381 Gregory Dr

Winston, OR 97496

$230,000
Price
2
Beds
1,323 Sq. Ft.
$174 / Sq. Ft.
1,323
Sq. Ft.
$174
per Sq. Ft.
a front view of a house with a garden and trees
a front view of a house with yard and green space
a front view of house with yard and trees
a view of a field with trees
a view of a house with a yard
a view of a house with a yard
a large bedroom with a bed and wooden floor
a room with lots of wooden furniture and a window
a kitchen with stainless steel appliances a refrigerator and a sink
a view of a room with window
a room with a door open and a microwave
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a view of a room with an empty space
a view of a livingroom with a staircase
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a bedroom with a bed and a dresser
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a view of empty room

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!...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!
  1. Listed by Nile Stark • RE/MAX Integrity • 541-345-8100

Property Details for 381 Gregory Drive

Style
Stories1, Ranch
Parking Features
Driveway
Garage Spaces
.00
Parking Total
.00
LISTING UPDATED: 02/03/2026 02:50 PM

Property Details for 381 Gregory Drive

StatusActive
MLS #518442030
Days on Market3
Taxes$3,081 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1948
Lot Size0.61 AC / 26,571 SF
CountyDouglas County

Location

Listing Courtesy of RE/MAX Integrity
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Building Information for 381 Gregory Drive

Stories1Year Built1948Building Size-Lot Size0.61 AC / 26,571 SF

Payment Calculator

$1,378 per month

30 year fixed, 6.15% Interest

Principal and Interest

$1,121

Property Taxes

$257

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 381 Gregory Drive

Summary
Location and General Information
  • Country: US
  • Directions: Main St to SE Edwards St, Right on SE Gregory
  • Road Surface: Paved
School Information
  • Elementary School: Mc Govern
  • High School: Douglas
  • Middle Or Junior School: Winston
Taxes and HOA
  • Tax Year: 2025
  • Tax Annual Amount: $3,080.84
  • Parcel Number: R53183
  • Tax Legal Description: SUKSDORF COOS JUNCT ORCH SUB, BLOCK 2, LOT PT 14, ACRES 0.61
Property
Lot Information
  • Acres: 0.61
  • Lot Size Square Feet: 26571.0
  • Lot Size Range: Sq Ft20000to Acres1
  • Lot Size: 20,000 Sq Ft to .99 Acres
  • SqFt Source: County
Property and Assessments
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Water Description: Public Water
  • Property Condition: Fixer
  • Year Built: 1948
Utilities
  • Fuel Description: Electricity, Gas
  • Heating Description: Wall Furnace, Wood Stove
  • Hot Water Description: Gas
  • Sewer Description: Public Sewer
Interior and Exterior Features
Exterior Features
  • Exterior Description: Lap Siding
  • Roof Type: Composition
Interior Features
  • Basement: Crawl Space
  • Foundation Details: Concrete Perimeter
  • Fireplace Description: Insert, Wood Burning
  • Fireplaces Total: 1
  • SqFt Calculated: 1323
  • SqFt Lower Level Total: 0
  • SqFt Main Level Total: 0
  • SqFt Upper Level Total: 1323
  • Bedrooms Total: 2
  • Stories: 1
  • Baths Total: 1.0
Master Bedroom
  • Room Description: Primary Bedroom
  • Primary Bedroom Level: Main
Bedroom 2
  • Room Description: _2nd Bedroom
  • Bedroom 2 Level: Main
Dining Room
  • Room Description: Dining Room
  • Dining Room Level: Main
Family Room
  • Room Description: Family Room
Kitchen
  • Room Description: Kitchen
  • Kitchen Room Level: Main
Living Room
  • Room Description: Living Room
  • Living Room Level: Main
Baths
  • Baths Lower Level Full: 0
  • Baths Lower Level Partial: 0
  • Baths Lower Level Total: 0.0
  • Baths Main Level Full: 1
  • BathsMainLevelPartial: 0
  • Baths Main Level Total: 1.0
  • Bathrooms Full: 1
  • Baths Partial: 0
  • Total Bathrooms: 1
  • Baths Upper Leve lFull: 0
  • Baths Upper Level Partial: 0
  • Baths Upper Level Total: 0.0
Multi Family
Multi-Family Information
  • SqFt Approximate Building Total: 1323

Public Records for 381 Gregory Drive

Taxable ValueLand-Additions-Total-
Tax Record2024$2,006 ($167 / month)
Home Facts
Beds2Total Finished SqFt1,323 SqFtAbove Grade Finished SqFt1,323 SqFtStories1Lot Size26,572 SqFtStyleSingle Family ResidenceYear Built1948CountyDOUGLASAPN28-06W-21DB-03700Fireplace TypeHas Fireplace

Schools near 381 Gregory Drive

This home is within Winston-Dillard School District 116.
Rating
School
Type
Grades
Distance
Mcgovern Elementary School
Public - 3 to 5
Winston Middle School
Public - 6 to 8
Douglas High School
Public - 9 to 12
Dillard Alternative High School
Public - 9 to 12
Rating
School
Distance
Mcgovern Elementary School
Public3 to 5

Winston Middle School
Public6 to 8

Douglas High School
Public9 to 12

Dillard Alternative High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 381 Gregory Drive, Winston, OR 97496

381 Gregory Drive is a single family home for sale in Winston, OR 97496. This property was listed for sale on February 3, 2026 by RE/MAX Integrity, it's currently listed at $230,000. This listing's school district is Winston-Dillard School District 116. Nearby schools include Mcgovern Elementary School, Winston Middle School and Douglas High School. 381 Gregory Drive is a 2-bed, 1-bath, 1,323 sqft single family home built in 1948.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX Integrity

All information provided is deemed reliable but is not guaranteed and should be independently verified. 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 brokerage firms other than Compass are marked with the RMLS logo and detailed information about these properties includes the names of the listing brokers. Copyright © 2026 RMLS, Portland, Oregon. Last updated: 02/03/2026 02:50 PM