Winston, OR Homes for Sale

• 

  

  

  /82

  $785,000

  • 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

  (458) 310-3863

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

• 

  

  

  /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

  (458) 310-3411

  

  0 Wil Way Unit 24094727, Winston, OR 97496
• 

  

  

  /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

  (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

  

  Ashton Faas

  Faas Realty

  (458) 217-1693

  

  0 Wil Way Unit 24292479, 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

  

  Tyler Head

  Turning Point Realty Group

  (458) 299-7413

  

  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,

  

  Tyler Head

  Turning Point Realty Group

  (458) 309-4957

  

  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

  

  Tyler Head

  Turning Point Realty Group

  (458) 291-0968

  

  2581 NW Brockway Rd, 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
• 

  

  /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
• 

  

  /48

  $439,900

  New Construction

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

  260 SE Logan St, Winston, OR 97496

  *** 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 designed, and ready for

  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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /30

  $149,900

  • Land
  • 5 Acres
  • $29,980 per Acre

  596 Raleigh Dr, Winston, OR 97496

  WOW! This level 5-acre property offers usable land, West Willis Creek frontage, a classic red barn, existing utilities, and a peaceful rural setting surrounded by hobby farms and open countryside! The manufactured home currently on the property serves as a placeholder while you design and build your dream home. Many of the hard-to-find improvements are already in place, including a well, a

  Anthony Beckham Different Better Real Estate

  

  596 Raleigh Dr, Winston, OR 97496
• 

  

  /48

  $725,000

  • 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

  $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
• 

  /2

  Call for Price

  • Land
  • 160 Acres

  0 Diamond Rock Rd Unit 727456026, Winston, OR 97496

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

  John Rosenthal Realty Marketing / Northwest

  

  0 Diamond Rock Rd Unit 727456026, Winston, OR 97496
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /10

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  572 Dillard Gardens Rd, Winston, OR 97496

  Charming property on the South Umpqua River features a 1,440 sf home set on 6.9 acres. The 2-bed 2-bath interior includes wood floors, an open living room with a fireplace insert, an open kitchen, large primary bedroom with an ensuite bath, laundry room and covered deck. Back patio and yard area is peaceful and quiet with flowers and shade trees. New septic system was installed in 2021. Detached

  Mike Nichols MORE Realty, Inc.

  

  572 Dillard Gardens Rd, Winston, OR 97496
• 

  

  /32

  $530,000

  $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
• 

  

  /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
• 

  

  /46

  $1,100,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,720 Sq Ft

  6700 Upper Olalla Rd, Winston, OR 97496

  Exquisite Lindal Custom Cedar home on 5 flat acres featuring a 2,400 sq ft shop with full bath, dual doors, and room for a 40’ motorhome, plus 3 RV hookups (2 across the driveway) with power, water, and RV dump by the shop. The gourmet kitchen is a chef’s dream with granite counters, dual sinks, pot filler, gas range with warming drawer, double ovens, hidden butcher block, and abundant storage,

  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
• 

  

  /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
• 

  

  /4

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  0 Berry Creek Rd, Winston, OR 97496

  This private, level 4-acre parcel offers convenient access to Ben Irving Reservoir and is the perfect setting for recreation, relaxation, or a future getaway retreat. The property features a large natural meadow surrounded by 20-year-old Douglas fir reprod, creating a peaceful and secluded atmosphere. Adjacent to BLM land, it provides direct access to endless outdoor opportunities. Improvements

  Ryan Fox Berkshire Hathaway HomeServices Real Estate Professionals

  

  0 Berry Creek Rd, 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
• 

  

  /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
• 

  

  /48

  $454,000

  • 2 Beds
  • 1 Bath
  • 2,056 Sq Ft

  0 Rice Creek Rd, Winston, OR 97496

  100% off-grid living on your own 20-acre slice of paradise! Located within "The Ranch" - a close-knit homesteading community of like-minded landowners who each steward their own property while embracing a shared off-grid lifestyle. Just 25 minutes southwest of Winston, Oregon, this property is accessed via a gated 4-mile gravel road through BLM and private timberlands. The resilient home features

  Aaron Cherry Oregon Life Homes

  

  0 Rice Creek Rd, Winston, OR 97496
• 

  

  /35

  $475,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  800 Byron Creek Rd, Winston, OR 97496

  Welcome to this charming country home set on over 5 acres of flat, usable land with Firewise Certification for peace of mind. The well maintained 3 bedroom with 1.5 bathrooms. Home is move-in ready, some of the furniture can be included with the right offer. House has a heat pump, pellet stove, generator, flooring- all done in last 4 years. The propane 22k generator automatically powers the home

  Rebekah Sexauer eXp Realty, LLC

  

  800 Byron Creek Rd, 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 $370,748.

Are home prices dropping in Winston?

Yes, home prices in Winston are down 2% in the last 12 months.

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

65 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, 97457, 97470 and 97469.

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 $359,900. If you put a 20% down payment of $72,000 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $1,820 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 $321,000, down 7% year-over-year. Homes in Winston sell in 84 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price $321,000	Median Single Family Sale Price $344,000
Median 2 Bedroom Sale Price $205,000	Median 1 Bedroom Sale Price $148,000
Average Price Per Sq Ft $230	Number of Homes for Sale 19
Last 12 months Home Sales 65	Months of Supply 3.50
Median List Price $359,900	Median Change From 1st List Price 3%
Median Home Sale Price YoY Change -7%