Winchester, OR Homes for Sale

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  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,581 Sq Ft

  556 N View Dr, Winchester, OR 97495

  Priced to sell!! Welcome to this beautifully maintained 4-bedroom home located in thedesirable Oak Valley Loop neighborhood. Thoughtfully cared for with fresh interior/exterior paint—this home blends comfort, style, and functionality. Step inside to soaring vaulted ceilings and bamboo floors, anchored by a cozy natural gas fireplace in the main living area. The spacious main-level primary suite

  

  Kristina Scott

  Umpqua Legacy Realty

  (458) 309-2302

  

  556 N View Dr, Winchester, OR 97495
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  /33

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,356 Sq Ft

  383 Ridgecrest Dr, Roseburg, OR 97471

  Owner carry option is available with approved terms!!Live Above the Clouds in Ridgeview’s Finest Remodel Perched high in the prestigious Ridgeview Gated Community, this exquisitely updated 4-bedroom, 2,356 sq ft home offers panoramic, unobstructed views of lush winery valleys and the majestic Callahan Mountains—visible from three of the four bedrooms. Step inside and experience luxury redefined.

  

  Kristina Scott

  Umpqua Legacy Realty

  (458) 217-1018

  

  383 Ridgecrest Dr, Roseburg, OR 97471
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  $719,900

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

  1062 Southridge Way, Roseburg, OR 97470

  Get ready to fall in love with this beautifully crafted custom home in the sought-after gated community of Winchester Ridge! With 3 spacious bedrooms, a bonus room or 4th bedroom, and 2.1 bathrooms spread across 2104 SF on 2.36 Acres, this property offers the perfect blend of elegance, comfort and room to roam. Step inside to a bright, open floor plan with soaring ceilings, walls of windows, and

  

  Kathy Flowers

  All-Pro Realty Advisors, LLC

  (458) 302-8031

  

  1062 Southridge Way, Roseburg, OR 97470
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  /45

  $287,500

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

  4545 Ridenour St, Roseburg, OR 97470

  Great opportunity for a home in the growing Winchester area! Featuring a fenced yard for pets or kids to play in. Terraced back yard, nice for hosting events. Relax in the sunroom or on the back patio during beautiful summer days. New RV hookups installed along with new bedroom and living room receptacles. Open kitchen area and large living room. Appliances are included! Master bedroom has 2

  

  Ashton Faas

  Different Better Real Estate

  (458) 310-2270

  

  4545 Ridenour St, Roseburg, OR 97470
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  $371,555 Open Sat 11PM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,459 Sq Ft

  1548 NW Eden St, Roseburg, OR 97470

  Priced below recent appraised value. Instant Equity! Perched atop a hill, this fully remodeled gem offers breathtaking panoramic views of the city and valley, making it a true sanctuary. Every inch of this home has been thoughtfully updated, blending modern comforts with classic charm. Featuring a brand-new roof, new exterior and interior paint, fully upgraded plumbing, HVAC and electrical

  Gina Pearl Premiere Property Group LLC

  

  1548 NW Eden St, Roseburg, OR 97470
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  /48

  $789,900

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

  1381 Echo Dr, Roseburg, OR 97470

  Welcome to 1381 Echo Drive in the desirable Echo Drive neighborhood, celebrated for its custom-built homes near the North Umpqua River and serene natural surroundings. Situated on 5 level acres, this spacious 5-bedroom, 3-bath home offers over 3,500 square feet of finished living space plus a semi-finished bonus / recreation space. Step inside to a thoughtfully designed floor plan featuring

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  1381 Echo Dr, Roseburg, OR 97470
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  /47

  $645,000

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  270 Glenwood Ct, Roseburg, OR 97471

  270 Glenwood Ct, Roseburg, OR – Conveniently located in the desirable Garden Valley area, this 3-bedroom, 2.5-bathroom home offers a country feel while still being close to town. Set on 5.65 flat, usable acres, the property blends comfort and functionality with natural beauty. Inside, you’ll find a spacious Casabella kitchen featuring granite countertops, stainless steel appliances, modern

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  270 Glenwood Ct, Roseburg, OR 97471
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  $790,000

  • 2 Beds
  • 2.5 Baths
  • 2,650 Sq Ft

  1346 Fisher Rd, Roseburg, OR 97471

  North Umpqua Riverfront Living + A Fisherman's Delight! Rare Legacy Property with Private Beach. A super opportunity to own an irreplaceable slice of Oregon paradise. Nestled on over an acre with a manicured yard and private river access, this custom cedar home is more than a residence, it’s a sanctuary for the soul. Tucked away in the desirable Fisher Road area of Roseburg, this custom-designed

