Winston, OR Homes under $500,000

/39
$439,000
- 3 Beds
- 2 Baths
- 1,310 Sq Ft
441 NW Galaxy Dr, Winston, OR 97496

Finished heated shop • Finished heated/cooled garage • Stunning views • Beautiful home overlooking the city w/panoramic views of surrounding mountains and valleys. Multiple decks and thoughtfully designated outdoor spaces for entertaining or relaxation. Fully finished and heated shop w/ vaulted ceilings, skylight and wood beams seamlessly attached to the fully finished heated/cooled garage

Nichole Sharman

Works Real Estate

(458) 854-7182

441 NW Galaxy Dr, Winston, OR 97496
/46
$479,900
- 4 Beds
- 2 Baths
- 2,534 Sq Ft
13224 Lookingglass Rd, Winston, OR 97496

Experience the unique allure of this beautifully updated, original homestead farmhouse nestled in Safari Estates. Thoughtful remodel and tasteful updates have modernized this 1900-built farmhouse, preserving its character while enhancing comfort. With 2,516 sq ft of living space, four bedrooms, and two full baths, this home blends historic charm with modern comfort. The kitchen has been remodeled

Deleta Dickson

eXp Realty, LLC

(458) 237-8628

13224 Lookingglass Rd, Winston, OR 97496
/28
$430,000
- Land
- 7 Acres
- $58,108 per Acre
0 Wil Way Unit 24094727, Winston, OR 97496

Rare investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Property has already been approved to be partitioned as either 2 larger parcels or a 28 lot subdivision! Currently no HOA or CC&Rs! Utilities conveniently are available nearby ready to be connected. The 2 parcels are also listed separately. Make an offer today before one or all

Ashton Faas

Different Better Real Estate

(458) 310-3411

0 Wil Way Unit 24094727, Winston, OR 97496
/37
$400,000
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
360 NE Rose Ridge Dr, Winston, OR 97496

Beautiful 3BD/2BTH home in Winston’s sought-after Rolling Meadows neighborhood! Built by Avery Homes in 2021, this one-level residence feels "like new" and is completely move-in ready. Enjoy an open-concept layout with durable LVP flooring, quartz countertops, and a bright, spacious living area perfect for everyday activities and entertaining. Energy-efficient solar panels installed in July 2024

Aaron Cherry Oregon Life Homes

360 NE Rose Ridge Dr, Winston, OR 97496
/48
$454,000
- 2 Beds
- 1 Bath
- 2,056 Sq Ft
0 Rice Creek Rd, Winston, OR 97496

100% off-grid living on your own 20-acre slice of paradise! Located within "The Ranch" - a close-knit homesteading community of like-minded landowners who each steward their own property while embracing a shared off-grid lifestyle. Just 25 minutes southwest of Winston, Oregon, this property is accessed via a gated 4-mile gravel road through BLM and private timberlands. The resilient home features

Aaron Cherry Oregon Life Homes

0 Rice Creek Rd, Winston, OR 97496
/32
$499,500
- 3 Beds
- 2 Baths
- 2,186 Sq Ft
240 Wil Way, Winston, OR 97496

Welcome to the highly desirable neighborhood of Safari Estates. This custom built 3-bedroom, 2 bath home offers stunning views of the rolling forested hills and is in the heart of wine country. The expansive living room is flooded with natural light, showcasing the breathtaking views through large windows that seamlessly connect the indoors to the outdoor patio space. The open-concept with

Jacob Sanchez Next Generation Real Estate LLC

240 Wil Way, Winston, OR 97496
/32
$489,000
- 2 Beds
- 2 Baths
- 1,764 Sq Ft
1941 Byron Creek Rd, Winston, OR 97496

Come home to your own private escape hidden in the trees! Beautiful parklike setting with amazing views and end of the road privacy. Property features include a huge, large covered RV storage, detached guest quarters, a storeroom & workshop. The manufactured home was custom built for the current owners with many custom touches. An expansive deck is perfect for gatherings or taking in the amazing

Andrew Stoner Roseburg Homes Realty

1941 Byron Creek Rd, Winston, OR 97496

Oregon Douglas County Winston

Home Trends in Winston, OR

On average, homes in Winston, OR sell after 159 days on the market compared to the national average of 70 days. The median sale price for homes in Winston, OR over the last 12 months is $379,500, down 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$379,500

Median Single Family Sale Price

$386,500

Average Price Per Sq Ft

$261

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.30

Median List Price

$389,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-6%

How to Buy a Home How to Finance a Home How to Sell a Home

In Winston, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 7 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Winston, OR and find the perfect fit for your homeownership goals.

Winston Types of Homes for Sale

Winston Mobile Homes for Sale

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Douglas County Homes for Sale

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate 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 Ten-X are marked with the RMLS™ logo, and detailed information about these properties includes the names of the listing brokers. Listing content is copyright © 2025 RMLS™, Portland, Oregon. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. All information provided is deemed reliable but is not guaranteed and should be independently verified.