Winston, OR Homes for Sale under $500,000

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

This rare riverfront horse property on the South Umpqua River is not to be missed! The home features a brand new 600 sq. ft. deck overlooking the property and river, new roof,a centrally located wood stove that heats the entire house, and is tucked away off the road for privacy. Horse facilities include an arena, barn, multiple stalls, and pasture. Additional amenities include an orchard,

Nancy Kruger Keller Williams Southern Oregon-Umpqua Valley

Exceptional Farm Forest–zoned timber property offers both natural beauty and strong investment potential. A recent professional timber cruise, inventory, and valuation completed by Resource Management Services highlights the value of this well-managed stand. Timber prices fluctuate but as of March, the net timber value is estimated at $174,749, consisting primarily of healthy, marketable Doug

Craig Warmouth Berkshire Hathaway HomeServices Real Estate Professionals