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500 Winston Section Rd, 
Winston, OR 97496

$775,000


4

Beds


2

Baths


3,746

Sq Ft


Single Family

Pending

Listed by

Cindy Beach

The Neil Company Real Estate

541-673-4417

Last updated:

May 17, 2026, 07:17 AM

MLS#

668322333

Source:

PORTLAND

About This Home

500 Winston Section Rd

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.

Home Facts

Single Family

2 Baths

4 Bedrooms

Built in 1910

Price Summary

775,000

$206 per Sq. Ft.

MLS #:

668322333

Last Updated:

May 17, 2026, 07:17 AM

Added:

18 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

3,746 Sq. Ft.


Structure

Structure

Architectural Style:

2 Story, Craftsman

Building Area:

3,746 Sq. Ft.

Year Built:

1910


Lot

Lot Size (Sq. Ft):

48,787


Finances & Disclosures

Finances

Price:

$775,000

Price per Sq. Ft:

$206 per Sq. Ft.

MLS Logo
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 Coldwell Banker Valley Brokers 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: May 17, 2026

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.