Winchester, OR Homes

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  $649,000

  • 6 Beds
  • 2 Baths
  • 3,580 Sq Ft

  331 Hemlock Ln, Roseburg, OR 97471

  Beautifully refinished home on 5 acres off desired Fisher Rd. area. This home has room for it all, and views all around. With 6 bedrooms, an office, living room and family room, there is no shortage of space and storage. There are 3 bedrooms upstairs, and 3 bedrooms and an office downstairs. The living room boasts 18' ceilings, a floor to ceiling fireplace, and a wet bar. The kitchen/dining room

  

  Wyndee Konopaski

  Keller Williams Southern Oregon-Umpqua Valley

  (458) 310-4954

  

  331 Hemlock Ln, Roseburg, OR 97471
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  /2

  $1,450 per month

  Oak Springs

  1 Bed

  331 NE Pomona St, Roseburg, OR 97470

  331 NE Pomona St, Roseburg, OR 97470
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  /30

  $205,000 Sold Apr 30, 2025

  26 NW Mountain View Dr, Roseburg, OR 97471

  • 2 Beds
  • 1.5 Baths
  • 1,296 Sq Ft
  • Built 1972

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 90 Days On Market

  Current Estimated Value $207,239

  Last Listing Agent Zach Field Different Better Real Estate

  

  26 NW Mountain View Dr, Roseburg, OR 97471
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  /48

  Est $970,494 Not Listed For Sale

  640 Cherokee Ave, Roseburg, OR 97471

  • 3 Beds
  • 2.5 Baths
  • 2,313 Sq Ft
  • Built 2011

  

  640 Cherokee Ave, Roseburg, OR 97471

  Last Sold Summary

  • 3% Below List Price
  • $433/SF
  • 94 Days On Market

  Last Sold Price $1,002,000

  Last Listing Agent Jennifer Kramer RE/MAX
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  $639,900

  • 4 Beds
  • 3 Baths
  • 2,954 Sq Ft

  286 Winchester Creek Ave, Winchester, OR 97495

  Experience refined living in Winchester Creek. This elegant two-story home with a full walk-out basement offers over 2,900 sq. ft. of beautifully designed space in one of North Roseburg’s mostdesirable communities.The main level features a spacious primary suite, a dedicated office, and an open-concept living and dining area ideal for entertaining. The kitchen offers a pantry and ample storage,

  

  Kristina Scott

  Umpqua Legacy Realty

  (458) 231-8692

  

  286 Winchester Creek Ave, Winchester, OR 97495
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  /14

  $1,375 per month

  Saddle Butte Duplexes

  2 Beds

  101 Village Dr, Winchester, OR 97495

  This is a completely remodeled 2+ bedroom/1.5 bath condo style duplex in a quiet neighborhood with beautiful landscaping! It is approximately 1150 square feet, single level. It features granite countertops, brand new cabinets, brand new luxury plank floor, and new appliances. The unit also includes: Washer/dryer hookup in the laundry room, dishwasher, heat and air, garage with storage, and

  101 Village Dr, Winchester, OR 97495
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  /48

  $732,500 Sold Aug 28, 2025

  1356 Echo Dr, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1987

  Last Sold Summary

  • 13% Below List Price
  • $372/SF
  • 104 Days On Market

  Current Estimated Value $729,783

  Last Listing Agent Deborah Whitaker Roseburg Realty

  

  1356 Echo Dr, Roseburg, OR 97470
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  /26

  Est $262,735 Not Listed For Sale

  617 NE Channon Ave, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1945

  

  617 NE Channon Ave, Roseburg, OR 97470

  Last Sold Summary

  • 2% Below List Price
  • $291/SF
  • 163 Days On Market

  Last Sold Price $268,461

  Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley
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  $650,000

  • 4 Beds
  • 3.5 Baths
  • 3,120 Sq Ft

  786 N View Dr, Roseburg North, OR 97495

  Perfect for multi-generational living, this 3,120 sq ft Winchester home features two primary suites—one on the main level and another upstairs. With 4 bedrooms, 3.5 bathrooms, two spacious living areas, and an upstairs flex space ideal for a home office, this home provides flexibility, comfort, and room to grow. Recent updates include updated flooring, fresh interior paint, new accent lighting,

  

  Kristina Scott

  Umpqua Legacy Realty

  (458) 243-4664

  

  786 N View Dr, Roseburg North, OR 97495
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  /34

  $310,000 Sold Oct 31, 2025

  1820 NW Otie St, Roseburg, OR 97470

  • 4 Beds
  • 2 Baths
  • 2,162 Sq Ft
  • Built 1973

  Last Sold Summary

  • 11% Below List Price
  • $143/SF
  • 29 Days On Market

  Current Estimated Value $364,792

  Last Listing Agent Neil Hummel The Neil Company Real Estate

  

