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Homes for Sale near Douglas High School

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  • /15

    $200,000

    • Land
    • 4.26 Acres
    • $46,948 per Acre

    0 Wil Way Unit 24292479, Winston, OR 97496

    Unique investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 217-1693

    0 Wil Way Unit 24292479, Winston, OR 97496
  • /45

    $699,900

    • 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
  • /28

    $375,000

    • Land
    • 7.4 Acres
    • $50,676 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

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 310-3411

    0 Wil Way Unit 24094727, Winston, OR 97496
  • /46

    $530,000

    • 3 Beds
    • 2.5 Baths
    • 1,621 Sq Ft

    125 Eagle Dr, Roseburg, OR 97471

    If you are looking for a home with breathtaking views, then look no further. This property has breathtaking views of the mountains and valleys. Located in the high demand Diamond Height Estates, this property offers over 5 acres of land to make your own. As you pull, you will be greeted by the beautiful designed, craftsman home. Behind the home, there are new raised garden beds with smart

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 254-5910

    125 Eagle Dr, Roseburg, OR 97471
  • /15

    $200,000

    • Land
    • 3.14 Acres
    • $63,694 per Acre

    0 Wil Way Unit 24278136, Winston, OR 97496

    Great investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 224-5797

    0 Wil Way Unit 24278136, Winston, OR 97496
  • /36

    $439,000

    • 7 Beds
    • 4.5 Baths
    • 3,861 Sq Ft

    2414 Brockway Rd, Winston, OR 97496

    Opportunity awaits! Whether you’re a savvy investor seeking passive income, a large family looking for a multi-generational setup, or a single household wanting a home with the luxury of renting out additional units, this three-home property offers countless possibilities.Located on historic Brockway Road, the property spans .58 acres and is lined with mature trees and lush landscaping, creating

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    2414 Brockway Rd, Winston, OR 97496
  • /48

    $545,000

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    712 Sibold Canyon Rd, Tenmile, OR 97481

    Over 92 acres privately situated in beautiful Sibold Canyon. This spacious 4bd/3bth home offers vaulted ceilings, generous living areas, and a large primary suite. Interior repair is needed in the kitchen/dining area due to a past plumbing leak - priced accordingly. Outdoor living features covered porches, an expansive deck, hot tub, garden beds, fruit trees, and workshop. A 23x35 three-car

    Aaron Cherry Oregon Life Homes

    712 Sibold Canyon Rd, Tenmile, OR 97481
  • /48

    $469,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,770 Sq Ft

    109 Citation Ct, Winston, OR 97496

    Welcome to 109 Citation Ct, a brand-new single-level home nestled in the highly sought-after Lookingglass Creek Estates subdivision in Winston, Oregon. This contemporary ranch-style residence offers 3 bedrooms, 2 bathrooms, and 1,770 sq. ft. of beautifully designed living space on a .20-acre lot with RV parking behind a private gate. Step inside to find luxury vinyl plank flooring, vaulted

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    109 Citation Ct, Winston, OR 97496
  • /48

    $625,000

    • 4 Beds
    • 2 Baths
    • 2,404 Sq Ft

    941 Colonial Rd, Roseburg, OR 97471

    Melrose! Shop! 5 acres! PRIVACY and VIEWS! Charming single-level home with incredible views on 5 acres in Roseburg, OR! This 4-bed, 2-bath home features vaulted ceilings, an open layout, and tons of natural light. The kitchen has been updated with hickory cabinets, granite counters and a spacious layout with ample cabinet storage and eating bar. Primary suite includes walk-in closet and a private

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    941 Colonial Rd, Roseburg, OR 97471
  • /45

    $66,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    125 SE Estate Loop, Winston, OR 97496

    Take in breathtaking views of Umpqua Valley and the surrounding mountains from this spacious manufactured home located in a welcoming 55+ community. Unwind on the large covered front porch. Featuring a metal roof, double-pane vinyl windows, and a sturdy concrete block foundation, this home offers lasting durability. Stay comfortable year-round with the newer heat pump installed in 2022.

