Homes for Sale near Douglas High School

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  /44

  $849,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,805 Sq Ft

  300 Mattie K Ln, Roseburg, OR 97471

  Beautiful country setting custom home located in Lookingglass Valley! Spacious, open floor plan with gourmet kitchen and cozy fireplace ideal for entertaining. Stainless steel appliances, dual oven, granite countertops, hickory cabinets, pantry, eat bar, solid hickory flooring. 2 New heat pumps and hot water heaters, laundry room. Primary bedroom has walk-in California style closet, walk-in

  Melony Marsh All-Pro Realty Advisors, LLC

  

  300 Mattie K Ln, Roseburg, OR 97471
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  /34

  $350,000

  $9K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,710 Sq Ft

  380 NW Cary St, Winston, OR 97496

  Schedule your private tour today of this adorable 4bd 2ba open floor plan home, located on a generous lot, with an extra deep garage and additional off-street parking for your RV or Boat. Just a 15-minute drive to Roseburg, close to local schools and just down the street from the Wildlife Safari.

  Willow Pearson Oregon Life Homes

  

  380 NW Cary St, Winston, OR 97496
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  /48

  $915,000

  Open Sat 11AM - 2PM $84K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,356 Sq Ft

  6404 Lookingglass Rd, Roseburg, OR 97471

  Possible owner carry? 2 HOMES! Sellers are motivated! Bring all offers! Dreaming of starting your very own vineyard? Maybe raising livestock? This unbelievably level 30 acre property can do it all! There are 2 homes. The main house is over 2300 sqft boasting 3 bedrooms and 3 full bathrooms. The kitchen is a chefs dream, complete with butcher block island! The open floor plan allows for large

  Brent Yop Winston Realty & Insurance

  

  6404 Lookingglass Rd, Roseburg, OR 97471
• 

  

  

  /20

  $515,000

  $35K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  572 Dillard Gardens Rd, Winston, OR 97496

  Peaceful and secluded home on the South Umpqua River. Set on 6.9 acres with water rights and an established cherry orchard. The home features wood floors, good natural light, a cozy living room, open kitchen and dining area and a large primary bedroom with an attached bath and walk in closet. Back yard filled with flowers and shade trees. New septic system installed in 2021. Zoned (F1) Exclusive

  Mike Nichols MORE Realty, Inc.

  

  572 Dillard Gardens Rd, Winston, OR 97496
• 

  

  

  /22

  $299,000

  $16K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,348 Sq Ft

  101 SW Peach Ln, Winston, OR 97496

  This single-level home features 3 bedrooms and 1 bathroom, offering comfortable and convenient living. Step outside to a spacious, fully fenced backyard perfect for pets, play or entertaining. Garden enthusiasts will appreciate the dedicated garden area, while multiple tool sheds provide ample storage for tools, equipment and hobbies. A large covered real patio creates an ideal space for

  Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

  

  101 SW Peach Ln, Winston, OR 97496
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  /24

  $95,000

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

  110 Charlene Ln, Tenmile, OR 97481

  Comfortable 3 BR/2 BA home located in a quiet manufactured home park community. Offering 1,512 sf of living space, this home features an open floor plan with living room and family room areas, providing plenty of space to relax or entertain. The lot includes a fenced front yard, extra parking area, and a large tool shed equipped with a 100-amp panel and a 30-amp hookup, ideal for projects,

  Christine Drake Berkshire Hathaway HomeServices Real Estate Professionals

  

  110 Charlene Ln, Tenmile, OR 97481
• 

  

  /23

  $70,000

  $30K PRICE DROP

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

  124 Country Side Ln, Winston, OR 97496

  Welcome home to this charming home located in a beautifully maintained 55+ community! With 3 bedrooms, 2 baths, and 1,296 sq. ft. of inviting living space, this home features vaulted ceilings, a bright open layout, and a manicured corner lot. The walk-through kitchen includes a breakfast bar, built-in microwave, stove, refrigerator, and a brand-new dishwasher. The spacious primary suite offers

  Jason Mann J Mann Realty

  

