(That You’ve Probably Never Walked Through)

Not all of Portland’s luxury living is where you’d expect it. Some of the city’s most desirable addresses are tucked away in forested hillsides, hidden from main roads, or wrapped in timeless architecture that feels like it belongs in a European village.

Whether you're searching for a grand historic estate or a modern custom home with privacy to spare, these are the neighborhoods where Portland's most exclusive real estate quietly shines. Most locals haven’t even driven through them—but if you know, you know.

Here’s a look at five of the most sought-after places to live in and around Portland.

#1

Old-world elegance steps from Washington Park.

Tucked just above the Rose Garden and Japanese Garden, Arlington Heights is known for its gorgeous historic architecture, grand staircases, and winding hillside streets. You'll find Colonials, Tudors, and Mediterranean-style estates here—many dating back to the early 1900s and lovingly preserved or tastefully updated.

The neighborhood’s elevation offers city, mountain, and forest views, and its proximity to trails, tennis courts, and cultural landmarks makes it as livable as it is luxurious. It’s quiet, close-in, and full of character—a rare combination.

Explore the grandeur of Arlington Heights and browse current homes for sale. →

#2

Private estates. River views. A class of its own.

Technically outside Portland city limits, Dunthorpe sits just south of the Sellwood Bridge, nestled between the Willamette River and the forested hills of Tryon Creek. It’s close enough to downtown Portland to be convenient—but secluded enough to feel like a private world.

What makes Dunthorpe unique? In addition to lush grounds and historic estates, it’s home to the Riverdale School District, one of the most exclusive and sought-after in the state. Homes here include grand Colonials, French-style manors, and Mediterranean villas, often with gated drives, guest houses, and river frontage.

Discover more and view homes for sale in Dunthorpe →

#3

Secluded. Expansive. Custom.

If your dream home includes a private drive, room to build, and daily visits from deer, Forest Park delivers. Backing up to the 5,200-acre urban forest that gives the area its name, these homes often sit on oversized lots—many an acre or more—and offer rare privacy within city limits.

This is a haven for buyers looking to build custom, modern homes designed to blend into the natural surroundings. Forest Park combines architectural freedom with proximity to NW Portland and downtown, making it one of the few places where luxury and nature live in perfect balance.

Experience the magic of Forest Park living and see current homes for sale. →

#4

Mid-century lines. Panoramic views. Quiet sophistication.

Perched just above the Alphabet District, Hillside offers striking views of downtown Portland, the West Hills, and even Mount Hood on a clear day. It’s a favorite among buyers who want the best of both worlds—quick access to city life and a home that feels miles away.

The homes here range from mid-century moderns to updated contemporaries, often with oversized windows, thoughtful landscaping, and smart indoor-outdoor flow. It’s a neighborhood where design matters and privacy is built into the terrain.

Explore this tucked away enclave of gorgeous homes for sale in Hillside. →

#5

Timeless elegance meets Portland’s skyline.

Southwest Hills is home to many of Portland’s legacy properties—classic homes with traditional architecture and commanding views. The winding roads and heavily treed lots give it a peaceful, almost country-like feel, despite being minutes from the city’s cultural core.

Here you’ll find larger homes with long driveways, wraparound porches, and expansive outdoor spaces, often tucked into the hills above Goose Hollow and the Alphabet District. It's long been a favorite of professionals, creatives, and those who value space and serenity with a view.

View all that Southwest Hills has to offer, including current homes for sale. →

Why These Neighborhoods Stand Out

While Portland is known for its creative spirit and laid-back culture, these neighborhoods show off a different side of the city—one where craftsmanship, space, and timeless beauty still lead the way. Whether you're looking for a design-forward custom home or a historic estate with soul, these pockets offer the kind of exclusivity that doesn’t scream—it simply lives well.

Data sourced from the 2025 Portland Monthly Neighborhood dataset, MLS Data, including Walk Score, Bike Score, Transit Score, and commuter stats.