Winston, OR Homes for Sale

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  /15

  $200,000

  • Land
  • 4.26 Acres
  • $46,948 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

• 

  

  

  /45

  $699,900

  • 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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  /28

  $375,000

  • Land
  • 7.4 Acres
  • $50,676 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

  $200,000

  • Land
  • 3.14 Acres
  • $63,694 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
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  /36

  $439,000

  • 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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  /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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  /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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  /40

  $289,900

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  260 SW Ford Ave, Winston, OR 97496

  Welcome to 260 SW Ford Ave in the heart of Winston, OR — a beautifully remodeled single-level home offering comfort, style, and exceptional move-in readiness. Fresh exterior paint gives the home a crisp, modern look, while inside you’ll find waterproof luxury vinyl plank flooring in the main living areas—including the living room, kitchen, bonus room, and laundry room—paired with brand-new carpet

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  260 SW Ford Ave, Winston, OR 97496
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  /42

  $375,000

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

  700 SE Tokay St, Winston, OR 97496

  Welcome to this inviting one level 3-bedroom, 2-bathroom home offering comfort, convenience, and modern touches throughout. Manicured front yard plus a manicured back yard that is completely fenced. The bright and open kitchen features stainless steel appliances and granite countertops, making meal prep a joy. Enjoy the ease of single-level living with a functional floor plan, perfect for both

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  700 SE Tokay St, Winston, OR 97496
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  /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
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  /12

  $334,900

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft

  185 Lebleu Ln, Winston, OR 97496

  Solid home in Winston with a newer roof and open concept floorplan. Welcome home to this well maintained single-story home with a modern layout, featuring an inviting open-concept layout designed for both comfort and privacy. The spacious primary bedroom includes an attached bathroom, offering a private retreat. The living room features a gas fireplace, perfect for relaxing evenings. Step outside

  Kurt Delahooke Keller Williams Realty Eugene and Springfield

  

  185 Lebleu Ln, Winston, OR 97496
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  /21

  $250,000

  • Land
  • 27.09 Acres
  • $9,228 per Acre

  0 E Willis Creek Rd, Winston, OR 97496

  27.09 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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  /39

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  617 Poison Oak Dr, Winston, OR 97496

  Escape to the country with this rustic home nestled on nearly 14 beautiful acres. Perfect for those dreaming of a mini-farm or simply wanting space for animals, and rural lifestyle. This property offers usable acreage mixed with stands of timber, seasonal creeks and endless potential. Surround yourself with sweeping mountain views and the serenity of nature, all while enjoying the freedom that

  Bob Lamonte Lamonte Real Estate Professionals

  

  617 Poison Oak Dr, Winston, OR 97496
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  /48

  $474,900

  • 4 Beds
  • 2 Baths
  • 2,534 Sq Ft

  13224 Lookingglass Rd, Winston, OR 97496

  Experience this beautifully updated, original homestead farmhouse nestled in Safari Estates. Thoughtful remodel and tasteful updates have modernized this 1900-built farmhouse, preserving its character while enhancing comfort. With 2,516 sq ft of living space, four bedrooms, and two full baths, this home blends historic charm with modern comfort. The kitchen has been remodeled with beautiful

  Deleta Dickson eXp Realty, LLC

  

  13224 Lookingglass Rd, Winston, OR 97496
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  /32

  $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 Homes Realty

  

  1941 Byron Creek Rd, Winston, OR 97496
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  /10

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  139 Teresa Ln, Winston, OR 97496

  Come take a look at your beautiful new forever home in this established neighborhood. Newer build in 2017 with many amenities. Kitchen boasting all stainless-steel appliances with a wonderful gas stove for the cook in the family, down to the granite countertop and eat in island great for entertaining with its open concept. Spacious master bedroom with a walk-in closet and granite vanity in the

  Angel Smith Trueblood Real Estate

  

  139 Teresa Ln, Winston, OR 97496
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  /48

  $459,000

  • 3 Beds
  • 2.5 Baths
  • 2,067 Sq Ft

  165 Danielle Dr, Winston, OR 97496

  Welcome home! Enjoy the space and warmth of this Safari Estates custom home. Featuring over 2,000 sq ft of living space. 3 bedrooms 2.5 baths with an upstairs laundry room make this home a great family setup. There is an office/Den that also doubles as a 4th bedroom if needed. Dramatic entry way with open concept kitchen/familyroom is what separates this home from the others ! Outside you will

  Brent Yop Winston Realty & Insurance

  

  165 Danielle Dr, Winston, OR 97496
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  /46

  $384,900

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  890 SE Thompson Ave, Winston, OR 97496

