Homes for Sale near Douglas High School

• 

  

  

  /15

  $185,000

  • 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

  

  Ashton Faas

  Different Better Real Estate

  (458) 217-1693

  

  0 Wil Way Unit 24292479, Winston, OR 97496
• 

  Explore Douglas High School

• 

  

  

  /27

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft

  380 SE Sunnyside Dr, Winston, OR 97496

  Welcome to 380 Sunnyside! This move-in-ready 3-bedroom, 2-bath home offers comfort, quality updates, and everyday convenience. Vaulted ceilings and peaceful territorial views create a bright, open feel from the moment you step inside. Recent upgrades include fresh interior paint, brand-new LVP flooring, and a newly built spacious deck, giving the home a modern look without the new construction

  

  Rockwell Group

  eXp Realty, LLC

  (458) 224-8911

  380 SE Sunnyside Dr, Winston, OR 97496
• 

  

  

  /38

  $260,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  146 Crater Rd, Camas Valley, OR 97416

  Beautiful 5 acres property in between rural Tenmile and Camas Valley OR. Tons of great potential with lots of water, gorgeous views, and great property. Adorable manufactured home with 2 beds/1 bath, and a single wide ADU located in the barn. Don't overlook this and miss out. Check it out today!

  

  Wyndee Konopaski

  Keller Williams Southern Oregon-Umpqua Valley

  (541) 991-5570

  

  146 Crater Rd, Camas Valley, OR 97416
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  /28

  $350,000

  • 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

  

  Ashton Faas

  Different Better Real Estate

  (458) 310-3411

  

  0 Wil Way Unit 24094727, Winston, OR 97496
• 

  

  

  /15

  $185,000

  • 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

  

  Ashton Faas

  Different Better Real Estate

  (458) 224-5797

  

  0 Wil Way Unit 24278136, Winston, OR 97496
• 

  

  /36

  $409,000

  • 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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  /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
• 

  

  /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
• 

  

  /48

  $650,000

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

  441 Gem Dr, Roseburg, OR 97471

  Experience the perfect blend of privacy and comfort in this stunning 2,484-square-foot retreat, nestled on 5 serene acres in the highly sought-after Diamond Heights neighborhood. The heart of the home features a spacious living room with soaring vaulted ceilings and a cozy wood stove, creating an inviting atmosphere for relaxation. Enjoy quiet mornings in the light-filled breakfast nook, where

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  441 Gem Dr, Roseburg, OR 97471
• 

  

  /23

  $55,000

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  119 Oak Leaf Ln, Winston, OR 97496

  Affordable living in a quiet 55+ community! This cozy 1-bedroom, 1-bath manufactured home offers a functional layout and easy, low-maintenance living. The kitchen comes equipped with a free-standing range and refrigerator, both included in the sale. Located in a peaceful, well-kept neighborhood with a friendly community atmosphere. Conveniently situated near local amenities while maintaining a

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  119 Oak Leaf Ln, Winston, OR 97496
• 

  

  /45

  $66,000

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

  125 SE Estate Loop, Winston, OR 97496

  Take in breathtaking views of Umpqua Valley and the surrounding mountains from this spacious manufactured home located in a welcoming 55+ community. Unwind on the large covered front porch. Featuring a metal roof, double-pane vinyl windows, and a sturdy concrete block foundation, this home offers lasting durability. Stay comfortable year-round with the newer heat pump installed in 2022.

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  125 SE Estate Loop, Winston, OR 97496
• 

  

  /48

  $1,095,000

  • 3 Beds
  • 3 Baths
  • 2,337 Sq Ft

  894 Colwell Hill Ln, Roseburg, OR 97471

  Welcome to your new wilderness retreat!Perched atop a hill and backed by 393 acres of BLM land, this property offers the perfect blend of privacy, exploration, and functionality. Surrounded by trees, you’ll feel miles from anywhere — yet you’re only 10 miles from Roseburg. The well-maintained grounds give off a peaceful, park-like ambience from the moment you arrive. While the property slopes in

