Winston, OR Homes for Sale under $500,000

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

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

Welcome to 623 SE Garden Way Dr, Winston, OR, where modern style, comfort, and convenience come together in one beautifully maintained single-level home. Built in 2019, this 3-bedroom, 2-bath residence offers an inviting open-concept layout with soaring vaulted ceilings and durable luxury vinyl flooring throughout, creating a bright, stylish, and low-maintenance living space. The well-appointed

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

Well-kept 3-bedroom, 2-bath home on a large fully fenced lot with a versatile detached finished bonus space. The main home features custom kitchen cabinetry, a large farmhouse sink, LVP flooring through the main living areas, and carpet in the bedrooms. The living room opens to an expansive Trex deck overlooking the backyard, and the spacious primary suite includes a walk-in closet. The home's

Jennifer Cox RE/MAX Integrity

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

Welcome home to this spacious single level home in one of Winston's nicest neighborhoods! With great curb appeal, a sprawling tastefully landscaped yard, and no HOA, this property stands out in many ways. The open kitchen with abundant cabinetry is highlighted by beautiful Quartzite countertops, an island with eating bar, pullout shelves, a pantry, and all appliances are included. There is a gas

Rich Raynor Heritage Real Estate

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

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

Welcome home to this inviting 3-bedroom, 2-bath residence tucked away in a quiet neighborhood. The open-concept living area features vaulted ceilings, creating a bright and spacious feel that’s perfect for everyday living and entertaining. Step outside to enjoy the covered porch and fully fenced backyard, complete with a large connected deck—ideal for relaxing, gathering, or enjoying the

Dannielle Glines Neath The Wind Realty, Inc.

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

This remarkable home showcases incredible attention to detail throughout, offering a spacious and unique floor plan designed for both comfort and functionality. The large kitchen features an eating bar, granite countertops, new appliances, abundant cabinet storage, overhead and can lighting, and walk-in pantry. The dining room offers beautiful built-in storage, adding both character and

Shae Ellison Platinum Realty

Move right into this beautifully built 3-bedroom, 2-bathroom home offering 1,245 square feet of thoughtfully designed living space. Set on a spacious, fully fenced lot with mountain views, this like-new construction blends modern comfort with low-maintenance living. Step inside to an open-concept living area featuring rich luxury vinyl plank flooring and a ductless mini-split system for efficient

Jase Nielsen J Mann Realty

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

Bring an offer, VERY motivated seller. 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.

Aaron Stansbury Keller Williams Realty Eugene and Springfield

This home sits on an oversized lot with room for RV parking, extra vehicles, and all your toys. It includes a two-bay garage plus a separate one-car garage—ideal for storage, hobbies, or a workshop. Hardwood floors run throughout the home, giving the 2-bedroom, 1-bath layout timeless appeal and tons of potential. Outside, enjoy a spacious cement patio in the back and a fully fenced yard in front,

Janet Stringfellow Oregon Life Homes

Brand-new construction in the desirable Lookingglass Creek Estates subdivision! This functionally designed home features an open floor plan with high-end finishes throughout. Offering 3 bedrooms, 2 bathrooms, & 1770 sqft. The kitchen offers beautiful custom soft-close cabinets, quartz countertops, pantry, and waterproof luxury vinyl plank flooring. The spacious primary suite offers a walk-in

Jacob Gilman The Neil Company Real Estate

This beautifully maintained home is tucked away in a cul-de-sac in the heart of Winston, offering both privacy and convenience. With three comfortable bedrooms and two well-appointed bathrooms, the open-concept layout creates a welcoming atmosphere that’s ideal for hosting gatherings. The kitchen features a spacious island, perfect for preparing meals and entertaining guests. Vaulted ceilings in

Christina Esterbrook J Mann Realty

Custom home site on 50 acres. Adjacent to Abacela vineyard with incredible views of the countryside. Set in the Umpqua Valley AVA. Zoned Residential Medium Density. Do not access this property without authorization.

Mike Nichols MORE Realty

New Information - This beautiful property qualifies for a Template Dwelling. Once conditions have been met and the "Template Dwelling" has been approved, this permit will allow up to 11 yrs to develop and build a residence. Currently Farm Forest–zoned timber property offers both natural beauty and strong investment potential. A recent professional timber cruise, inventory, and valuation completed

Craig Warmouth Berkshire Hathaway HomeServices Real Estate Professionals

JUST REDUCED!! This 3 Bedroom/1 Bath, family home on over 1/3-acre has been completely updated for your enjoyment. There are many new items, including roof, mini split system, LVP flooring throughout, interior and exterior paint, plumbing and outside waterline. The bathroom/laundry room has been completely renovated. The yards are fully fenced, and there is a nice large deck on the back

Debra Moore Currieco Real Estate

Nestled in the highly desired Lookingglass Creek Estates Subdivision in Winston. This brand-new home provides exceptional design and craftsmanship, with a popular floor plan that ensures comfort and style. The heart of this home, the kitchen, is adorned with quartz countertops & custom cabinets that extend to the bathrooms, adding elegance and durability. The property comes with the added

Jacob Gilman The Neil Company Real Estate

Wonderful little cottage for the first time home buyer or the investor needing one more rental in there portfolio. This home is located on a double lot. Per city of Winston, lot is dividable. Build an additional house on its own lot, or leave it as-is and build an ADU or shop in your backyard. Come check this out and make your appointment today.

Angel Smith Trueblood Real Estate