  1820 NW Otie St, Roseburg, OR 97470
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  /22

  Est $342,356 Not Listed For Sale

  581 NE Newton Creek Rd, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1965

  

  581 NE Newton Creek Rd, Roseburg, OR 97470

  Last Sold Summary

  • 2% Below List Price
  • $306/SF
  • 10 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Aaron Daniel Lamonte Real Estate Professionals
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  /43

  $875,000 Pending

  • 6 Beds
  • 3.5 Baths
  • 4,607 Sq Ft

  101 Aster St, Winchester, OR 97495

  Unique opportunity to own this beautiful Winchester home. A large corner lot, fully fenced, and private. Optimal outdoor area, with circular driveway, tons of parking, RV hook-up, 20x20 outbuilding, covered patio, lots of privacy and room to entertain. Come inside this grand home with high ceilings, a main level master, and second level master. Hardwood floors expand throughout the main level

  

  Wyndee Konopaski

  Keller Williams Southern Oregon-Umpqua Valley

  (458) 254-5748

  

  101 Aster St, Winchester, OR 97495
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  /31

  $860,000 Sold Dec 23, 2025

  650 Southridge Way, Roseburg, OR 97470

  • 4 Beds
  • 3 Baths
  • 2,758 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Below List Price
  • $312/SF
  • 5 Days On Market

  Current Estimated Value $863,043

  Last Listing Agent Christina Esterbrook J Mann Realty

  

  650 Southridge Way, Roseburg, OR 97470
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  /34

  Est $321,562 Not Listed For Sale

  2999 NE Parker Rd, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • Built 2024

  

  2999 NE Parker Rd, Roseburg, OR 97470

  Last Sold Summary

  • 1% Below List Price
  • $272/SF
  • 0 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley
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  $2,500,000

  • 4 Beds
  • 5.5 Baths
  • 5,185 Sq Ft

  375 Bella Hills Ln, Roseburg, OR 97471

  Experience the pinnacle of Umpqua Valley living at 375 Bella Hills Lane—an extraordinary 80+ acre, agriculturally zoned estate with sweeping views of the Umpqua River. Peaceful, private, and rich with opportunity, this exceptional agriculturally zoned property offers limitless potential—ideal for a boutique vineyard, agricultural operations, multigenerational living, income-producing retreat, or

  

  Kristina Scott

  Umpqua Legacy Realty

  (458) 310-3629

  

  375 Bella Hills Ln, Roseburg, OR 97471
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  /48

  $720,000 Sold Jul 09, 2025

  390 Singing Waters Rd, Winchester, OR 97495

  • 2 Beds
  • 2 Baths
  • 1,928 Sq Ft
  • Built 2010

  Last Sold Summary

  • 1% Below List Price
  • $373/SF
  • 4 Days On Market

  Current Estimated Value $720,236

  Last Listing Agent Veronica Gillespie eXp Realty, LLC

  

  390 Singing Waters Rd, Winchester, OR 97495
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  /48

  Est $951,685 Not Listed For Sale

  776 Cherokee Ave, Roseburg, OR 97471

  • 3 Beds
  • 2.5 Baths
  • 2,442 Sq Ft
  • Built 2013

  

  776 Cherokee Ave, Roseburg, OR 97471

  Last Sold Summary

  • 1% Below List Price
  • $393/SF
  • 5 Days On Market

  Last Sold Price $960,000

  Last Listing Agent Jennifer Kramer RE/MAX
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  /45

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft

  1660 NE Alameda Ave, Roseburg, OR 97470

  Here's a unique opportunity for the beautiful Rocky Ridge Community! Relatively newer built home for a great price. As you enter, you will immediately notice the vaulted ceilings giving a very spacious feeling with the open floor plan. The light laminate flooring provides a lively sense to the home with nice natural lighting. The kitchen has gorgeous granite with stainless steel appliances and

  

  Ashton Faas

  Different Better Real Estate

  (458) 310-2120

  

  1660 NE Alameda Ave, Roseburg, OR 97470
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  /2

  $124,000 Sold Jun 06, 2025

  1066 NW Plateau Dr, Roseburg, OR 97471

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $158/SF
  • 12 Days On Market

  Current Estimated Value $161,000

  Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  1066 NW Plateau Dr, Roseburg, OR 97471
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  /37

  Est $458,952 Not Listed For Sale

  1791 NE Rocky Dr, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft
  • Built 2012

  

