Winston, OR Homes for Sale

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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

  

  Kristina Scott

  Umpqua Legacy Realty LLC

  9114 Old Highway 99 S, Winston, OR 97496
• Explore Winston

• 

  

  

  /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

  

  Ashton Faas

  Faas Realty

  

  0 Wil Way Unit 24278136, Winston, OR 97496
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  /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

  

  Ashton Faas

  Faas Realty

  

  0 Wil Way Unit 24292479, Winston, OR 97496
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  /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

  

  Ashton Faas

  Faas Realty

  

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

  

  Tyler Head

  Turning Point Realty Group

  

  150 Wil Way, Winston, OR 97496
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  /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

  

  Tyler Head

  Turning Point Realty Group

  

  2581 NW Brockway Rd, Winston, OR 97496
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  /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

  

  Tyler Head

  Turning Point Realty Group

  

  160 Wil Way, Winston, OR 97496
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  /48

  $439,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft

  260 SE Logan St, Winston, OR 97496

  *** BUILDER INCENTIVE *** Lower Payments Available on this House! Seller offering flexible buyer incentives with acceptable offer, including potential rate buy down, closing cost assistance, or improvement credits. Attractive opportunity for both financed and cash buyers.*** There’s something special about stepping into a home that’s never been lived in—where everything is fresh, thoughtfully

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  260 SE Logan St, Winston, OR 97496
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  /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
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  /48

  $409,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft

  265 SE Logan St, Winston, OR 97496

  Welcome to Rolling Meadows Estates, Winston's newest neighborhood community where quality craftsmanship, modern design, and Southern Oregon lifestyle come together. Surrounded by attractive newer homes and a growing sense of community, this is an opportunity to enjoy the benefits of new construction in one of Winston's most exciting new developments.Built by Premier Home Construction, a respected

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  265 SE Logan St, Winston, OR 97496
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  /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
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  /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
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  /27

  $259,000

  • 2 Beds
  • 1 Bath
  • 939 Sq Ft

  71 SE Ronald St, Winston, OR 97496

  Charming remodeled cottage-style home situated on a large quarter acre lot offering comfortable single-level living. This updated residence features new interior paint, newer roof and siding, and thoughtful modern upgrades throughout. The kitchen includes stainless steel appliances, adding a sleek and functional touch to the heart of the home. Enjoy a bright and inviting layout with practical

  Joshua Glaspie ICON Real Estate Group

  

  71 SE Ronald St, Winston, OR 97496
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  /39

  $190,000

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  0 Rice Creek Rd, Winston, OR 97496

  Escape to your own off-grid retreat on a 20-acre shared property in a gated community with coded access. This is a unique property on jointly owned lot, in an off grid community. Seller is selling 50% share in 20 acre lot. Land use agreement in place. This beautifully crafted 1,000 SF cabin showcases exceptional handcrafted woodwork and rustic charm throughout. Features include 1 bedroom plus a

  Starlight Turner Starlight Realty

  

  0 Rice Creek Rd, Winston, OR 97496
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  /10

  $235,000

  • Land
  • 42,253 Sq Ft
  • $242,268 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
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  /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
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  /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
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  /2

  $249,000

  • Land
  • 27.31 Acres
  • $9,118 per Acre

  0 E Willis Creek Rd, Winston, OR 97496

  27.31 acres offering the opportunity to build your dream home either atop the property with expansive views or tucked into the peaceful valley below. City water is available, and additional utilities are accessible via a recorded easement. Boundary lines shown in photos are approximate; buyers to perform their own due diligence regarding property lines, buildability, utilities, and intended use.

  Tim Rist DORE

  

  0 E Willis Creek Rd, Winston, OR 97496
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  /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
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  /6

  $485,000

  • 3 Beds
  • 3 Baths

  51 SW Brantley Dr, Winston, OR 97496

  INVESTMENT PROPERTY OPPORTUNITY! Well-maintained 4-unit apartment building located in a quiet, centrally located neighborhood. This property features a desirable unit mix with two spacious 2-bedroom, 2-bath units and two comfortable 1-bedroom, 1-bath units, offering strong rental appeal for a variety of tenants. Conveniently situated close to schools, shopping, dining, and local amenities, with

  Vera-Anne Wallace Vera-Anne International Real Estate

  

  51 SW Brantley Dr, Winston, OR 97496
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
• 

  

  /24

  $85,000

  • 2 Beds
  • 2 Baths
  • 1,188 Sq Ft

  205 Twin Oaks Loop, Winston, OR 97496

  Tucked away at the back of Twin Oaks 55+ Park, this cozy and well-cared-for home offers a little extra peace and privacy. The yard is easy to keep up with, the carport has plenty of room, and inside you’ll find vaulted ceilings throughout that make the space feel open and comfortable. County records show 2 bedrooms, but the home lives as a 3-bedroom, giving you nice flexibility for guests,

  Jennifer Cox RE/MAX Integrity

  

  205 Twin Oaks Loop, Winston, OR 97496
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  /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
• 

  

  /23

  $550,000

  • 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
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  /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

  $70,000

  $30K 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
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  /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
• 

  

  /48

  $409,000

  Open House 8/02

  • 3 Beds
  • 2.5 Baths
  • 1,761 Sq Ft

  600 SE Parkway Dr, Winston, OR 97496

  Immaculate, move-in ready 3-bedroom, 2.5-bath home in one of Winston's premier neighborhoods, just minutes from Wildlife Safari and Roseburg! This beautifully updated home features an open-concept floor plan with a spacious vaulted living room, rich wood flooring, abundant natural light, and a sliding glass door leading to the private backyard retreat. The well-appointed kitchen offers a gas

  Julie Bancroft The Neil Company Real Estate

  

  600 SE Parkway 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
• 

  

  /30

  $260,000

  • 2 Beds
  • 1 Bath
  • 1,070 Sq Ft

  3707 Willis Creek Rd, Winston, OR 97496

  Rare rural opportunity priced at land and utility value — for the investor, builder, or country-living dreamer ready to create something truly their own in the hills of Douglas County, Oregon. Utilities are already in place — a significant head start on any rural build. The property is served by Pacific Power electric and Winston City Water (public water), with an on-site septic system. Septic

  Michelle Kohlhoff Sundance Realty LLC

  

  3707 Willis Creek 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

  $280,000

  • 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

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 $372,493.

Are home prices dropping in Winston?

Yes, home prices in Winston are down 3% in the last 12 months.

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

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

Is Winston, OR a safe city?

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

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

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

What are the most popular neighborhoods in Winston, OR?

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

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

The median home price in Winston is $364,900. If you put a 20% down payment of $73,000 and had a 30-year fixed mortgage with an interest rate of 6.43%, 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.

How are the schools in Winston, OR?

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

Home Prices in Winston, OR

The median home sale price in Winston, OR is $319,000, down 8% year-over-year. Homes in Winston sell in 86 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price $319,000	Median Single Family Sale Price $353,400
Median 2 Bedroom Sale Price $222,500	Median 1 Bedroom Sale Price $148,000
Average Price Per Sq Ft $230	Number of Homes for Sale 23
Last 12 months Home Sales 66	Months of Supply 4.20
Median List Price $364,900	Median Change From 1st List Price 3%
Median Home Sale Price YoY Change -8%