Oakland Homes with Custom Style

Welcome to the charming city of Oakland, Oregon, nestled in the heart of Douglas County. With its picturesque landscapes and rich history, Oakland offers a unique blend of small-town charm and vibrant community spirit. Known for its historic downtown area, Oakland boasts beautifully preserved buildings that tell the story of its past, making it a delightful place to explore.

As you wander through the streets, you'll find a diverse array of shops, cafes, and local businesses that contribute to the city's warm and inviting atmosphere. The surrounding natural beauty is equally captivating, with lush forests, rolling hills, and the stunning Umpqua River nearby, providing ample opportunities for outdoor enthusiasts to hike, fish, and enjoy the great outdoors.

For those seeking a home that reflects their personal style, Oakland is a treasure trove of custom-built residences. Here, you’ll discover homes that are not just structures but expressions of individuality and creativity. From charming craftsman-style houses to modern designs, each property showcases unique architectural elements and thoughtful landscaping. Whether you prefer a cozy cottage or a spacious family home, Oakland's real estate market offers an array of options tailored to your tastes.

Living in Oakland means enjoying a close-knit community where neighbors become friends, and local events bring everyone together. With its stunning scenery, rich history, and a variety of custom-style homes, Oakland, Oregon, is more than just a place to live—it's a place to thrive. Come and experience the allure of Oakland for yourself!

Newest Oakland Homes with Custom Style

$699,900

3 Beds ⋅ 2 Baths ⋅ 430216774 MLS

Welcome to this well-maintained 3-bedroom, 2-bathroom 2021 Hi-Line home in a private wooded setting surrounded by mature trees and abundant wildlife. A seasonal creek is located on the property, adding to the natural setting. Inside, the home offers a comfortable and functional floor plan with three bedrooms, two full bathrooms, spacious living areas, and plenty of natural light. Large windows provide views of the surrounding trees, and the layout offers flexibility for everyday living, guests, or a home office. The property offers excellent workspace and storage with a 40' x 48' detached shop, providing plenty of room for a workshop, equipment, hobbies, recreational vehicles, storage, or other projects. The attached garage adds additional parking and storage, while the home is wired for a generator. A private driveway provides access to the home and shop. Outside, the concrete patio offers a convenient space for outdoor dining, entertaining, or relaxing. The wooded surroundings, mature trees, wildlife, and seasonal creek provide a private setting to enjoy the outdoors. With newer construction, a large detached shop, attached garage, private driveway, generator wiring, and a natural wooded setting, this property offers a great combination of comfortable living, workspace, and versatility.

5655 HIGHWAY 138, Oakland

$715,000

3 Beds ⋅ 2 Baths ⋅ 702851696 MLS

Rural living at its best! Escape from the outside world once you step onto this tranquil setting. The heart of this beautiful custom built, 3 bed, 2 bath home features an open floor plan with a loft allowing an abundance of natural light into the main living space. Stunning views from the deck overlooking the pasture with a pond stocked with bass. The scenic year-round creek running through the property offers a great place for solitude or to cool your feet off in the summer! Perfect set-up for the equestrian with a large barn, ample space for pastures, turnouts, and an area already setup for a riding arena. There is a 2000 sqft shop with heated concrete floor, bathroom, and living space. This pristine 20 acres is truly a must see property!

401 DE COSTA LN, Oakland

$2,300,000

5 Beds ⋅ 3 Baths ⋅ 603344021 MLS

1488 Red Hill Rd offers a once-in-a-lifetime opportunity to own far more than just a property — it’s a lifestyle rooted in beauty, agriculture, hospitality, and endless potential. Set against breathtaking mountain, valley, and vineyard views, this remarkable estate captures the very essence of Southern Oregon wine country living. The timeless single-level custom home spans an impressive 6,180 square feet and is ready for your personal touches and vision. Designed for entertaining and comfortable living alike, the home features soaring beamed ceilings in the grand great room and dining area, stunning stone fireplaces, and windows that frame the spectacular surrounding landscape. Equestrian enthusiasts will appreciate the two barns, cross-fenced pastures, and riding arena creating a true horse lover’s paradise. A separate guest cottage provides additional flexibility for extended family, guests, caretakers, or potential income opportunities. The crown jewel of the estate is the 38+ acres of established vineyard located within the prestigious Red Hill Douglas County AVA. The rich volcanic soil formed from uplifted ancient seafloor, combined with ideal elevation and climate, creates premier grape-growing conditions known for producing exceptional wines. With incredible natural beauty, agricultural value, equestrian amenities, and possible event venue opportunities, this extraordinary property offers endless possibilities in one of Douglas County’s most sought-after wine regions. Call for your private tour today!