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  894 Colwell Hill Ln, Roseburg, OR 97471
• 

  

  /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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  /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
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  /44

  $699,500

  • 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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  /41

  $499,900 New Construction

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

  160 Wil Way, Winston, OR 97496

  OPEN HOUSE! Monday 4/27 1-5pm 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

  Tyler Head Turning Point Realty Group

  

  160 Wil Way, Winston, OR 97496
• 

  

  /32

  $555,000

  • 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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  /48

  $775,000

  • 4 Beds
  • 2 Baths
  • 3,746 Sq Ft

  500 Winston Section Rd, Winston, OR 97496

  Step back in time without sacrificing modern convenience in this breathtaking 1910 Craftsman home. Nestled among lush orchards & located directly next door to the iconic Brosi Farmstand & Bakery, this estate offers a lifestyle defined by heritage, craftsmanship, & natural beauty. Every inch of this well-maintained home celebrates the Craftsman era, featuring original woodwork, hardwood floors,

  Cynthia Beach The Neil Company Real Estate

  

  500 Winston Section Rd, Winston, OR 97496
• 

  

  /40

  $675,000

  • 2 Beds
  • 2.5 Baths
  • 2,304 Sq Ft

  9740 Upper Olalla Rd, Winston, OR 97496

  Country setting 29.80 acres, Chalet-style home, 2304 sqft , 2 BR ( could be 3 BR) 2.5 BA. LR has a fireplace with woodstove insert and massive natural stone chimney. Good size kitchen, laundry room with extra sink. Merchantable timber, access to Seneca timber and BLM land for horseback riding, mushroom hunting, ATV's and hiking. Beautiful mountain views, year-round Olalla Creek with water right

  Thuy Chrestenson KNIPE REALTY ERA POWERED

  

  9740 Upper Olalla Rd, Winston, OR 97496
• 

  

  /48

  $775,000

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft

  1868 Larson Rd, Roseburg, OR 97471

  This exceptional property offers a rare combination of beauty, tranquility, and refined living. Set on a gentle sloped 12.89 acres of land and that is located at the end of a private road. The grounds are thoughtfully designed with exquisite landscaping, featuring lush garden beds with automatic drip system. The mature trees add a park like setting outdoor among spaces that invite relaxation and

  Gina Evenich The Neil Company Real Estate

  

  1868 Larson Rd, Roseburg, OR 97471
• 

  

  /40

  $499,900 New Construction

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

  150 Wil Way, Winston, OR 97496

  OPEN HOUSE! Monday 1-5 pm 4/27 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,

  Tyler Head Turning Point Realty Group

  

  150 Wil Way, Winston, OR 97496
• 

  

  /42

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,431 Sq Ft

  605 Deerwood Ct, Winston, OR 97496

  This custom-built Passive Solar home, constructed in 1979, offers a rare blend of timeless beauty, retro charm, and thoughtful modern updates. This Passive Solar home is thoughtfully designed to work with the sun and climate, providing comfort, efficiency, and sustainability without relying heavily on mechanical systems. Ideally located near local river recreation and just a short drive to the

  Lisa Ollivant RE/MAX Integrity

  

  605 Deerwood Ct, Winston, OR 97496
• 

  

  /20

  $279,000

  • Land
  • 40 Acres
  • $6,975 per Acre

  584 Buzz Mountain Ln, Roseburg, OR 97471

  Discover this stunning 40-acre secluded parcel in Lookingglass, offering breathtaking views and exceptional privacy. The property features a house pad and roughed-in utilities, making it easier to start building your dream home. A gated entrance ensures security, while the parcel borders BLM land guarantees open space and natural beauty right next door. Whether you're seeking a peaceful retreat

  Lindsey Heard The Neil Company Real Estate

  

  584 Buzz Mountain Ln, Roseburg, OR 97471
• 

  

