# 339 PIONEER Way, Winchester, OR 97495 > **TL;DR:** 3bd/3ba single family, $429,000 ($207/sqft), built 1977, 2,072 sqft. > View, A/C, 1-car garage. Est. $2,294/mo. Listed 105 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $429,000 | | Price/sqft | $207 | | Bedrooms | 3 | | Bathrooms | 2 full, 1 half | | Square Feet | 2,072 | | Year Built | 1977 | | Lot Size | 10,890 sqft (0.25 acres) | | Stories | 1 | | Garage | 1-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 105 | ## Why This Home Stands Out - **Views** - Valley, Territorial ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,169 | | Estimated Insurance | $125 | | **Total** | **$2,294** | ## Nearby Schools - **Elementary:** Winchester - **Middle:** Joseph Lane - **High:** Roseburg ## Key Amenities - View - A/C - 1-car garage ## Property Highlights - Built in 1977 - 0.25 acre lot ## Description ### Agent Description Welcome to this beautifully updated residence in one of Winchester's sought-after neighborhoods. Nestled on a quiet, dead-end street with a welcoming atmosphere, this home offers the perfect blend of comfort, style, and convenience. Filled with natural light from expansive windows, the thoughtfully designed floor plan features 3 spacious bedrooms, including a luxurious primary suite with a stunning walk-in closet complete with custom built-in storage and a dedicated vanity. Quartz countertops, tiled showers, and tasteful updates throughout create a fresh, modern feel. Designed for today's lifestyle, the home also offers a versatile bonus room with French doors-ideal as a home office or potential 4th bedroom. Plus an additional flex space - perfect for a family room, game room, or media room. The well-appointed kitchen features abundant cabinetry and two pantry/storage closets. The layout of the home and living spaces, make entertaining effortless. Additional storage includes a coat closet, oversized linen closet, utility/storage room, and generous cabinetry in the laundry room. Step outside to enjoy the spacious front and backyard, offering plenty of room for gatherings, play, or simply relaxing. The garage features an epoxy-coated floor, and the attached shop provides additional workspace with a bank of cabinets or the potential to convert into a covered carport. Large driveway that can easily fit 6 vehicles. Ideal location--less than five minutes from I-5, approx 10 minutes to Umpqua Community College, and less than 1 mile from the beautiful North Umpqua River, where swimming, rafting, kayaking, and fishing can be enjoyed all summer long. If you have been searching for a move-in-ready home in a peaceful, established neighborhood with room to entertain and an unbeatable location, this Winchester gem is one you won't want to miss! Motivated sellers - please bring ALL offers! Agent is owner. ## Location - **Address:** 339 PIONEER Way, Winchester, OR 97495 - **County:** Douglas - **Neighborhood:** RY WINCHESTER AREA (NON-RIVER) - **Coordinates:** 43.283859, -123.35009 - **Google Maps:** https://www.google.com/maps?q=43.283859,-123.35009 ## Listing Agent - **Name:** Amanda Legaspino - **Brokerage:** EXP REALTY LLC - **Broker Phone:** (888) 814-9613 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/339-Pioneer-Way_Winchester_OR_97495_M14106-36238?f=listhub&s=RMLSOR&m=176433898&c=propsimple) ## Photos ![339 PIONEER Way - Photo 1](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f2442573734r.jpg) ![339 PIONEER Way - Photo 2](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f1388441053r.jpg) ![339 PIONEER Way - Photo 3](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f2393340752r.jpg) ![339 PIONEER Way - Photo 4](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f439679717r.jpg) ![339 PIONEER Way - Photo 5](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f1979002862r.jpg) ![339 PIONEER Way - Photo 6](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f1126201289r.jpg) ![339 PIONEER Way - Photo 7](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f3604187774r.jpg) ![339 PIONEER Way - Photo 8](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f3536595539r.jpg) ![339 PIONEER Way - Photo 9](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f1284155246r.jpg) ![339 PIONEER Way - Photo 10](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f2014513303r.jpg) ![339 PIONEER Way - Photo 11](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f2152900500r.jpg) ![339 PIONEER Way - Photo 12](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f2430174097r.jpg) ![339 PIONEER Way - Photo 13](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f3607296380r.jpg) ![339 PIONEER Way - Photo 14](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f460243786r.jpg) ![339 PIONEER Way - Photo 15](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f1421285447r.jpg) ![339 PIONEER Way - Photo 16](http://lh.rdcpix.com/be8edc6a194c4c2ed1566a97831696e7l-f321923396r.jpg) --- **MLS#:** 176433898 | **Updated:** 2026-10-31 **Source:** listhub *Copyright © 2026 Regional Multiple Listing Services. 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/339-pioneer-way-winchester-or-97495-01c2fe31b47a4393b5e2f1c4a05f90e2) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/339-pioneer-way-winchester-or-97495-01c2fe31b47a4393b5e2f1c4a05f90e2#listing", "url": "https://www.propertysimple.ai/listing/339-pioneer-way-winchester-or-97495-01c2fe31b47a4393b5e2f1c4a05f90e2", "name": "339 PIONEER Way, Winchester, OR 97495", "description": "Welcome to this beautifully updated residence in one of Winchester's sought-after neighborhoods. Nestled on a quiet, dead-end street with a welcoming atmosphere, this home offers the perfect blend of comfort, style, and convenience. 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The garage features an epoxy-coated floor, and the attached shop provides additional workspace with a bank of cabinets or the potential to convert into a covered carport. Large driveway that can easily fit 6 vehicles. Ideal location--less than five minutes from I-5, approx 10 minutes to Umpqua Community College, and less than 1 mile from the beautiful North Umpqua River, where swimming, rafting, kayaking, and fishing can be enjoyed all summer long. If you have been searching for a move-in-ready home in a peaceful, established neighborhood with room to entertain and an unbeatable location, this Winchester gem is one you won't want to miss! Motivated sellers - please bring ALL offers! 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