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Winston Homes for Sale

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  • /15

    $185,000

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

    0 Wil Way Unit 24278136, Winston, OR 97496

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

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 224-5797

    0 Wil Way Unit 24278136, Winston, OR 97496
  • /15

    $185,000

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

    0 Wil Way Unit 24292479, Winston, OR 97496

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

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 217-1693

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

    $350,000

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

    0 Wil Way Unit 24094727, Winston, OR 97496

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

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 310-3411

    0 Wil Way Unit 24094727, Winston, OR 97496
  • /40

    $499,900

    New Construction Open Sat 2PM - 5PM $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,999 Sq Ft

    150 Wil Way, Winston, OR 97496

    Open House 5/30 2-5 pm New Home by JW Construction Inc. This beautifully crafted 2,143 sq ft home offers 3 bedrooms and 2 1/2 bathrooms with a thoughtful layout and excellent separation of space. Set on a low-maintenance lot with views of trees and the surrounding mountains, 140 Wil Way combines modern design with comfort and convenience. The open-concept main level features high ceilings,

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    (458) 309-4957

    150 Wil Way, Winston, OR 97496
  • /44

    $499,900

    New Construction Open Sat 2PM - 5PM
    • 3 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    2581 NW Brockway Rd, Winston, OR 97496

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

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    (458) 291-0968

    2581 NW Brockway Rd, Winston, OR 97496
  • /41

    $499,900

    New Construction Open Sat 2PM - 5PM $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    160 Wil Way, Winston, OR 97496

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

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    (458) 299-7413

    160 Wil Way, Winston, OR 97496
  • /48

    $385,000

    Open Sun 2PM - 4PM
    • 3 Beds
    • 2 Baths
    • 1,613 Sq Ft

    186 Woodduck St, Winston, OR 97496

    Well-maintained home in a quiet neighborhood in the heart of Winston. Move-in ready with brand new floors recently installed. Minimal outdoor maintenance. Garden shed and room to park a 5th wheel. Don’t miss your opportunity to own a solid, easy-living home in a great location.

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    186 Woodduck St, Winston, OR 97496
  • /48

    $439,900

    New Construction
    • 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
  • /36

    $409,000

    $30K PRICE DROP
    • 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
  • /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

    $489,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,928 Sq Ft

    263 Wil Way, Winston, OR 97496

    Welcome to Your Like-New Custom Home in Winston, Oregon!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality craftsmanship and thoughtful design are evident in every detail. The open-concept floor plan features soaring vaulted ceilings, beautiful flooring, and a warm, inviting layout that flows effortlessly for both everyday living and entertaining.At the

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    263 Wil Way, Winston, OR 97496
  • /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
  • /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
  • /32

    $530,000

    Open Sat 1PM - 3PM $79K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,660 Sq Ft

    102 Sarah Bear Ln, Winston, OR 97496

    Meticulous quality 4 br 3 bath 2660 sq ft home, with real hard wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, spacious gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance front yard, covered patio. The gourmet kitchen has

    Valynn Currie Currieco Real Estate

    102 Sarah Bear Ln, Winston, OR 97496
  • /42

    $549,900

    $99K PRICE DROP
    • 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
  • /44

    $699,500

    $20K PRICE DROP
    • 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
  • /15

    $229,000

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

    90 SE Darrell Ave, Winston, OR 97496

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

    Rebekah Sexauer eXp Realty, LLC

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

    $312,000

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

    0 NW Brockway Rd, Winston, OR 97496

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

    Cynthia Beach The Neil Company Real Estate

    0 NW Brockway Rd, Winston, OR 97496
  • /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

    $165,000

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

    101 NE Darrell Ave, Winston, OR 97496

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

    Nancy Wood Oregon Life Homes

    101 NE Darrell Ave, Winston, OR 97496
  • /34

    $355,000

    $4K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,710 Sq Ft

    380 NW Cary St, Winston, OR 97496

    Schedule your private tour today of this adorable 4bd 2ba open floor plan home, located on a generous lot, with an extra deep garage and additional off-street parking for your RV or Boat. Just a 15-minute drive to Roseburg, close to local schools and just down the street from the Wildlife Safari.

