Hillside

Tucked into the West Hills of Northwest Portland, the Hillside neighborhood is one of the city’s most distinctive and quietly celebrated residential enclaves. Folded into narrow, winding streets that defy the grid, Hillside rises above the vibrant NW 23rd Avenue corridor with sweeping views of the Portland skyline, the Willamette River, and — on clear days — Mount Hood and the Cascades. It is bordered by the Northwest District to the east, Forest Park to the west and north, Arlington Heights to the south, and Sylvan-Highlands to the southwest. As an experienced and knowledgeable REALTOR® in the area, Hillside is the area I chose when I moved to my current home.

Also frequently referenced alongside Kings Heights, Hillside is anchored at its center by the historic Hillside Community Center (635 NW Culpepper Terrace) — formerly the Catlin Gabel School, designed by renowned Oregon architect Pietro Belluschi. When developers threatened to convert it to condominiums, residents pooled resources to purchase and preserve it. That story captures the spirit of this neighborhood: deeply invested, fiercely independent, and committed to place.

Housing Styles and Architecture

Hillside’s residential character is defined by the winding topography that shapes every lot and sightline. The housing stock spans the full range of early 20th-century Portland styles, including classic Bungalows, Colonial Revival, Cape Cod, Four Square, Mediterranean, and Old Portland vernacular homes. Many were built between 1900 and 1940, with some mid-century additions rounding out the mix.

Lush, mature old-growth trees line nearly every street, creating a canopy that heightens the sense of seclusion. Because of the steep terrain, front yard space is often limited, though many properties feature private backyard areas with views. A small number of contemporary condominium buildings — including the architecturally notable The Westerly (a 14-story tower by Ankrom Moisan Architects, completed 2008) and The Westover (5 stories, completed 1999) — offer lower-maintenance living at the neighborhood’s eastern edge along NW Westover Road.

The overwhelming majority of residents own their homes, contributing to a strong sense of continuity and stewardship.

Median Home Sale Price (recent 12-month period): approximately $1,136,250, reflecting the neighborhood’s position among Portland’s most established residential areas. (Verify against current MLS data before publishing — this figure is from an earlier pull.)

Parks, Landmarks & Nearby Places

Hillside enjoys exceptional proximity to some of Portland’s most celebrated green spaces and landmarks.

Hillside Park — 653 NW Culpepper Terrace. A 3.41-acre neighborhood park featuring basketball courts, tennis courts, a playground, a soccer field, and both paved and unpaved paths. The adjacent Hillside Community Center includes a gymnasium, classrooms, rock climbing wall, kitchen, and youth programming ranging from ballet to ceramics.

Forest Park — One of the largest urban forests in the United States, Forest Park borders Hillside to the north and west, offering more than 70 miles of trails through Douglas fir and western red cedar. Trails accessible from the neighborhood include the Wildwood Trail and the Cumberland Trail.

Macleay Park — Nearly 140 acres of forested canyon, accessible via the Wildwood Trail and beloved for its dense Pacific Northwest woodland character.

Pittock Mansion — 3229 NW Pittock Dr. A 16,000-square-foot French Renaissance estate built in 1914 by Oregonian newspaper publisher Henry Pittock. The grounds are free to walk and offer commanding views of downtown Portland, the river, and multiple Cascade peaks. Interior tours are ticketed.

Washington Park — Just south of Hillside across West Burnside, Washington Park encompasses the Oregon Zoo, the Portland Japanese Garden, the International Rose Test Garden, the Portland Children’s Museum, and the World Forestry Center. MAX Light Rail serves the park directly.

The Barbara Walker Crossing — A footbridge on the 30-mile Wildwood Trail spanning West Burnside Road, allowing uninterrupted trail access between Forest Park and Washington Park-area trails.

Kings Heights Staircase — A historic 157-step staircase beneath a canopy of lush vegetation connecting NW Westover Road and NW Summit Avenue — a favorite among local walkers.

Adams Community Garden — 4300 NW Cornell Road. A community growing space at the neighborhood’s northern edge.

Providence Park — The 25,000-seat home of the Portland Timbers (MLS) and Portland Thorns (NWSL), located at the neighborhood’s southeastern boundary near West Burnside and NW 18th Avenue. An easy downhill walk or short drive.

Public Schools Serving Hillside

Students in the Hillside neighborhood attend Portland Public Schools (PPS). School assignments are determined by address; verify boundaries at pps.net.

Elementary: Chapman Elementary School — Northwest Portland’s beloved neighborhood elementary, known for strong community involvement.
Middle School: West Sylvan Middle School — Located in the West Hills, consistently well-regarded within PPS.
High School: Lincoln High School — A comprehensive high school in Goose Hollow, rebuilt and reopened in 2022 with state-of-the-art facilities.