  124 Country Side Ln, Winston, OR 97496
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  /43

  $99,000

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

  180 Twin Oaks Loop, Winston, OR 97496

  WOW! Enjoy affordable living in the sought-after 55+ Twin Oaks community! This spacious 3-bedroom, 2-bath double-wide offers 1404 square feet of comfortable living space with a thoughtful split-bedroom floor plan and vaulted ceilings. The oversized living room flows into the dining area, where a built-in hutch adds both charm and extra storage. The kitchen features granite tile countertops,

  Anthony Beckham Different Better Real Estate

  

  180 Twin Oaks Loop, Winston, OR 97496
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  /10

  $134,900

  • Land
  • 26,136 Sq Ft
  • $224,833 per Acre

  7944 Lookingglass Rd, Roseburg, OR 97471

  Discover the perfect blend of county charm and ready-to-build convenience on this fully fenced 0.6-acre level lot. Enjoy peace and security with a fully fenced lot and an electric gated entrance. A spacious 1,100-square-foot barn offers incredible value and potential, whether you are looking for the ultimate space to shelter your animals or create the shop of your dreams! With most of the

  Danielle Wright Oregon Life Homes

  

  7944 Lookingglass Rd, Roseburg, OR 97471
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  /45

  $399,000

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

  1090 E Willis Creek Rd, Winston, OR 97496

  A Place Where Memories Are Made, Private 9+ Acre RetreatStrategically located at the end of a private drive, this remarkable property offers the peace and privacy that is becoming increasingly hard to find. Set well back from the road, this hidden retreat invites you to slow down and enjoy the simple pleasures of country living. Take notice of the quiet, with towering trees, abundant wildlife,

  Marilyn Kittelman Cutting Edge Real Estate

  

  1090 E Willis Creek Rd, Winston, OR 97496
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  /48

  $829,000

  • 3 Beds
  • 2 Baths
  • 2,228 Sq Ft

  8160 Lookingglass Rd, Roseburg, OR 97471

  Ranch-style home on almost 17 acres in the desirable Lookingglass area with a pond, shops, and usable land! This property has everything you need in one beautiful place. Inside, the single-level home features a split-bedroom design, built-ins, and ample storage throughout. The kitchen is equipped with stainless steel appliances (including a gas range) and offers plenty of counter space, while the

  Najla Slater Stellar Realty Northwest

  

  8160 Lookingglass Rd, Roseburg, OR 97471
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  /17

  $339,000

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

  185 SE Lebleu Ln, Winston, OR 97496

  Picture enjoying your morning coffee on the back deck looking out over a peach orchard! This very tidy and well-maintained 3 bedroom, 2 bath house is situated in a quiet neighborhood and borders Brosi Orchards. Step inside to the living room with vaulted ceilings and gas fireplace, perfect for relaxing after a long day. Smartly designed layout with private master suite on one end of the home.

  Sandra Hart The Neil Company Real Estate

  

  185 SE Lebleu Ln, Winston, OR 97496
• 

  

  /23

  $365,000

  $24K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  10 SW Peach Ln, Winston, OR 97496

  Welcome to 10 SW Peach Ln, where every day feels like a peaceful retreat and every corner invites you to slow down and savor the moment. This special property blends warmth, character, and an unforgettable backyard oasis designed to elevate your everyday living.Step outside and imagine hosting summer gatherings on the resort-style brick patio, unwinding beside the soothing sounds of your private

  Kimberly Krebs Stellar Realty Northwest

  

  10 SW Peach Ln, Winston, OR 97496
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  /46

  $1,100,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,720 Sq Ft

  6700 Upper Olalla Rd, Winston, OR 97496

  Stunning custom cedar home on 5 level acres offering the perfect blend of luxury, functionality, and country living. This Lindal-style home features a spacious 2,400 sq ft shop with a full bath, dual garage doors, and enough space for a 40-foot motorhome. Property also includes 3 RV hookups with power, water, and RV dump access, ideal for guests, multi-use living, or recreational storage.The

  Dan Gandee Real Broker

  