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  1346 Fisher Rd, Roseburg, OR 97471
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  /48

  $1,199,000

  • 4 Beds
  • 4 Baths
  • 3,304 Sq Ft

  1435 Wilbur Rd, Roseburg, OR 97470

  Rich timber finishes enhance this exceptional estate, setting it apart from typical log cabins. Experience unparalleled luxury and privacy at 1435 Wilbur Rd, Roseburg, OR—an exquisite luxury log home nestled on 80 pristine acres of serene woodland. This masterfully crafted residence blends rustic elegance with sophisticated design, featuring soaring 28-foot ceilings, exposed beams, and expansive

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  1435 Wilbur Rd, Roseburg, OR 97470
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  /27

  $348,300

  • Land
  • 128.96 Acres
  • $2,701 per Acre

  0 NE Rocky Dr Unit 24990635, Roseburg, OR 97470

  128.96 acres total; 125.61 acres withing the city limits of Roseburg, and 3.35 acres outside city limits. Access to property off of Rocky Drive & NE Gardiner St which is unimproved at this time. Potential for major subdivision, condos, or a single home. Original subdivision plans available at listing office. prices at $2,700/acre.

  Greg Johnson G Stiles Realty

  0 NE Rocky Dr Unit 24990635, Roseburg, OR 97470
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  $5,495,000

  • 4 Beds
  • 2 Baths
  • 1,966 Sq Ft

  1104 Rio Nes Ln, Roseburg, OR 97470

  Carlin Ranch; a unique opportunity in Douglas county w/ a 859.75 acre historic property w/a rich heritage dating back to 1850. This secluded, end-of-road ranch offers breathtaking natural beauty, abundant wildlife,& significant water access. Key features include 2.6 miles of North Umpqua River, & +/- 50 acres of water rights. Situated within a historically established Columbian Whitetail Deer

  Garrett Zoller Land Leader

  

  1104 Rio Nes Ln, Roseburg, OR 97470
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  /16

  $99,000

  • Land
  • 3.23 Acres
  • $30,650 per Acre

  0 NE Rocky Dr Unit 4400 20539110, Roseburg, OR 97470

  3.23-acre parcel on Rocky Dr in Roseburg. Per city one home can be built on this parcel as it sits, Buyers to verify. Buyers responsible for all due diligence including approved uses and utilities. An additional 1.78-acre adjacent parcel is also available.

  Jacob Gilman The Neil Company Real Estate

  0 NE Rocky Dr Unit 4400 20539110, Roseburg, OR 97470
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  /2

  $120,000

  • 2 Beds
  • 1 Bath
  • 798 Sq Ft

  1119 NE Crescent Alley, Roseburg, OR 97470

  Investments opportunity, priced to sell, multi-residential zoning.

  Nathan Johnson G. Stiles Realty

  

  1119 NE Crescent Alley, Roseburg, OR 97470
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  $780,000

  • 4 Beds
  • 2.5 Baths
  • 2,780 Sq Ft

  2744 NW Daysha Dr, Roseburg, OR 97471

  Modern Luxury Living, Perfected!Experience refined sophistication in this modern stucco and stone estate, framed by elegant columns and an iron-fenced yard, where architectural beauty and everyday comfort meet.Inside, an open, light-filled layout features high ceilings and a vaulted living room that create an airy, inviting atmosphere. The designer kitchen is the centerpiece of the home,

  Wendy Rigsby All-Pro Realty Advisors, LLC

  

  2744 NW Daysha Dr, Roseburg, OR 97471
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  $529,990 Open Sat 10AM - 12PM

  • 3 Beds
  • 2.5 Baths
  • 1,732 Sq Ft

  159 Live Oak Ct, Roseburg, OR 97470

  Stunning Retreat with river views, river access, and high-end upgrades! Welcome to your dream home on the North Umpqua River! This beautifully updated 3-bedroom, 2.5-bathroom home offers breathtaking river views, private river access, and a serene lifestyle surrounded by nature. Step inside to find soaring ceilings and an open, airy layout anchored by a remodeled chef's kitchen featuring granite

  Julie Bancroft The Neil Company Real Estate

  

  159 Live Oak Ct, Roseburg, OR 97470
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  $925,000 Open Thu 1PM - 2:30PM

  • 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

  

