Douglas Co: NE Roseburg/inside Roseburg SD Homes with 2 Story Style

Welcome to Douglas County, nestled in the heart of Oregon, where the charming city of Roseburg offers a perfect blend of natural beauty and vibrant community life. Known for its picturesque landscapes, Roseburg is surrounded by lush forests, rolling hills, and the majestic Umpqua River, making it an ideal location for outdoor enthusiasts and families alike. The region boasts a mild climate, ensuring that residents can enjoy a variety of seasonal activities, from hiking and fishing to wine tasting in the nearby vineyards.

Within the Roseburg School District, families can take advantage of quality education options, fostering a nurturing environment for children to thrive. The community is known for its friendly atmosphere, where neighbors become friends and local events bring everyone together. With a rich history and a strong sense of community, Roseburg is a place where you can truly feel at home.

When it comes to housing, Roseburg offers an array of charming two-story homes that cater to various lifestyles. These spacious residences provide ample room for families to grow, featuring open floor plans, modern amenities, and beautiful outdoor spaces. Imagine enjoying a cup of coffee on your balcony while soaking in the serene views or hosting gatherings in your expansive backyard. With plenty of character and style, these two-story homes are not just places to live; they are spaces to create lasting memories.

Whether you're a first-time homebuyer or looking to settle down in a welcoming community, Roseburg's two-story homes offer the perfect combination of comfort, convenience, and charm. Come explore the possibilities in this enchanting corner of Douglas County!

Newest Douglas Co: NE Roseburg/inside Roseburg SD Homes with 2 Story Style

$569,900

4 Beds ⋅ 2 Baths ⋅ 396042645 MLS

WOW! Perched in the desirable Rocky Ridge area, this custom 4-bedroom, 2.5-bath home offers nearly 2,700 square feet of thoughtfully designed living space on just over half an acre. Enjoy sweeping views of the city, surrounding mountains, and spectacular sunsets while benefiting from the privacy and peaceful atmosphere that make this neighborhood so sought after. Designed for both comfort and entertaining, the home features a spacious main-level primary suite complete with a jetted tub, slate flooring and shower, dual granite vanities, and a generous walk-in closet. The gourmet kitchen is equipped with granite countertops, custom cabinetry, high-end stainless steel appliances, and a large walk-in pantry, all flowing seamlessly into the spacious dining area with custom built-ins. Soaring ceilings, wood flooring, abundant natural light, and a beautiful gas fireplace create a warm and inviting main living area, while the open staircase leads to three additional bedrooms, each with a walk-in closet, and a versatile upper-level family room. The flexible layout provides space for gathering, entertaining, working from home, or simply spreading out. Outside, the wraparound deck takes full advantage of the incredible views and serves as the perfect place to enjoy a quiet morning or take in the evening sunset. The level, fenced backyard offers plenty of room for recreation, gardening, a future pool, or your own custom outdoor retreat. A stamped concrete driveway and oversized attached 3-car garage add both convenience and curb appeal. Combining quality craftsmanship, generous living spaces, stunning views, and a prime Rocky Ridge location, this is a home designed to be enjoyed for years to come. Schedule your private tour today!

1548 NE ROCKY RIDGE DR, Roseburg

$489,500

4 Beds ⋅ 3 Baths ⋅ 271779634 MLS

Stunning custom built home in Winchester! Enjoy views of the North Umpqua River and bridge views from the large wrap-around deck. Inside features a grand great room, granite counters, an upgraded range, vinyl windows, new ductless HVAC, and built-in storage. Ideal for large or multi-family potential: downstairs offers extended living area, office, and play space. Outside, enjoy a huge yard with fruit trees, RV parking, and river access. Minutes to schools, shopping, and easy I-5 access. Schedule a tour today!