  1791 NE Rocky Dr, Roseburg, OR 97470

  Last Sold Summary

  • $278/SF
  • 35 Days On Market

  Last Sold Price $457,000

  Last Listing Agent Melony Marsh All-Pro Realty Advisors, LLC
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  /46

  $705,000

  • 3 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  1062 Southridge Way, Roseburg, OR 97470

  Enter through the gates of Winchester Ridge and follow your private drive to this beautifully crafted custom home set on 2.36 serene acres. Offering 3 bedrooms plus a flexible bonus room (or 4th bedroom), 2.1 baths, and 2,104 SF, this home blends elegance, comfort, and space to unwind. Inside, soaring ceilings, expansive windows, and abundant natural light create a bright, open atmosphere. The

  

  Kathy Flowers

  All-Pro Realty Advisors, LLC

  (458) 302-8031

  

  1062 Southridge Way, Roseburg, OR 97470
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  /43

  $350,000 Sold Sep 26, 2025

  2297 NE Vine St, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Below List Price
  • $258/SF
  • 54 Days On Market

  Current Estimated Value $347,546

  Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  2297 NE Vine St, Roseburg, OR 97470
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  /33

  Est $431,798 Not Listed For Sale

  276 N View Dr, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 2003

  

  276 N View Dr, Roseburg, OR 97470

  Last Sold Summary

  • 12% Above List Price
  • $256/SF
  • 55 Days On Market

  Last Sold Price $386,500

  Last Listing Agent Merlynn M. Cruz Cutting Edge Real Estate
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  /34

  $1,795,000

  • Land
  • 556.02 Acres
  • $3,228 per Acre

  2268 Sunshine Rd, Roseburg, OR 97470

  553± acres of rolling hills, timber, water, and open sky! An opportunity to own a true piece of Southern Oregon. Just minutes outside of Roseburg, this expansive EFU-zoned (Exclusive Farm Use – Grazing) property offers a rare blend of privacy, usability, and long-term potential. The land unfolds with a diverse mix of open pasture, timbered ridges, and natural creek corridors. Expansive valley and

  

  Nick Shivers

  eXp Realty, LLC

  (458) 299-0687

  

  2268 Sunshine Rd, Roseburg, OR 97470
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  /25

  $202,000 Sold Aug 05, 2025

  424 NE Kirby Ave, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1987

  Last Sold Summary

  • 8% Below List Price
  • $180/SF
  • 3 Days On Market

  Current Estimated Value $205,941

  Last Listing Agent Cindy Mahaffy RE/MAX Integrity

  

  424 NE Kirby Ave, Roseburg, OR 97470
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  Not Listed For Sale

  18 Mary Ann Ln, Roseburg, OR 97470

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1984

  

  18 Mary Ann Ln, Roseburg, OR 97470

  Last Sold Summary

  • $49/SF
  • 4 Days On Market

  Last Sold Price $79,000

  Last Listing Agent Neil Hummel The Neil Company Real Estate
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  /48

  $535,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 3,360 Sq Ft

  3257 NE Follett St, Roseburg, OR 97470

  Rare in-town acreage with space, privacy, and views. Situated on 1.52 acres, this expansive 5-bedroom, 2.5-bath home offers over 3,300 square feet of flexible living space with an open floor plan designed for both comfort and functionality. Enjoy city views while still feeling tucked away and private, with room to spread out indoors and out.The layout lends itself to multiple uses: perfect for

  

  Chelsie Siemens

  Fathom Realty Oregon, LLC

  (458) 307-2201

  

  3257 NE Follett St, Roseburg, OR 97470
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  /43

  $560,000 Sold Aug 11, 2025

  1260 NE Granite Ridge St, Roseburg, OR 97470

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $262/SF
  • 4 Days On Market

  Current Estimated Value $562,961

  Last Listing Agent Sherri Brown The Neil Company Real Estate

  

  1260 NE Granite Ridge St, Roseburg, OR 97470
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  /29

  Not Listed For Sale

  506 Shadow Ranch Ln, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1978

  

  506 Shadow Ranch Ln, Roseburg, OR 97470

  Last Sold Summary

  • $83/SF
  • 76 Days On Market

  Last Sold Price $96,000

  Last Listing Agent Anthony Beckham Different Better Real Estate
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  /48

  $1,595,000

  • 4 Beds
  • 6 Baths
  • 3,843 Sq Ft

  130 Stengar Ln, Roseburg, OR 97471

  Experience the pinnacle of riverfront living on the historic North Umpqua River. From the moment you pull into the elegant circle drive, it is clear this estate was crafted with a rare level of intention. This isn't just a house; it’s a masterwork of detail where no corner was cut and every amenity was chosen to elevate your daily life.Step inside to find a warm, inviting atmosphere defined by