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    125 SE Estate Loop, Winston, OR 97496
  • /40

    $289,900

    • 3 Beds
    • 1 Bath
    • 1,180 Sq Ft

    260 SW Ford Ave, Winston, OR 97496

    Welcome to 260 SW Ford Ave in the heart of Winston, OR — a beautifully remodeled single-level home offering comfort, style, and exceptional move-in readiness. Fresh exterior paint gives the home a crisp, modern look, while inside you’ll find waterproof luxury vinyl plank flooring in the main living areas—including the living room, kitchen, bonus room, and laundry room—paired with brand-new carpet

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    260 SW Ford Ave, Winston, OR 97496
  • /48

    $1,150,000

    • 3 Beds
    • 3 Baths
    • 2,337 Sq Ft

    894 Colwell Hill Ln, Roseburg, OR 97471

    Welcome to your new wilderness retreat!Perched atop a hill and backed by 393 acres of BLM land, this property offers the perfect blend of privacy, exploration, and functionality. Surrounded by trees, you’ll feel miles from anywhere — yet you’re only 10 miles from Roseburg. The well-maintained grounds give off a peaceful, park-like ambience from the moment you arrive. While the property slopes in

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    894 Colwell Hill Ln, Roseburg, OR 97471
  • /42

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    700 SE Tokay St, Winston, OR 97496

    Welcome to this inviting one level 3-bedroom, 2-bathroom home offering comfort, convenience, and modern touches throughout. Manicured front yard plus a manicured back yard that is completely fenced. The bright and open kitchen features stainless steel appliances and granite countertops, making meal prep a joy. Enjoy the ease of single-level living with a functional floor plan, perfect for both

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    700 SE Tokay St, Winston, OR 97496
  • /7

    $734,000

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

    1068 Rice Creek Rd, Winston, OR 97496

    This gated, 8.52-acre property is fenced and cross-fenced, offering plenty of country living space. This beautiful ranch-style home features updates, a newer roof, and recent interior and exterior paint. The gourmet kitchen includes double ovens and a walk-in pantry. The large living room features a fireplace. The huge primary bedroom includes a walk-in closet and a two-headed shower. One of the

    Greg Johnson G Stiles Realty

    1068 Rice Creek Rd, Winston, OR 97496
  • /12

    $334,900

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

    185 Lebleu Ln, Winston, OR 97496

    Solid home in Winston with a newer roof and open concept floorplan. Welcome home to this well maintained single-story home with a modern layout, 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 for relaxing evenings. Step outside

    Kurt Delahooke Keller Williams Realty Eugene and Springfield

    185 Lebleu Ln, Winston, OR 97496
  • /21

    $250,000

    • Land
    • 27.09 Acres
    • $9,228 per Acre

    0 E Willis Creek Rd, Winston, OR 97496

    27.09 acres to build your dream home either on top of the property or in the valley. City water is available, and other utilities are accessible via a recorded easement. In photos, red boundary lines are approximate and buyer is to perform due diligence. All showings are to be with a licensed realtor. Please make note that this property is a combination of only R66808 & R66885. 0 E. Willis Creek

    Art Dillahay Oregon Life Homes

    0 E Willis Creek Rd, Winston, OR 97496
  • /21

    $150,000

    • Land
    • 10.56 Acres
    • $14,205 per Acre

    3541 Willis Creek Rd, Winston, OR 97496

    10.56 Acres Bordering Public Land Nestled at 3541 Willis Creek Rd, this 10.56-acre property offers a rare chance to own a slice of Oregon's natural beauty. With a newly cut-in road leading to a potential home site, you'll enjoy a stunning view of the valley-a perfect backdrop for your future home. The essentials are already in place: Community water with a meter installed near the south end

    Cliff Farley Mossy Oak Properties Oregon Field and Stream Realty

    3541 Willis Creek Rd, Winston, OR 97496
  • /16

    $2,599,000

    • Land
    • 324.62 Acres
    • $8,006 per Acre

    5961 Lookingglass Rd Unit 8, Roseburg, OR 97471

    Prime horse property! Rare opportunity to purchase 300+ acres in highly sought-after Lookingglass Valley. Quiet and peaceful prime grazing land with rich soil, perfect for cattle or horses. Formerly registered short horn ranch. Pasture currently leased for the season. 2 ponds, 1 is lower during the summer months. Manufactured home can be renovated or replaced with a beautiful custom ranch home. 2

    Melony Marsh All-Pro Realty Advisors, LLC

    5961 Lookingglass Rd Unit 8, Roseburg, OR 97471
  • /39

    $275,000

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    617 Poison Oak Dr, Winston, OR 97496

    Escape to the country with this rustic home nestled on nearly 14 beautiful acres. Perfect for those dreaming of a mini-farm or simply wanting space for animals, and rural lifestyle. This property offers usable acreage mixed with stands of timber, seasonal creeks and endless potential. Surround yourself with sweeping mountain views and the serenity of nature, all while enjoying the freedom that

    Bob Lamonte Lamonte Real Estate Professionals

    617 Poison Oak Dr, Winston, OR 97496
  • /48

    $3,800,000

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    8690 Lookingglass Rd, Roseburg, OR 97471