  6700 Upper Olalla Rd, Winston, OR 97496
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  /30

  $255,000

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,070 Sq Ft

  3707 Willis Creek Rd, Winston, OR 97496

  Rare rural opportunity priced at land and utility value — for the investor, builder, or country-living dreamer ready to create something truly their own in the hills of Douglas County, Oregon. Utilities are already in place — a significant head start on any rural build. The property is served by Pacific Power electric and Winston City Water (public water), with an on-site septic system. Septic

  Michelle Kohlhoff Sundance Realty LLC

  

  3707 Willis Creek Rd, Winston, OR 97496
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  /41

  $169,900

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  600 SE Edgewood St, Winston, OR 97496

  WOW! Affordable 2-bedroom 1-bath home set on nearly half an acre in the heart of Winston. With 0.43 acres of usable ground, a fully fenced yard, mature shade trees, and room for RVs, trailers, boats, equipment, gardens, and outdoor projects, or possible future development, there's plenty of flexibility here! Inside features an open living area with updated laminate flooring, abundant natural

  Anthony Beckham Different Better Real Estate

  

  600 SE Edgewood St, Winston, OR 97496
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  /26

  $270,000

  $48K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  340 SE Darrell Ave, Winston, OR 97496

  ***JUST LOWEREDD PRICE BY $48,000!!!*** Solid 3-bedroom, single-level home with a functional layout, attached garage, and fully fenced yard with covered patio, and front porch.The home features a ductless heat pump for efficient heating and cooling, along with comfortable interior living spaces. Roof replaced within the last few years. Primary bedroom includes a walk-in closet and crown molding.

  Aaron Stansbury Keller Williams Realty Eugene and Springfield

  

  340 SE Darrell Ave, Winston, OR 97496
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  /32

  $268,000

  $12K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  509 NW Elwood Dr, Winston, OR 97496

  This adorable 3-bedroom, 1-bathroom home is the perfect starter home or an excellent addition to your investment portfolio. The kitchen was remodeled earlier this year. Conveniently located close to an elementary school, shopping, and everyday amenities, this home combines comfort with convenience. Whether you’re a first-time homebuyer, looking to downsize, or searching for a rental property,

  Jada Whited Oregon Life Homes

  

  509 NW Elwood Dr, Winston, OR 97496
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  /4

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  0 Berry Creek Rd, Winston, OR 97496

  This private, level 4-acre parcel offers convenient access to Ben Irving Reservoir and is the perfect setting for recreation, relaxation, or a future getaway retreat. The property features a large natural meadow surrounded by 20-year-old Douglas fir reprod, creating a peaceful and secluded atmosphere. Adjacent to BLM land, it provides direct access to endless outdoor opportunities. Improvements

  Ryan Fox Berkshire Hathaway HomeServices Real Estate Professionals

  

  0 Berry Creek Rd, Winston, OR 97496
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  /19

  $18,499

  $11K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,022 Sq Ft

  228 Estate Loop, Winston, OR 97496

  2 bed, 1 bath home in a desirable 55+ park featuring spacious living areas and a well-appointed kitchen with breakfast bar. Attached dining area includes built-ins for added storage and charm. Separate laundry room, plus a bathroom with walk-in shower for convenience. Outside features include covered porch, carport with attached storage area. Located close to shopping, dining, and other amenities.

  Jason Mann J Mann Realty

  

  228 Estate Loop, Winston, OR 97496
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  /4

  $2,000,000

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft

  80 NW Lost Ln, Winston, OR 97496

  Great Property for future Developing. 2007 Manufactured Home on .68 of a Ac. City Water and Sewer.

  Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

  

  80 NW Lost Ln, Winston, OR 97496
• 

  

  /44

  $245,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  2325 Tenmile Valley Rd, Tenmile, OR 97481

  Charming 2-bedroom, 1-bath home nestled on a peaceful half-acre in Tenmile, Oregon. Enjoy the tranquility of country living while being just a short drive from the Oregon Coast, Ben Irving Reservoir, and Wildlife Safari in Winston.Inside, you’ll find vaulted ceilings, an open-concept living space with an eating bar/pass-through, a dining area with a built-in hutch, and durable laminate flooring

  Shae Ellison Platinum Realty

  

