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Winston Homes for Sale

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  • /28

    $430,000

    • Land
    • 7 Acres
    • $58,108 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

    Different Better Real Estate

    (458) 310-3411

    0 Wil Way Unit 24094727, Winston, OR 97496
  • /39

    $439,000

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft

    441 NW Galaxy Dr, Winston, OR 97496

    Finished heated shop • Finished heated/cooled garage • Stunning views • Beautiful home overlooking the city w/panoramic views of surrounding mountains and valleys. Multiple decks and thoughtfully designated outdoor spaces for entertaining or relaxation. Fully finished and heated shop w/ vaulted ceilings, skylight and wood beams seamlessly attached to the fully finished heated/cooled garage

    Agent Photo

    Nichole Sharman

    Works Real Estate

    (458) 854-7182

    441 NW Galaxy Dr, Winston, OR 97496
  • /45

    $780,000

    • 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

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 232-3589

    635 Wil Way, Winston, OR 97496
  • /46

    $479,900

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

    13224 Lookingglass Rd, Winston, OR 97496

    Experience the unique allure of 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

    Agent Photo

    Deleta Dickson

    eXp Realty, LLC

    (458) 237-8628

    13224 Lookingglass Rd, Winston, OR 97496
  • /15

    $230,000

    • Land
    • 4.26 Acres
    • $53,991 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

    Different Better Real Estate

    (458) 217-1693

    0 Wil Way Unit 24292479, Winston, OR 97496
  • /15

    $230,000

    • Land
    • 3.14 Acres
    • $73,248 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

    Different Better Real Estate

    (458) 224-5797

    0 Wil Way Unit 24278136, Winston, OR 97496
  • /21

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,348 Sq Ft

    595 SE Parkway Dr, Winston, OR 97496

    Exquisitely clean and well-maintained single-level home in desired Winston neighborhood close to schools and parks. Very sharp, low-maintenance landscaping with small grassy area in the back and mature shrubs and perennials throughout the property. This home was built in 1996 but looks almost brand new. Offering 3 bedrooms, 2 full bathrooms, vaulted living room, vinyl windows, dark wood laminate

    Jacob Gilman The Neil Company Real Estate

    595 SE Parkway Dr, Winston, OR 97496
  • /47

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    465 SE Gregory Dr, Winston, OR 97496

    Welcome to this inviting single-level home in Winston, Oregon! Built in 2021, this 3-bedroom, 2-bathroom residence offers 1,620 square feet of bright, open living space. The spacious living room seamlessly connects to a dining area and well-equipped kitchen with a center island, pantry, and all major appliances—perfect for entertaining or everyday comfort. Step through double doors to enjoy a

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

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

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    621 SE Rose Ridge Dr, Winston, OR 97496

    Welcome to 621 SE Rose Ridge Dr in Winston’s desirable Orchard View neighborhood—a beautifully maintained single-level home built in 2020. This 3-bedroom, 2-bath home offers approximately 1,620 sq ft of thoughtfully designed living space on a landscaped 6,534 sq ft lot. The open-concept great room features vaulted ceilings, while the gourmet kitchen includes solid surface countertops, a stainless

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    621 SE Rose Ridge Dr, Winston, OR 97496
  • /37

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    360 NE Rose Ridge Dr, Winston, OR 97496

    Beautiful 3BD/2BTH home in Winston’s sought-after Rolling Meadows neighborhood! Built by Avery Homes in 2021, this one-level residence feels "like new" and is completely move-in ready. Enjoy an open-concept layout with durable LVP flooring, quartz countertops, and a bright, spacious living area perfect for everyday activities and entertaining. Energy-efficient solar panels installed in July 2024

    Aaron Cherry Oregon Life Homes

    360 NE Rose Ridge Dr, Winston, OR 97496
  • /31

    $59,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    111 Sharway Ln, Winston, OR 97496

    This charming 2-bedroom, 1-bath manufactured home is fully furnished and move-in ready, located in a well-kept 55+ community with low space rent, offering an ideal mix of comfort and convenience. The property includes a recently built carport, two storage sheds, and a beautifully landscaped yard that enhances its curb appeal. With a roof that’s just 5 years old and a brand-new HVAC system