  /21

  $250,000

  • Land
  • 27.31 Acres
  • $9,154 per Acre

  0 E Willis Creek Rd, Winston, OR 97496

  27.31 acres to build your dream home either on top of the property or in the valley. City water is available, and other utilities are accessible via a recorded easement. In photos, red boundary lines are approximate and buyer is to perform due diligence. All showings are to be with a licensed realtor. Please make note that this property is a combination of only R66808 & R66885. 0 E. Willis Creek

  Art Dillahay Oregon Life Homes

  

  0 E Willis Creek Rd, Winston, OR 97496
• 

  

  /21

  $150,000

  • Land
  • 10.56 Acres
  • $14,205 per Acre

  3541 Willis Creek Rd, Winston, OR 97496

  10.56 Acres Bordering Public Land Nestled at 3541 Willis Creek Rd, this 10.56-acre property offers a rare chance to own a slice of Oregon's natural beauty. With a newly cut-in road leading to a potential home site, you'll enjoy a stunning view of the valley-a perfect backdrop for your future home. The essentials are already in place: Community water with a meter installed near the south end

  Cliff Farley Mossy Oak Properties Oregon Field and Stream Realty

  3541 Willis Creek Rd, Winston, OR 97496
• 

  

  /48

  $3,800,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  8690 Lookingglass Rd, Roseburg, OR 97471

  Welcome to Lookingglass Vineyard, a remarkable 142.94-acre estate nestled in the highly sought-after South Valley Wine Loop of the renowned Umpqua Valley AVA. This established and producing vineyard features 99.94± acres planted in Pinot Noir and an additional 1/2-acre parcel with other select varietals, offering an exceptional opportunity for both lifestyle and investment. The vineyard is fully

  Jennifer Kramer RE/MAX Integrity

  

  8690 Lookingglass Rd, Roseburg, OR 97471
• 

  

  /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
• 

  

  /48

  $469,900

  • 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
• 

  

  /15

  $229,000

  • 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
• 

  

  /15

  $149,900

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft

  463 SE Gregory Dr, Winston, OR 97496

  1993 manufactured home with addition. Has 1130 sq ft with deck. On .21 acre lot. 3 br 2 baths. Includes range, refrig, microwave, dishwasher, trash compactor, washer/dryer. Assumable VA loan. Has playhouse and storage building.

  Valynn Currie Currieco Real Estate

  

  463 SE Gregory Dr, Winston, OR 97496
• 

  

  /15

  $180,000

  • 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
• 

  

  /20

  $475,000

  • 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
• 

  

  /21

  $195,000

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

  751 SE Meadowood Dr, Winston, OR 97496

  1995 Double-wide manufactured home on a good sized lot in Winston. Not perfect but a lot of home for the money. Central heat and air conditioning, carport and lots of room for a garden. A great home for the money. Affordable living, close to park and community center. Roof has just been replaced.

  Timothy A Smith RE/MAX Integrity

  

  751 SE Meadowood Dr, Winston, OR 97496
• 

  

  /30

  $259,000

  • Land
  • 16.59 Acres
  • $15,612 per Acre

  505 Sibold Canyon Rd, Tenmile, OR 97481

  Private 16.5+ acres in beautiful Sibold Canyon with a cleared, level homesite ready for your build. Power is available onsite, offering a valuable head start. Enjoy pasture ground, fruit trees, and peaceful frontage along seasonal Porter Creek. Trails and an access road wind through the timbered hillside for recreation and exploration. Wildlife is frequently seen throughout the property. A unique

  Aaron Cherry Oregon Life Homes

  

  505 Sibold Canyon Rd, Tenmile, OR 97481
• 

  

  /44

  $874,000

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

  300 Mattie K Ln, Roseburg, OR 97471

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

  Melony Marsh All-Pro Realty Advisors, LLC

  

  300 Mattie K Ln, Roseburg, OR 97471
• 

  

  /34

  $359,000

  • 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
• 

  

  /48

  $975,000 Open House 5/16

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

  6404 Lookingglass Rd, Roseburg, OR 97471

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

  Brent Yop Winston Realty & Insurance

  

  6404 Lookingglass Rd, Roseburg, OR 97471
• 

  

  /11

  $189,000

  • 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

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