24

Winston, OR Houses for Sale

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  • /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

    Agent Photo

    Deleta Dickson

    eXp Realty, LLC

    (458) 237-8628

    13224 Lookingglass Rd, Winston, OR 97496
  • /39

    $429,900

    • 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

    Agent Photo

    Nichole Sharman

    Works Real Estate

    (458) 854-7182

    441 NW Galaxy Dr, Winston, OR 97496
  • /45

    $699,500

    • 4 Beds
    • 3.5 Baths
    • 3,072 Sq Ft

    635 Wil Way, Winston, OR 97496

    One of a kind property that is a true gem. Panoramic views of the Abacela Vineyards, the Wildlife Safari, the beautiful city, and the stunning valleys. While being tucked away at the end of the road for extra privacy. Nestled on over 20 acres, this parcel adjoins the Wildlife Safari. Imagine watching exotic animals from your back yard! The home is a gorgeous 2019 build featuing many high quality

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 232-3589

    635 Wil Way, Winston, OR 97496
  • /37

    $390,000

    • 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
  • /47

    $489,900

    • 3 Beds
    • 2 Baths
    • 1,928 Sq Ft

    263 Wil Way, Winston, OR 97496

    Welcome to Your Like-New Custom Home in Winston, OR!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality and thoughtful design shine through every detail. The open concept floor plan boasts soaring vaulted ceilings, stunning floors, and an inviting layout that flows seamlessly for both everyday living and entertaining. At the heart of the home, the gourmet

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    263 Wil Way, Winston, OR 97496
  • /27

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    631 SE Rose Ridge Dr, Winston, OR 97496

    This is a gem! Single-level upgraded home built in 2020. This custom property combines quality construction with modern finishes throughout. Step inside to an open and inviting floor plan featuring vaulted living room and 9 foot ceilings, recessed lighting, ceiling fans, and a perfect blend of rich wood and stylish tile flooring in the main living areas and bathrooms. The gourmet kitchen is a

    Jacob Gilman The Neil Company Real Estate

    631 SE Rose Ridge Dr, Winston, OR 97496
  • /46

    $424,000

    • 3 Beds
    • 2 Baths
    • 1,832 Sq Ft

    128 Watusi Ct, Winston, OR 97496

    Very desirable single level home in Lookingglass Estates. Built in 2008 with great curb appeal and no HOA. The cul-de-sac location offers a level quarter acre lot with lovely landscaping & fenced backyard. Enjoy easy care maintenance with in-ground sprinklers, "Leaf Filter" gutter system, fruit trees, garden boxes and hot tub. Inside you’ll appreciate the open concept, split floor plan with 3BR /

    Thomas Gulan RE/MAX Integrity

    128 Watusi Ct, Winston, OR 97496
  • /20

    $575,000

    • 3 Beds
    • 1.5 Baths
    • 2,026 Sq Ft

    308 Helweg Rd, Winston, OR 97496

    Prime 12.91-acre agricultural property zoned (FC) Exclusive Farm Use-Cropland with 10 acres of primary pond and supplemental river irrigation rights (priority date 1983). This land is perfectly positioned for a profitable homestead, organic farm, or u-pick business. Previously used for hay production and livestock, the soil and water offer a solid foundation for success. The existing home and

    Aaron Cherry Oregon Life Homes

    308 Helweg Rd, 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

    $585,000

    • 4 Beds
    • 3 Baths
    • 2,660 Sq Ft

    102 Sarah Bear Ln, Winston, OR 97496

    Stately quality 4 br 3 bath home, real wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, over sized gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance, covered patio. The gourmet kitchen has granite, pantry, new gas appliances,

    Valynn Currie Currieco Real Estate

    102 Sarah Bear Ln, Winston, OR 97496
  • /44

    $319,900

    • 4 Beds
    • 2 Baths
    • 1,288 Sq Ft

    68 NW Rose St, Winston, OR 97496

    24x36 Shop & 7x40 inground heated lap pool!! This property offers the perfect blend of comfort, functionality, and outdoor living. The standout features are hard to miss - an impressive 24x36 shop ideal for hobbies, storage, or projects, and a 7x40 inground heated lap pool that's perfect for both exercise and relaxation. Whether you're working, unwinding, or entertaining, this backyard setup has