1488 RED HILL RD, Oakland

$675,000

3 Beds ⋅ 2 Baths ⋅ 715225428 MLS

Private, peaceful, and surrounded by beautiful valley views, this exceptional 7.05-acre property offers the space and setting you've been waiting for. Tucked behind a secure gated entrance, the property feels like your own private retreat while still being conveniently close to town. Enjoy open views, a seasonal creek, private pond, and plenty of usable acreage with room to create the lifestyle you've envisioned.Inside, the immaculate 3-bedroom, 2.5-bath home offers 1,766 square feet of comfortable living space with an open floor plan, luxury vinyl plank flooring, wood-burning fireplace, and large windows that bring the beauty of the surrounding landscape indoors. The spacious primary suite features a walk-in closet, updated walk-in shower, and direct access to the expansive deck. A newer roof adds peace of mind.The outdoor living is just as impressive. Relax on the covered deck or concrete patio while enjoying stunning sunrises and sunsets overlooking your private backyard. Beautifully landscaped grounds feature an underground sprinkler system, greenhouse, fenced garden, chicken coop, private pond, and seasonal creek. With plenty of usable land and excellent potential for a horse property or hobby farm, there's room for gardens, animals, recreation, and more.For your projects, equipment, toys, or hobbies, the impressive 36' x 32' detached shop offers abundant space, complemented by covered parking and additional outbuildings.If you've been searching for privacy, views, acreage, and a property that truly offers room to live, work, and enjoy the outdoors, this one is worth seeing. A rare opportunity to own your own private slice of the country—welcome home!

445 GREEN VALLEY RD, Oakland

$754,000

3 Beds ⋅ 3 Baths ⋅ 310133687 MLS

There is a certain ease to life in this 3+ bed, 3 bath home located on a rare find of 8.8 acres located in Oakland city limits! Features a den/studio with closet and glass French doors, office area with slider that opens onto deck, and spacious laundry/storage room with separate entry onto its own wood deck. Living room with fireplace and dining room both have floor to ceiling windows to enjoy the magnificent views and natural light! Kitchen has propane down draft range, new stainless steel refrigerator, prep sink, granite counter tops, and lots of windows to look onto the deck and the views beyond. Entry door leads to deck that spans the entire west side of the home! Plus a great room/guest quarters with separate entrance that includes a mini kitchen and can be shut off from main area of home. Upstairs features a game room/sitting area, dormer windows, and spacious bedroom with bath. Hardwood floors on both levels. Outside has a concrete patio, sidewalk, flower garden, walnut trees, wooded area, path to Calapooya, and a level area once used for a garden! There is also a gazebo with fire pit for evening gatherings! 400 sqft workshop basement. New roof in 2025 and exterior paint May 2026. Expansive concrete parking and 2 detached metal carports. Well for exterior watering, lean-to attached to pump house for garden tools, PLUS 1.6 acre irrigation rights from the Calapooya (home is on city water). Large, level graveled lot on the south side of home with circular drive and room to park your RV, boat, ATV's, and build a shop! Or apply for a zone change and subdivide to increase your options. Private setting, yet close to schools and sporting events. Lots of possibilities on this rare property! Listing Broker is related to Sellers. Seller is very motivated and encourages any/all offers!

905 NE THIRD ST, Oakland

$799,000

5 Beds ⋅ 4 Baths ⋅ 699245704 MLS

**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!****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

$15,500,000

5 Beds ⋅ 4 Baths ⋅ 305448302 MLS

Nestled in Oregon's scenic Umpqua Valley, this extraordinary 2,670-acre ranch offers a rare blend of luxury, tranquility, & commercial potential. Atop a prominent knoll stands a grand 7,936-sqft Tudor-style mansion that commands sweeping 360-degree views of rolling pasture, woodlands, & distant hills. The home's 3-levels are a testament to craftsmanship & attention to detail featuring 5 spacious bedrooms, 4 full bathrooms, 2 powder rooms, custom millwork, stained-glass accents, chandeliers, & multiple fireplaces for an atmosphere of timeless elegance. Seeking a quiet reading space? Step into the charming, castle-like library. The rolling ladder & private balcony enhances its storybook feel. The basement is a haven for wellness. It features a hot tub, tanning bed, sauna & steam room, & fully equipped exercise room. Prefer a drink? Head to the full bar or select a bottle from the wine cellar. The kitchen offers style & functionality with a built-in Sub-Zero refrigerator, custom copper range hood, ample workspace, & storage. Currently operating as a working cattle ranch, the property includes a general-purpose building with a Helicopter hangar & landing pad, caretaker's apartment, meat-processing room, & workshop. A state-registered, one-mile private airstrip caters to aviation needs with potential for further development. Conveniently located along Interstate 5 & close to Historic Oakland. Heaven's Gate Ranch is fully approved by the county for destination resort development with civil engineering, site maps, & utility designs already completed. The new owner will receive comprehensive documentation including plans for a 100-room hotel, restaurant, convention center, & 200-lot residential subdivision—providing an advantage for streamlined development & customization. These approvals & plans save years of work & expense. Heaven's Gate Ranch marries majestic living with the rare potential to craft a world-class destination resort. It is a once-in-a-lifetime opportunity.

331 METZ HILL RD, Oakland

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