Winston, OR Homes for Sale

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  /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 Winston

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  /45

  $679,900

  • 4 Beds
  • 3.5 Baths
  • 3,072 Sq Ft

  635 Wil Way, Winston, OR 97496

  One of a kind property that is a true gem. Panoramic views of the Abacela Vineyards, the Wildlife Safari, the beautiful city, and the stunning valleys. While being tucked away at the end of the road for extra privacy. Nestled on over 20 acres, this parcel adjoins the Wildlife Safari. Imagine watching exotic animals from your back yard! The home is a gorgeous 2019 build featuing many high quality

  

  Ashton Faas

  Different Better Real Estate

  (458) 232-3589

  

  635 Wil Way, Winston, OR 97496
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  /27

  $357,900

  • 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
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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
• 

  

  /48

  $469,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  109 Citation Ct, Winston, OR 97496

  Welcome to 109 Citation Ct, a brand-new single-level home nestled in the highly sought-after Lookingglass Creek Estates subdivision in Winston, Oregon. This contemporary ranch-style residence offers 3 bedrooms, 2 bathrooms, and 1,770 sq. ft. of beautifully designed living space on a .20-acre lot with RV parking behind a private gate. Step inside to find luxury vinyl plank flooring, vaulted

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  109 Citation Ct, Winston, OR 97496
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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
• 

  

  /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
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  /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
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  /48

  $265,000 Open Fri 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  771 SE Hall St, Winston, OR 97496

  Welcome to 771 SE Hall St in Winston where comfort meets convenience in this spacious 3 bedroom 2 bath home featuring 1650 square feet of well designed living space on a 0.16 acre lot. Curb appeal abounds with a freshly painted covered front porch and an expansive driveway providing tons of parking for vehicles or recreational toys. Peace of mind comes included with a newer roof and a newer hot

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  771 SE Hall St, Winston, OR 97496
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  /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
• 

  

  /7

  $734,000

  • 4 Beds
  • 2.5 Baths
  • 2,362 Sq Ft

  1068 Rice Creek Rd, Winston, OR 97496

  This gated, 8.52-acre property is fenced and cross-fenced, offering plenty of country living space. This beautiful ranch-style home features updates, a newer roof, and recent interior and exterior paint. The gourmet kitchen includes double ovens and a walk-in pantry. The large living room features a fireplace. The huge primary bedroom includes a walk-in closet and a two-headed shower. One of the

  Greg Johnson G Stiles Realty

  1068 Rice Creek Rd, Winston, OR 97496
• 

  

  /41

  $499,900 New Construction

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

  160 Wil Way, Winston, OR 97496

  OPEN HOUSE! Sunday 3/29 1-3pm 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
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  /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
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  /32

  $555,000 Open House 4/12

  • 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 wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, over sized gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance, covered patio. The gourmet kitchen has granite, pantry, new

  Valynn Currie Currieco Real Estate

  

  102 Sarah Bear Ln, Winston, OR 97496
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  /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
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  /40

  $499,900 New Construction

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

  150 Wil Way, Winston, OR 97496

  OPEN HOUSE! Sunday 1-3pm 3/29 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
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  /35

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  800 Byron Creek Rd, Winston, OR 97496

  Welcome to this charming country home set on over 5 acres of flat, usable land with Firewise Certification for peace of mind. The well maintained 3 bedroom with 1.5 bathrooms. Home is move-in ready, some of the furniture can be included with the right offer. House has a heat pump, pellet stove, generator, flooring- all done in last 4 years. The propane 22k generator automatically powers the home

  Rebekah Sexauer eXp Realty, LLC

  

  800 Byron Creek Rd, Winston, OR 97496
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  /42

  $599,000

  • 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
• 

  

  /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
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  /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
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  /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
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  /36

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  669 NW T St, Winston, OR 97496

  Welcome to this beautiful 2022 built home in Winston, Oregon, offering comfort, privacy, and stunning open views. Conveniently located close to local amenities with easy access to the Oregon Coast and the world-famous Wildlife Safari. Situated on a private and spacious flag lot, the property backs to a school field, creating an open feel with peaceful mountain views and added privacy.Inside,

  Shae Ellison Platinum Realty

  

  669 NW T St, Winston, OR 97496
• 

  

