Winchester, OR 2-Story Homes for Sale

Welcome to 1381 Echo Drive in one of the Umpqua Valley's most desirable neighborhoods, celebrated for its custom-built homes near the North Umpqua River and serene natural surroundings. Situated on 5 level acres, this spacious 5-bedroom, 3-bath home offers over 3,500 square feet of finished living space plus a semi-finished bonus / rec space. Step inside to a thoughtfully designed floor plan

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

Welcome to 2744 NW Daysha Dr, Roseburg, OR! This stunning and spacious 4-bedroom, 2.5-bathroom home perfectly combines modern style, comfort, and functionality, all situated in a highly desirable neighborhood. Located just minutes away from shopping centers, medical facilities, and the movie theater. This property offers an ideal lifestyle for families and professionals alike. The exterior of the

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

Meticulously Maintained Home in Prestigious Rocky Ridge.Step into this beautifully cared-for 3-bedroom, 2-bathroom home offering 2,294 square feet of comfortable living space, thoughtfully designed to suit every lifestyle. Inside, you are greeted with the gorgeous hardwood floors leading to the vaulted living room featuring built-in shelves and French doors that open to the covered patio.

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

Entertainer’s Dream with Spectacular Umpqua Valley ViewsWelcome to this stunning custom home, designed for luxurious living and effortless entertaining. From the moment you step through the grand entry with its gleaming marble tile floors and elegant tray ceiling, you'll be captivated by the attention to detail and quality craftsmanship throughout.Enjoy sweeping views of the Umpqua Valley and

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

Welcome to this stunning property featuring a spacious Casabella kitchen, complete with modern finishes and plenty of storage space for all your culinary needs. The home boasts beautiful engineered hardwood floors throughout, providing a warm and inviting atmosphere. Enjoy breathtaking views of the Callahan Mountains from the comfort of your home, with the added bonus of a fenced and cross-fenced

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

North Umpqua Riverfront Living – Rare Legacy Property with Private Beach. A rare opportunity to own an irreplaceable slice of Oregon paradise. Nestled on over an acre of manicured grounds with private river access, this custom cedar home is more than a residence—it’s a sanctuary for the soul. Tucked away in the desirable Fisher Road area of Roseburg, this custom-built cedar home offers peace,

Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

Welcome to this beautiful 4-bedroom, 2.5-bath home located in a peaceful cul-de-sac with breathtaking views. Enjoy formal living and dining rooms, a spacious kitchen with a center island, and a versatile bonus room perfect for a home office, gym, or playroom. The primary suite offers comfort and privacy, while the additional bedrooms provide plenty of space for family or guests. Step outside to a

Karissa Pangelina Keller Williams Southern Oregon-Umpqua Valley

Cruise down scenic North Bank Road to this beautifully remodeled 5.2-acre retreat in one of the area’s most desirable settings. This spacious split-level home offers over 2,500 square feet of updated living—ideal for multigenerational living or simply enjoying the peaceful rural lifestyle. Step inside to discover brand-new luxury vinyl plank flooring, fresh interior and exterior paint, and a

Jeffrey Enserink Lamonte Real Estate Professionals

Tucked away on a scenic mountaintop just minutes from town, this 2,428 sq. ft. Colonial style retreat blends timeless charm with modern comfort. Wake up to serene sunrises on the back deck and unwind with breathtaking valley sunsets from the front porch. Set on 14.2 acres, this peaceful property offers a private sanctuarysurrounded by nature. Inside, the home features 2 bedrooms, 2.5 bathrooms, a

J. Ryan Smith Berkshire Hathaway HomeServices Real Estate Professionals

Two houses! This is an amazing property that can be a family estate or an income producing property. Main house is 1977SF with 4 beds/2baths, fenced yard, covered patio, loft and bedroom upstairs. Primary bedroom is on the main level with a sun room that could also serve as a home office. Second house is 575 SF w/ 1 bed/1bath and a fenced yard of its own, and attached 2 car garage. Laundry hook

Wyndee Konopaski Keller Williams Southern Oregon-Umpqua Valley

Beautiful custom home in a peaceful Winchester neighborhood! From the moment you step onto the covered front entry, this home invites you in. Inside, vaulted ceilings, expansive windows, and skylights create a bright, open atmosphere filled with natural light. The living room features a fireplace and French doors that lead to the spacious deck with stunning sunset views. The remodeled kitchen is

Najla Slater Berkshire Hathaway HomeServices Real Estate Professionals

Beautifully refinished home on 5 acres off desired Fisher Rd. area. This home has room for it all, and views all around. With 6 bedrooms, an office, living room and family room, there is no shortage of space and storage. There are 3 bedrooms upstairs, and 3 bedrooms and an office downstairs. The living room boasts 18' ceilings, a floor to ceiling fireplace, and a wet bar. The kitchen/dining room

Wyndee Konopaski Keller Williams Southern Oregon-Umpqua Valley

Beautiful riverfront property at the end of Sunshine Rd. The home features 5 bedrooms, 3.5 baths, 2848 sqft, new heating system, hardwood floors on main level that is Madrone 3/4 - 6 inch planks (locally sourced & processed), wrap-around deck, hot tub, & green house. Lower level could be second living quarters. Garages for 4 cars, RV garages for 2, and shop. Owner says, "Great fishing & old water

John McVeigh The Neil Company Real Estate

Three bed, three bath home situated in the valley, five minutes from Downtown. Home features beautiful views of the valley, frequent wildlife visits, and the woods behind for hiking enthusiasts. Well is shared with neighbor. There are some foundation issues.

