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Homes for Sale in 97496

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  • /83

    $735,000

    $50K PRICE DROP
    • 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

    Agent Photo

    Kristina Scott

    Umpqua Legacy Realty LLC

    (458) 310-3863

    9114 Old Highway 99 S, Winston, OR 97496
  • /15

    $185,000

    $90K PRICE DROP
    • Land
    • 4.26 Acres
    • $43,427 per Acre

    0 Wil Way Unit 24292479, Winston, OR 97496

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

    Agent Photo

    Ashton Faas

    Faas Realty

    (458) 217-1693

    0 Wil Way Unit 24292479, Winston, OR 97496
  • /28

    $350,000

    $150K PRICE DROP
    • Land
    • 7.4 Acres
    • $47,297 per Acre

    0 Wil Way Unit 24094727, Winston, OR 97496

    Rare investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Property has already been approved to be partitioned as either 2 larger parcels or a 28 lot subdivision! Currently no HOA or CC&Rs! Utilities conveniently are available nearby ready to be connected. The 2 parcels are also listed separately. Make an offer today before one or all

    Agent Photo

    Ashton Faas

    Faas Realty

    (458) 310-3411

    0 Wil Way Unit 24094727, Winston, OR 97496
  • /15

    $185,000

    $90K PRICE DROP
    • Land
    • 3.14 Acres
    • $58,917 per Acre

    0 Wil Way Unit 24278136, Winston, OR 97496

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

    Agent Photo

    Ashton Faas

    Faas Realty

    (458) 224-5797

    0 Wil Way Unit 24278136, Winston, OR 97496
  • /45

    $314,900

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

    301 NW Midway St, Winston, OR 97496

    Beautifully remodeled home on almost half an acre right in the heart of Winston! Fully fenced for kids and pets to roam freely. Backyard is ready for someone to make it their own. Work shed in the back with power and lighting for those special projects. Along with a good sized garage for plenty of parking. The home was remodeled top to bottom. As you enter, notice the excellent natural lighting

    Agent Photo

    Ashton Faas

    Faas Realty

    (458) 646-4901

    301 NW Midway St, Winston, OR 97496
  • /41

    $499,900

    New Construction $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    160 Wil Way, Winston, OR 97496

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

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    (458) 299-7413

    160 Wil Way, Winston, OR 97496
  • /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 5/30 2-5 pm 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,

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    (458) 309-4957

    150 Wil Way, Winston, OR 97496
  • /44

    $499,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    2581 NW Brockway Rd, Winston, OR 97496

    Open House 5/30 2-5pm New listing! This beautifully crafted new construction home offers 2,576 square feet with 3 bedrooms and 2.5 bathrooms, thoughtfully designed with quality finishes and modern comfort throughout.The open-concept floor plan features vaulted ceilings, abundant natural light, and recessed lighting, creating a bright and inviting living space. The kitchen is designed for both

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    (458) 291-0968

    2581 NW Brockway Rd, Winston, OR 97496
  • /48

    $409,900

    New Construction Open Sat 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,555 Sq Ft

    265 SE Logan St, Winston, OR 97496

    Welcome to Rolling Meadows Estates, Winston's newest neighborhood community where quality craftsmanship, modern design, and Southern Oregon lifestyle come together. Surrounded by attractive newer homes and a growing sense of community, this is an opportunity to enjoy the benefits of new construction in one of Winston's most exciting new developments.Built by Premier Home Construction, a respected

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    265 SE Logan St, Winston, OR 97496
  • /48

    $375,000

    $10K PRICE DROP
    • 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
  • /48

    $439,900

    New Construction Open Sat 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,629 Sq Ft

    260 SE Logan St, Winston, OR 97496

    *** BUILDER INCENTIVE *** Lower Payments Available on this House! Seller offering flexible buyer incentives with acceptable offer, including potential rate buy down, closing cost assistance, or improvement credits. Attractive opportunity for both financed and cash buyers.*** There’s something special about stepping into a home that’s never been lived in—where everything is fresh, thoughtfully

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    260 SE Logan St, Winston, OR 97496
  • /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
  • /35

    $22,500

    • Land
    • 6,098 Sq Ft
    • $160,714 per Acre

    111 SE Lebleu Ln, Winston, OR 97496

    Developable residential lot zoned R1, offering a gentle slope and utilities available including electricity, sewer, and water. Enjoy a pleasant view overlooking nearby vineyards in the valley, providing a peaceful setting for your future home. Conveniently located within driving distance to the Umpqua River and Wildlife Safari, offering access to outdoor recreation and local attractions. Great

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    111 SE Lebleu Ln, Winston, OR 97496
  • /27

