Dillard, OR Houses for Sale

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  $785,000

  • 3 Beds
  • 3 Baths
  • 2,722 Sq Ft

  9114 Old Highway 99 S, Winston, OR 97496

  Escape to the peace and beauty of rural Oregon with this beautifully remodeled country retreat set on 5.4 usable acres of fenced pastureland. Offering the perfect blend of modern comfort and small-acreage functionality, this stunning single-level home features 2,722 sq. ft. with 3 bedrooms, 3 full baths, and a versatile flex space ideal for a home office or hobby room. Each bedroom includes its

  

  Kristina Scott

  Umpqua Legacy Realty LLC

  (458) 310-3863

  9114 Old Highway 99 S, Winston, OR 97496
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  /48

  $395,000

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

  133 Silverado St, Roseburg, OR 97471

  This move-in ready home has been thoughtfully updated with a more open concept layout, creating a bright and inviting living space. The new kitchen features a center island and flows seamlessly into the main living area, making it ideal for everyday living and entertaining. Other interior updates include refinished trim, new flooring, and stylish finishes throughout. Primary room has ensuite with

  

  Wyndee Konopaski

  Keller Williams Southern Oregon-Umpqua Valley

  (458) 299-7039

  

  133 Silverado St, Roseburg, OR 97471
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  /47

  $409,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,291 Sq Ft

  176 Homestead Dr, Myrtle Creek, OR 97457

  Beautiful acreage in a serene valley. This slice of paradise is has so much to offer. Large variety of fruit trees including baby grafted pear tree, apple tree, yellow and red plum trees. There are grapes and wild cucumber as well. As you approach the entrance, you will notice the newly built deck. Along with a new rocked carport for extra parking. The home has had several recent updates made: in

  

  Ashton Faas

  Different Better Real Estate

  (458) 309-3053

  

  176 Homestead Dr, Myrtle Creek, OR 97457
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  /47

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  12589 Old Highway 99 S, Myrtle Creek, OR 97457

  Situated on just under 2 acres, this single-level 1,848 sq ft ranch-style home offers 3 bedrooms and 2 bathrooms with a functional, open-flow layout. Recent updates include new flooring and fresh interior paint throughout, creating a clean and move-in-ready living space.The land is level and fully usable, well-suited for homesteading, animals, and gardening. The property is thoughtfully set up

  

  Sabrina Jorgensen

  Fathom Realty Oregon, LLC

  (458) 877-3615

  

  12589 Old Highway 99 S, Myrtle Creek, OR 97457
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  /48

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft

  186 Woodduck St, Winston, OR 97496

  Well-maintained home in a quiet neighborhood in the heart of Winston. Move-in ready with brand new floors recently installed. Minimal outdoor maintenance. Garden shed and room to park a 5th wheel. Don’t miss your opportunity to own a solid, easy-living home in a great location.

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  186 Woodduck St, Winston, OR 97496
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  /48

  $439,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft

  260 SE Logan St, Winston, OR 97496

  There’s something special about stepping into a home that’s never been lived in—where everything is fresh, thoughtfully designed, and ready for your story to begin. Welcome to 260 Logan St, a brand-new one-level home that blends modern comfort with effortless living. From the moment you walk in, you’ll appreciate the clean, cohesive feel of luxury vinyl plank flooring throughout—no carpet—paired

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  260 SE Logan St, Winston, OR 97496
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  /36

  $409,000

  $30K PRICE DROP

  • 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
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  /48

  $395,000

  • 5 Beds
  • 2 Baths
  • 2,058 Sq Ft

  1997 Castle Ave, Roseburg, OR 97471

  Welcome to 1997 Castle Ave—a beautifully updated 5-bedroom, 2-bath home that blends modern style with incredible space and versatility. Opportunities like this are rare, offering both function and charm in one inviting package. From the moment you arrive, the curb appeal draws you in. Step into a light-filled living room, where a stylish tile entry transitions into warm laminate flooring. The

