32

Winston, OR Homes for Sale with Garage

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  • /83

    $735,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,722 Sq Ft

    9114 Old Highway 99 S, Winston, OR 97496

    Escape to the peace and beauty of rural Oregon with this beautifully remodeled country retreat set on 5.4 usable acres of fenced pastureland. Offering the perfect blend of modern comfort and small-acreage functionality, this stunning single-level home features 2,722 sq. ft. with 3 bedrooms, 3 full baths, and a versatile flex space ideal for a home office or hobby room. Each bedroom includes its

    Agent Photo

    Kristina Scott

    Umpqua Legacy Realty LLC

    9114 Old Highway 99 S, Winston, OR 97496
  • /45

    $525,000

    • 3 Beds
    • 2 Baths
    • 4,024 Sq Ft

    2620 Brockway Rd, Winston, OR 97496

    Beautiful Craftsman-style home with fantastic curb appeal and a slate-tile covered front porch. This spacious 3-bedroom plus office home offers 1,752 square feet of finished living space, along with a full 2,272-square-foot unfinished walkout basement.The main level features a large open kitchen with gas cooking, an island, granite countertops, pantry, stainless steel appliances, and a hammered

    Agent Photo

    Tyler Head

    Turning Point Realty Group

    2620 Brockway Rd, Winston, OR 97496
  • /41

    $499,900

    New Construction $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

    160 Wil Way, Winston, OR 97496
  • /40

    $499,900

    New Construction $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

    150 Wil Way, Winston, OR 97496
  • /44

    $499,900

    New Construction
    • 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

    2581 NW 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
  • /48

    $375,000

    $10K PRICE DROP
    • 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
  • /10

    $199,000

    $36K PRICE DROP
    • Land
    • 42,253 Sq Ft
    • $205,155 per Acre

    740 Ireland Rd, Winston, OR 97496

    Peaceful Country Escape with Endless Potential! Just minutes from Winston, about 75 miles to the coast and close to Ben Irving Reservoir Area. Embrace the quiet country lifestyle on this beautiful 0.97-acre parcel, offering the perfect blend of rural tranquility and functional utility. Framed by gorgeous, views of the surrounding woods and mountains, this property is a blank canvas ready for your

    Cynthia Beach The Neil Company Real Estate

    740 Ireland Rd, Winston, OR 97496
  • /46

    $509,999

    • 4 Beds
    • 2 Baths
    • 2,091 Sq Ft

    330 Wil Way, Winston, OR 97496

    Custom-built in 2014 and thoughtfully designed by the owner, this 2,091 SF ranch style home offers 4 bedrooms and 2 full bathrooms on a spacious corner lot. The inviting great room showcases vaulted ceilings, abundant natural light, and a stunning floor-to-ceiling stone fireplace that serves as the centerpiece of the home. The open-concept kitchen features stainless steel appliances, including a

    Shea Martin United Real Estate Properties

    330 Wil Way, Winston, OR 97496
  • /17

    $315,000

    Pre-Foreclosure
    • 3 Beds
    • 2 Baths
    • 1,594 Sq Ft

    340 NW Elizabeth Ave, Winston, OR 97496

    This 3-bedroom, 2-bath home offers a functional layout with plenty of potential for its next owner. A few minor repairs will help unlock its full charm, making it an excellent opportunity for buyers looking to personalize a home without taking on a major renovation. Conveniently located in Winston near everyday amenities, this property is ready for its next chapter.

    Tiffanie Frasier Keller Williams Southern Oregon-Umpqua Valley

    340 NW Elizabeth Ave, Winston, OR 97496
  • /48

    $469,900

    $19K PRICE DROP
    • 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
  • /48

    $699,000

    $26K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,362 Sq Ft

    1068 Rice Creek Rd, Winston, OR 97496

    Security gated 8.52-acre property! This beautiful ranch-style home features, updates, paved driveway, newer roof, interior & exterior paint, gourmet kitchen, double ovens, large walk-in pantry, lots of outdoor light, large living room with a cozy fireplace, great views, huge primary bedroom with a walk-in closet and bathroom with 2-headed shower, 4th bedroom could easily be used as an office, new

