500 Winston Section Rd

Winston, OR 97496

$775,000
Price
4
Beds
3,746 Sq. Ft.
$207 / Sq. Ft.
3,746
Sq. Ft.
$207
per Sq. Ft.
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Exterior
Porch
Porch
Porch
Entrance/Foyer
Living Room
Living Room
Living Room
Living Room
Dining Room
Dining Room
Dining Room
Kitchen
Kitchen
Kitchen
Laundry
Porch, Screened in
Bathroom
Family Room
Family Room
Staircase
Bonus Room
Balcony
Bedroom, Primary
Bedroom, Primary
Bedroom
Bedroom
Bedroom
Bathroom
Den/Office
Gazebo
Backyard
Gazebo
Backyard
Barn
Barn
Barn
Garage
Accessory Dwelling Unit
Accessory Dwelling Unit
Accessory Dwelling Unit
Driveway

Description

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...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.
  1. Listed by Cindy Beach • The Neil Company Real Estate

Property Details for 500 Winston Section Road

Style
Stories2, Craftsman
Parking Features
Driveway, Off Street
Zoning
F1
View
Mountain, Trees Woods
Garage Spaces
3.00
Parking Total
3.00
LISTING UPDATED: 05/04/2026 02:37 PM

Property Details for 500 Winston Section Road

StatusActive
MLS #668322333
Days on Market4
Taxes$4,088 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1910
Lot Size1.12 AC / 48,787 SF
CountyDouglas County
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Location

Listing Courtesy of The Neil Company Real Estate
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Building Information for 500 Winston Section Road

Stories3Year Built1910Building Size-Lot Size1.12 AC / 48,787 SF

Payment Calculator

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$4,243 per month

30 year fixed, 6.46% Interest

Principal and Interest

$3,903

Property Taxes

$341

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 500 Winston Section Road

Summary
Location and General Information
  • Country: US
  • Directions: I-5 Exit 119, west on Hwy 99, left on Pepsi Rd, turns into Winston Section Rd
  • Road Surface: Paved
School Information
  • Elementary School: Brockway
  • Elementary School 2: Mc Govern
  • High School: Douglas
  • Middle Or Junior School: Winston
Parking
  • Garage Type: Detached
Taxes and HOA
  • Tax Year: 2025
  • Tax Annual Amount: $4,087.64
  • Parcel Number: R38697
  • Tax Legal Description: TRACT M&B V114 P88, ACRES 1.12
Property
Lot Information
  • Acres: 1.12
  • Lot Description: Flood Zone, Gated, Irrigated Irrigation Equipment, Level, Orchard
  • Lot Size Square Feet: 48787.0
  • Lot Size Range: Acres1to3
  • Lot Size: 1 to 2.99 Acres
  • SqFt Source: Assessor
Property and Assessments
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Water Description: Public Water
  • Property Condition: Resale
  • Year Built: 1910
Utilities
  • Cooling Description: None
  • Fuel Description: Electricity, Gas
  • Heating Description: Forced Air
  • Hot Water Description: Electricity
  • Sewer Description: Public Sewer
Interior and Exterior Features
Exterior Features
  • Exterior Description: Lap Siding, Shingle Siding
  • Exterior Features: Barn, Fenced, Garden, Gas Hookup, Gazebo, Guest Quarters, Outbuilding, Porch, Sprinkler, Tool Shed, Yard
  • Roof Type: Composition
Interior Features
  • Basement: Daylight, Full Basement, Other
  • Foundation Details: Concrete Perimeter
  • Window Features: Storm Window, Wood Frames
  • Fireplace Description: Gas, Wood Burning
  • Fireplaces Total: 3
  • Interior Features: Garage Door Opener, Hardwood Floors, High Ceilings, Laundry, Separate Living Quarters Apartment Aux Living Unit, Vinyl Floor, Wallto Wall Carpet, Wood Floors
  • SqFt Calculated: 2978
  • SqFt Lower Level Total: 768
  • SqFt Main Level Total: 1608
  • SqFt Upper Level Total: 1370
  • Bedrooms Total: 4
  • Stories: 3
  • Baths Total: 2.0
Master Bedroom
  • Room Description: Primary Bedroom
  • Primary Bedroom Level: Upper
Bedroom 2
  • Room Description: _2nd Bedroom
  • Bedroom 2 Level: Upper
Bedroom 3
  • Room Description: _3rd Bedroom
  • Bedroom 3 Level: Upper
Dining Room
  • Room Description: Dining Room
  • Dining Room Level: Main
Family Room
  • Room Description: Family Room
  • Family Room Level: Main
Kitchen
  • Room Description: Kitchen
  • Kitchen Appliances: Dishwasher, Disposal, Free Standing Gas Range, Free Standing Refrigerator, Instant Hot Water, Island, Range Hood, Stainless Steel Appliance
  • 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: 2
  • Baths Partial: 0
  • Total Bathrooms: 2
  • Baths Upper Leve lFull: 1
  • Baths Upper Level Partial: 0
  • Baths Upper Level Total: 1.0
Additional Room 1
  • Additional Room 1 Description: _4th Bedroom
  • Additional Room 1 Level: Upper
Additional Room 2
  • Additional Room 2 Description: Office
  • Additional Room 2 Level: Upper
Additional Room 3
  • Additional Room 3 Description: Bonus Room
  • Additional Room 3 Level: Upper
Amenities
Amenities Information
  • Internet Service Type: Cable
Multi Family
Multi-Family Information
  • SqFt Approximate Building Total: 3746

Property History for 500 Winston Section Road

DateEvent & SourcePriceAppreciation
Dec 5, 2023

Sold (Public Record)

Public Record #1523020418

$625,000—
DateEvent & SourcePrice
12/05/2023

Sold (Public Record)

Public Record #1523020418

$625,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 500 Winston Section Road

Taxable ValueLand-Additions-Total-
Tax Record2025$4,088 ($341 / month)
Home Facts
Beds4Total Finished SqFt2,978 SqFtAbove Grade Finished SqFt2,978 SqFtUnfinished Basement SqFt768 SqFtStories2Lot Size48,787 SqFtStyleMiscellaneous ResidentialYear Built1910Year Renovated1945ZoningF1CountyDOUGLASAPN28-06W-15C-01300Fireplace TypeHas Fireplace

Schools near 500 Winston Section Road

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
Brockway Elementary School
Public - PK to 2
Rating
School
Distance
Mcgovern Elementary School
Public3 to 5

Winston Middle School
Public6 to 8

Douglas High School
Public9 to 12

Brockway Elementary School
PublicPK to 2

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 500 Winston Section Road, Winston, OR 97496

500 Winston Section Road is a single family home for sale in Winston, OR 97496. This property was listed for sale on April 30, 2026 by The Neil Company Real Estate, it's currently listed at $775,000. It has been on the market for a total of 4 days and was last sold on December 5, 2023. This listing's school district is Winston-Dillard School District 116. Nearby schools include Mcgovern Elementary School, Winston Middle School and Douglas High School. 500 Winston Section Road is a 4-bed, 2-bath, 3,746 sqft single family home built in 1910.

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 The Neil Company Real Estate

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: 05/04/2026 02:37 PM