  101 Aster St, Winchester, OR 97495
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  $599,000

  • 4 Beds
  • 3 Baths
  • 2,536 Sq Ft

  7978 N Bank Rd, Roseburg, OR 97470

  Roseburg rated #2 Place to Live in PNW by World Atlas! Recognized for its rivers, unique geology & natural beauty, this is the destination for those seeking lifestyle and legacy and this private 5-acre retreat puts you in the heart of it all. Set well off the road behind a gated entry the property is well maintained and the cherished home for its current owners the past 11+ years. They

  Marilyn Kittelman Cutting Edge Real Estate

  

  7978 N Bank Rd, Roseburg, OR 97470
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  $724,000

  • 4 Beds
  • 3 Baths
  • 2,648 Sq Ft

  3314 Fisher Rd, Roseburg, OR 97471

  Welcome to 3314 Fisher Rd, A rare slice of riverfront living with 4 bedrooms, 3 bathrooms, and 2,648 sq ft to call home. This split-level has so much to offer. The daylight basement comes with its own private entrance, full kitchenette, bedroom, bathroom, and living/dining space making it perfect for extended family, guests, or even rental income. Upstairs, the main living area is built for

  Anthony Beckham Different Better Real Estate

  

  3314 Fisher Rd, Roseburg, OR 97471
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  /48

  $799,929

  • 3 Beds
  • 2.5 Baths
  • 2,092 Sq Ft

  692 Echo Dr, Roseburg, OR 97470

  Discover luxury living at its finest in this completely remodeled, high-end home nestled along the serene banks of the North Umpqua River. (Complete remodel in 2023 by Lieberman Construction.) This rare gem offers an unmatched combination of modern elegance and natural beauty, set in a lush, park-like setting with sprawling gardens and valuable irrigation rights. Step inside to find an expansive

  Tracy Grubbs eXp Realty, LLC

  

  692 Echo Dr, Roseburg, OR 97470
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  /48

  $749,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  290 Singing Waters Rd, Roseburg North, OR 97495

  Peaceful setting on the North Umpqua River close to town. Paved, private boat access ramp to gorgeous, quiet area on the river (no road noise or thru traffic). Home has been completely cosmetically renovated with quality upgrades. The kitchen includes new stainless steel appliances, composite granite sink, and quartz countertops with Carrera marble backsplash. The kitchen is also open to the main

  Tami Morin The Neil Company Real Estate

  

  290 Singing Waters Rd, Roseburg North, OR 97495
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  $629,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 3 Baths
  • 3,278 Sq Ft

  370 Wild Fern Dr, Winchester, OR 97495

  Perched in the treetops, this custom Winchester home feels like your own private retreat. The expansive windows, skylights, and vaulted ceilings bring the outdoors in, filling the open living space with natural light and framing the gorgeous sunset views. The living room, complete with fireplace, flows through to the spacious deck, perfect for entertaining or relaxing. The remodeled kitchen feels

  Najla Slater Stellar Realty Northwest

  

  370 Wild Fern Dr, Winchester, OR 97495
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  $624,900

  • 3 Beds
  • 2.5 Baths
  • 2,632 Sq Ft

  Unlisted Address

  Discover an intelligently designed mid-century modern home in the heart of the Umpqua Valley, where timeless elegance meets contemporary comfort. This stunning property is perfectly suited as a primary residence, peaceful second home, or a desirable vacation rental, offering a harmonious blend of sophisticated design and a vibrant lifestyle. Step inside and experience a world of refined elegance

  Adam Joyce Value Home Realty

  

  Unlisted Address
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  $575,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  1223 Sable Dr, Roseburg, OR 97470

  Riverfront property located on the North Umpqua River. Enjoy this peaceful setting just minutes from town. This single-story 3 bedroom/2 bath home with attached two-car garage and large enclosed shop or RV garage sits on 1.36 level acres and has easy access to the Umpqua River. Water rights. In-ground irrigation established. Don't miss this opportunity.

  Meryl Pearson Oregon Life Homes

  

  1223 Sable Dr, Roseburg, OR 97470
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  $549,900

  • 3 Beds
  • 3 Baths
  • 3,460 Sq Ft

  148 Wild Fern Dr, Winchester, OR 97495

  Located in one of the most desirable subdivisions in Douglas County, this stunning chalet style home is ready for you to make it your new home. The living room features a stunning wall of windows, a gas fireplace insert and hardwood floors. The hardwood floors continue through the dining room and into the spacious kitchen, which boasts granite countertops, eating bar, and built-in oven, microwave

  Rich Raynor Heritage Real Estate

  

  148 Wild Fern Dr, Winchester, OR 97495
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  /48

  $640,000

  • 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

  

  331 Hemlock Ln, Roseburg, OR 97471
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  $598,000

  • 4 Beds
  • 2.5 Baths
  • 2,690 Sq Ft

  1548 NE Rocky Ridge Dr, Roseburg, OR 97470

  Luxurious Custom home in Rocky Ridge area located on just over half acre with amazing views of city, mountains and sunsets. The nearly 2700 square feet includes 4 bedrooms, 2.5 baths, gourmet kitchen, living room and family room. Luxury features throughout include main level Master Suite with jetted tub, slate flooring and shower, granite countertops with double sinks and large walk-in closet.

