Listing provided courtesy of The Neil Company Real Estate- MLS# 668322333MLS Provider

500 WINSTON SECTION RDWinston, OR 97496

Single Family · 4 Beds · 2 Full Baths · 3,746 Sq. ft. | 1.12 Acres
$775,000 Pending

500 WINSTON SECTION RD Overview

Time on Site:
60 days
Visits:
0

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.

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500 WINSTON SECTION RD Facts & Features

  • Type Single Family
  • Sq. ft. 3,746
  • Price/Sq.ft. $207
  • Lot 1.12 Acres

Details

General

School Information

  • Elementary School: Brockway
  • Middle Or Junior School: Winston
  • High School: Douglas

Building Information

  • Year Built: 1910

Location/Region

  • Country: US
  • County Or Parish: Douglas
  • MLS Area Major: 257 - Douglas Co: Winston/southwest of Roseburg

Tax Information

  • Tax Annual Amount: 4087.64
  • Tax Year: 2025

General Information

  • Disclosures: Disclosure
  • Listing Terms: Cash,Conventional,Other
  • Parcel Number: R38697
  • Property Condition: Resale
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Zoning: F1

Interior

Parking Information

  • Garage Spaces: 3.0

Beds/Baths

  • Bathrooms Full: 2
  • Bathrooms Partial: 0
  • Bathrooms Total: 2
  • Bedrooms Total: 4

Building Interior

  • Building Area Total: 3746.0

General Information

  • Appliances: Dishwasher,Disposal,Free-Standing Gas Range,Free-Standing Refrigerator,Instant Hot Water,Island,Range Hood,Stainless Steel Appliance(s)
  • Basement: Daylight,Full Basement,Other
  • Cooling: None
  • Fireplace Features: Gas,Wood Burning
  • Fireplaces Total: 3
  • Foundation Details: Concrete Perimeter
  • Heating: Forced Air
  • 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
  • Stories: 3
  • Window Features: Storm Window(s),Wood Frames

Exterior

Parking Information

  • Parking Features: Driveway,Off Street
  • Parking Total: 3.0

Lot Information

  • Lot Features: Flood Zone,Gated,Irrigated/Irrigation Equipment,Level,Orchard
  • Lot Size Acres: 1.12
  • Lot Size Square Feet: 48787.0
  • Road Surface Type: Paved
  • Water Source: Public Water

Building Exterior/Construction

  • Architectural Style: 2 Story,Craftsman
  • Roof: Composition

General Information

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

500 WINSTON SECTION RD Neighborhood

Community

97496 (Winston) Demographics

43
Median Age
88
Population Density (per sq. mile)
29%
College Educated
$46,488
Estimated Median Income
1,925
Estimated Total Home Owners
1,042
Estimated Total Renters
65% / 35%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.
* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

500 WINSTON SECTION RD Market Data

Based on the last 30 days in this zip code

$409,377
Average List Price
$247
Average Price per Square Foot
5
Properties Sold
133
Average Days on Market
57
Properties for Sale
Calculations provided by Reliance Network

500 WINSTON SECTION RD History

Date Event Value Agent
5/8/2026Source: Regional MLS Status Change
Pending
4/30/2026Source: Regional MLS Added to Database
April 30, 2026
12/6/2023Source: Regional MLS Status Change
Sold
10/19/2023Source: Regional MLS Status Change
Pending