170 HURRICANE LN, Winchester

$614,000

3 Beds ⋅ 2 Baths ⋅ 179377451 MLS

Wake up to valley views with the Callahan Mountains creating the backdrop from this hillside home just above town. The covered front porch is the perfect place for morning coffee, while the fenced yard and patio offer just enough outdoor space to enjoy without spending every weekend on yard work.Inside, a tiled entry opens to an easy-flowing great room where the kitchen, dining, and living areas come together. The kitchen features smooth granite countertops, a cook island, custom-faced refrigerator, and plenty of workspace. High ceilings, built-in shelving, and a gas fireplace give the living room a welcoming feel.The main-level primary suite offers a quiet retreat with patio access, a large bathroom with dual sinks, a jetted soaking tub, tile walk-in shower, and a walk-in closet that connects directly to the laundry room. A second bedroom on the main level works equally well as a guest room or home office.Upstairs, you'll find another bedroom suite with a walk-in closet plus a media room complete with projector and screen. Already plumbed for a sink, the space is ready for whatever fits your lifestyle, whether that's movie nights, hobbies, a game room, or guest accommodations.The garage offers tall ceilings with room for extra storage, and the location puts shopping, restaurants, medical care, and downtown conveniences just minutes away. If you've been looking for a home that offers views, a practical floor plan, and spaces that simply make everyday life easier, this one is worth a look.

1984 NE SUNSET LOOP DR, Roseburg

$599,900

4 Beds ⋅ 2 Baths ⋅ 277360378 MLS

This beautiful custom home is located in one of Douglas County's premier neighborhoods and there is no HOA! The all level lot is nearly 1/2 acre in size and boasts an amazing amount of parking. Bring your automobiles, RVs, boats, golf carts, trailers, or whatever you have, as there is room for all! The home's interior features a spacious kitchen with built in-oven and microwave, a downdraft gas range/oven, island, eating bar, dining nook, refrigerator with water and ice, disposal and tile flooring. The comfortable living room is centered around a classy gas fireplace and has a cathedral ceiling. The primary bedroom is good sized and has direct access to the back patio, (which would be a great place to install a hot tub), along with a bathroom with a walk-in shower, garden tub, double sink vanity and a walk-in closet. The den/office has 2 doors, with one being a french door. The family room makes a great spot to enjoy your favorite indoor activities. There is a formal dining room directly off the kitchen. The upper level is very unique and has two bedrooms. Enjoy the wonderful summer weather in the fully fenced expansive back and side yards, and on the covered patio on the rear of the home, which is accessible directly from the kitchen, making for great outdoor entertaining and living. In addition to all the parking in, and adjacent to the driveway, there is a lot of parking behind the gated fence on the right side of the home. Detached carport structure and storage shed are included. All this and low county taxes! If this sounds like a place you would enjoy calling yours, don't delay, call for a viewing appointment today!

251 MARTHA DR, Winchester

$299,900

3 Beds ⋅ 2 Baths ⋅ 353390392 MLS

Welcome to easy living in the desirable Four Seasons community, where comfort, convenience, and low-maintenance homeownership come together in one of Roseburg's most accessible locations. Beautifully maintained, this inviting condo offers the perfect blend of modern amenities and everyday practicality.Step inside to a bright and welcoming main level featuring durable laminate flooring throughout and an open-concept design ideal for both everyday living and entertaining. The spacious living room flows seamlessly into the dining area and kitchen, complete with tile countertops, a gas range, and an island with an eating bar—creating a comfortable space for meals, conversation, and gathering with family and friends.Upstairs, fresh interior paint creates a clean and inviting atmosphere throughout the upper level. The vaulted primary suite provides a peaceful retreat with double sinks, a soaking tub, and a walk-in shower. Two additional bedrooms offer flexibility for guests, hobbies, or a home office. A conveniently located upstairs laundry room helps simplify daily routines.Outside, enjoy your private fenced backyard with an extended deck—perfect for outdoor dining, entertaining, or simply relaxing at the end of the day.Additional features include central gas heating, electric air conditioning, a tankless gas water heater, and an attached one-car garage.One of the greatest benefits of living at Four Seasons is the location. Centrally located in Roseburg, you'll enjoy convenient access to shopping, restaurants, medical services, professional offices, and everyday necessities. Whether running errands, meeting friends for lunch, or attending appointments, everything you need is just minutes away.With attractive curb appeal, stacked rock accents, fresh upper-level interior paint, and move-in-ready condition, this home offers a comfortable, carefree lifestyle in a sought-after community. Spend less time on maintenance and more time enjoying the things that matter.