    $259,000

    • 2 Beds
    • 1 Bath
    • 939 Sq Ft

    71 SE Ronald St, Winston, OR 97496

    Charming remodeled cottage-style home situated on a large quarter acre lot offering comfortable single-level living. This updated residence features new interior paint, newer roof and siding, and thoughtful modern upgrades throughout. The kitchen includes stainless steel appliances, adding a sleek and functional touch to the heart of the home. Enjoy a bright and inviting layout with practical

    Joshua Glaspie ICON Real Estate Group

    71 SE Ronald St, Winston, OR 97496
  • /39

    $190,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    0 Rice Creek Rd, Winston, OR 97496

    Escape to your own off-grid retreat on a 20-acre shared property in a gated community with coded access. This is a unique property on jointly owned lot, in an off grid community. Seller is selling 50% share in 20 acre lot. Land use agreement in place. This beautifully crafted 1,000 SF cabin showcases exceptional handcrafted woodwork and rustic charm throughout. Features include 1 bedroom plus a

    Starlight Turner Starlight Realty

    0 Rice Creek Rd, Winston, OR 97496
  • /28

    $340,000

    $10K PRICE DROP
    • 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
  • /48

    $469,900

    $19K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,764 Sq Ft

    1941 Byron Creek Rd, Winston, OR 97496

    Come home to your own private escape hidden in the trees! Beautiful parklike setting with amazing views and end of the road privacy. Property features include a huge, large covered RV storage, detached guest quarters, a storeroom & workshop. The manufactured home was custom built for the current owners with many custom touches. An expansive deck is perfect for gatherings or taking in the amazing

    Andrew Stoner Roseburg Realty

    1941 Byron Creek Rd, Winston, OR 97496
  • /48

    $725,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,362 Sq Ft

    1068 Rice Creek Rd, Winston, OR 97496

    Security gated 8.52-acre property! This beautiful ranch-style home features, updates, paved driveway, newer roof, interior & exterior paint, gourmet kitchen, double ovens, large walk-in pantry, lots of outdoor light, large living room with a cozy fireplace, great views, huge primary bedroom with a walk-in closet and bathroom with 2-headed shower, 4th bedroom could easily be used as an office, new

    Joan Smith The Neil Company Real Estate

    1068 Rice Creek Rd, Winston, OR 97496
  • /6

    $485,000

    • 3 Beds
    • 3 Baths

    51 SW Brantley Dr, Winston, OR 97496

    INVESTMENT PROPERTY OPPORTUNITY! Well-maintained 4-unit apartment building located in a quiet, centrally located neighborhood. This property features a desirable unit mix with two spacious 2-bedroom, 2-bath units and two comfortable 1-bedroom, 1-bath units, offering strong rental appeal for a variety of tenants. Conveniently situated close to schools, shopping, dining, and local amenities, with

    Vera-Anne Wallace Vera-Anne International Real Estate

    51 SW Brantley Dr, Winston, OR 97496
  • /44

    $685,000

    $34K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    411 Woodland Dr, Roseburg, OR 97471

    What if your favorite getaway was home?Set above Lookingglass Creek with stunning views of Abacela Vineyard, this property offers the kind of lifestyle that's getting harder to find. Spend summer afternoons at your own swimming hole, grow fresh produce in the fenced garden and greenhouse, and enjoy the satisfaction of having water rights, irrigation, a K-line system, and pump already in place.The

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471
  • /15

    $229,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    90 SE Darrell Ave, Winston, OR 97496

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

    Rebekah Sexauer eXp Realty, LLC

    90 SE Darrell Ave, Winston, OR 97496
  • /11

    $312,000

    • Land
    • 13.5 Acres
    • $23,111 per Acre

    0 NW Brockway Rd, Winston, OR 97496

    Premier 13.5 Mixed-Use Development Opportunity! A trifecta of buildability and prestige. Position your next project in the path of progress with this exceptional parcel. Located strategically within the Urban Growth Area and zoned as mixed use (CHIS), this site offers density potential combined with the unparalleled natural beauty of the region which include mountain and vineyard views. The

    Cynthia Beach The Neil Company Real Estate

    0 NW Brockway Rd, Winston, OR 97496
  • /35

    $160,000

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    105 Stephanie Ct, Winston, OR 97496

    Welcome home to this well-maintained single-level home offering comfort, convenience, and an inviting open-concept design. The spacious living area flows seamlessly into a beautifully appointed kitchen featuring abundant cabinet storage, a pantry, stainless steel appliances, and a large island perfect for meal prep, casual dining, or gathering with family and friends.Luxury vinyl plank flooring

    Tammi Ellison eXp Realty, LLC

    105 Stephanie Ct, Winston, OR 97496
  • /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
  • /15

    $165,000

    $15K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 784 Sq Ft

    101 NE Darrell Ave, Winston, OR 97496

    Charming affordable singlewide manufacture home on .18 of an acre, located on a corner lot. This 2 bedroom, 1 bath home has a covered front porch and back deck with a chain link fenced yard. Storage shed and off street parking.

