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$775,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 2,978 Sq. Ft.
  • Updated 14 hours ago
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Step back in time without sacrificing modern convenience in this breathtaking 1910 Craftsman home. Nestled among lush orchards & located directly next door to the iconic Brosi Farmstand & Bakery, this estate offers a lifestyle defined by heritage, craftsmanship, & natural beauty. Every inch of this well-maintained home celebrates the Craftsman era, featuring original woodwork, hardwood floors, hand-troweled ceilings, & period light fixtures. The grand entrance features front sitting rooms on both sides, one with a fireplace. Off the hallway is a cozy library/TV room with a fireplace & charming window seat. Choose between the formal dining room for elegant gatherings or the secondary sunlit dining space for casual mornings. The spacious kitchen features a center island & flows into the laundry room equipped with folding station, sink, & outdoor access. The home offers 4 bedrooms & 2 bathrooms, including a primary bedroom with its own fireplace. Upstairs has a large open landing that leads to a secondary sitting room with private balcony overlooking the front yard & orchards. There's a dedicated office with serene mountain & orchard views. The grounds are designed for both utility & grand-scale entertaining with a historic barn repurposed for weddings, parties, or a gallery. The 3-car garage & ADU includes an attached guest suite, perfect for a high-end Airbnb or multi-generational living. Also included are a large garden shed, storage shed, & woodshed. A circle drive provides ample parking, with gated entrances (one automatic) for secure backyard access. Landscaping includes a built-in sprinkler system & features flower gardens, a tranquil fountain, grape arbor, & boasts 2 apple, 2 cherry, & 1 walnut tree. Relax on the spacious front porch or enjoy the screened-in back porch for bug-free summer evenings. Experience the legacy of one of the area's most distinguished historical homes-offering all the charm of the past without the restrictions of a historical registry.

Full Property Details for 500 Winston Section Rd

General

  • Price: $775,000
  • Taxes: $4,087 (2025)
  • Status: Active
  • Type: Single Family
  • Source: RWMLS
  • MLS ID: 668322333
  • Updated: 4/30/2026
  • Added to Site: 1 day(s) ago

Interior

  • Interior Features: Garage Door Opener, Hardwood Floors, High Ceilings, Laundry, Separate Living Quarters/Apartment/Aux Living Unit, Vinyl Floor, Wall to Wall Carpet, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Fireplace(s): Gas, Wood Burning
  • Appliances: Dishwasher, Disposal, Free-Standing Gas Range, Free-Standing Refrigerator, Instant Hot Water, Island, Range Hood, Stainless Steel Appliance(s)

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Upper - Full Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Upper
  • Bedroom 2: Upper
  • Bedroom 3: Upper
  • Bedroom 4: Upper

Other Rooms

  • Living Room: Main
  • Family Room: Main
  • Kitchen: Main
  • Dining Room: Main
  • Office/Den/Study: Upper

Exterior

  • Exterior Features: Barn(s), Fenced, Garden, Gas Hookup, Gazebo, Guest Quarters, Outbuilding, Porch, Sprinkler, Tool Shed, Yard

Parking

  • Garage: Yes
  • Total Spaces: 3
  • Parking Features: Driveway, Off Street

Location

  • County: Douglas
  • Driving Directions: I-5 Exit 119, west on Hwy 99, left on Pepsi Rd, turns into Winston Section Rd

School Information

  • Elem School District: McGovern
  • Elementary School: Brockway
  • Middle School: Winston
  • High School: Douglas

Community

  • Community Name: 257 - Douglas Co: Winston/southwest of Roseburg

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Forced Air
  • Heating Fuel: Electricity, Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public Water

Structural Information

  • Property Detached: Yes
  • Architectural Style: 2 Story, Craftsman
  • Basement Desc.: Daylight, Full Basement, Other
  • Roof: Composition
  • Windows: Storm Window(s), Wood Frames
  • Stories/Levels: 3
  • Square Feet: 2,978
  • Year Built: 1910
  • Property Condition: Resale

Lot Features

  • Lot Size (Acres): 1.12
  • Lot Size (Sq. Ft.): 48,787
  • Lot Size: 1 to 2.99 Acres
  • Frontage: Paved
  • Lot Features: Flood Zone, Gated, Irrigated/Irrigation Equipment, Level, Orchard

Financial Considerations

  • Tax Amount: $4,087.64
  • Tax Year: 2025
  • Terms: Cash, Conventional, Other

Disclosures and Reports

  • Legal Description: TRACT M&B V114 P88, ACRES 1.12
  • Disclosures/Reports: Disclosure
  • Property ID: R38697

Listed by The Neil Company Real Estate (541) 673-4417, Cindy Beach (949) 533-9190

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Listing agent

— 500 Winston Section Rd —

  • Cindy Beach

    The Neil Company Real Estate

    541-673-4417

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NMLS#: 1598647

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Be ready to buy your new home!

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NMLS#: 1598647

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Save up to an additional 20% by bundling your home and auto together!

Schools serving 500 Winston Section Rd

School District:Winston-Dillard School District 116
NameGradesDistance
Mcgovern Elementary School
600 NW Elwood, Winston, OR 97496
4-61.4 mi
Brockway Elementary School
2520 Northwest Brockway Road, Winston, OR 97496
K-32.3 mi
Winston Middle School
330 Thompson Avenue, Winston, OR 97496
7-81.2 mi
Douglas High School
1381 Northwest Douglas Boulevard, Winston, OR 97496
9-122.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 500 Winston Section Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/30/2026
Listed
$775,000
24%
MLS
12/05/2023
Sold
$625,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 500 Winston Section Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,088
3%
$331,090
3%
2024
$3,974
3%
$321,447
3%
2023
$3,863
6%
$312,085
6%
2021
$3,649
-3%
$294,171
—
2022
$3,747
3%
$294,171
3%
2021
$3,649
5%
$285,603
3%
2019
$3,466
3%
$277,285
3%
2018
$3,376
3%
$269,209
3%
2017
$3,291
3%
$261,368
3%
2016
$3,205
2%
$253,756
3%
2015
$3,131
2%
$246,366
3%
2014
$3,069
3%
$239,191
3%
2013
$2,979
—
$232,225
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by The Neil Company Real Estate (541) 673-4417, Cindy Beach (949) 533-9190

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500 Winston Section Rd, Winston, OR 97496 (MLS# 668322333) is a Single Family property with 4 bedrooms and 2 full bathrooms. 500 Winston Section Rd is currently listed for $775,000 and was received on April 30, 2026. Want to learn more about 500 Winston Section Rd? Do you have questions about finding other Single Family real estate for sale in Winston? You can browse all Winston real estate or contact a Coldwell Banker agent to request more information.

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