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  1997 Castle Ave, Roseburg, OR 97471
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  /36

  $459,000

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  311 SE Grape Ave, Winston, OR 97496

  Great investment opportunity on a spacious 0.74-acre lot! This property features a 3-bedroom, 1-bath single-level home with approximately 1,250 sq ft of living space, plus a duplex on the same lot—offering excellent potential for rental income or multi-generational living. The main home includes a full basement, forced air heating, and public utilities. Situated on a level to gently sloped lot

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  311 SE Grape Ave, Winston, OR 97496
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  /42

  $319,000

  $36K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  490 Char St, Roseburg, OR 97471

  Charming 3-bedroom, 1-bath ranch-style home in the desirable Rolling Hills neighborhood. This single-level home features an inviting layout with ceiling fans, newly remodeled kitchen, and a light-filled dining area with exterior access. The kitchen offers a built-in microwave and dishwasher for convenience. Enjoy outdoor living with a fenced yard, patio, sprinklers, and RV parking. The peaceful

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  490 Char St, Roseburg, OR 97471
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  /47

  $499,900

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

  263 Wil Way, Winston, OR 97496

  Welcome to Your Like-New Custom Home in Winston, Oregon!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality craftsmanship and thoughtful design are evident in every detail. The open-concept floor plan features soaring vaulted ceilings, beautiful flooring, and a warm, inviting layout that flows effortlessly for both everyday living and entertaining.At the

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  263 Wil Way, Winston, OR 97496
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  /48

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,295 Sq Ft

  356 Dark Horse St, Roseburg, OR 97471

  Nestled on a quiet street, this charming 3 bed, 2 bath home offers 1,295 sq ft of comfortable one-level living on 0.16 acres. Enjoy vaulted ceilings, an open concept layout with laminate and tile floors, and a private covered front porch. The primary suite features an ensuite, ceiling fan, and walk-in closet. Fenced front and backyard, a large garage with storage and workbench, plus a cozy rear

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  356 Dark Horse St, Roseburg, OR 97471
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  /41

  $499,900

  New Construction $25K PRICE DROP

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

  160 Wil Way, Winston, OR 97496

  OPEN HOUSE! 5/17 1-4pm 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

  Tyler Head Turning Point Realty Group

  

  160 Wil Way, Winston, OR 97496
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  /20

  $475,000

  $125K PRICE DROP

  • 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
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  /48

  $475,000

  • 4 Beds
  • 3 Baths
  • 2,764 Sq Ft

  208 Jamie Loop, Roseburg, OR 97471

  Welcome to this spacious and versatile 2,764 sq ft home, offering 4 bedrooms and 3 full bathrooms on a beautifully sized 0.54-acre lot, providing room to breathe both inside and out.The main level features three bedrooms and two full bathrooms, while the lower level offers a fourth bedroom or office and an additional full bath, ideal for guests, remote work, or multi-generational

  Amanda Nash Oregon Life Homes

  

  208 Jamie Loop, Roseburg, OR 97471
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  /40

  $429,000

  • 3 Beds
  • 2 Baths
  • 2,028 Sq Ft

  2029 Castle Ave, Roseburg, OR 97471

  Completely renovated from top to bottom, this stunning 3-bedroom, 2-bath home is truly move-in ready with everything new! Featuring oversized rooms, a bright open layout, and stylish modern finishes throughout, this home offers comfort and space for everyday living. Enjoy the convenience of ample parking, a garage, and plenty of room for guests, or extra vehicles. Step outside to a huge flat

  Karissa Pangelina Keller Williams Southern Oregon-Umpqua Valley

  

  2029 Castle Ave, Roseburg, OR 97471
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  /40

  $499,900

  New Construction $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,999 Sq Ft

  150 Wil Way, Winston, OR 97496

  OPEN HOUSE! 5/17 1-4pm New Home by JW Construction Inc.This beautifully crafted 2,143 sq ft home offers 3 bedrooms and 2 1/2 bathrooms with a thoughtful layout and excellent separation of space. Set on a low-maintenance lot with views of trees and the surrounding mountains, 140 Wil Way combines modern design with comfort and convenience.The open-concept main level features high ceilings, recessed

