# 411 WOODLAND Dr, Winston, OR 97496 > **TL;DR:** 4bd/2ba single family, $669,000 ($299/sqft), built 1968, 2,240 sqft. > Waterfront, A/C, 2-car garage. Est. $3,578/mo. Listed 363 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $669,000 | | Price/sqft | $299 | | Bedrooms | 4 | | Bathrooms | 2 full | | Square Feet | 2,240 | | Year Built | 1968 | | Lot Size | 275,299 sqft (6.32 acres) | | Stories | 2 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 363 | ## Why This Home Stands Out - **Waterfront** - Waterfront location listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $3,383 | | Estimated Insurance | $195 | | **Total** | **$3,578** | ## Nearby Schools - **Elementary:** Brockway - **Middle:** Winston - **High:** Douglas ## Key Amenities - Waterfront - A/C - 2-car garage ## Property Highlights - Built in 1968 - 6.32 acre lot - 2 stories - Waterfront ## Description ### Agent Description What if your favorite getaway was home? Set above Lookingglass Creek with stunning views of Abacela Vineyard, this property offers the kind of lifestyle that's getting harder to find. Spend summer afternoons at your own swimming hole, grow fresh produce in the fenced garden and greenhouse, and enjoy the satisfaction of having water rights, irrigation, a K-line system, and pump already in place.The land is set up for living well and staying busy in all the best ways. A fantastic finished shop provides space for projects and hobbies, while the large carport with multiple storage rooms keeps equipment, toys, and tools organized. Covered RV parking with 50-amp service makes it easy to host visitors or keep your next adventure ready to roll.Whether you're raising kids who would rather explore a creek than stare at a screen, or you're looking for a property that supports gardening, traveling, creating, and enjoying the outdoors, this is a place that adapts to the way you want to live.Comfortable, functional, and surrounded by some of Douglas County's most beautiful scenery, this two-story ranch offers more than a home. It offers a reason to spend less time rushing and more time enjoying where you are. ## Location - **Address:** 411 WOODLAND Dr, Winston, OR 97496 - **County:** Douglas - **Coordinates:** 43.122315, -123.445518 - **Google Maps:** https://www.google.com/maps?q=43.122315,-123.445518 ## Listing Agent - **Name:** Nataly Mattox - **Brokerage:** RE/MAX Integrity - **Broker Phone:** (541) 673-3272 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/411-Woodland-Dr_Winston_OR_97496_M98735-42135?f=listhub&s=RMLSOR&m=289799981&c=propsimple) ## Photos ![411 WOODLAND Dr - Photo 1](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f4057255068r.jpg) ![411 WOODLAND Dr - Photo 2](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1588917851r.jpg) ![411 WOODLAND Dr - Photo 3](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f728612400r.jpg) ![411 WOODLAND Dr - Photo 4](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f982945626r.jpg) ![411 WOODLAND Dr - Photo 5](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1628351185r.jpg) ![411 WOODLAND Dr - Photo 6](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2548543635r.jpg) ![411 WOODLAND Dr - Photo 7](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3675960161r.jpg) ![411 WOODLAND Dr - Photo 8](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2809193755r.jpg) ![411 WOODLAND Dr - Photo 9](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2907800898r.jpg) ![411 WOODLAND Dr - Photo 10](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3994716204r.jpg) ![411 WOODLAND Dr - Photo 11](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1118189770r.jpg) ![411 WOODLAND Dr - Photo 12](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3805306258r.jpg) ![411 WOODLAND Dr - Photo 13](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f4050892419r.jpg) ![411 WOODLAND Dr - Photo 14](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f818756662r.jpg) ![411 WOODLAND Dr - Photo 15](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2939469908r.jpg) ![411 WOODLAND Dr - Photo 16](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f4218432953r.jpg) ![411 WOODLAND Dr - Photo 17](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2369569828r.jpg) ![411 WOODLAND Dr - Photo 18](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1934579345r.jpg) ![411 WOODLAND Dr - Photo 19](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3993296137r.jpg) ![411 WOODLAND Dr - Photo 20](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2015400849r.jpg) ![411 WOODLAND Dr - Photo 21](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1315396198r.jpg) ![411 WOODLAND Dr - Photo 22](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f565403721r.jpg) ![411 WOODLAND Dr - Photo 23](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2755079659r.jpg) ![411 WOODLAND Dr - Photo 24](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1584402839r.jpg) ![411 WOODLAND Dr - Photo 25](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f4097834389r.jpg) ![411 WOODLAND Dr - Photo 26](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f102643567r.jpg) ![411 WOODLAND Dr - Photo 27](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1463069207r.jpg) ![411 WOODLAND Dr - Photo 28](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3677501057r.jpg) ![411 WOODLAND Dr - Photo 29](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2119631385r.jpg) ![411 WOODLAND Dr - Photo 30](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1464001125r.jpg) ![411 WOODLAND Dr - Photo 31](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1375738875r.jpg) ![411 WOODLAND Dr - Photo 32](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f4038039309r.jpg) ![411 WOODLAND Dr - Photo 33](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f575414031r.jpg) ![411 WOODLAND Dr - Photo 34](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3681148102r.jpg) ![411 WOODLAND Dr - Photo 35](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1535793783r.jpg) ![411 WOODLAND Dr - Photo 36](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f227614620r.jpg) ![411 WOODLAND Dr - Photo 37](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1946178246r.jpg) ![411 WOODLAND Dr - Photo 38](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3658875139r.jpg) ![411 WOODLAND Dr - Photo 39](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2696759082r.jpg) ![411 WOODLAND Dr - Photo 40](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1484794422r.jpg) ![411 WOODLAND Dr - Photo 41](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f2688374154r.jpg) ![411 WOODLAND Dr - Photo 42](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3431804818r.jpg) ![411 WOODLAND Dr - Photo 43](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f3001673917r.jpg) ![411 WOODLAND Dr - Photo 44](http://lh.rdcpix.com/ef50a10b4c5e76dc595027ae0c68177el-f1064543811r.jpg) --- **MLS#:** 289799981 | **Updated:** 2026-10-26 **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/411-woodland-dr-winston-or-97496-2b03fcb7d6ab4d4f83dddf6be7ff8bb0) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/411-woodland-dr-winston-or-97496-2b03fcb7d6ab4d4f83dddf6be7ff8bb0#listing", "url": "https://www.propertysimple.ai/listing/411-woodland-dr-winston-or-97496-2b03fcb7d6ab4d4f83dddf6be7ff8bb0", "name": "411 WOODLAND Dr, Winston, OR 97496", "description": "What if your favorite getaway was home? Set above Lookingglass Creek with stunning views of Abacela Vineyard, this property offers the kind of lifestyle that's getting harder to find. 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