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    111 Sharway Ln, Winston, OR 97496
  • /47

    $377,500

    • 3 Beds
    • 1 Bath
    • 1,434 Sq Ft

    10 SE Kegler Ave, Winston, OR 97496

    Set on a full acre at the edge of town, this property blends flexibility, functionality, and a 1,200 sq ft shop that’s hard to ignore! The 3-bedroom, 1-bath home includes an oversized living room with exposed wood accents and rustic-style posts that bring a bit of texture and charm. Heating and cooling are handled with ductless systems, and there’s a gas fireplace to keep things cozy. The kitchen

    Anthony Beckham Different Better Real Estate

    10 SE Kegler Ave, Winston, OR 97496
  • /28

    $395,000

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft

    140 Teresa Ln, Winston, OR 97496

    This modern, beautiful home is located in the highly sought-after Winston neighborhood. The home has been recently remodeled down to the studs and includes brand new HVAC, new appliances, and new roof. Step inside to find luxury vinyl plank flooring, recessed lighting, and soaring vaulted ceilings, and an abundance of windows that create a spacious and inviting atmosphere. The open-concept

    Jason Mann J Mann Realty

    140 Teresa Ln, Winston, OR 97496
  • /32

    $499,500

    • 3 Beds
    • 2 Baths
    • 2,186 Sq Ft

    240 Wil Way, Winston, OR 97496

    Welcome to the highly desirable neighborhood of Safari Estates. This custom built 3-bedroom, 2 bath home offers stunning views of the rolling forested hills and is in the heart of wine country. The expansive living room is flooded with natural light, showcasing the breathtaking views through large windows that seamlessly connect the indoors to the outdoor patio space. The open-concept with

    Jacob Sanchez Next Generation Real Estate LLC

    240 Wil Way, Winston, OR 97496
  • /12

    $58,000

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft

    250 NE Jorgen St, Winston, OR 97496

    Affordable living or investment opportunity in Douglas County! This 2-bedroom, 1-bath manufactured home sits on a generously sized lot. Fix the existing home to suit your needs, or place another home to maximize your investment! New rubber roof, bathroom floor, and vinyl in 2014.

    Derrick Roser Keller Williams Realty Eugene and Springfield

    250 NE Jorgen St, 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
  • /29

    $147,000

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    140 NW Bree Dr, Winston, OR 97496

    This beautifully maintained 3-bedroom, 2-bath home offers a bright and inviting open floor plan with a split-bedroom layout for added privacy. The master suite features a generous walk-in closet and an en-suite bathroom, creating a comfortable retreat. Enjoy durable Luxury Vinyl Plank (LVP) flooring throughout, vaulted ceilings, and newer double-pane vinyl windows that fill the home with natural

    Darla Duke Lamonte Real Estate Professionals

    140 NW Bree Dr, Winston, OR 97496
  • /8

    $2,500,000

    • Land
    • 15 Acres
    • $166,113 per Acre

    215 Parkinson Rd, Winston, OR 97496

    Lovely acreage on South Umpqua River. Zoned agriculture. Water rights from 1953. 44x60 barn has been partially renovated. Running water at barn. Use your imagination on the uses for this wonderful acreage on the river. Buyer to do all due diligence regarding every aspect of the property. Seller makes no disclosures.

    Nick Knight Knight Realty Group LLC

    215 Parkinson Rd, Winston, OR 97496
  • /27

    $350,000

    • 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

    Jerry Norman Oregon Life Homes

    120 SE Edwards Ave, Winston, OR 97496
  • /20

    $299,500

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft

    120 SW Brantley Dr, Winston, OR 97496

    Charming 3 bedroom, 2 bath home with attached 2 car garage & multiple outbuildings. Large cement patio with lots of outdoor living area. Sits on a large lot, (over 3/5ths of an acre) with lots of fruit trees & room to roam! Must see to appreciate this lovely home!