    Willow Pearson Oregon Life Homes

    380 NW Cary St, Winston, OR 97496
  • /39

    $290,000

    • 4 Beds
    • 2 Baths
    • 1,782 Sq Ft

    70 SE Darrell Ave, Winston, OR 97496

    Stunning newly remodeled manufactured home tucked away in a private neighborhood in Winston! This spacious 4 bed, 2 bath home features a desirable split floor plan with vaulted ceilings and bright natural light throughout.Completely updated from top to bottom with new flooring, fresh interior and exterior paint, new windows, doors, carpet, and a brand-new roof. The main bathroom has been

    Shae Ellison Platinum Realty

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

    $179,000

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

    1580 Winston Section Rd, Winston, OR 97496

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

    Cynthia Beach The Neil Company Real Estate

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

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,348 Sq Ft

    101 SW Peach Ln, Winston, OR 97496

    This single-level home features 3 bedrooms and 1 bathroom, offering comfortable and convenient living. Step outside to a spacious, fully fenced backyard perfect for pets, play or entertaining. Garden enthusiasts will appreciate the dedicated garden area, while multiple tool sheds provide ample storage for tools, equipment and hobbies. A large covered real patio creates an ideal space for

    Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

    101 SW Peach Ln, Winston, OR 97496
  • /23

    $90,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    124 Country Side Ln, Winston, OR 97496

    Welcome home to this charming home located in a beautifully maintained 55+ community! With 3 bedrooms, 2 baths, and 1,296 sq. ft. of inviting living space, this home features vaulted ceilings, a bright open layout, and a manicured corner lot. The walk-through kitchen includes a breakfast bar, built-in microwave, stove, refrigerator, and a brand-new dishwasher. The spacious primary suite offers

    Jason Mann J Mann Realty

    124 Country Side Ln, Winston, OR 97496
  • /17

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft

    165 Collins Rd, Winston, OR 97496

    Single-level home in Creekside Meadows, built in 2018 with granite counters, open floor plan, and no-step entry. Fenced backyard with front and rear irrigation, 2-car attached garage, central air. Public water and sewer. Conveniently located near Douglas High and Brockway Elementary.

    Jerry Norman Oregon Life Homes

    165 Collins Rd, Winston, OR 97496
  • /25

    $318,000

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

    340 SE Darrell Ave, Winston, OR 97496

    Solid 3-bedroom, single-level home with a functional layout, attached garage, and fully fenced yard with covered patio, and front porch.The home features a ductless heat pump for efficient heating and cooling, along with comfortable interior living spaces. Roof replaced within the last few years. Primary bedroom includes a walk-in closet and crown molding. The terraced backyard includes fruit

    Aaron Stansbury Keller Williams Realty Eugene and Springfield

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

    $265,000

    $5K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 1,224 Sq Ft

    66 NW Cary St, Winston, OR 97496

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

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

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

    $29,900

    • 2 Beds
    • 1 Bath
    • 1,022 Sq Ft

    228 Estate Loop, Winston, OR 97496

    2 bed, 1 bath home in a desirable 55+ park featuring spacious living areas and a well-appointed kitchen with breakfast bar. Attached dining area includes built-ins for added storage and charm. Separate laundry room, plus a bathroom with walk-in shower for convenience. Outside features include covered porch, carport with attached storage area. Located close to shopping, dining, and other amenities.

    Jason Mann J Mann Realty

    228 Estate Loop, Winston, OR 97496
  • /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

    $10K PRICE DROP
    • 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
    • 19,602 Sq Ft
    • $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
  • /19

    $72,000

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    235 Twin Oaks Loop, Winston, OR 97496

    Cozy residence that's located in the 55+ Winston Twin Oaks Mobile Estates community! This manufactured double-wide home offers three bedrooms and 2 baths, with features including a spacious primary bedroom and bath, large living room, dining area, kitchen with appliances, laundry room, and a carport with shed. Space rent includes water, sewer, and garbage, for $725 a month (there is an

    Kimberly Krebs Stellar Realty Northwest

    235 Twin Oaks Loop, 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

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 with some transit options. Winston is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. 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 2 out of 10.
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 6.53%, your estimated principal and interest payment would be $1,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $78K a year to afford the median home price in Winston. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winston is $66K.
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, 97457, 97470 and 97469.
What are the most popular neighborhoods near Winston, Winston, OR?
The most popular neighborhoods near Winston, Winston, OR are Dillard, Green, West Harvard, Hucrest and Melrose.
Are home prices dropping in Winston?
Yes, home prices in Winston are down 4% in the last 12 months.

Home Trends in Winston, OR

Housing Trends

Median Sale Price
$321,000
Median Single Family Sale Price
$344,000
Average Price Per Sq Ft
$230
Number of Homes for Sale
16
Last 12 months Home Sales
65
Months of Supply
3.00
Median List Price
$359,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-7%
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