Oakland Homes with 2 Story Style

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

111 EDJON LN, Oakland
$525,000
4 Beds ⋅ 2 Baths ⋅ 187998518 MLS
A piece of history awaits it's next chapter - This Umpqua River 1900's 2-story Homestead has endless possibilities with 25 acres, mostly sloped with some pockets of flat/use-ability, plenty of room for multiple gardens, fruit trees, animals, motorcycles, fishing, you name it! Property includes 5 tax lots, R73512, R73561, R73526, R73463, R73505, water right certificate, Umpqua River frontage, seasonal creek, 28 x 34 Shop, & additional outbuildings. This 2 level, 4 bedroom, 2 bathroom home holds a 1900's charm including some original cabinetry, tall ceilings, some original windows/doors, claw foot bathtub, pellet stove, updated kitchen, and a dreamy wrap around porch for you to enjoy your morning coffee amidst the tree's & mountain views! Home does need a little TLC & seller's are selling in 'as is' condition. Don't miss this unique opportunity to build your dream of living in a 1900's Old Homestead property along the Umpqua River!!

111 EDJON LN, Oakland
978 WILDFLOWER LN, Oakland
$987,000
2 Beds ⋅ 3 Baths ⋅ 168069525 MLS
Tucked into a private, wooded setting in Oakland, this distinctive 2-bed, 3-bath home offers 2,077 sqft of living space & strong connection to the surrounding landscape. Soaring ceilings, expansive windows, warm wood accents, & hardwood floors create a home filled with natural light & character. Spacious & versatile living areas center around a welcoming living room with a fireplace & large bay window seat showcasing the beautiful landscape. The kitchen offers a functional layout, abundant lighting, & solid wood cabinetry, while the adjoining dining area continues the home's open, light-filled environment. The laundry room offers a utility sink, upper & lower cabinets, & shelving. The main bath is equipped with a standup shower & extra built-in cabinets. There are two primary suites, one on the main level & one upstairs. Both are very spacious & feature dramatic windows, vaulted ceilings, & full attached bathrooms. An enclosed atrium/sunroom creates another unique area to enjoy the natural surroundings throughout the seasons with tongue & grove paneling, skylights, & a wall of sliding doors. Substantial garage space & workshop provide plenty of room for vehicles, equipment, projects, & storage. There are two oversized 2 car garages with rollup doors, & an additional finished workshop with heat/cool. Outside, multiple new deck areas extend the living space outdoors, while mature trees provide privacy & frame impressive views of the hills & countryside. Not only is this property a private mountain retreat, but it's also an incredible investment opportunity with significant timber value. A professional timber cruise has been performed, showing 1495 MBF of timber with a gross value of over $980,000. With versatile indoor & outdoor spaces, substantial garage & workshop capacity, investment opportunity, in a setting tucked away among the trees close to town, this property offers a unique opportunity to enjoy privacy, space, & the natural beauty of rural Oakland.

978 WILDFLOWER LN, Oakland
8824 GREEN VALLEY RD, Oakland
$949,000
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
3450 HOGAN 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, electric gate entrance, and some timber. Zoned Farm-Forest for low taxes. Set-up for multi-family living, the seller says the 20 acre section of land is also buildable - buyer to verify. Portable saw mill is negotiable. This is country living at its best!

3450 HOGAN RD, Oakland
106 GREEN VALLEY RD, Oakland
$1,695,000
4 Beds ⋅ 2 Baths ⋅ 360882115 MLS
Exceptional 42± acre estate with a custom 4-bedroom home, expansive outdoor living, 14 acres of junior water rights and creek frontage. A remodeled accessory building offers flexible office, studio or hobby space, and a newer insulated shop supports any use. Approximately 20 acres of level, fertile bottom ground opens the door to multiple dry cropland uses such as orchard, vineyard, pasture or your own vision. Currently home to an established Christmas tree operation of approx. 15,000 trees - run it or make the land your own. Turnkey today!

106 GREEN VALLEY RD, Oakland
1300 FAIR OAKS RD, Oakland
$799,000
5 Beds ⋅ 4 Baths ⋅ 699245704 MLS
***Sellers are offering credit for buyer's closing costs or rate buy-down!!!*** **WAIT… Is this a Victorian Dollhouse, a French Countryside B&B, or your next home?! **Honestly… you’re going to have to see it for yourself. This one-of-a-kind property is packed with charm, character, and the kind of thoughtful details you just don’t find every day. Every inch has been intentionally designed and lovingly cared for by the sellers over the years — from the plants and winding pathways to the custom finishes throughout the home. And it doesn’t stop at the curb appeal… **TWO functioning kitchens. **More bedrooms than originally listed — those 2 upstairs bonus rooms have closets and are now technically bedrooms...YAY! **Ample storage. **A HUGE shop with a wood stove for year-round projects. **A dreamy yard built for entertaining, celebrations & unforgettable gatherings. **Whether you’re imagining cozy mornings at home, hosting the holidays, running a creative workshop, or simply enjoying a property that feels completely unlike anything else… This one deserves a spot at the top of your must-see list. Come wander the paths. Explore the rooms. Check out the shop. Take in the yard. Then decide for yourself: Victorian Dollhouse… or French Countryside B&B?**Schedule your showing today — this is one you’ll want to experience in person!

1300 FAIR OAKS RD, Oakland
511 OAK ST, Oakland
$450,000
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
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.

How much is your home worth?

Get instant property value now!