    Judith Zuver Winston Realty & Insurance

    120 SW Brantley Dr, Winston, OR 97496
  • /6

    $359,000

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

    185 Lebleu Ln, Winston, OR 97496

    Welcome home to this well maintained single-story home with a modern floorplan, 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 to enjoy unrestricted views of nature from the backyard,

    Kurt Delahooke Keller Williams Realty Eugene and Springfield

    185 Lebleu Ln, Winston, OR 97496
  • /19

    $60,000

    • 1 Bed
    • 1 Bath
    • 384 Sq Ft

    119 Oak Leaf Ln, Winston, OR 97496

    Small but mighty! This well-maintained 384 sq ft home, built in 2021, offers a comfortable and convenient living space in a peaceful 55+ community. Featuring laminate flooring throughout, the home includes a cozy bedroom and a bright, functional bathroom. Washer and dryer hookups are available for added convenience, and a private storage unit provides extra space for your belongings. Spacious

    Cindi Mills RE/MAX Integrity

    119 Oak Leaf Ln, Winston, OR 97496
  • /5

    $92,000

    • Land
    • 0.64 Acre
    • $143,750 per Acre

    873 SE Edgewood St, Winston, OR 97496

    0.64 Acre Buildable Lot zoned RR. Out of flood plain. At the end of a quiet dead St. Buyer to do all due diligence to verify buildability. Has not been septic approved.

    Nick Knight Knight Realty Group LLC

    873 SE Edgewood St, Winston, OR 97496
  • /47

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,374 Sq Ft

    231 NE Darrell Ave, Winston, OR 97496

    Great location with a custom built one level home located on .39 of an acre at the end of the road in Winston with City Services! Home built in 1981 with approximately 1,374 square feet, 3 bedrooms and 2 full bathrooms, primary bedroom and bathroom has a walk-in closet and slider door to deck, nice Kitchen with oodles of oak cabinets, lots of counter space, plus a pantry, Living room has

    Cynthia Johnson Johnson Group Real Estate, LLC

    231 NE Darrell Ave, Winston, OR 97496
  • /32

    $590,000

    • 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

    $294,900

    • 3 Beds
    • 1 Bath
    • 1,668 Sq Ft

    551 NW T St, Winston, OR 97496

    Charming, beautifully updated, move-in-ready home in Winston! The perfect blend of turn key and affordability. Fresh, modern flooring, kitchen, bath, light fixtures and fun finishes give this home its clean aesthetic while the lovely fireplace and mid century details add warmth and character. New roof, new ductless ac units up and downstairs and so much more! Don’t miss this gem!

    Bob Lamonte Lamonte Real Estate Professionals

    551 NW T St, Winston, OR 97496
  • /39

    $345,000

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

    151 Sherry St, Winston, OR 97496

    Step into this charming 1965 Ranch-style home, nestled in a peaceful neighborhood on a generous double lot in the heart of Winston, Oregon. With 3 bedrooms, 1.5 bathrooms, and a large, fully fenced corner lot, this property offers both privacy and convenience. This home boasts ample storage space throughout, with built-in shelving and closets to keep your living areas tidy. The cozy and airy

    RaNae Sams Oregon Life Homes

    151 Sherry St, Winston, OR 97496
  • /15

    $240,000

    • 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.

    Timothy A Smith RE/MAX Integrity

    751 SE Meadowood Dr, Winston, OR 97496
  • /14

    $199,999

    • 2 Beds
    • 1 Bath
    • 735 Sq Ft

    110 SE Darrell Ave, Winston, OR 97496

    YOU WON'T WANT TO MISS THIS OPPORTUNITY. Cute updated 2 bedroom home with small utility room. Kitchen with appliances. Updated hot water heater, flooring, interior and exterior paint. Living room offers gas heater and a front bonus area. Partially fenced yard with garden shed in back. Nice corner lot with driveway. Call for your showing today!

