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381 SE Gregory Dr, Winston, OR 97496

$230,000

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Property Description

Seize this opportunity with this charming single-story 1948 ranch style home boasting 2 bedrooms, 1 bath, and about 1,323 sq ft of living space on a generous 0.61-acre lot. Surrounded by mature trees and offering a peaceful, rural-suburban feel in the heart of Douglas County. This mid-century gem features timeless details like a prominent brick chimney, large picture windows for natural light, horizontal siding, and a low-profile layout perfect for easy single-level living. Great potential awaits! Ideal for investors, renovators, or hands-on buyers looking to restore a classic Northwest ranch and add value in a community with easy access to Roseburg, outdoor recreation, and Southern Oregon's natural beauty. Priced for quick action-your blank-canvas project in a desirable area starts here!

381 SE Gregory Dr | MLS# 518442030

This single family home located at 381 SE Gregory Dr, Winston, OR 97496 is currently listed for sale with an asking price of $230,000. This property was built in 1948 and has 2 bedrooms and 1 full baths with 1323 sq. ft. Search Winston real estate on www.williamraven.realtor today.

Property Features

Property Type: Residential - Single Family
Basement: Crawl Space
Fireplaces: 1
Fuel Type: Electricity, Gas
Heating: Wall Furnace, Wood Stove
Home Style: 1 Story, Ranch
Lot Size: 0.61 Acres
Roof Type: Composition
Stories: 1.0
Taxes: $3,081
Year Built: 1948
Square Feet: 1,323

Feature Descriptions

Bathroom: 1.0 (Main)
Days on Site: 26
Exterior: Lap Siding
Fireplace: Insert, Wood Burning
Hot Water: Gas
Parking Notes: Driveway
Sewer: Public Sewer
Square Footage: 1323 (Upper)
Water: Public Water

Local Schools

High School: Douglas
Middle School: Winston
Elementary School: McGovern

Listed By / Shown By

Listed By

Agency Name: RE/MAX Integrity
Agency Contact: 541-345-8100

Shown By

Agent Name: William Raven Broker
Agent Phone: (541) 280-9701
Agency Title: Bend Premier Real Estate

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Estimated Payment

$ 1,486.84 per month $1,163.01 Principal & Interest $256.75 Property Tax $67.08 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 03/03/2026. The listing information on this page last changed on 03/03/2026. 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 Tue 03/03/2026 12:04:50 AM EST) or RMLS (last updated Mon 03/02/2026 11:58:17 PM EST) or COAR/MLSCO (last updated Tue 03/03/2026 12:01:16 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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