    Nancy Wood Oregon Life Homes

    101 NE Darrell Ave, Winston, OR 97496
  • /30

    $205,000

    • 2 Beds
    • 1 Bath
    • 1,323 Sq Ft

    381 SE Gregory Dr, Winston, OR 97496

    Incredible and rare opportunity in Winston, Oregon! Developers, investors, and visionaries take notice. This charming 1940s 2-bedroom, 1-bath home is full of character and ready for its next chapter. With a little vision and elbow grease, this property offers endless possibilities.Situated on a spacious, level lot with mature greenery, the property presents potential for future development,

    Shae Ellison Platinum Realty

    381 SE Gregory Dr, Winston, OR 97496
  • /47

    $489,900

    $10K PRICE DROP
    • 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
  • /34

    $355,000

    $4K 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
  • /17

    $550,000

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

    572 Dillard Gardens Rd, Winston, OR 97496

    Charming property on the South Umpqua River features a 1,440 sf home set on 6.9 acres. The 2-bed 2-bath interior includes wood floors, an open living room with a fireplace insert, an open kitchen, large primary bedroom with an ensuite bath, laundry room and covered deck. Back patio and yard area is peaceful and quiet with flowers and shade trees. New septic system was installed in 2021. Detached

    Mike Nichols MORE Realty, Inc.

    572 Dillard Gardens Rd, Winston, OR 97496
  • /32

    $530,000

    Open Sat 11AM - 1PM $79K 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
  • /11

    $179,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    1580 Winston Section Rd, Winston, OR 97496

    This 3-bedroom, 2-bathroom "fixer upper" sits on a peaceful 0.18-acre corner lot, offering a quiet atmosphere and beautiful mountain views right from your doorstep. While the home is ready for interior renovation, the floor plan features three bedrooms, two bathrooms, laundry room, large kitchen, creating a cozy feeling once restored. A standout is the 576 sqft detached garage/shop, where half

    Cynthia Beach The Neil Company Real Estate

    1580 Winston Section Rd, Winston, OR 97496
  • /22

    $315,000

    • 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
  • /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
  • /16

    $499,000

    Pre-Foreclosure
    • 4 Beds
    • 3 Baths
    • 2,270 Sq Ft

    150 SW Brantley Dr, Winston, OR 97496

    Spacious Tri-Level Home on 1 Acre with Dual Garages, Fruit Trees & Outdoor LivingWelcome to this beautifully maintained tri-level home offering 4 bedrooms, a bonus room, 3 full bathrooms, and multiple living spaces designed for comfort and flexibility.The upper level features 3 bedrooms and 2 bathrooms, while the lower level includes a private 4th bedroom and full bathroom, perfect for guests,

    Kayla Knight Trueblood Real Estate

    150 SW Brantley Dr, Winston, OR 97496
  • /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
  • /25

    $318,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    340 SE Darrell Ave, Winston, OR 97496

    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. The terraced backyard includes fruit

    Aaron Stansbury Keller Williams Realty Eugene and Springfield

    340 SE Darrell Ave, Winston, OR 97496
  • /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
  • /46

    $245,000

    $15K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,224 Sq Ft

    66 NW Cary St, Winston, OR 97496

    Beautifully maintained 2BD/1BA residence on a generous corner lot in a convenient location—just a short walk to local shops, dining, and school. This thoughtfully designed home offers a spacious living room and an expansive bonus room with rich original hardwood floors; the bonus room may also serve as a private 3rd bedroom or flex space. The well-appointed kitchen features an island, abundant

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    66 NW Cary St, Winston, OR 97496
  • /19

    $24,999

    $5K 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
  • /29

    $259,900

    • 3 Beds
    • 1 Bath
    • 1,085 Sq Ft

    224 5th St, Dillard, OR 97432

    Welcome to this charming 3-bedroom, 1-bath home nestled in the desirable community of Dillard, Oregon. Inside, you'll find updated laminate flooring throughout, creating a clean and modern feel. The spacious kitchen offers plenty of room for cooking, gathering, and entertaining, with ample cabinetry and workspace for all your needs.Step outside and discover what makes this property truly special.

    Mike Jacoby eXp Realty, LLC

    224 5th St, Dillard, OR 97432

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