Key Features

Panoramic views of the Portland skyline, Willamette River, Mt. Hood, and the Cascades
Direct trail access to Forest Park, Macleay Park, and the 30-mile Wildwood Trail
Historic early 20th-century architecture on narrow, winding streets — virtually no straight roads
The Hillside Community Center, a preserved neighborhood landmark designed by Pietro Belluschi
Pittock Mansion and its grounds — free to explore — just steps from residential streets
Immediate proximity to the NW 23rd Avenue / Nob Hill commercial corridor
Walking and biking trails connecting directly to Washington Park and the Oregon Zoo (via MAX)
The historic Kings Heights Staircase — 157 steps through old-growth canopy
Primarily owner-occupied housing stock with a strong neighborhood association
Approximately 7–10 minutes by car to downtown Portland; accessible on foot or bike for the active commuter

What Locals Love

Hillside has remarkable access to everything Portland has to offer, while retaining a remote “in the woods” feeling. Downtown is about 6 minutes away down Burnside and Beaverton’s Cedar Hills Boulevard with its’ myriad of stores and entertainment venues is only about 12-15 minutes away. Locals can enjoy the theatre or concerts downtown or the beautiful International Rose Test garden, the Japanese Garden, and Washington Park and the zoo without a lot of driving.
Being located right on the edge of Forest Park means that you have easy access to Forest Park trail system
The Kings Heights staircase and the Albermarle Terrace to Westover shortcut leads you right onto 23rd Street (Trendy-Third) in the heart of the Alphabet District/Nob Hill.

Things to Consider

Although most homes have garages, overnight street parking is not allowed on many streets.
THe area is very hilly and is well above the snow line so a 4-wheel vehicle and tires rated for snow are required. In fact, when it does snow, the Police require you to pull over and put on chains or prove your tires have the little snowflake on them.
Bicyclists will find the steep hills a challenge (or maybe a thrill?)
Lots of towering trees, protected by city law, can pose a risk of falling in heavy storms.

Popular Restaurants, Cafes & Pubs

Hillside itself is primarily residential, but its position directly above the NW 23rd Avenue / Nob Hill corridor puts residents within easy reach of one of Portland’s finest dining and café districts.

Phil’s Meat Market & Delicatessen — Located at the Uptown Shopping Center (SE corner of Hillside). A neighborhood institution serving deli sandwiches, premium seafood, and quality cuts of meat. 🌐 philsmeatmarket.com

Kizuki Ramen & Izakaya — Also in the Uptown Shopping Center. Authentic Japanese ramen and izakaya-style small plates in a welcoming, casual setting.

Barista — 539 NW 23rd Ave. A destination espresso bar with a beautifully appointed interior — leather booths, parquet floors, and gold-rimmed mirrors. 🌐 baristapdx.com

St. Jack — 1610 NW 23rd Ave. A rustic French bistro serving coq au vin, duck confit, and a curated wine list. The happy hour is a neighborhood favorite. 🌐 stjackpdx.com

Papa Haydn — 701 NW 23rd Ave. A Portland institution for over four decades, celebrated for its legendary desserts, brunch, and upscale American cuisine. 🌐 papahaydn.com

The Fireside — 801 NW 23rd Ave. A handsome gastropub with dual fireplaces serving Pacific Northwest cuisine, craft cocktails, and weekend brunch. 🌐 pdxfireside.com

Ken’s Artisan Bakery — 338 NW 21st Ave. A Portland legend for naturally leavened breads, pastries, soups, and sandwiches. 🌐 kensartisan.com

St. Honoré Boulangerie — 2335 NW Thurman St. Authentic French boulangerie with exceptional croissants, baguettes, tarts, and café fare. 🌐 sthonore.com

Kells Irish Pub & Brewery — 210 NW 21st Ave. A long-running Irish brew pub with house-crafted IPA, Irish lager, and Red Ale; hearty pub fare; welcoming patio. 🌐 kellsbrewpub.com

Case Study Coffee Roasters — 802 NW 23rd Ave. Housed inside a stunning white Victorian home, this café is a favorite for specialty coffee and a quintessentially Portland atmosphere. 🌐 casestudycoffee.com

Transportation & Access

Hillside’s location above NW Portland gives it excellent access to downtown and the broader metro while maintaining a decidedly residential character. Most residents commute by car, with a drive to downtown Portland taking approximately 7–10 minutes via West Burnside or NW Westover Road. Portland International Airport is approximately 30 minutes away.

TriMet Bus service connects the neighborhood to NW 23rd Avenue and downtown Portland. The Portland Streetcar NS Line terminates in the Northwest District, linking to the Pearl District, Downtown, and South Waterfront. MAX Light Rail serves nearby Washington Park, providing easy access to the zoo, gardens, and connections throughout the metro.

For those who prefer active transportation, the neighborhood’s hidden staircases, forest trails, and downhill routes into the Northwest District make walking and cycling viable options — particularly for the outbound leg. The return trip uphill is best made via TriMet.

About PDXHomesforSale.com

Lauren Perreault is a Principal Broker at Fiv Realty, licensed in Oregon, Washington, and California, with more than 21 years of experience in Portland Metro real estate. Whether you’re exploring Hillside or any other corner of the Portland area, Lauren combines deep local knowledge with a data-driven approach to help buyers and sellers make informed decisions.

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