    Ryan Fox Berkshire Hathaway HomeServices Real Estate Professionals

    68 NW Rose St, Winston, OR 97496
  • /27

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,421 Sq Ft

    120 SE Edwards Ave, Winston, OR 97496

    Welcome to this 3-bedroom, 2-bath single-level custom home. Thoughtfully designed with comfort and functionality in mind, this 1,421 sq ft residence offers a spacious open-concept layout, vaulted ceilings, and abundant natural light throughout. The kitchen features wood cabinetry, stainless steel appliances, and a breakfast bar perfect for casual meals or entertaining guests. The primary suite

    Jerry Norman Oregon Life Homes

    120 SE Edwards Ave, Winston, OR 97496
  • /34

    $268,000

    • 3 Beds
    • 1 Bath
    • 1,085 Sq Ft

    224 5th St, Winston, OR 97496

    MOTIVATED SELLER!! Charming 3-Bedroom Home on Oversized Lot – Perfect for Entertaining! Discover comfort and charm in this updated 3-bedroom, 1-bath home situated on an expansive .36-acre lot with a spacious backyard designed for entertaining, you’ll love spending time outdoors under the beautiful custom built covered porch—perfect for enjoying your morning coffee or relaxing in the evening. Step

    Terri LeVasseur J Mann Realty

    224 5th St, Winston, OR 97496
  • /20

    $299,500

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft

    120 SW Brantley Dr, Winston, OR 97496

    Charming 3 bedroom, 2 bath home with attached 2 car garage & multiple outbuildings. Large cement patio with lots of outdoor living area. Sits on a large lot, (over 3/5ths of an acre) with lots of fruit trees & room to roam! Must see to appreciate this lovely home!

    Judith Zuver Winston Realty & Insurance

    120 SW Brantley Dr, Winston, OR 97496
  • /17

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft

    185 Lebleu Ln, Winston, OR 97496

    Buyer incentive offered if under contract by 9/15. Solid 3 bed, 2 bath in Winston with a newer roof. Welcome home to this well maintained single-story home with a modern floorplan, featuring an inviting open-concept layout designed for both comfort and privacy. The spacious primary bedroom includes an attached bathroom, offering a private retreat. The living room features a gas fireplace, perfect

    Kurt Delahooke Keller Williams Realty Eugene and Springfield

    185 Lebleu Ln, Winston, OR 97496
  • /25

    $695,000

    • 3 Beds
    • 2 Baths
    • 2,167 Sq Ft

    1090 E Willis Creek Rd, Winston, OR 97496

    Secluded private 2167 sq ft 3 br 2 bath contemporary home on 9.81 acres. Has open beam ceilings, wood stove, barn, wood shop, 2 gar garage. Garden area, city water, creek. Mostly level property. Charming kitchen with large pantry and skylight, ample dining room overlooking the garden and yard. Living room has bay window and room to entertain. Covered parking for boat or RV.

    Valynn Currie Currieco Real Estate

    1090 E Willis Creek Rd, Winston, OR 97496
  • /47

    $377,500

    • 3 Beds
    • 1 Bath
    • 1,434 Sq Ft

    10 SE Kegler Ave, Winston, OR 97496

    Set on a full acre at the edge of town, this property blends flexibility, functionality, and a 1,200 sq ft shop that’s hard to ignore! The 3-bedroom, 1-bath home includes an oversized living room with exposed wood accents and rustic-style posts that bring a bit of texture and charm. Heating and cooling are handled with ductless systems, and there’s a gas fireplace to keep things cozy. The kitchen

    Anthony Beckham Different Better Real Estate

    10 SE Kegler Ave, Winston, OR 97496
  • /44

    $739,000

    • 4 Beds
    • 2.5 Baths
    • 2,362 Sq Ft

    1068 Rice Creek Rd, Winston, OR 97496

    Gated 8.5 acres country living, fenced X Fenced, beautiful ranch style updated home. Newer roof, newer paint in and out, gourmet kitchen w/DBL ovens & cooking pantry, large living room with fireplace, huge primary bedroom with walk in closet 2 headed shower & 3 nice sized bedrooms, one bedroom can be use for office space. 36x40 Shop with office & 1/2 bath & extra garage with tool room. City

    Joan Smith G. Stiles Realty

    1068 Rice Creek Rd, Winston, OR 97496
  • /28

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft

    140 Teresa Ln, Winston, OR 97496

    This modern, beautiful home is located in the highly sought-after Winston neighborhood. The home has been recently remodeled down to the studs and includes brand new HVAC, new appliances, and new roof. Step inside to find luxury vinyl plank flooring, recessed lighting, and soaring vaulted ceilings, and an abundance of windows that create a spacious and inviting atmosphere. The open-concept

