Oakland Homes with 2 Story Style

Welcome to Oakland, Oregon – a charming city nestled in the heart of Douglas County, where picturesque landscapes meet a rich tapestry of history and community spirit. With its quaint small-town atmosphere, Oakland offers residents a unique blend of tranquility and accessibility, making it an ideal place to call home.

Known for its stunning natural beauty, Oakland is surrounded by lush forests, rolling hills, and the serene Umpqua River, providing endless opportunities for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply taking in the breathtaking views, this vibrant city has something for everyone. The historic downtown area is filled with delightful shops, local eateries, and a warm sense of community, inviting you to explore and connect with your neighbors.

In Oakland, homes with a two-story style are particularly sought after, offering spacious living and a perfect blend of comfort and functionality. These residences often feature open floor plans, allowing for seamless entertaining and family gatherings. The second stories provide added privacy, with bedrooms that offer stunning views of the surrounding landscape. Many two-story homes in Oakland come equipped with modern amenities while retaining the charm of classic architectural designs, making them a perfect fit for families, professionals, or anyone looking to enjoy the best of Oregon living.

If you’re searching for a place where community, nature, and beautiful homes converge, Oakland, Oregon, awaits you. Discover the joy of two-story living in this enchanting city, where every day feels like a getaway!

Newest Oakland Homes with 2 Story Style

$998,000

3 Beds ⋅ 2 Baths ⋅ 234446332 MLS

First time ever on the market, this remarkable property has been in the same family for three generations. If you've been searching for space, privacy, & a truly move-in-ready home, this exceptional 123-acre Green Valley estate is the opportunity you've been waiting for. There's a reason families put down roots in Green Valley & stay for generations. Surrounded by lush landscapes, peaceful mountain views, & unmatched privacy—all just minutes from I-5, you can enjoy the best of rural living without sacrificing convenience. Adding to the property's long-term value, more than 100 acres were professionally reforested in 2024 with 21,800 Douglas Fir seedlings, creating an investment in the future alongside an incredible place to call home. The 3-bdrm, 2-bath home offers comfortable, open-concept living with a spacious kitchen, dining area, & living room that flow seamlessly together. Step outside onto the covered deck, where you can enjoy quiet mornings with a cup of coffee or unwind while dining outdoors. Downstairs, the full daylight basement offers outstanding flexibility. Already plumbed for a second kitchen, it has the potential to become a separate living space for multigenerational living, guests, or rental income. Just off the entry, a generously-sized, bonus mudroom provides endless possibilities; create a second laundry room, walk-in pantry, hobby space, or customize it to fit your lifestyle. Water on this property is plentiful thanks to multiple natural springs. The primary spring continuously gives abundant water, even during the summer months, & a supplemental holding tank provides peace of mind with reliable water storage. Properties of this caliber rarely become available. Combining generations of stewardship, productive timberland, abundant water, breathtaking scenery, & a beautiful home, this is truly a one-of-a-kind opportunity. Schedule your private showing today! Information deemed reliable; for marketing purposes. Buyer to perform all due diligence.

8824 GREEN VALLEY RD, Oakland

$999,000

3 Beds ⋅ 3 Baths ⋅ 785344995 MLS

Great country home with room for animals and everyone! 45.04 acres with a 3 bedroom, 3 bath home. Featuring main level primary bedroom, den/office on the main level, vaulted ceilings, wood/pellet stove, new roof, new heat pump, new flooring, new bathroom, and RV parking with hookups. The property also features a 36x30 shop, about a 50x40 barn, 20x20 shop, 12x12 woodshed, 35x50 lean-to, well house, store unit, septic, 3000 gal water storage tank, tool barn, and electric gate entrance. This is country living at its best!

3450 HOGAN RD, Oakland

$249,000

3 Beds ⋅ 1 Baths ⋅ 237306613 MLS

Built in 1883, this classic Oakland home has historic character with thoughtful updates and everyday functionality. 3BED/1.5BATHS with 900 square feet. Recent updates include a kitchen with new cabinetry and laminate countertops, LVP flooring, fresh interior paint in select rooms, new carpet on the stairs and upstairs bedroom, and a brand-new water heater. Forced-air heating and pellet stove. Covered front porch, yard with storage shed, and plenty of off-street parking. Conveniently located just minutes from historic downtown Oakland, local schools, and parks, this home is an excellent opportunity to enjoy one of Douglas County's most beloved small towns.