  Tyler Head Turning Point Realty Group

  

  150 Wil Way, Winston, OR 97496
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  /24

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,959 Sq Ft

  192 Reston Ave, Winston, OR 97496

  Home comes with a riding mower, and a gas/propane generator.Spacious Home with Unique Extras – A Rare Find!3-bedroom, 2-bath home offers 1959 square feet of comfortable living space, plus an array of hard-to-find extras that make this property truly special. You'll love the massive 25x50 garage, perfect for car enthusiasts, hobbyists, or home-based businesses, complete with a dedicated paint

  Robin Troy Hybrid Real Estate

  

  192 Reston Ave, Winston, OR 97496
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  /24

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  867 N Summerwood St, Roseburg, OR 97470

  Elevated living with a view! Experience the best of Southern Oregon living in this beautifully maintained 3-bedroom, 2-bathroom home. Designed to maximize its natural surroundings, this 1,562 sq. ft. residence offers a seamless blend of indoor comfort. The defining feature of this property is the back deck located directly off the main living and dining areas. Perfectly positioned for

  Cynthia Beach The Neil Company Real Estate

  

  867 N Summerwood St, Roseburg, OR 97470
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  /39

  $400,000

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,989 Sq Ft

  439 Chandler Dr, Roseburg, OR 97471

  This beautiful two-story home showcases true pride of ownership throughout. Step inside to a welcoming entry with soaring ceilings, warm laminate flooring, and a cozy fireplace anchoring the inviting living room. The main level also features a dedicated office, convenient half bath, and a spacious open kitchen complete with granite countertops, breakfast bar, abundant cabinetry, and a

  Jason Mann J Mann Realty

  

  439 Chandler Dr, Roseburg, OR 97471
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  /20

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,573 Sq Ft

  4341 Happy Valley Rd, Roseburg, OR 97471

  Incredible valley view from porch and deck of this traditional 1930s farm house. Has 2.08 acres, outbuilding and garden area. Appliances included. Wood heat. Good roof, newer deck.

  Valynn Currie Currieco Real Estate

  

  4341 Happy Valley Rd, Roseburg, OR 97471
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  /47

  $359,000

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

  144 Bunting Ct, Roseburg, OR 97471

  Beautifully maintained 3-bedroom, 2-bath home offering 1,440 sq. ft. of comfortable living in a quiet, desirable area. This move-in ready home features a welcoming layout, generous living spaces, and a serene setting perfect for relaxed everyday living

  Michael Brown Oregon Life Homes

  

  144 Bunting Ct, Roseburg, OR 97471
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  /22

  $270,000

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  783 Callahan Dr, Roseburg, OR 97471

  MOVE IN READY, NICE LOCATION and backed up to farm land. This 2 bedroom home has the perfect amount of space to accommodate your needs and make you feel right at home. Heating and Air Conditioning for all season comfort. Offers a front and back yard with underground sprinklers. Back yard completely fenced. Plus a single car garage with driveway. Low HOA for neighborhood. Call to make a showing

  Lacey Williams Trueblood Real Estate

  

  783 Callahan Dr, Roseburg, OR 97471
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  /35

  $389,000

  $1K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  114 Umpqua View Dr, Roseburg, OR 97471

  Prepare to be impressed by this beautifully updated home with nice views, nestled in a quiet neighborhood. This meticulously maintained property showcases pride of ownership in every detail, featuring tasteful decor and careful attention throughout. The home boasts high-end, water-resistant, and scratch-resistant luxury vinyl flooring throughout its interior. The kitchen is equipped with a pantry

  Cindy Mahaffy RE/MAX Integrity

  

  114 Umpqua View Dr, Roseburg, OR 97471
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  /28

  $350,000

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft

  170 Church St, Dillard, OR 97432

  South Umpqua River front home with beautiful mature landscaping. This home was thoroughly remodeled in 2012 with new kitchen, HVAC, and most plumbing. Small work shop, and RV parking area. Enjoy watching the water off the relaxing deck of this adorable riverfront home.