  You won't want to miss this beautifully maintained 3-bedroom, 2.5-bath Hi line home in Winston. Built in 2016, offering over 1,700 sq ft of thoughtfully designed living space. The open and functional layout includes a main-floor bonus room—perfect for a home office, playroom, or guest retreat—while abundant natural light fills the living areas, creating a warm and inviting atmosphere. The kitchen

  Anthony Beckham Different Better Real Estate

  

  890 SE Thompson Ave, Winston, OR 97496
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  /35

  $169,900

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

  222 NW Broc Dr, Winston, OR 97496

  Wow! Discover wonderful value with this 2024-built, 1,512 sq. ft. three-bedroom, two-bath manufactured home located in a quiet, private co-op with low $449 space rent and a very exceptional price point. Step inside to an inviting interior featuring laminate flooring, carpeted bedrooms and living room, and a spacious primary suite complete with an oversized en-suite bath, double vanity, and a deep

  Anthony Beckham Different Better Real Estate

  

  222 NW Broc Dr, Winston, OR 97496
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  /15

  $239,000

  • 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
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  /35

  $405,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  364 NW Teal St, Winston, OR 97496

  Welcome to this move-in ready, well-maintained one-level home in a highly desirable subdivision on the outskirts of Winston. Featuring 3 bedrooms, 2 bathrooms and dedicated home office. This property offers both comfort and convenience. Open floorplan with master suite privately positioned at the opposite end of the house for added tranquility. 3-car attached garage provides ample storage and

  Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

  

  364 NW Teal St, Winston, OR 97496
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  /20

  $89,000

  • Land
  • 0.12 Acre
  • $741,667 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
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  /37

  $525,000 New Construction

  • 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

  Tyler Head Turning Point Realty Group

  

  160 Wil Way, Winston, OR 97496
• 

  

  /41

  $830,000

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

  375 Porter Creek Rd, Winston, OR 97496

  Discover the perfect blend of vineyard lifestyle and modern comfort in this beautifully updated 41-acre estate, nestled in the heart of Oregon’s Umpqua Valley AVA. Surrounded by timber, a year-round creek, and a seasonal pond, this scenic retreat offers privacy, natural beauty, and endless potential.At the heart of the property is a spacious 3,000 sq ft home featuring four large bedrooms and

  Lorrie Normann Triple Oaks Realty LLC

  

  375 Porter Creek Rd, Winston, OR 97496
• 

  /2

  Call for Price

  • Land
  • 160 Acres

  0 Diamond Rock Rd Unit 727456026, Winston, OR 97496

  160± acre Diamond Rock Road Recreation and Timber Tract is located within Umpqua National Forest, six miles south of South Umpqua River community of Tiller, and two miles from Drew at County Road 1. Diamond Rock Road (FS3201 Road) provides access to Drew, and continues through the Tract south, to both private and USFS lands. The entire Tract was impacted by 2015 Stouts Fire, and was replanted

  John Rosenthal Realty Marketing / Northwest

  

  0 Diamond Rock Rd Unit 727456026, Winston, OR 97496
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  /20

  $500,000

  • 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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  /27

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  120 SE Edwards Ave, Winston, OR 97496

  Welcome to this 3-bedroom, 2-bath single-level custom home. Thoughtfully designed with comfort and functionality in mind, this 1,421 sq ft residence offers a spacious open-concept layout, vaulted ceilings, and abundant natural light throughout. The kitchen features wood cabinetry, stainless steel appliances, and a breakfast bar perfect for casual meals or entertaining guests. The primary suite is

  Jerry Norman Oregon Life Homes

  

  120 SE Edwards Ave, Winston, OR 97496
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  /36

  $199,000

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

  301 NW Midway St, Winston, OR 97496

  AMAZING INVESTMENT OPPORTUNITY!!! Cosmetic fixer upper features 3 Bedrooms, 2 baths, 2 car garage, spacious lot nearly half an acre & fully fenced with outbuildings. Tons of parking for RV's, cars or other toys. Central heat, indoor laundry room & vinyl windows. Bring your tools, your ideas & your cash!!

