5366 Pioneer Road, Medford, OR 97501 - **County:** Jackson - **Coordinates:** 42.272749, -122.884609 - **Google Maps:** https://www.google.com/maps?q=42.272749,-122.884609 ## Virtual Tour & Media - **Video Tour:** https://apex-video-tours.aryeo.com/sites/elvzyxbg/unbranded ## Listing Agent - **Name:** Janet L Lopez - **Brokerage:** Top Agents Real Estate Company - **Broker Phone:** (541) 227-6288 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/5366-Pioneer-Rd_Medford_OR_97501_M21517-70817?f=listhub&s=ODOR&m=220220969&c=propsimple) ## Photos ![5366 Pioneer Road - Photo 1](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3535200491r.jpg) ![5366 Pioneer Road - Photo 2](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f1119356889r.jpg) ![5366 Pioneer Road - Photo 3](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3931076332r.jpg) ![5366 Pioneer Road - Photo 4](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f2561955329r.jpg) ![5366 Pioneer Road - Photo 5](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f2622727115r.jpg) ![5366 Pioneer Road - Photo 6](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3811580492r.jpg) ![5366 Pioneer Road - Photo 7](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3905650284r.jpg) ![5366 Pioneer Road - Photo 8](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f1270236503r.jpg) ![5366 Pioneer Road - Photo 9](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f2394044373r.jpg) ![5366 Pioneer Road - Photo 10](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f100377958r.jpg) ![5366 Pioneer Road - Photo 11](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3563394665r.jpg) ![5366 Pioneer Road - Photo 12](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3940314884r.jpg) ![5366 Pioneer Road - Photo 13](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3345886416r.jpg) ![5366 Pioneer Road - Photo 14](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f1338279879r.jpg) ![5366 Pioneer Road - Photo 15](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f1132811773r.jpg) ![5366 Pioneer Road - Photo 16](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3600762985r.jpg) ![5366 Pioneer Road - Photo 17](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f801685976r.jpg) ![5366 Pioneer Road - Photo 18](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f47246396r.jpg) ![5366 Pioneer Road - Photo 19](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f1686319949r.jpg) ![5366 Pioneer Road - Photo 20](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f1445729853r.jpg) ![5366 Pioneer Road - Photo 21](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f538513044r.jpg) ![5366 Pioneer Road - Photo 22](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3280858065r.jpg) ![5366 Pioneer Road - Photo 23](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f2607569117r.jpg) ![5366 Pioneer Road - Photo 24](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3441961190r.jpg) ![5366 Pioneer Road - Photo 25](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3815463316r.jpg) ![5366 Pioneer Road - Photo 26](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f1339920438r.jpg) ![5366 Pioneer Road - Photo 27](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f269438320r.jpg) ![5366 Pioneer Road - Photo 28](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f2576190889r.jpg) ![5366 Pioneer Road - Photo 29](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3214323437r.jpg) ![5366 Pioneer Road - Photo 30](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f573812655r.jpg) ![5366 Pioneer Road - Photo 31](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f222588717r.jpg) ![5366 Pioneer Road - Photo 32](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3241878345r.jpg) ![5366 Pioneer Road - Photo 33](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3424382626r.jpg) ![5366 Pioneer Road - Photo 34](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f564921633r.jpg) ![5366 Pioneer Road - Photo 35](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f3403156585r.jpg) ![5366 Pioneer Road - Photo 36](http://lh.rdcpix.com/a48a9318c6c3e60959045a1fe6efe93bl-f2990166535r.jpg) --- **MLS#:** 220220969 | **Updated:** 2026-10-27 **Source:** listhub *Copyright © 2026 Oregon Data Share. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/5366-pioneer-road-medford-or-97501-29f6ae2a8a8a4c178ea3739eef2bde3f) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/5366-pioneer-road-medford-or-97501-29f6ae2a8a8a4c178ea3739eef2bde3f#listing", "url": "https://www.propertysimple.ai/listing/5366-pioneer-road-medford-or-97501-29f6ae2a8a8a4c178ea3739eef2bde3f", "name": "5366 Pioneer Road, Medford, OR 97501", "description": "A little piece of country paradise in the heart of Southern Oregon! The main home offers 3 bedrooms, 2 full baths all on one level, with an upgraded kitchen and guest bath. But! 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