  Christina Ronk Harcourts Integrity Team Real Estate Services, LLC.

  

  170 Church St, Dillard, OR 97432
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  /31

  $372,900

  $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  176 Othello Ave, Roseburg, OR 97471

  This well-maintained single-level residence is ideally situated on a desirable corner lot and offers a functional and inviting layout. Built in 2007 by Hayden Homes, this 3-bedroom, 2-bath home features a thoughtfully designed split floor plan, vaulted ceilings, a formal dining area and a spacious living room suited for both everyday living and entertaining. The kitchen is equipped with a bright

  Carol Thompson RE/MAX Integrity

  

  176 Othello Ave, Roseburg, OR 97471
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  /26

  $309,500

  • 3 Beds
  • 1 Bath
  • 1,041 Sq Ft

  274 Georginna Dr, Roseburg, OR 97471

  Welcome to this charming 3-bedroom, 1-bath home at 274 Georgina Dr in Roseburg, Oregon! This cozy residence offers comfort, functionality, and a lifestyle that blends indoor ease with outdoor enjoyment.Step inside to find a warm and inviting layout perfect for everyday living. The home features a nice-sized garage, providing ample space for parking, storage, or even a workshop.Out back, you’ll

  Raymond Coburn eXp Realty, LLC

  

  274 Georginna Dr, Roseburg, OR 97471
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  /35

  $350,000

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  223 Armande Loop, Roseburg, OR 97471

  This property is a newer 3 bed 2 bath home that is move-in ready with fresh interior paint, newer flooring, and stainless steel appliances. Features a large primary bedroom with bathroom attached and a walk in closet. The open kitchen flows into to main living room that include desirable vaulted ceilings. You’ll find central heating and air conditioning throughout the home. An oversized laundry

  Joshua Glaspie ICON Real Estate Group

  

  223 Armande Loop, Roseburg, OR 97471
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  /48

  $599,000

  $396K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,025 Sq Ft

  383 Little Valley Rd, Roseburg, OR 97471

  Attention developers and investors!!! Awesome property surrounded by residential developments which is one of the last remaining large parcels in the area with great potential for subdividing! There are top of the world mountain and valley views from the knoll that the single level home sits on. Some of the home features include hardwood floors, beamed ceilings, French doors, and vaulted ceiling.

  Jennifer Kramer RE/MAX Integrity

  

  383 Little Valley Rd, Roseburg, OR 97471
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  /20

  $625,000

  • 7 Beds
  • 5 Baths
  • 3,686 Sq Ft

  161 Vintage Ln, Myrtle Creek, OR 97457

  222.67 acres of pasture and woodland with 2 homes and a duplex. Great rental investment property or Family compound. Has community water, 3 septic systems, fenced, pasture is leased. Main house is 2 bedroom 2 bath, second dwelling 3 bedroom 1 bath. Duplexes are 1 bedroom 1 bath each.shop, garage. Sold As Is. Has pipeline easement.

  Michael Roberts Currieco Real Estate

  

  161 Vintage Ln, Myrtle Creek, OR 97457
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  /34

  $322,500

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  2205 Landers Ave, Roseburg, OR 97471

  Welcome to this warm and inviting home that blends comfort with thoughtful updates throughout. Over the past two years, this property has been refreshed with upgrades that make everyday living easy, including a tankless water heater, added attic insulation, fresh interior paint, and updated kitchen countertops. The layout feels bright and functional, with comfortable living spaces and bedrooms

  Karina DiStefano Lamonte Real Estate Professionals

  

  2205 Landers Ave, Roseburg, OR 97471
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  /41

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,932 Sq Ft

  549 Bailey Dr, Roseburg, OR 97471

  Riverfront treasure with incredible views from full length newer covered deck. Serene private custom 3 br 2.5 bath home on 1.49 acres. 1932 sq ft, 1 level built in 1980. Gourmet kitchen with ample counterspace with antique working stove. The yards are manicured with easy access to the river. Master suit has river view, slider to deck, walk-in shower. Viewing patio down by the river with bench.