  /20

  $230,000

  • 2 Beds
  • 1 Bath
  • 1,323 Sq Ft

  381 SE Gregory Dr, Winston, OR 97496

  Seize this opportunity with this charming single-story 1948 ranch style home boasting 2 bedrooms, 1 bath, and about 1,323 sq ft of living space on a generous 0.61-acre lot. Surrounded by mature trees and offering a peaceful, rural-suburban feel in the heart of Douglas County. This mid-century gem features timeless details like a prominent brick chimney, large picture windows for natural light,

  Nile Stark RE/MAX Integrity

  

  381 SE Gregory Dr, 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
• 

  

  /20

  $80,000

  • Land
  • 0.12 Acre
  • $666,667 per Acre

  271 SE Robinson St, Winston, OR 97496

  Build Your Dream Home on This Prime Lot!Nice Lot – Prime Location – All Utilities – Investment Opportunity!Discover the perfect canvas for your future home. This spacious lot comes with full utilities—water, electricity, and sewer—ready for you to build. Nestled in a good location, it’s ideal for families, investors, or anyone looking to live in town. Don’t miss out on this incredible

  Kayla Wehe Lamonte Real Estate Professionals

  

  271 SE Robinson St, 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
• 

  

  /23

  $119,000

  • 3 Beds
  • 2 Baths
  • 1,377 Sq Ft

  221 NW Bree Dr, Winston, OR 97496

  Meticulously maintained 3-bedroom, 2-bath manufactured home located in a quiet and private all-ages co-op community with a low $449 monthly space rent, including water and sewer. Built in 1998, this home offers a functional and inviting layout with a split-bedroom design and a separate family/media room just off the main living area, providing flexibility for everyday living or entertaining. The

  Brenda Smith Stellar Realty Northwest

  

  221 NW Bree 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
• 

  

  /22

  $375,000 Open House 4/11

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  182 Woodduck St, Winston, OR 97496

  Quality contemporary 3 bedroom, 2 bath 1452 sq ft home built in 2005 in Hunters Crossing. Has Double garage, vaulted ceilings, appliances included. Newly painted. Laminate floors throughout, covered patio in private fenced yard low maintenance. Will finance all ways. Turn key ready. RV Parking/boat parking.

  Valynn Currie Currieco Real Estate

  

  182 Woodduck St, Winston, OR 97496
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  /34

  $359,000 Open House 4/11

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

  380 NW Cary St, Winston, OR 97496

  Open house April 11th from 12 - 2pm.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
• 

  

  /11

  $199,900

  • 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
• 

  

  /23

  $90,000

  • 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
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  /30

  $399,999

  • 2 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  270 Sabrina Ln, Winston, OR 97496

  Tucked away in the peaceful countryside of Douglas County, this unique 8-acre property offers the perfect blend of self-sufficiency, privacy, and convenience—just a 15-minute drive from Winston, Oregon. The two-story home features approximately 1,050 square feet of comfortable living space, surrounded by nature and open skies that create a true sense of seclusion.The land is thoughtfully equipped

  Robinson Parker Oregon Life Homes

  

  270 Sabrina Ln, Winston, OR 97496
• 

  

  /16

  $850,000

  • Land
  • 37.86 Acres
  • $22,451 per Acre

  0 Danielle Dr Unit 122251646, Winston, OR 97496

  Prime development opportunity in Winston, Oregon! This expansive 38-acre property has potential for 90 buildable residential lots, perfect for a new housing community. Situated in a peaceful location with easy access to local amenities, this land offers a great investment potential for developers. Ideal for those looking to create a vibrant neighborhood in a growing area. Don’t miss out on this

  Jeremy Parmenter TLC Realty

  

  0 Danielle Dr Unit 122251646, Winston, OR 97496
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  /48

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 2,720 Sq Ft

  6700 Upper Olalla Rd, Winston, OR 97496

  Exquisite Lindal Custom Cedar home on 5 flat acres featuring a 2,400 sq ft shop with full bath, dual doors, and room for a 40’ motorhome, plus 3 RV hookups (2 across the driveway) with power, water, and RV dump by the shop. The gourmet kitchen is a chef’s dream with granite counters, dual sinks, pot filler, gas range with warming drawer, double ovens, hidden butcher block, and abundant storage,

  Dan Gandee Real Broker

  

  6700 Upper Olalla Rd, Winston, OR 97496
• 

  

  /4

  $2,000,000

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft

  80 NW Lost Ln, Winston, OR 97496

  Great Property for future Developing. 2007 Manufactured Home on .68 of a Ac. City Water and Sewer.

  Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

  

  80 NW Lost Ln, Winston, OR 97496
• 

  

  /21

  $127,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  180 Twin Oaks Loop, Winston, OR 97496

  application and park requirements, No other fees to HOA except basic space rent 604$+121$ w/s/g Property Listing: 180 Twin Oaks Loop, Winston, OR Renovated 3-Bedroom,2-Bathroom Double Wide in 55+ Community Welcome to this beautifully renovated 3-bedroom, 2-bathroom home located in the sought-after Twin Oaks Mobile Park Estates, a quiet and well-maintained 55+ community in Winston, OR. This

  Raymond Coburn eXp Realty, LLC

  

  180 Twin Oaks Loop, Winston, OR 97496
• 

  

  /10

  $249,500

  • Land
  • 0.45 Acre
  • $554,444 per Acre

  0 SW Main St, Winston, OR 97496

  Looking for a retail, office or hospitality location in Winston? This lot is strategically located near the intersection of Hwy 42 & Hwy 99 with easy access to I-5 and on the route to Oregon's coastal destinations! This lot is the best that Winston has to offer...

  Jody Tatone RE/MAX Integrity

  

  0 SW Main St, Winston, OR 97496

Showing Results 1 - 40, Page 1 of 2

Why Live in Winston

Winston, Oregon, is a small community of nearly 6,000 residents nestled along the South Umpqua River and surrounded by forested landscapes. Known for its Wildlife Safari, Winston offers a driving tour featuring over 500 animals and 80 species. The town's parks, such as Riverbend Park and Winston Dillard County Park, provide playgrounds, skate parks, picnic areas, and summer concert series. Harold and Sid Nichols Park includes a public boat ramp, popular for fishing and kayaking. Winston's homes range from starter properties to high-end estates, with single-level ranch homes being the most common. Lot sizes vary from under 10,000 square feet to over 20 acres, and new developments like Rolling Meadows are underway. Dining options are concentrated around Southeast Main Street and Northwest Douglas Boulevard, with spots like Winston Diner & Drive-Thru and Willee's Cafe and Spirits. Grocery Outlet and Brosi's Sugartree Farms cater to local shopping needs, while nearby Abacela Winery and Freed Estates Vineyard offer tasting rooms. Highway 99 provides scenic routes through the area, including the Rogue-Umpqua Scenic Byway. Flooding can be a concern in local parks and boat ramps after heavy rainfall or snowmelt.

Learn more about living in Winston

Frequently Asked Questions

What is the average home price in Winston, OR?

Homes for sale in Winston, OR have an average home price of $370,055.

Are home prices dropping in Winston?

Yes, home prices in Winston are down 2% in the last 12 months.

How many homes have sold over the last 12 months in Winston, OR?

66 homes have sold in Winston, OR over the last 12 months.

Is Winston, OR a safe city?

In general, the safest neighborhoods in Winston, OR with lower crime scores are Green, Dillard, Tenmile and Camas Valley.

What are the most popular zip codes in Winston, OR?

The most popular zip codes in Winston, OR include 97496, 97471, 97457, 97470 and 97416.

What are the most popular neighborhoods in Winston, OR?

The most popular neighborhoods in Winston, OR with the most homes for sale are Green, Dillard, Tenmile and Camas Valley.

How much do you need to make to afford a house in Winston?

The median home price in Winston is $372,000. If you put a 20% down payment of $74,400 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $1,860 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $80K a year to afford the median home price in Winston. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Winston, OR?

Winston, OR has highly rated public and private schools. Some of the best schools in Winston based on Niche Grades are John C. Fremont Middle School, McGovern Elementary School and Roseburg High School. The neighborhoods in Winston with the highest rated schools are Green, Dillard and Tenmile. Browse all the schools in Winston, OR to learn more.

Home Trends in Winston, OR

On average, homes in Winston, OR sell after 81 days on the market compared to the national average of 55 days. The median sale price for homes in Winston, OR over the last 12 months is $325,000, down 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$325,000

Median Single Family Sale Price

$344,000

Average Price Per Sq Ft

$228

Number of Homes for Sale

15

Last 12 months Home Sales

66

Months of Supply

2.70

Median List Price

$372,000

Median Change From 1st List Price

3%

Median Home Sale Price YoY Change

-6%