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500 Winston Section Rd, Winston, OR 97496

$775,000

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Property 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 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.

500 Winston Section Rd | MLS# 668322333

This single family home located at 500 Winston Section Rd, Winston, OR 97496 is currently listed for sale with an asking price of $775,000. This property was built in 1910 and has 4 bedrooms and 2 full baths with 3746 sq. ft. Search Winston real estate on evanmann.bendpremierrealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Daylight, Full Basement, Other
Cooling: None
Fenced: Yes
Fireplaces: 3
Fuel Type: Electricity, Gas
Garage: 3
Heating: Forced Air
Home Style: 2 Story, Craftsman
Lot Size: 1.12 Acres
Roof Type: Composition
Stories: 3.0
Taxes: $4,088
Year Built: 1910
Square Feet: 3,746

Feature Descriptions

Bathroom: 1.0 (Main), 1.0 (Upper)
Days on Site: 5
Exterior: Barn, Fenced, Garden, Gas Hookup, Gazebo, Guest Quarters, Outbuilding, Porch, Sprinkler, Tool Shed, Yard
Exterior: Lap Siding, Shingle Siding
Fireplace: Gas, Wood Burning
Hot Water: Electricity
Interior: Garage Door Opener, Hardwood Floors, High Ceilings, Laundry, Separate Living Quarters-Apartment-Aux Living Unit, Vinyl Floor, Wall to Wall Carpet, Wood Floors
Kitchen: Dishwasher, Disposal, Free-Standing Gas Range, Free-Standing Refrigerator, Instant Hot Water, Island, Range Hood, Stainless Steel Appliance(s)
Lot: Flood Zone, Gated, Irrigated-Irrigation Equipment, Level, Orchard
Parking Notes: Detached, Driveway, OffStreet
Sewer: Public Sewer
Special View Info: Mountain, Trees/Woods
Square Footage: 768 (Lower), 1608 (Main), 1370 (Upper)
Water: Public Water

Local Schools

High School: Douglas
Middle School: Winston
Elementary School: Brockway

Listed By / Shown By

Listed By

Agency Name: The Neil Company Real Estate
Agency Phone: 541-673-4417

Shown By

Agent Name: Evan Mann, Broker
Agent Phone: (541) 977-6666
Agency Title: Bend Premier Real Estate

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Estimated Payment

$ 4,485.53 per month $3,918.82 Principal & Interest $340.67 Property Tax $226.04 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/07/2026. The listing information on this page last changed on 05/07/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 05/07/2026 4:21:48 AM EST) or RMLS (last updated Thu 05/07/2026 1:50:21 AM EST) or COAR/MLSCO (last updated Thu 05/07/2026 1:31:26 AM EST). Real estate listings held by brokerage firms other than Bend Premier Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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