    Welcome to Lookingglass Vineyard, a remarkable 142.94-acre estate nestled in the highly sought-after South Valley Wine Loop of the renowned Umpqua Valley AVA. This established and producing vineyard features 99.94± acres planted in Pinot Noir and an additional 1/2-acre parcel with other select varietals, offering an exceptional opportunity for both lifestyle and investment. The vineyard is fully

    Jennifer Kramer RE/MAX Integrity

    8690 Lookingglass Rd, Roseburg, OR 97471
  • /20

    $25,000

    • Land
    • 1.5 Acres
    • $16,667 per Acre

    0 Reston Rd, Roseburg, OR 97471

    WOW! Located just a 15-minute drive from Winston, this 1.5-acre property offers a large, level, graveled lot with endless potential. Zoned FF, this property is ideal for those looking for recreational land or exploring the possibilities of future development. With low property taxes, this affordable property is a blank slate perfect for a variety of uses. Whether you’re envisioning a private

    Anthony Beckham Different Better Real Estate

    0 Reston Rd, Roseburg, OR 97471
  • /48

    $474,900

    • 4 Beds
    • 2 Baths
    • 2,534 Sq Ft

    13224 Lookingglass Rd, Winston, OR 97496

    Experience 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 with beautiful

    Deleta Dickson eXp Realty, LLC

    13224 Lookingglass Rd, Winston, OR 97496
  • /32

    $469,900

    • 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
  • /10

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    139 Teresa Ln, Winston, OR 97496

    Come take a look at your beautiful new forever home in this established neighborhood. Newer build in 2017 with many amenities. Kitchen boasting all stainless-steel appliances with a wonderful gas stove for the cook in the family, down to the granite countertop and eat in island great for entertaining with its open concept. Spacious master bedroom with a walk-in closet and granite vanity in the

    Angel Smith Trueblood Real Estate

    139 Teresa Ln, Winston, OR 97496
  • /48

    $459,000

    • 3 Beds
    • 2.5 Baths
    • 2,067 Sq Ft

    165 Danielle Dr, Winston, OR 97496

    Welcome home! Enjoy the space and warmth of this Safari Estates custom home. Featuring over 2,000 sq ft of living space. 3 bedrooms 2.5 baths with an upstairs laundry room make this home a great family setup. There is an office/Den that also doubles as a 4th bedroom if needed. Dramatic entry way with open concept kitchen/familyroom is what separates this home from the others ! Outside you will

    Brent Yop Winston Realty & Insurance

    165 Danielle Dr, Winston, OR 97496
  • /46

    $384,900

    • 3 Beds
    • 2.5 Baths
    • 1,768 Sq Ft

    890 SE Thompson Ave, Winston, OR 97496

    You won't want to miss this beautifully maintained 3-bedroom, 2.5-bath Hi line home in Winston. Built in 2016, offering over 1,700 sq ft of thoughtfully designed living space. The open and functional layout includes a main-floor bonus room—perfect for a home office, playroom, or guest retreat—while abundant natural light fills the living areas, creating a warm and inviting atmosphere. The kitchen

    Anthony Beckham Different Better Real Estate

    890 SE Thompson Ave, Winston, OR 97496
  • /44

    $719,000

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    411 Woodland Dr, Roseburg, OR 97471

    Discover a lifestyle rooted in fresh air, room to roam, and time spent outside. This two-story ranch sits above sweeping views of Abacela Vineyard and offers Lookingglass Creek frontage with irrigation rights, K-line system, and pump already in place. Enjoy your own private swimming hole, raised-bed fenced garden, and greenhouse—perfect for growing, tinkering, and staying active year-round.The

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471
  • /15

    $239,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    90 SE Darrell Ave, Winston, OR 97496

    This charming 2-bedroom, 2-bathroom manufactured home in Winston, Oregon offers comfortable, modern living in a convenient location close to shopping, dining and other local amenities. Nestled on its own land, this home combines privacy with easy access to town.Inside, you’ll love the open-design floor plan that creates a bright, spacious feel throughout the living room, dining area and

    Rebekah Sexauer eXp Realty, LLC

    90 SE Darrell Ave, Winston, OR 97496
  • /35

    $405,000

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft

    364 NW Teal St, Winston, OR 97496

    Welcome to this move-in ready, well-maintained one-level home in a highly desirable subdivision on the outskirts of Winston. Featuring 3 bedrooms, 2 bathrooms and dedicated home office. This property offers both comfort and convenience. Open floorplan with master suite privately positioned at the opposite end of the house for added tranquility. 3-car attached garage provides ample storage and

    Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

    364 NW Teal St, Winston, OR 97496
  • /20

    $89,000

    • Land
    • 0.12 Acre
    • $741,667 per Acre

    271 SE Robinson St, Winston, OR 97496

    Build Your Dream Home on This Prime Lot!Nice Lot – Prime Location – All Utilities – Investment Opportunity!Discover the perfect canvas for your future home. This spacious lot comes with full utilities—water, electricity, and sewer—ready for you to build. Nestled in a good location, it’s ideal for families, investors, or anyone looking to live in town. Don’t miss out on this incredible

    Kayla Wehe Lamonte Real Estate Professionals

    271 SE Robinson St, Winston, OR 97496
  • /37

    $525,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    160 Wil Way, Winston, OR 97496

    New Home by JW Construction Inc.This beautiful one-level home offers just over 2,000 square feet with three bedrooms and two and a half bathrooms. The open great room features vaulted ceilings, luxury vinyl plank flooring, recessed lighting, and a gas fireplace. A large sliding door opens to an expansive deck, perfect for entertaining or relaxing. The kitchen is designed for both style and

    Tyler Head Turning Point Realty Group

    160 Wil Way, Winston, OR 97496
  • /28

    $768,000

    • 3 Beds
    • 2 Baths
    • 2,070 Sq Ft

    264 Mattie K Ln, Roseburg, OR 97471

    This lovely 3-bedroom, 2-bath, 2,070 sq ft home in Lookingglass, Oregon, sits at the end of a private drive on 1.69 acres of peaceful, wooded land filled with tall pines and firs. Built in 2009, it offers an abundance of natural light through large windows and includes ceiling fans in every room for year-round comfort. The property is ideal for a mini farm, featuring a fenced, irrigated garden

    Greg Messick RealtyNET, LLC

    264 Mattie K Ln, Roseburg, OR 97471
  • /41

    $830,000

    • 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
  • /20

    $500,000

    • 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
  • /27

    $325,000

    • 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 is

    Jerry Norman Oregon Life Homes

    120 SE Edwards Ave, Winston, OR 97496
  • /15

    $269,000

    • Land
    • 16.59 Acres
    • $16,215 per Acre

    505 Sibold Canyon Rd, Tenmile, OR 97481

    Private 16.5+ acres in beautiful Sibold Canyon with frontage along seasonal Porter Creek. Former homesite is cleared and ready for your new home with well, septic, and power onsite. Approx. 2 acres of level pasture and fruit trees sit near the original homesite. Remaining acreage offers sloped terrain with trails and an access road for recreation, wildlife viewing, and potential building sites.

    Aaron Cherry Oregon Life Homes

    505 Sibold Canyon Rd, Tenmile, OR 97481
  • /39

    $675,000

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    166 Whitson Ln, Myrtle Creek, OR 97457

    Stunning 126.67-Acre Property with Breathtaking Views and Two HomesThis exceptional 126.67-acre property offers unparalleled views of the picturesque Umpqua Valley and the scenic South Umpqua River below. The property is divided into two tax lots, each with its own unique appeal and potential.The first lot features a beautifully remodeled 3-bedroom, 2-bathroom home with 1,416 sq ft of living

    Theresa Montoya Vantage Point Brokers, LLC

    166 Whitson Ln, Myrtle Creek, OR 97457
  • /36

    $199,000

    • 3 Beds
    • 2 Baths
    • 1,156 Sq Ft

    301 NW Midway St, Winston, OR 97496

    AMAZING INVESTMENT OPPORTUNITY!!! Cosmetic fixer upper features 3 Bedrooms, 2 baths, 2 car garage, spacious lot nearly half an acre & fully fenced with outbuildings. Tons of parking for RV's, cars or other toys. Central heat, indoor laundry room & vinyl windows. Bring your tools, your ideas & your cash!!

    Tracy Grubbs eXp Realty, LLC

    301 NW Midway St, Winston, OR 97496
  • /35

    $142,500

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    112 Twin Oaks Loop, Winston, OR 97496

    WOW! BRAND NEW 2025 manufactured home in the tidy senior living 55+ Twin Oaks community! This 3-bed, 2-bath home features an open floor plan with a large kitchen island, stainless steel appliances, and modern finishes throughout. The primary suite includes double sinks and a walk-in shower. Covered carport and storage shed add convenience. Space rent $725/month and includes water, sewer, and

    Anthony Beckham Different Better Real Estate

    112 Twin Oaks Loop, Winston, OR 97496
  • /32

    $575,000

    • 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

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