    Joan Smith The Neil Company Real Estate

    1068 Rice Creek Rd, Winston, OR 97496
  • /15

    $215,000

    $24K 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
  • /31

    $98,000

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft

    190 Twin Oaks Loop, Winston, OR 97496

    Welcome to this cozy 3-bedroom, 2-bathroom home located in the sought-after Twin Oaks Mobile Park Estates. Situated in a quiet and well-maintained 55+ community in Winston, Oregon, this charming property offers the perfect blend of comfort and conveniences. This home features a spacious, functional open floor plan. The living room flows seamlessly into a modern kitchen, which comes complete with

    Kimberley Ferguson eXp Realty, LLC

    190 Twin Oaks Loop, Winston, OR 97496
  • /35

    $160,000

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    105 Stephanie Ct, Winston, OR 97496

    Welcome home to this well-maintained single-level home offering comfort, convenience, and an inviting open-concept design. The spacious living area flows seamlessly into a beautifully appointed kitchen featuring abundant cabinet storage, a pantry, stainless steel appliances, and a large island perfect for meal prep, casual dining, or gathering with family and friends.Luxury vinyl plank flooring

    Tammi Ellison eXp Realty, LLC

    105 Stephanie Ct, Winston, OR 97496
  • /41

    $775,000

    $95K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,000 Sq Ft

    375 Porter Creek Rd, Winston, OR 97496

    Significant priced improvement! Discover the perfect blend of vineyard lifestyle and modern comfort in this recently 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

    Lorrie Normann Triple Oaks Realty LLC

    375 Porter Creek Rd, Winston, OR 97496
  • /30

    $205,000

    • 2 Beds
    • 1 Bath
    • 1,323 Sq Ft

    381 SE Gregory Dr, Winston, OR 97496

    Incredible and rare opportunity in Winston, Oregon! Developers, investors, and visionaries take notice. This charming 1940s 2-bedroom, 1-bath home is full of character and ready for its next chapter. With a little vision and elbow grease, this property offers endless possibilities.Situated on a spacious, level lot with mature greenery, the property presents potential for future development,

    Shae Ellison Platinum Realty

    381 SE Gregory Dr, 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
  • /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
  • /21

    $525,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    572 Dillard Gardens Rd, Winston, OR 97496

    Charming farmhouse on the South Umpqua River. Features a 1,440 sf home on 6.9 acres. The 2 bedroom 2 bathroom interior has wood floors, good natural light, a cozy living room, an open kitchen and dining area, a large primary bedroom with an attached bath and walk in closet. Multi-use laundry room. Covered deck opens to the patio and yard filled with flowers and shade trees. New septic system

    Mike Nichols MORE Realty, Inc.

    572 Dillard Gardens Rd, 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
  • /43

    $99,000

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

    180 Twin Oaks Loop, Winston, OR 97496

    Affordable living in the 55+ Twin Oaks community! This 3-bedroom, 2-bath double-wide offers a comfortable split-bedroom floor plan, updated flooring, and plenty of space to make your own. A front ramp provides easy access. Space rent is approximately $725 per month and includes water, sewer, and garbage. Conveniently located near shopping, dining, parks, and Wildlife Safari. Park approval and

    Anthony Beckham Different Better Real Estate

    180 Twin Oaks Loop, Winston, OR 97496
  • /16

    $380,000

    $119K PRICE DROP Pre-Foreclosure
    • 4 Beds
    • 3 Baths
    • 2,270 Sq Ft

    150 SW Brantley Dr, Winston, OR 97496

    Spacious Tri-Level Home on 1 Acre with Dual Garages, Fruit Trees & Outdoor Living Welcome to this beautifully maintained tri-level home offering 4 bedrooms, a bonus room, 3 full bathrooms, and multiple living spaces designed for comfort and flexibility.The upper level features 3 bedrooms and 2 bathrooms, while the lower level includes a private 4th bedroom and full bathroom, perfect for guests,

    Kayla Knight Trueblood Real Estate

    150 SW Brantley Dr, Winston, OR 97496
  • /23

    $389,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    10 SW Peach Ln, Winston, OR 97496

    Welcome to 10 SW Peach Ln, where every day feels like a peaceful retreat and every corner invites you to slow down and savor the moment. This special property blends warmth, character, and an unforgettable backyard oasis designed to elevate your everyday living.Step outside and imagine hosting summer gatherings on the resort-style brick patio, unwinding beside the soothing sounds of your private