330 NE 1ST ST, Oakland

$440,000

2 Beds ⋅ 2 Baths ⋅ 737342368 MLS

Set on more than 20 acres of gently sloping forestland, this architecturally distinctive Linwood post-and-beam chalet offers a peaceful mountain retreat where quality craftsmanship, privacy, and nature come together - all just 25 minutes from Roseburg and 45 minutes from Eugene. As the forerunner to Linwood Homes' popular Venice/Avondale model, the home showcases timeless design with a dramatic prow front, soaring walls of glass, vaulted cedar ceilings, and an inviting wraparound deck with recently rebuilt decking and railings overlooking the surrounding forest and abundant wildlife. The private setting offers an appealing balance of seclusion and convenience. Dual road frontage on Old Homestead Rd and Indian Creek Dr provides direct access to both the upper and lower portions of the property. Inside, the home is ready for your personal vision and updates, providing an excellent opportunity to build equity while preserving the character and craftsmanship of this unique post-and-beam design. All kitchen appliances + washer/dryer are included. Roof was replaced in 2018. Whether you're searching for a full-time residence, a recreational getaway, or a private retreat surrounded by nature, this scenic property offers exceptional privacy, distinctive architecture, and the opportunity to make it your own. Estate sale. Property sold "as-is."

670 OLD HOMESTEAD RD, Oakland

$1,795,000

4 Beds ⋅ 2 Baths ⋅ 360882115 MLS

Exceptional 42± acre luxury estate featuring a custom 4-bedroom home, expansive outdoor living, water rights, creek frontage, and a thriving Christmas tree farm with approx. 16,000 Nordmann, Concolor., Grand etc A remodeled accessory building offers flexible office, studio, or hobby space, while the newer insulated shop supports farm use. Enjoy a profitable seasonal business and an opportunity to deeply connect with the community just a few weekends each year.

106 GREEN VALLEY RD, Oakland

$830,000

5 Beds ⋅ 4 Baths ⋅ 699245704 MLS

Victorian Dollhouse or French Countryside B&B? You're going to want to see this beauty and decide for yourself! With so many custom finishes, and spacious rooms, this home really brings you in.... It truly is a one of a kind as every inch of this property was thought out by sellers over the years - every plant and path adds to it's charm. Not only does the home have ample storage with 2 functioning kitchens, but the large shop will leave you dreaming up projects year-round with it's wood stove to keep warm. Don't forget to check out that yard; painted perfectly for entertaining and celebrations. Edit: 2 "bonus" rooms upstairs have closets and are now technical bedrooms! Schedule your showing today!

1300 FAIR OAKS RD, Oakland

$465,000

4 Beds ⋅ 2 Baths ⋅ 632984617 MLS

Located in the heart of Oakland’s Historic District, this beautifully maintained 1900 Victorian blends timeless character with thoughtful modern updates. Offering 2,589 sq ft, 4 bedrooms, and 2 full bathrooms, this home combines historic charm with everyday comfort and functionality. Inside, you’ll find original oak floors with a rich walnut stain throughout the main living areas. A downstairs bedroom retains its original wool carpet, adding to the home’s historic appeal. The spacious mudroom/laundry room adds convenience and character, while the updated downstairs bathroom features period-inspired finishes. The kitchen offers ample workspace with stainless steel appliances and granite tile countertops. The inviting living room centers around an open fireplace, creating a warm and comfortable gathering space. Upstairs features three additional bedrooms and a full bathroom with a walk-in shower and classic soaking tub. Outside, the backyard offers a peaceful setting with a brick walkway, covered deck, and hot tub under a gazebo for year-round enjoyment. The property also includes raised garden beds, a greenhouse, drip irrigation, and in-ground sprinklers. This well-maintained Victorian offers a rare opportunity to enjoy historic character alongside modern amenities in one of Oakland’s most recognizable neighborhoods. Schedule your private showing today!

511 OAK ST, Oakland

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