  2325 Tenmile Valley Rd, Tenmile, OR 97481
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  /48

  $634,900

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

  635 Wil Way, Winston, OR 97496

  WOW! Panoramic valley views, over 20 acres of RM-zoned land, and a location bordering Wildlife Safari make this 4-bedroom, 3.5-bath, 3,072 SF home one of Southern Oregon’s most unique offerings. Positioned at the end of the road, it enjoys exceptional privacy while overlooking Abacela Vineyards, rolling valleys, and Wildlife Safari, with potential for 360-degree views. RM zoning adds rare

  Anthony Beckham Different Better Real Estate

  

  635 Wil Way, Winston, OR 97496
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  /48

  $1,199,900

  • 3 Beds
  • 2.5 Baths
  • 2,856 Sq Ft

  1349 Willis Creek Rd, Winston, OR 97496

  Quiet country living on private acreage! Offered for the first time ever, this exceptional estate presents a rare opportunity to own a truly special piece of the Pacific Northwest. Featuring two separate residences, this property is perfectly suited for multi-generational living, guest accommodations, or potential rental income. The primary home offers over 2,800 square feet of inviting living

  Jordan Anderson The Anderson Agency

  

  1349 Willis Creek Rd, Winston, OR 97496
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  /30

  $399,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft

  675 SE Brush Ct, Winston, OR 97496

  This beautifully maintained home is tucked away in a cul-de-sac in the heart of Winston, offering both privacy and convenience. With three comfortable bedrooms and two well-appointed bathrooms, the open-concept layout creates a welcoming atmosphere that’s ideal for hosting gatherings. The kitchen features a spacious island, perfect for preparing meals and entertaining guests. Vaulted ceilings in

  Christina Esterbrook J Mann Realty

  

  675 SE Brush Ct, Winston, OR 97496
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  /40

  $459,990

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  535 SE Parkway Dr, Winston, OR 97496

  Enjoy your own Fourth of July fireworks show from the comfort of your rear deck with front-row views of the surrounding area! Meticulously maintained single-level home located in the highly desirable Parkway Subdivision. Offering 1,442 square feet of comfortable living space, this home features 3 bedrooms and 2 bathrooms and is situated on a generously sized lot with beautiful views of the

  Lisa Ollivant RE/MAX Integrity

  

  535 SE Parkway Dr, Winston, OR 97496
• 

  

  /45

  $599,000

  • 5 Beds
  • 2 Baths
  • 2,405 Sq Ft

  1177 Dairy Loop Rd, Roseburg, OR 97471

  Country living in the desirable Lookingglass area! This farmhouse sits on 10.6 level acres featuring a seasonal pond, pasture area, fruit trees, gardening space with raised beds, chicken coop, and multiple outbuildings including a barn, storage areas, and covered parking. Whether you have animals, hobbies, equipment, or simply want room to spread out, this property offers the space and setting to

  Najla Slater Stellar Realty Northwest

  

  1177 Dairy Loop Rd, Roseburg, OR 97471
• 

  

  /10

  $350,000

  • Land
  • 50 Acres
  • $7,000 per Acre

  0 Lookingglass Rd Unit TL 203, Winston, OR 97496

  50 acres in the Umpqua Valley AVA. Great location by Abacela vineyard with incredible views of the countryside. Zoned Residential Medium Density. Potential for a custom home and residential development. Do not access this property without authorization.

  Mike Nichols MORE Realty, Inc.

  

  0 Lookingglass Rd Unit TL 203, Winston, OR 97496
• 

  

  /39

  $659,000

  • 3 Beds
  • 2 Baths
  • 2,038 Sq Ft

  460 Little Branch Ln, Roseburg, OR 97471

  Welcome to your own private retreat on approximately 7 beautiful acres just outside of Roseburg, Oregon. Offering the perfect blend of country living and modern comfort, this spacious 2,038-square-foot single-level home is designed for those who appreciate room to spread out both inside and out.Step inside to an inviting open floor plan that creates a seamless flow between the living room and

  Rebekah Sexauer eXp Realty, LLC

  

  460 Little Branch Ln, Roseburg, OR 97471
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  /48

  $495,000

  $130K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  624 Willis Creek Rd, Winston, OR 97496