  Patti Archambault All-Pro Realty Advisors, LLC

  

  1548 NE Rocky Ridge Dr, Roseburg, OR 97470
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  $549,000

  • 3 Beds
  • 3 Baths
  • 3,152 Sq Ft

  1556 NE Kennedy Loop Dr, Roseburg, OR 97470

  This home is a dream for people who are 55 or older, active, and still want a large, spacious, elegant, beautiful home in a serene gated 55+ community! This stunning residence offers 3,152 square feet of luxurious living space designed for comfort and elegance. Featuring three spacious bedrooms and three beautifully appointed bathrooms, this home is perfect for both relaxation and entertaining.

  Joanne Graham eXp Realty, LLC

  

  1556 NE Kennedy Loop Dr, Roseburg, OR 97470
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  $240,000

  • 3 Beds
  • 1 Bath
  • 896 Sq Ft

  1650 NE Winter St, Roseburg, OR 97470

  This charming 3 bedroom, 1 bath bungalow is set in the heart of one of Roseburg’s great established neighborhoods! This home may be smaller in size, but it makes up for it with smart design, a warm vibe, and plenty of hidden storage—including a spacious attic. Step outside to your own backyard oasis: a large, private, fully fenced yard featuring fruit trees, a covered deck perfect for weekend

  Anthony Beckham Different Better Real Estate

  

  1650 NE Winter St, Roseburg, OR 97470
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  $164,900

  • 2 Beds
  • 1 Bath
  • 1,441 Sq Ft

  3248 NE Johnson St, Roseburg, OR 97470

  WOW! INVESTOR SPECIAL! Tucked away on the end of a quiet street, this property offers a rare sense of privacy and potential. Set on a .28-acre lot that backs up to open, undeveloped land, this 2-bedroom, 1-bath home is 1,441 square feet and is ready for its next chapter. Inside, vaulted ceilings with exposed wood beams add character and warmth to the open floor plan. Large windows bring in

  Anthony Beckham Different Better Real Estate

  

  3248 NE Johnson St, Roseburg, OR 97470
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  $454,900

  • 3 Beds
  • 2.5 Baths
  • 1,852 Sq Ft

  1734 NE Shale Ct, Roseburg, OR 97470

  Welcome to this beautiful 3-bedroom, 2.5-bathroom home located in the highly desirable Rocky Ridge neighborhood. Situated on a spacious .53-acre lot in a quiet cul-de-sac, this property offers the perfect blend of comfort, privacy, and charm. Inside, you’ll find a warm and inviting layout featuring luxury vinyl plank flooring throughout the main level and a cozy gas fireplace in the great room

  Jennifer Kramer RE/MAX Integrity

  

  1734 NE Shale Ct, Roseburg, OR 97470
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  /27

  $775,000

  • Land
  • 118.92 Acres
  • $6,517 per Acre

  955 Kester Rd, Roseburg, OR 97470

  This rare equestrian and cattle property combines privacy, convenience, and endless potential; all just 5 minutes from Roseburg. Property consists of 118+ acres and its the perfect opportunity for those dreaming of self-sufficient living, a private ranch retreat, or developing a premier horse facility. See map for approximate property lines per lot to be verified by buyer. The property is primed

  Dan Gandee Real Broker

  

  955 Kester Rd, Roseburg, OR 97470
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  $125,000

  • 2 Beds
  • 1 Bath
  • 846 Sq Ft

  885 NE Sunset St Unit 22, Roseburg, OR 97470

  Darling, light and bright upper floor condo in the Highland Park condo complex. Large living room & 2 nice sized bedrooms, private patio, plenty of closet space. Completely remodeled . New laminate flooring throughout, kitchen cabinets and countertop, bathroom, fresh paint, new appliances. All appliances included. Low association dues, included water, garbage, landscaping, exterior maint. Onsite

  Elena Mackey eXp Realty, LLC

  

  885 NE Sunset St Unit 22, Roseburg, OR 97470
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  $439,000

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  1884 NE Sunset St, Roseburg, OR 97470