1487 NE FOUR SEASONS DR, Roseburg

$260,000

3 Beds ⋅ 1 Baths ⋅ 125911706 MLS

Nestled in the heart of downtown Roseburg among some of the area's most beautiful historic homes, this enchanting 1937 residence offers timeless character just moments from the very best the city has to offer. Enjoy the convenience of nearby parks, the post office, courthouse, shopping, dining, and everyday amenities—all within easy reach.This stunning 3-bedroom, 1.5-bath home has been lovingly maintained and thoughtfully preserved to honor its original craftsmanship. Rich in warmth and personality, you'll find a cozy wood-burning fireplace, original small-plank oak flooring, intricate tile work, graceful archways, and charming built-ins throughout.Upstairs, vaulted peaked ceilings showcase rustic wood lap siding, exposed brick accents, a second wood stove, and beautiful stained-glass art windows that create a truly magical retreat. Every corner of this home reflects a perfect blend of comfort, charm, and historic elegance.Outside, enjoy a private fenced backyard ideal for relaxing or entertaining. The spacious walk-in basement offers a dedicated laundry area and abundant storage, while the detached garage provides additional space for hobbies, tools, or seasonal items.One-of-a-kind and full of soul, this downtown Roseburg gem is a rare opportunity to own a piece of the city's enduring charm.

1426 SE DOUGLAS AVE, Roseburg

$490,000

4 Beds ⋅ 2 Baths ⋅ 152479269 MLS

Priced to sell and offering exceptional value in Winchester's sought-after Oak Valley Loop neighborhood! This beautifully maintained 4-bedroom, 2.5-bath home offers 2,581 square feet of thoughtfully designed living space, combining timeless finishes, everyday comfort, and room to grow.Step inside to soaring vaulted ceilings, rich bamboo flooring, and a warm natural gas fireplace that creates an inviting focal point in the main living area. The spacious main-level primary suite provides a private retreat, featuring a luxurious ensuite bath with a tiled walk-in shower, double vanity, relaxing jetted tub, and generous walk-in closet.Designed with both entertaining and daily living in mind, the kitchen showcases granite countertops, stainless steel appliances, under-cabinet lighting, a walk-in pantry, and an eating bar that seamlessly connects to the formal dining area. Step outside to the deck and enjoy effortless indoor-outdoor living, perfect for summer barbecues, morning coffee, or evening gatherings.Upstairs, a versatile bonus loft offers additional living space, while three generously sized bedrooms—each with its own walk-in closet—provide comfort and flexibility for family, guests, hobbies, or a home office.An extra-deep two-car garage, abundant storage throughout, fresh interior and exterior paint, and mature landscaping add to the home's appeal. The fully fenced backyard creates a private outdoor oasis, offering plenty of space to relax, garden, or play.With a Real Market Value of $593,570, this home presents an incredible opportunity to own in one of Winchester's most desirable neighborhoods. Conveniently located near schools, shopping, and recreation, 556 N View Drive delivers the perfect blend of space, quality, and value. Schedule your private tour today!

556 NORTH VIEW DR, Winchester

$419,000

3 Beds ⋅ 2 Baths ⋅ 513159959 MLS

Beautifully maintained 2-story home located in the desirable Rocky Ridge community! This 3-bedroom, 2.5-bath residence offers 1,860 square feet of comfortable living space and a spacious 3-car attached garage. Nestled on a quiet cul-de-sac, you'll enjoy stunning mountain views and a peaceful setting. The thoughtfully designed floor plan features central air, a private patio, and plenty of room for everyday living and entertaining. Residents of this sought-after neighborhood have access to nearby walking trails and a community playground, making it easy to enjoy the outdoors. Conveniently located close to schools, shopping, and amenities, this home combines comfort, convenience, and scenic beauty in one exceptional package.

1696 NE RUBY CT, Roseburg

$724,900

4 Beds ⋅ 2 Baths ⋅ 343266536 MLS

Perched at nearly 1,250 feet in a desirable gated neighborhood, this custom 4-bedroom home offers sweeping mountain, valley, and forest views in a setting filled with birds, wildlife, and privacy. Inside, 2,587 square feet of thoughtfully designed living space features soaring ceilings, abundant natural light, and distinctive architectural details. The kitchen is equipped with a Bertazzoni professional gas range with griddle, a 42-inch Viking built-in stainless steel side-by-side refrigerator, granite surfaces, abundant cabinetry, and a large center island. The inviting living area features custom built-ins, a fireplace, and expansive windows that showcase the surrounding landscape. A standout sunroom with accordion-style doors opens to the private deck, creating seamless indoor-outdoor living and flexible space for a home office, reading room, fitness area, or playroom. Designed for comfort, efficiency, and low-maintenance living, the home includes upgraded insulated walls, triple-pane windows, mini-split heating and cooling units in every bedroom, a tankless water heater, and portable generator readiness. The portable generator and house connection are included, along with recently installed smoke and carbon monoxide detectors (February 2026). Outside, the oversized driveway provides ample parking, while the spacious 3-car garage accommodates a full-size truck and includes heavy-duty overhead storage rated to 800 pounds. The fenced yard, Rain Bird irrigation system, mature landscaping, and private outdoor spaces make it easy to enjoy the surroundings without extensive upkeep. The washer and dryer are also included, making this home truly move-in ready. If you're looking for exceptional views, energy-efficient construction, quality finishes, and a low-maintenance lifestyle in one of Roseburg's most sought-after gated communities, this property delivers. Schedule your private tour today!