  Tracy Grubbs eXp Realty, LLC

  

  301 NW Midway St, Winston, OR 97496
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  /35

  $142,500

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  112 Twin Oaks Loop, Winston, OR 97496

  WOW! BRAND NEW 2025 manufactured home in the tidy senior living 55+ Twin Oaks community! This 3-bed, 2-bath home features an open floor plan with a large kitchen island, stainless steel appliances, and modern finishes throughout. The primary suite includes double sinks and a walk-in shower. Covered carport and storage shed add convenience. Space rent $725/month and includes water, sewer, and

  Anthony Beckham Different Better Real Estate

  

  112 Twin Oaks Loop, Winston, OR 97496
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  /32

  $575,000

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

  102 Sarah Bear Ln, Winston, OR 97496

  Stately quality 4 br 3 bath home, 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 gas appliances,

  Valynn Currie Currieco Real Estate

  

  102 Sarah Bear Ln, Winston, OR 97496
• 

  

  /23

  $99,500

  • 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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  /38

  $350,000

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

  210 NW Timothy Ave, Winston, OR 97496

  Extremely nice 1999 triple-wide on a beautiful corner lot. Features 3 bedrooms, 2 baths with a large kitchen, living, and family rooms. There is also a gas fireplace, new heat pump, and an extra large 2-car garage. Outside has a covered deck, patio, mature landscaping, and fenced yard with sprinkler and drip system.

  John McVeigh The Neil Company Real Estate

  

  210 NW Timothy Ave, Winston, OR 97496
• 

  

  /25

  $249,000

  • 3 Beds
  • 1 Bath
  • 994 Sq Ft

  350 SE Park St, Winston, OR 97496

  Perfect home for a first-time buyer or an excellent investment opportunity! Situated on a large corner lot in a desirable neighborhood within walking distance to the city park. This move-in-ready home features beautiful kitchen cabinets and a versatile storage/she shed. Don’t miss out on this great opportunity!

  Michael Brown Oregon Life Homes

  

  350 SE Park St, Winston, OR 97496
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  /48

  $748,000

  • 3 Beds
  • 2.5 Baths
  • 1,845 Sq Ft

  1470 E Willis Creek Rd, Winston, OR 97496

  Build a second home? 3 tax lots. 80+5+5 acres each & one of the 5-acre lots is buildable! Connected to city water with a 2500 reserve tank. Nestled on 90 acres of private land, this stunning 3-bedroom, 2.5-bath log home offers the perfect retreat for those seeking tranquility and connection with nature. The main home is a masterpiece of rustic craftsmanship, featuring soaring vaulted ceilings,

  Rhonda Marshall Knipe Realty ERA Powered

  

  1470 E Willis Creek Rd, Winston, OR 97496
• 

  

  /27

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft

  291 SE Shigley St, Winston, OR 97496

  Contemporary custom 2014 sq ft. tri level home on .21 acre level lot. Has 8x24 green house, deck, hot tub, new furnace, new solar system paid for. Range, refrigerator, dishwasher, freezer, washer dryer included. Quality built home, double garage, RV parking. Views of mountains. Park around the corner. Estate sale. Motivated seller. Needs cosmetics but excellent bones.

  Valynn Currie Currieco Real Estate

  

  291 SE Shigley St, Winston, OR 97496
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  /49

  $700,000

  • 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
• 

  

  /18

  $272,000

  • 3 Beds
  • 2 Baths
  • 1,835 Sq Ft

  151 Sherry St, Winston, OR 97496

  Charming 3 bedroom (possibly 4 bedroom), 2 bath home with lots of storage & room to roam! Large, fenced corner lot & covered patio for outdoor enjoyment. With a little TLC, this home could sparkle again.

  Judith Zuver Winston Realty & Insurance

  

  151 Sherry St, Winston, OR 97496
• 

  

  /32

  $59,000

  • Land
  • 0.18 Acre
  • $327,778 per Acre

  105 Lebleu Ln, Winston, OR 97496

  Seller willing to owner carry. US Bank offers both lot and constructions loan. Discover the perfect canvas for your dream home at 105 SE Lebleu, a buildable lot nestled on the fringe of a blossoming neighborhood. Embrace the opportunity to create a bespoke living space surrounded by the tranquil beauty of orchards, farms, and the majestic mountains beyond. Don't miss the chance to claim this

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  105 Lebleu 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

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 $360,068.

Are home prices dropping in Winston?

Yes, home prices in Winston are down 1% 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, Camas Valley and Tenmile.

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

The most popular zip codes in Winston, OR include 97496, 97471, 97470, 97457 and 97481.

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, Camas Valley and Tenmile.

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

The median home price in Winston is $359,900. If you put a 20% down payment of $72,000 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $1,770 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $76K 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 Camas Valley. Browse all the schools in Winston, OR to learn more.

Home Trends in Winston, OR

On average, homes in Winston, OR sell after 65 days on the market compared to the national average of 53 days. The median sale price for homes in Winston, OR over the last 12 months is $337,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$337,000

Median Single Family Sale Price

$340,000

Average Price Per Sq Ft

$227

Number of Homes for Sale

25

Last 12 months Home Sales

66

Months of Supply

4.50

Median List Price

$359,900

Median Change From 1st List Price

2%

Median Home Sale Price YoY Change

-3%