  Valynn Currie Currieco Real Estate

  

  549 Bailey Dr, Roseburg, OR 97471
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  /44

  $699,500

  $20K PRICE DROP

  • 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
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  /48

  $765,000

  • 3 Beds
  • 2 Baths
  • 2,484 Sq Ft

  269 Bailey Dr, Roseburg, OR 97471

  This exceptional riverfront property offers luxury, comfort, & breathtaking natural surroundings in one of Roseburg’s most desirable settings. This custom-built single-level home sits along the banks of the beautiful South Umpqua River, offering incredible views & the peaceful sound of the water. The home features a thoughtfully designed living space with an open-concept that creates a bright and

  Jennifer Kramer RE/MAX Integrity

  

  269 Bailey Dr, Roseburg, OR 97471
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  /26

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  206 Church St, Dillard, OR 97432

  Beautifully remodeled home in a cozy rural neighborhood near the scenic South Umpqua River. This move-in ready property features granite kitchen countertops and new windows and roof, offering both comfort and peace of mind.The main level includes the living room, kitchen, primary bedroom, full bath, and an oversized laundry room that could easily serve as an office, craft room, or flexible

  Marilyn Kittelman Cutting Edge Real Estate

  

  206 Church St, Dillard, OR 97432
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  /34

  $359,000

  Open Sat 12PM - 2PM

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

  380 NW Cary St, Winston, OR 97496

  OPEN HOUSE - Saturday May 23rd 12:00pm - 2:00pm 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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  /36

  $345,000

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  106 Umpqua View Dr, Roseburg, OR 97471

  Single-level home, built in 2001, offers 1580sqft with 3 bedrooms, 2 bathrooms and a Brand-New Roof! Inside, you’ll find vaulted ceilings, laminate flooring and large picture windows that fill the home with natural light. The spacious primary suite features a walk-in closet and a walk-in shower for added convenience. The kitchen is both functional and inviting, complete with a pantry, stainless

  Carol Thompson RE/MAX Integrity

  

  106 Umpqua View Dr, Roseburg, OR 97471
• 

  

  /17

  $550,000

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

  572 Dillard Gardens Rd, Winston, OR 97496

  Charming farmhouse on the South Umpqua River. Features a 1,440 sf home with 2 beds and 2 baths set on 6.9 acres with an established cherry orchard. Home interior is warm and inviting with wood floors, fireplace insert, open living and kitchen areas, ensuite bath in the primary bed, and a dedicated laundry room that opens to a covered deck. Back patio and yard are surrounded with flowers and shade

  Mike Nichols MORE Realty, Inc.

  

  572 Dillard Gardens Rd, Winston, OR 97496
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  /32

  $555,000

  $54K PRICE DROP

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

  102 Sarah Bear Ln, Winston, OR 97496

  Meticulous quality 4 br 3 bath 2660 sq ft home, with real hard wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, spacious gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance front yard, covered patio. The gourmet kitchen has

  Valynn Currie Currieco Real Estate

  

  102 Sarah Bear Ln, Winston, OR 97496
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  /36

  $369,999

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,712 Sq Ft

  1993 Linnell Ave, Roseburg, OR 97471

  Welcome home to this spacious 3-bedroom, 2-bath property designed for comfort and flexibility. The inviting living room features a cozy fireplace, perfect for relaxing nights in. A bonus family room offers extra space for entertaining, dining, movie nights, or a home office. Step outside to a fully fenced yard—great for pets, play, or outdoor gatherings. Need more room? You’ll love the bonus room

  Karissa Pangelina Keller Williams Southern Oregon-Umpqua Valley

  

  1993 Linnell Ave, Roseburg, OR 97471

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