    Jason Mann J Mann Realty

    140 Teresa Ln, Winston, OR 97496
  • /47

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,374 Sq Ft

    231 NE Darrell Ave, Winston, OR 97496

    Great location with a custom built one level home located on .39 of an acre at the end of the road in Winston with City Services! Home built in 1981 with approximately 1,374 square feet, 3 bedrooms and 2 full bathrooms, primary bedroom and bathroom has a walk-in closet and slider door to deck, nice Kitchen with oodles of oak cabinets, lots of counter space, plus a pantry, Living room has

    Cynthia Johnson Johnson Group Real Estate, LLC

    231 NE Darrell Ave, Winston, OR 97496
  • /41

    $870,000

    • 4 Beds
    • 3 Baths
    • 3,000 Sq Ft

    375 Porter Creek Rd, Winston, OR 97496

    Discover the perfect blend of vineyard lifestyle and modern comfort in this beautifully updated 41-acre estate, nestled in the heart of Oregon’s Umpqua Valley AVA. Surrounded by timber, a year-round creek, and a seasonal pond, this scenic retreat offers privacy, natural beauty, and endless potential.At the heart of the property is a spacious 3,000 sq ft home featuring four large bedrooms and

    Lorrie Normann Triple Oaks Realty LLC

    375 Porter Creek Rd, Winston, OR 97496
  • /39

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,835 Sq Ft

    151 Sherry St, Winston, OR 97496

    Step into this charming 1965 Ranch-style home, nestled in a peaceful neighborhood on a generous double lot in the heart of Winston, Oregon. With 3 bedrooms, 1.5 bathrooms, and a large, fully fenced corner lot, this property offers both privacy and convenience. This home boasts ample storage space throughout, with built-in shelving and closets to keep your living areas tidy. The cozy and airy

    RaNae Sams Oregon Life Homes

    151 Sherry St, Winston, OR 97496
  • /14

    $199,999

    • 2 Beds
    • 1 Bath
    • 735 Sq Ft

    110 SE Darrell Ave, Winston, OR 97496

    BRAND NEW ROOF IN 2025 AT THE SAME LOW PRICE! Cute updated 2 bedroom home with small utility room. Kitchen with newer appliances. Brand New Roof and hot water heater and recently updated flooring, interior and exterior paint. Living room offers gas heater and a front bonus area. Partially fenced yard with garden shed in back. Nice corner lot with driveway. Call for your showing today!

    Lacey Williams Trueblood Real Estate

    110 SE Darrell Ave, Winston, OR 97496
  • /48

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 1,845 Sq Ft

    1470 E Willis Creek Rd, Winston, OR 97496

    Build a second home? 3 tax lots. 80+5+5 acres each & one of the 5-acre lots is buildable! Connected to city water with a 2500 reserve tank. Nestled on 90 acres of private land, this stunning 3-bedroom, 2.5-bath log home offers the perfect retreat for those seeking tranquility and connection with nature. The main home is a masterpiece of rustic craftsmanship, featuring soaring vaulted ceilings,

    Rhonda Marshall Knipe Realty ERA Powered

    1470 E Willis Creek Rd, Winston, OR 97496

Why Live in Winston

Winston, Oregon, is a small community of nearly 6,000 residents nestled along the South Umpqua River and surrounded by forested landscapes. Known for its Wildlife Safari, Winston offers a driving tour featuring over 500 animals and 80 species. The town's parks, such as Riverbend Park and Winston Dillard County Park, provide playgrounds, skate parks, picnic areas, and summer concert series. Harold and Sid Nichols Park includes a public boat ramp, popular for fishing and kayaking. Winston's homes range from starter properties to high-end estates, with single-level ranch homes being the most common. Lot sizes vary from under 10,000 square feet to over 20 acres, and new developments like Rolling Meadows are underway. Dining options are concentrated around Southeast Main Street and Northwest Douglas Boulevard, with spots like Winston Diner & Drive-Thru and Willee's Cafe and Spirits. Grocery Outlet and Brosi's Sugartree Farms cater to local shopping needs, while nearby Abacela Winery and Freed Estates Vineyard offer tasting rooms. Highway 99 provides scenic routes through the area, including the Rogue-Umpqua Scenic Byway. Flooding can be a concern in local parks and boat ramps after heavy rainfall or snowmelt.

Home Trends in Winston, OR

Housing Trends

Median Sale Price
$342,000
Median Single Family Sale Price
$347,450
Average Price Per Sq Ft
$236
Number of Homes for Sale
18
Last 12 months Home Sales
68
Months of Supply
3.20
Median List Price
$362,450
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
0%
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