  This rare riverfront horse property on the South Umpqua River is not to be missed! The home features a brand new 600 sq. ft. deck overlooking the property and river, new roof,a centrally located wood stove that heats the entire house, and is tucked away off the road for privacy. Horse facilities include an arena, barn, multiple stalls, and pasture. Additional amenities include an orchard,

  Nancy Kruger Keller Williams Southern Oregon-Umpqua Valley

  

  624 Willis Creek Rd, Winston, OR 97496
• 

  

  /45

  $775,000

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

  375 Porter Creek Rd, Winston, OR 97496

  Significant priced improvement! Discover the perfect blend of vineyard lifestyle and modern comfort in this recently 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. A spacious 3,000 sq ft home featuring four large bedrooms, large

  Lorrie Normann Triple Oaks Realty LLC

  375 Porter Creek Rd, Winston, OR 97496
• 

  /2

  $209,900

  $10K PRICE DROP

  • Land
  • 40 Acres
  • $5,248 per Acre

  0 Willis Creek Rd Unit 124013990, Winston, OR 97496

  Exceptional Farm Forest–zoned timber property offers both natural beauty and strong investment potential. A recent professional timber cruise, inventory, and valuation completed by Resource Management Services highlights the value of this well-managed stand. Timber prices fluctuate but as of March, the net timber value is estimated at $174,749, consisting primarily of healthy, marketable Doug

  Craig Warmouth Berkshire Hathaway HomeServices Real Estate Professionals

  

  0 Willis Creek Rd Unit 124013990, Winston, OR 97496
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  /28

  $320,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  351 SE Darrell Ave, Winston, OR 97496

  This 3 Bedroom/1 Bath, family home on over 1/3-acre has been completely updated for your enjoyment. There are many new items, including roof, mini split system, LVP flooring throughout, interior and exterior paint, plumbing and outside waterline. The bathroom/laundry room has been completely renovated. The yards are fully fenced, and there is a nice large deck on the back overlooking the large

  Debra Moore Currieco Real Estate

  

  351 SE Darrell Ave, Winston, OR 97496
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  /8

  $590,000

  • Land
  • 4.77 Acres
  • $123,690 per Acre

  350 View Point Terrace, Winston, OR 97496

  Excellent investment opportunity! 31 platted lots prime for development in the growth seeking city of Winston! This early 1980's subdivision is prominently located next to a newer construction community to strengthen the potential development value. Pacific Power just confirmed power is available! Call Winston city manager with all your building/development questions as he will accommodate all

  Michael Fischer Oregon Life Homes

  

  350 View Point Terrace, Winston, OR 97496
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  /39

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  895 Mulberry Ln, Roseburg, OR 97471

  Welcome to your slice of Southern Oregon paradise! Enjoy sweeping views from the deck overlooking the serene countryside. Whether you're exploring the acreage amongst the trees or taking in the beauty of the private pond, you'll love life on Mulberry Lane just 10 minutes to the amenities and conveniences of town.

  Leah Hyland Haven Lane Realty

  

  895 Mulberry Ln, Roseburg, OR 97471
• 

  

  /16

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  261 SE Darrell Ave, Winston, OR 97496

  Wonderful little cottage for the first time home buyer or the investor needing one more rental in there portfolio. This home is located on a double lot. Per city of Winston, lot is dividable. Build an additional house on its own lot, or leave it as-is and build an ADU or shop in your backyard. Come check this out and make your appointment today.

  Angel Smith Trueblood Real Estate

  

  261 SE Darrell Ave, Winston, OR 97496
• 

  

  /13

  $99,000

  $10K PRICE INCREASE

  • Land
  • 5.78 Acres
  • $17,128 per Acre

  0 Willis Creek Rd Unit 23389927, Winston, OR 97496

  One of the last vacant lots on Willis Creek Rd. .76 acres between roadway and the creek. 5.02 wooded acres up the hill that levels off to a rather flat area for building site. With a bit of road grading and building pad clearing. This location offers seclusion in the trees with views of the surrounding hills and valley.

  Thomas Gulan RE/MAX Integrity

  

  0 Willis Creek Rd Unit 23389927, Winston, OR 97496

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