    Lacey Williams Trueblood Real Estate

    110 SE Darrell Ave, Winston, OR 97496
  • /4

    $225,000

    • Land
    • 0.71 Acre
    • $316,901 per Acre

    0 SE Gregory Dr, Winston, OR 97496

    Ready to go multifamily with construction plans. See attached plans for 3 triplex buildings. Utilities are to property line. Water & sewer available. Great opportunity for a hard to find multifamily property. CLA for more information

    Larry KW Alberts Keller Williams Realty Eugene and Springfield

    0 SE Gregory Dr, Winston, OR 97496
  • /16

    $850,000

    • Land
    • 38 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
  • /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
  • /48

    $725,000

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    411 Woodland Dr, Roseburg, OR 97471

    End of road privacy in a quiet setting, this great two-story ranch-style home offers an unparalleled lifestyle with breathtaking views of the renowned Abacela Vineyard! Imagine waking up every day to the gentle beauty of the surrounding landscape, where the flowing waters of Lookingglass Creek add to the peaceful ambiance. The property features creek frontage with coveted irrigation rights,

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471
  • /6

    $39,900

    • Land
    • 0.42 Acre
    • $95,000 per Acre

    0 NW Galaxy Dr, Winston, OR 97496

    Winston residential building lot. Fully developed street with nice homes. Cul-de-sac location. Covenants allow for stick built single-family or duplex.

    Benjamin Tatone Roseburg Homes Realty

    0 NW Galaxy Dr, Winston, OR 97496
  • /10

    $1,500,000

    • Land
    • 4.54 Acres
    • $330,396 per Acre

    140 NW Lost Ln, Winston, OR 97496

    2 Tax Lots (4.54 ac.) With collaborative effort of the City of Winston, this property has undergone the design process to include an 80 Unit multi-family apartment complex, detached garage structures on-site leasing office, Ramadas, swimming pool, sand volleyball pit and kids playground. In addition documents for a 20 unit short stay building are in process and nearly complete. Should you choose

    Beverly Heyer Safari Village Real Estate

    140 NW Lost Ln, Winston, OR 97496
  • /12

    $54,995

    • Land
    • 0.22 Acre
    • $249,977 per Acre

    2700 Brockway Rd, Winston, OR 97496

    End of road privacy and stunning views of the surrounding countryside, including gorgeous Abacela Winery and Vineyard! Build your dream home in the elegant Safari Estates on this larger 0.22 acres parcel. Surrounded by beautiful home and exceptional scenery and only minutes away to Wildlife Safari and downtown Winston! Easy freeway access with close proximity to hospitals and medical facilities

    David Platz The Neil Company Real Estate

    2700 Brockway Rd, Winston, OR 97496
  • /8

    $590,000

    • Land
    • 4.77 Acres
    • $123,690 per Acre

    350 View Point Terrace, Winston, OR 97496

    Excellent investment opportunity! 31 platted lots prime for development in the growth seeking city of Winston! This early 1980's subdivision is prominently located next to a newer construction community to strengthen the potential development value. Pacific Power just confirmed power is available! Call Winston city manager with all your building/development questions as he will accommodate all

    Michael Fischer Oregon Life Homes

    350 View Point Terrace, 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

Frequently Asked Questions Why Live in Winston

Is Winston a good place to live?
Winston is a good place to live. Winston is considered car-dependent and somewhat bikeable. Winston has 1 park for recreational activities. It has a median age of 43. The average household income is $66,222 which is below the national average. College graduates make up 13.7% of residents. A majority of residents in Winston are home owners, with 31.2% of residents renting and 68.8% of residents owning their home. A local real estate agent serving Winston can help you decide if this neighborhood is the right one for you. Learn more on our Winston neighborhood guide.
Is Winston, OR a safe neighborhood?
Winston, OR is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.
What are the best public schools in Winston?
The best public schools that serve Winston are:
What are the most popular zip codes in Winston, Winston, OR?
The most popular zip codes in Winston, Winston, OR include 97496, 97471, 97470, 97457 and 97416.
What are the most popular neighborhoods near Winston, Winston, OR?
The most popular neighborhoods near Winston, Winston, OR are Dillard, Green, Lookingglass, West Harvard and Hucrest.
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