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Denny Osborn, Broker
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(541) 771-1578
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411 Woodland Dr, Winston, OR 97496

$685,000

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Property 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.

411 Woodland Dr | MLS# 289799981

This single family home located at 411 Woodland Dr, Winston, OR 97496 is currently listed for sale with an asking price of $685,000. This property was built in 1968 and has 4 bedrooms and 2 full baths with 2240 sq. ft. Search Winston real estate on dennyosborn.bendpremierrealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Daylight
Cooling: Heat Pump
Fenced: Yes
Fireplaces: 2
Fuel Type: Electricity, Propane
Garage: 2
Heating: Heat Pump
Home Style: Daylight Ranch
Lot Size: 6.32 Acres
Roof Type: Composition
Stories: 2.0
Taxes: $2,448
Year Built: 1968
Square Feet: 2,240

Feature Descriptions

Bathroom: 1.0 (Lower), 1.0 (Main)
Body of Water: Lookingglass Creek
Days on Site: 221
Exterior: T-111 Siding
Exterior: Barn, Cross Fenced, Deck, Dog Run, Fenced, Free-Standing Hot Tub, Garden, Greenhouse, Outbuilding, Porch, Private Road, Raised Beds, RV Hookup, RV-Boat Storage, Tool Shed, Workshop
Fireplace: Pellet Stove, Stove, Wood Burning
Hot Tub: Yes
Hot Water: Propane
Interior: Ceiling Fan(s), High Speed Internet, Laundry, Vinyl Floor, Wall to Wall Carpet, Washer-Dryer
Kitchen: Dishwasher, Disposal, Free-Standing Range, Free-Standing Refrigerator, Microwave
Lot: Gentle Sloping, Level, Pasture, Private, Private Road
Parking Notes: Detached, ParkingPad, RVAccessParking
Sewer: Septic Tank, Standard Septic
Special View Info: Mountain, Vineyard
Square Footage: 1120 (Lower), 1120 (Main)
Water: Public Water
Waterfront: Creek

Local Schools

High School: Douglas
Middle School: Winston
Elementary School: Brockway

Listed By / Shown By

Listed By

Agency Name: RE/MAX Integrity
Agency Phone: 541-673-3272

Shown By

Agent Name: Denny Osborn, Broker
Agent Phone: (541) 771-1578
Agency Title: Bend Premier Real Estate

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Estimated Payment

$ 3,867.52 per month $3,463.73 Principal & Interest $204.00 Property Tax $199.79 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/10/2026. The listing information on this page last changed on 06/10/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 06/10/2026 2:33:27 AM EST) or RMLS (last updated Wed 06/10/2026 1:50:27 AM EST) or COAR/MLSCO (last updated Wed 06/10/2026 1:31:20 AM EST). Real estate listings held by brokerage firms other than Bend Premier Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

The content relating to real estate for sale on this web site comes in part from the IDX program of the RMLS of Portland, Oregon. Real estate listings held by other brokerage firms are marked with the RMLS logo, and detailed information about these properties includes the names of the listing brokers. Listing content is copyright © 2026 RMLS, Portland, Oregon. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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