    Kimberly Krebs Stellar Realty Northwest

    10 SW Peach Ln, Winston, OR 97496
  • /46

    $1,100,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,720 Sq Ft

    6700 Upper Olalla Rd, Winston, OR 97496

    Stunning custom cedar home on 5 level acres offering the perfect blend of luxury, functionality, and country living. This Lindal-style home features a spacious 2,400 sq ft shop with a full bath, dual garage doors, and enough space for a 40-foot motorhome. Property also includes 3 RV hookups with power, water, and RV dump access, ideal for guests, multi-use living, or recreational storage.The

    Dan Gandee Real Broker

    6700 Upper Olalla Rd, Winston, OR 97496
  • /41

    $169,900

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    600 SE Edgewood St, Winston, OR 97496

    WOW! Affordable 2-bedroom 1-bath home set on nearly half an acre in the heart of Winston. With 0.43 acres of usable ground, a fully fenced yard, mature shade trees, and room for RVs, trailers, boats, equipment, gardens, and outdoor projects, or possible future development, there's plenty of flexibility here! Inside features an open living area with updated laminate flooring, abundant natural

    Anthony Beckham Different Better Real Estate

    600 SE Edgewood St, 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
  • /32

    $275,000

    Open Sun 1PM - 3PM $5K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    509 NW Elwood Dr, Winston, OR 97496

    This adorable 3-bedroom, 1-bathroom home is the perfect starter home or an excellent addition to your investment portfolio. The kitchen was remodeled earlier this year. Conveniently located close to an elementary school, shopping, and everyday amenities, this home combines comfort with convenience. Whether you’re a first-time homebuyer, looking to downsize, or searching for a rental property,

    Jada Whited Oregon Life Homes

    509 NW Elwood Dr, Winston, OR 97496
  • /48

    $634,900

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

    635 Wil Way, Winston, OR 97496

    WOW! Panoramic valley views, over 20 acres of RM-zoned land, and a location bordering Wildlife Safari make this 4-bedroom, 3.5-bath, 3,072 SF home one of Southern Oregon’s most unique offerings. Positioned at the end of the road, it enjoys exceptional privacy while overlooking Abacela Vineyards, rolling valleys, and Wildlife Safari, with potential for 360-degree views. RM zoning adds rare

    Anthony Beckham Different Better Real Estate

    635 Wil Way, Winston, OR 97496
  • /48

    $1,199,900

    • 3 Beds
    • 2.5 Baths
    • 2,856 Sq Ft

    1349 Willis Creek Rd, Winston, OR 97496

    Quiet country living on private acreage! Offered for the first time ever, this exceptional estate presents a rare opportunity to own a truly special piece of the Pacific Northwest. Featuring two separate residences, this property is perfectly suited for multi-generational living, guest accommodations, or potential rental income. The primary home offers over 2,800 square feet of inviting living

    Jordan Anderson The Anderson Agency

    1349 Willis Creek Rd, Winston, OR 97496
  • /45

    $775,000

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

    375 Porter Creek Rd, Winston, OR 97496

    Significant priced improvement! Discover the perfect blend of vineyard lifestyle and modern comfort in this recently 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. A spacious 3,000 sq ft home featuring four large bedrooms, large

    Lorrie Normann Triple Oaks Realty LLC

    375 Porter Creek Rd, Winston, OR 97496
  • /44

    $685,000

    $34K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    411 Woodland Dr, Roseburg, OR 97471

    What if your favorite getaway was home?Set above Lookingglass Creek with stunning views of Abacela Vineyard, this property offers the kind of lifestyle that's getting harder to find. Spend summer afternoons at your own swimming hole, grow fresh produce in the fenced garden and greenhouse, and enjoy the satisfaction of having water rights, irrigation, a K-line system, and pump already in place.The

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471

Home Price Trends

Median Sale Price
$316,000
Median Single Family Sale Price
$325,000
Median 2 Bedroom Sale Price
$205,000
Median 1 Bedroom Sale Price
$148,000
Average Price Per Sq Ft
$228
Number of Homes for Sale
20
Last 12 months Home Sales
66
Months of Supply
3.60
Median List Price
$359,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-8%
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