1196 SOUTHRIDGE WAY, Roseburg

$584,000

4 Beds ⋅ 2 Baths ⋅ 221400910 MLS

Opportunities to own something truly one-of-a-kind don’t come around often. Introducing one of Roseburg’s most iconic residences: the 1875 Historic John Rast House, restored in 2020 and rich with preserved character. Ideally situated in the heart of Roseburg, just minutes from downtown, local dining, and convenient access to I-5, Hwy 42, and Hwy 138, this timeless property offers exceptional versatility for a variety of buyers and uses. Listed on the National Register of Historic Places, it also benefits from a property tax abatement. Set on .38 acres of meticulously landscaped grounds, the Gothic Revival home welcomes you with striking architecture-covered porches, balconies, steep gables, and ornate features. The fully fenced property includes a gated entry, expansive driveway/parking, and RV/EV accommodations. Inside, historic charm is preserved, from crown molding to original hardwood floors and period fixtures. A spacious family room with a wood-burning fireplace and abundant natural light, flows into an inviting living room with cedar paneling. The formal dining room features built-ins and generous space for hosting, while the kitchen blends vintage character with modern convenience. Upstairs, you’ll find three large bedrooms, a full bathroom, and a den currently showcasing historical pieces from the Rast family. A detached ADU offers excellent potential for guests, extended living, or rental income. Enjoy peaceful mornings on the back deck or unwind beneath the covered gazebo, surrounded by mature landscaping, and multiple storage sheds. The 2020 restoration included a new foundation, roof, gutters, electrical, plumbing, insulation, paint, and HVAC mini-splits. The C3 zoning allows for a wide range of uses including business, investment, or primary residency. Some homes await you to write their story. This home invites you to share in a story woven throughout centuries and brought to life by restoration and care.

236 SE STEPHENS ST, Roseburg

$275,000

3 Beds ⋅ 2 Baths ⋅ 611614311 MLS

This bright and inviting 3-bedroom, 2.5 bath end unit condominium offers approximately 1,590 sq. ft. of comfortable living space in the desirable Waterstone Crossing community in Roseburg. The two-story layout features a spacious living room, dining area, and large bay windows that fill the home with natural light. The kitchen includes black granite counter tops, a dishwasher (included), breakfast bar, and garbage disposal, with convenient first-floor laundry area nearby. Kitchen appliances are Samsung and refrigerator, stove, and dishwasher are included. Recent updates include a new water heater and new heat pump, providing added comfort and efficiency. Additional highlights include 3 parking spaces, low maintenance living with exterior maintenance, landscaping, and garbage included in the HOA, a new roof was installed in 2016. Perfect for first-time buyers, downsizing, or anyone seeking easy condo living close to town amenities.

202 NE RIFLE RANGE ST Unit #6, Roseburg

$269,000

2 Beds ⋅ 1 Baths ⋅ 652702621 MLS

Welcome to this well-cared-for home that blends timeless character with everyday comfort. From the moment you step inside, you’ll notice the classic Craftsman details, high ceilings, and the warm, inviting feel that makes this home truly special.The spacious living room offers plenty of room to relax or gather, while the main-level primary bedroom adds convenience to your daily routine. The kitchen is generously sized and functional, with an easy flow into the main living spaces.Thoughtful updates bring modern comfort, including a beautifully updated bathroom, on-demand water heater, and a ductless heating and cooling system—all while preserving the home’s original charm.Outside, the fully fenced backyard offers privacy and flexibility, with ample parking and space for an RV, boat, or additional vehicles.Simple, comfortable, and full of character—come see what makes this home feel so special.

334 NE NASH ST, Roseburg

Start Your Search

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.