  Come check out this meticulously maintained single-level home, built in 2008, this home offers a desirable open floor plan with well planned 3-bed/2-bath layout is perfect for everyday living and entertaining.Seller updates include new carpet in the living room and primary suite, along with modern appliances— refrigerator and Speed Queen washer/dryer purchased within the last two years and used

  Andrew Stoner Roseburg Homes Realty

  

  1884 NE Sunset St, Roseburg, OR 97470
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  /31

  $434,900

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

  675 NE Cummins St, Roseburg, OR 97470

  Welcome to this attractive single-level home on a dead-end street in east Roseburg. Built in 2006, this 3-bedroom, 2-bath home offers a spacious layout with vaulted ceilings and a cozy gas fireplace perfect for relaxing on cooler days. The kitchen includes an eating bar and appliances, while the dining area opens to a covered back deck designed for year-round enjoyment. Step outside and you’ll

  Carol Block Stellar Realty Northwest

  

  675 NE Cummins St, Roseburg, OR 97470
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  /35

  $430,000

  • 3 Beds
  • 2.5 Baths
  • 1,828 Sq Ft

  368 Page Rd, Winchester, OR 97495

  Come see this beautifully maintained home just 4 houses down from Winchester Elementary School. This home comes with ample parking, a large 864 SF shop (24x36) plus room to park an RV. Large backyard for hosting with a lot of potential/room for a pool, newly installed carpet, 4 security cameras included in sale. Please call today to book your private showing!

  Hannah Kelsey Alpine Real Estate 1, LLC

  

  368 Page Rd, Winchester, OR 97495
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  /9

  $1,990,000

  • Land
  • 17.13 Acres
  • $116,170 per Acre

  0 Umpqua College Rd, Roseburg, OR 97470

  Rare North Umpqua Opportunity! Perched above the Winchester Dam, this 17.13-acre R-1 zoned property offers breathtaking views of the North Umpqua River and endless recreational opportunities—boating, swimming, paddleboarding, and world-class fishing. With a minimum 1-acre lot size, the land holds significant division and development potential. Sewer and power are available at the lower property

  Jason Mann J Mann Realty

  

  0 Umpqua College Rd, Roseburg, OR 97470
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  /44

  $315,000

  • 5 Beds
  • 3 Baths
  • 2,094 Sq Ft

  130 Walter Ct, Roseburg, OR 97471

  Spacious Triple-Wide on Double Lot – Endless Potential in Roseburg! Located at the end of a quiet cul-de-sac in a desirable Roseburg neighborhood, this large 5-bedroom, 3-bathroom triple-wide manufactured home sits on a rare double lot, offering ample space, privacy, and opportunity. With over 2,000 sq ft of living space, this home has a generous layout perfect for multi-generational living, home

  Tracy Grubbs eXp Realty, LLC

  

  130 Walter Ct, Roseburg, OR 97471
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  /48

  $1,299,900

  • 4 Beds
  • 3 Baths
  • 2,608 Sq Ft

  6743 N Bank Rd, Roseburg, OR 97470

  Discover a rare opportunity to own a private, gated riverfront retreat on the beautiful North Umpqua River. This versatile 11+ acre property is perfect for multi-family living, income opportunities, and a self-sufficient lifestyle—all with unmatched natural beauty. The main residence is a well-kept 4 bedroom, 3 bathroom home featuring a large bonus room for office, hobby, or guest use. A second

  Jordan Anderson The Anderson Agency

  

  6743 N Bank Rd, Roseburg, OR 97470
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  /12

  $225,000

  • Land
  • 2.65 Acres
  • $84,906 per Acre

  0 NE Carmen St, Roseburg, OR 97470

  Discover 2.65 acres of opportunity—right in town, yet offering the peace and space of country living. This beautiful property is zoned R6 and ready for you to build your dream home—or potentially two! The county has previously indicated the possibility of two home sites (buyer to verify). A rare find with room to grow, just minutes from city amenities while still feeling tucked away.

  Anthony Beckham Different Better Real Estate

  

  0 NE Carmen St, Roseburg, OR 97470
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  $235,000

  • Land
  • 5.14 Acres
  • $45,720 per Acre

  1245 Sunshine Rd, Roseburg, OR 97470

  Discover the perfect blend of space and opportunity on this 5-acre property located just outside of Roseburg. With 3 homesite locations, a high-flow well, and septic approval in place, this parcel is ready for your vision—whether you’re looking to build a family estate, create investment opportunities, or establish a beautiful new home with a separate site for a shop. 2 RV plugs with a 350 gallon

  Shae Ellison Platinum Realty

  

  1245 Sunshine Rd, Roseburg, OR 97470

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