Mel Rodrigues The Neil Company Real Estate

Check out this spacious 4-bedroom home with daylight basement & dual covered decks! Welcome to 251 Winchester Creek Ave, this beautifully maintained 4-bedroom, 3-bathroom home offering 1,858 sq/ft of well-designed living space in a peaceful and private setting. Nestled against a hillside backdrop of lush trees and natural landscape, this home seamlessly blends comfort, functionality, and outdoor

Andrew Stoner Roseburg Homes Realty

Experience elevated living in this stunning, move-in-ready 1,718 sq ft, 3-bedroom, 2.5-bath condominium, perfectly perched to capture million-dollar panoramic views of downtown Roseburg, the majestic surrounding mountains, and unforgettable sunrises and sunsets. Step into an open-concept layout where natural light pours through floor-to-ceiling picture windows, creating a seamless connection

Anthony Beckham Different Better Real Estate

Welcome to 375 Bella Hills Ln, an extraordinary 80-acre estate nestled in part of Oregon’s wine country with breathtaking views of the Umpqua River. This peaceful and private property offers endless potential—whether you're dreaming of a vineyard, multigenerational living, or a tranquil retreat surrounded by nature.The main residence is a thoughtfully designed 3-bedroom, 5.1/2-bath home featuring

Stephen Bates UNITED REAL ESTATE PROPERTIES

Diamond in the works! This classic 1950s home is well on its way to a complete transformation—more than halfway through a full remodel with major upgrades already completed. All remodeling has been permitted, and house plans and contractor bids are available to help you take the project across the finish line.Sellers have replaced all electrical and plumbing, added a spacious kitchen and

Tammi Ellison eXp Realty, LLC

Welcome to this beautifully appointed 2,688 sq ft home nestled on a serene 0.41-acre lot in one of Winchester’s most sought-after neighborhoods. Thoughtfully designed for comfort and functionality, this spacious residence features two luxurious primary suites, including one conveniently located on the main level—complete with dual walk-in closets for ample storage.Enjoy sweeping mountain and

Jennifer Kramer RE/MAX Integrity

Located in one of the most desirable subdivisions in Douglas County, this stunning chalet style home is ready for you to make it your new home. The living room features a stunning wall of windows, a gas fireplace insert and hardwood floors. The hardwood floors continue through the dining room and into the spacious kitchen, which boasts granite countertops, eating bar, and built-in oven, microwave

Rich Raynor Heritage Real Estate

Turnkey duplex on a spacious 0.39-acre double lot WITH A SHOP!—plus potential to build a second duplex! Clean, well-maintained units with strong rental history, ample parking, and consistent demand in a high-rent, low-vacancy area near the college. Opportunities like this don’t last—call today!

Micah Davis Oregon Life Homes

Luxurious Custom home in Rocky Ridge area located on just over half acre with amazing views of city, mountains and sunsets. The nearly 2700 square feet includes 4 bedrooms, 2.5 baths, gourmet kitchen, living room and family room. Luxury features throughout include main level Master Suite with jetted tub, slate flooring and shower, granite countertops with double sinks and large walk-in closet.

Patti Archambault All-Pro Realty Advisors, LLC

2-bedroom, 2 bath manufactured home with 1,152 sq ft on a 0.15 acre lot. Includes a workshop. Year built 1973. Located on NW Joseph St in Roseburg. Buyer to perform all due diligence.

Bryan McKeun RE/MAX Integrity

This stunning custom-built masterpiece spans 22.66 acres and offers breathtaking views of the famous North Umpqua River! Situated above the Winchester Dam, This property is perfect for boating, swimming, paddle boarding and fishing enthusiasts. From the grand entrance to the expansive deck featuring unobstructed river views, an inground pool, and a newly remodeled, fully contained 911-square-foot

Jason Mann J Mann Realty

Freshly remodeled beautiful home with spectacular views by day or by night in Roseburg! It features a brand-new HVAC system, luxury vinyl plank flooring, gorgeous kitchen with granite, farm sink, stainless steel appliances, and large eating bar! The great room and dining area are spacious and a perfect place for gathering. The slider leading out to the expansive, covered deck for year around

Jennifer Kramer RE/MAX Integrity

Discover your own piece of paradise with this incredible gardener's oasis, located on nearly 90 acres just outside Roseburg. This beautifully updated farmhouse and guest quarters offer the perfect blend of country charm and modern convenience. The property features lush, usable pastureland and a gardener's dream setup, with nearly an acre of deer-fenced raised garden beds and a variety of

Ryan Fox Berkshire Hathaway HomeServices Real Estate Professionals

This home is a dream for people who are 55 or older, active, and still want a large, spacious, elegant, beautiful home in a serene gated 55+ community! This stunning residence offers 3,152 square feet of luxurious living space designed for comfort and elegance. Featuring three spacious bedrooms and three beautifully appointed bathrooms, this home is perfect for both relaxation and entertaining.

Joanne Graham eXp Realty, LLC

Get ready to fall in love with this beautifully crafted custom home in the sought-after gated community of Winchester Ridge! With 3 spacious bedrooms, a bonus/game room, and 2.1 bathrooms spread across 2,104 sq. ft. on 2.36 acres, this property offers the perfect blend of elegance, comfort, and room to roam. Step inside to a bright, open floor plan with soaring ceilings, walls of windows, and

Kathy Flowers All-Pro Realty Advisors, LLC

Very nice 3 bedroom, 2.5 bath home built in 2005. All appliances currently in the home are included. Located close to I-5, shopping and medical. Great views of North Roseburg and the surrounding neighborhood. Come see and make this your new home.

Roger Snyder Berkshire Hathaway HomeServices Real Estate Professionals