Oakland Homes under $400,000

Welcome to Oakland, Oregon – a hidden gem nestled in the heart of Douglas County! Known for its charming small-town atmosphere and rich history, Oakland offers residents a unique blend of community spirit and natural beauty. With its picturesque landscapes, including rolling hills and lush greenery, Oakland is the ideal place for those seeking a serene lifestyle away from the hustle and bustle of city living.

The city is steeped in history, boasting a well-preserved downtown area filled with antique shops, cozy cafes, and friendly local businesses. Whether you're taking a leisurely stroll down the scenic streets or enjoying a picnic at one of the nearby parks, Oakland’s warm and welcoming environment is sure to make you feel right at home.

For homebuyers looking for affordability without sacrificing quality, Oakland has a variety of homes available for under $400,000. This price range opens doors to charming single-family homes, cozy cottages, and spacious lots where you can create your dream sanctuary. With the current real estate market, this is an excellent opportunity for first-time homebuyers, families, or anyone seeking a peaceful retreat.

In addition to its affordable housing options, Oakland offers access to outdoor adventures, including hiking, fishing, and exploring the beautiful Umpqua National Forest. If you’re ready to embrace a vibrant community and a lifestyle surrounded by nature, Oakland, Oregon, is the perfect place to call home. Discover your future here and experience all that this delightful city has to offer!

Newest Oakland Homes under $400,000

$375,000

3 Beds ⋅ 2 Baths ⋅ 403981297 MLS

Welcome to 215 SE Fifth St in historic Oakland! This charming 3-bedroom, 2.5-bath home is full of character. It offers a functional layout, thoughtful updates, and plenty of outdoor space to enjoy.Inside, you’ll find an updated bathroom featuring new flooring and a new vanity, along with new toilets throughout the home. The kitchen is equipped with a newer sink, refrigerator, gas stove, and dishwasher. Additional improvements include a newer hot water heater and a 30-year composition roof, adding to the home’s appeal.Step outside onto the deck and take in the surrounding mountain views while enjoying all this property has to offer. The outdoor space features a fire pit, fruit trees, a chicken coop with a fenced area for chickens or other animals. There is a shop/shed right off the deck for additional storage or a place to work on projects. The property has also been surveyed, with property pins in the ground.Conveniently located near Oakland schools and downtown Oakland, this home offers a wonderful combination of character, functionality, and inviting indoor and outdoor spaces. Come see all that 215 SE Fifth St has to offer—it just might be the place you’ll want to call home!

215 SE 5TH ST, Oakland

$315,000

3 Beds ⋅ 2 Baths ⋅ 186027717 MLS

WOW! Come experience the joys of small-town living, just a 20-minute drive from Roseburg! This conveniently located 3-bedroom, 2-bathroom home offers nearly 1,225 square feet of comfortable living space on a spacious corner lot in a quiet neighborhood. The schools are close by, and local favorites like The Secret Wine Society, Lamplighter Cafe & Lounge, Oakland Flour Mill Antiques & Gifts, Oakland Coffee Company, the library and disc golf course are all just a few minutes walk away. Built in 1955, this charming home has been lovingly brought into the 21st century while still preserving its desirable mid-century character. Enjoy the longevity and security of a newer metal roof, vinyl windows, and plenty of parking, including ample room for an RV. Step inside the cozy interior and discover newer stainless steel appliances, a gas stove, hardwood flooring, tiled kitchen countertops, and plenty of natural charm throughout. Outside, you’ll find ample space for gardening and growing your own herbs and veggies, along with a handy tool shed for storing all your supplies. Conveniently located, thoughtfully updated, and full of character, this home is ready for its next chapter. Call today to schedule your private tour before it’s too late!

729 NE LOCUST ST, Oakland

$159,900

2 Beds ⋅ 1 Baths ⋅ 455959794 MLS

Situated on a nice piece of all usable property, with plenty of room for gardening, small livestock, or just enjoying the elbow room and the relaxing view, this budget friendly home has a lot to offer. The home is connected to city water and natural gas is run to the home, but not currently connected. The manufactured home has been integrated into an addition, and due to the age of the manufactured home, this property will require a cash sale or special lending. Check with your agentregarding loan options.

1549 OLD TOWN LOOP RD, Oakland

$295,000

3 Beds ⋅ 2 Baths ⋅ 792712726 MLS

INVESTMENT OPPORTUNITY IN THE HEART OF OAKLAND! ??This unique property has so much to offer—whether you’re looking for a place to call home, additional rental income, or a great investment opportunity!The main home features 3 bedrooms and 2 bathrooms, a dedicated laundry room, and an unfinished daylight basement offering plenty of additional storage space.PLUS a separate approx 626 sq ft 1 bedroom, 1 bathroom apartment!Complete with its own living room, kitchen, and additional storage or office space—perfect for rental income, extended family, guests, or multi-generational living.Outside, you’ll find a large fully fenced and gated lot with a shop, tool shed, additional outbuildings, fruit trees, garden space, a covered porch, RV parking, and plenty of room for all your toys and projects.A wonderful opportunity with income-producing potential and room to make it your own. Properties offering this much versatility don’t come along every day!

421 WELLS RD, Oakland

$349,000

2 Beds ⋅ 2 Baths ⋅ 740876745 MLS

Bring your animals to this private 5 acre sanctuary. This 1400 sq ft 2 bedroom 2 bath is a must see. With just a little TLC this could be exactly what you have been looking for. Sit on this huge front porch that is screened in and enjoy the beautiful scenery and also plenty of room for entertaining those guest. Also a nice back deck as well. This property also has a large barn, chicken coop and lean-to. Lots of trees and plants including, walnut, pear, apple, plum, dogwood, concord grapes, elderberries, cranberries and lilacs. Plenty of room not only for those animals but a RV, Boats and trailers.Irrigation rights out of coons creek.

425 TIGERLILY LN, Oakland

$309,000

3 Beds ⋅ 1 Baths ⋅ 257638674 MLS

Nestled in the charming town of Oakland, Oregon, this solid older home offers endless potential. Featuring a good roof and a strong foundation, this well-loved property is ready for its next chapter. Mature trees and beautiful flowers create a picturesque setting, adding to the home's timeless appeal.Inside, this classic time capsule awaits your personal touch. Bring your vision and update the interior to match your style while preserving its unique character. With an attractive price and plenty of opportunity to build equity, this quaint Oakland home is the perfect canvas for homeowners, investors, or anyone looking to create something special.

210 SE 4TH ST, Oakland

$229,000

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

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.