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  130 Stengar Ln, Roseburg, OR 97471
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  /48

  $260,000 Sold Jul 28, 2025

  1770 NE Beulah Dr Unit 24, Roseburg, OR 97470

  • 3 Beds
  • 2.5 Baths
  • 1,718 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $151/SF
  • 80 Days On Market

  Current Estimated Value $267,291

  Last Listing Agent Jennifer Drumright eXp Realty, LLC

  

  1770 NE Beulah Dr Unit 24, Roseburg, OR 97470
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  /23

  Not Listed For Sale

  403 Shadow Ranch Ln, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1978

  

  403 Shadow Ranch Ln, Roseburg, OR 97470

  Last Sold Summary

  • $24/SF
  • 67 Days On Market

  Last Sold Price $22,500

  Last Listing Agent Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley
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  /48

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 3,731 Sq Ft

  1330 Fisher Rd, Roseburg, OR 97471

  Private North Umpqua River retreat on 1.09 acres! Enjoy stunning river views, an in-ground pool, heated hardwood floors, gourmet kitchen, and multiple decks designed to take in the peaceful sounds of the river. A paved circular driveway welcomes you home and leads to an oversized three car garage with additional covered storage along the side, plus a separate workshop perfect for hobbies,

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  1330 Fisher Rd, Roseburg, OR 97471
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  /38

  $80,000 Sold Sep 17, 2025

  12 NE Mary Ann Ln, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $56/SF
  • 20 Days On Market

  Last Listing Agent Tracy Grubbs eXp Realty, LLC

  

  12 NE Mary Ann Ln, Roseburg, OR 97470
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  /19

  Not Listed For Sale

  127 Northpark Ln, Roseburg, OR 97470

  • 1 Bed
  • 1 Bath
  • 504 Sq Ft
  • Built 1972

  

  127 Northpark Ln, Roseburg, OR 97470

  Last Sold Summary

  • $58/SF
  • 89 Days On Market

  Last Sold Price $29,000

  Last Listing Agent Jason Mann J Mann Realty
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  /48

  $312,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,572 Sq Ft

  1463 Four Seasons Dr Unit 10, Roseburg, OR 97470

  Welcome to this beautifully maintained and thoughtfully updated condo in the highly sought-after Four Seasons community, located at 1463 Four Seasons Dr in Roseburg. With inviting curb appeal featuring stacked rock accents and a newer roof installed in 2023, this home offers both style and peace of mind from the moment you arrive. Step inside to a spacious and light-filled main level where the

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  1463 Four Seasons Dr Unit 10, Roseburg, OR 97470
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  /48

  $544,000 Sold Dec 11, 2025

  91 N River Dr, Roseburg, OR 97470

  • 5 Beds
  • 3 Baths
  • 2,892 Sq Ft
  • Built 1975

  Last Sold Summary

  • 1% Below List Price
  • $188/SF
  • 10 Days On Market

  Current Estimated Value $544,350

  Last Listing Agent Veronica Gillespie eXp Realty, LLC

  

  91 N River Dr, Roseburg, OR 97470
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  /29

  Not Listed For Sale

  714 Shadow Ranch Ln, Roseburg, OR 97470

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft
  • Built 1980

  

  714 Shadow Ranch Ln, Roseburg, OR 97470

  Last Sold Summary

  • $56/SF
  • 78 Days On Market

  Last Sold Price $100,000

  Last Listing Agent Wyndee Konopaski Keller Williams Southern Oregon-Umpqua Valley
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  /48

  $530,000

  • 3 Beds
  • 2 Baths
  • 1,877 Sq Ft

  849 N View Dr, Winchester, OR 97495

  Charming and ideally located at 849 N View Dr, this home offers a seamless blend of comfort, functionality, and convenience. The thoughtfully designed layout features 3 bedrooms and 2 bathrooms with inviting living spaces bathed in natural light, creating a warm and welcoming atmosphere. Enjoy a fenced yard, sprinkler system, RV parking, and a garage, perfect for both relaxation and practicality.

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  849 N View Dr, Winchester, OR 97495
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  /20

  $68,000 Sold Oct 08, 2025

  1005 Shadow Ranch Ln, Roseburg, OR 97470

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1983

  Last Sold Summary

  • 9% Below List Price
  • $52/SF
  • 27 Days On Market

  Last Listing Agent Jerry Norman Oregon Life Homes

  

  1005 Shadow Ranch Ln, Roseburg, OR 97470

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