Wound into the hills of northwest Portland, is a neighborhood whose unique charm is largely derived from the eclectic mix of homes that fill its streets. The appropriately named Hillside features a collection of houses that draw from a range of architectural styles, all perched amidst the area’s picturesque landscape.
Hillside is largely filled with single-family homes, built along the neighborhood’s sloping roads, though there are some condos here as well. The single-family homes in Hillside cover styles ranging from Colonial Revival to Mediterranean. Many of the options here were built in the early part of the 20th century, but home seekers can also find some options built midcentury and later. The way homes are oriented on Hillside’s hilly streets means that front yard space is generally limited, but some properties include backyard space. Price tags here span from the $300,000s for a one-bedroom and one-bathroom condo to more than $2 million for a home pushing 5,000 or 6,000 square feet. “What makes our city so special is it's very irregular. You’ll have a $500,000 house next to a $2 million house,” says local Realtor Libby Benz of Windermere Realty Trust, who frequently works in the Hillside area.
Hillside is primarily residential, but children and their families can find multiple schools in the Portland Public Schools system nearby. Kids can start at Chapman Elementary for kindergarten to fifth grade, a school with a B-plus overall grade on Niche and a list of afterschool activities that includes yoga. From Chapman, students in Hillside move on to the A-minus-rated West Sylvan Middle, which has its own Lego robotics club. Lincoln High, which has an A grade, is next, a school with career and technical education programs in audio engineering, business and management, computer science and robotics, construction, design and applied arts, future endeavors, hospitality and tourism, and media studies/mass communications.
The terrain of Hillside is a boon for nature lovers. One destination of note is Macleay Park, which is almost 140 acres total and stretches into Hillside. It’s a heavily wooded sanctuary full of Douglas fir and western red cedar trees, with multiple trails carving through it. One of the paths that cuts into Hillside is the Wildwood Trail, which is almost 30 miles in total. The beginning of the shorter, half-mile Cumberland Trail is also located in Hillside.
Those looking for indoor recreation can head over to the Hillside Community Center. That facility includes a rock climbing wall and a basketball court, and is home to a range of youth programs and camps, from ballet classes to ceramics classes.
For shopping or a bite to eat, locals can head to the southeast corner of Hillside, where the Uptown Shopping Center is located. There they can nab a sandwich at Phil's Meat Market & Delicatessen or a bowl at Kizuki Ramen & Izakaya. There’s also a Fred Meyer just down the street, convenient for groceries and more. “It’s very, very popular,” Benz says of this slice of the city. “With boutiques and small restaurants and pubs. It’s a wonderful part of the city.”
Residents can perhaps follow a meal at the Uptown Shopping Center with a visit to the 25,000-seat Providence Park for a Portland Timbers soccer game. Providence Park is situated across from the Fred Meyers. Also, history lovers in Hillside may choose to spend an afternoon at the historic Pittock Mansion, a 16,000-square-foot French Renaissance home that was built in 1914 by Henry Pittock, who was publisher of The Oregonian newspaper. The 23-room colossus is now a museum full of period furnishings and artifacts.
Hillside features multiple stops in the area’s TriMet bus system. TriMet covers the Portland metro area with more than 80 bus lines.
Also, despite its secluded feel, Hillside is only a couple of miles from Portland’s downtown, a quick drive without even having to hop on the highway. But Interstate 405 isn’t too far away either, which connects to Interstate 5 for trips across the state line and into Vancouver, Washington, about 9 miles away.
Hillside locals are known to organize a variety of events for the community. The list includes everything from a Family Fun Night in the spring to a Fourth of July picnic and parade to a Halloween Festival.
According to the CAP Index, instances of larceny, burglary and motor vehicle theft rank above national averages in Hillside.
Mandi Mack
TRADITION REAL ESTATE PARTNERS
(971) 328-4330
196 Total Sales
1 in Hillside
$325,000 Price
Doug Bergmann
John L. Scott
(503) 479-4267
33 Total Sales
1 in Hillside
$1,200,000 Price
Summer Browner
Keller Williams Realty Professionals
(360) 803-3063
91 Total Sales
1 in Hillside
$1,419,752 Price
Amy Rhew
Real Broker
(971) 407-5148
78 Total Sales
1 in Hillside
$460,000 Price
Suzanne Clark
Cascade Hasson Sotheby's International Realty
(503) 831-9908
99 Total Sales
1 in Hillside
$1,315,000 Price
Shawn Watson
RE/MAX NORTHWEST - BRANCH OFFICE
(971) 308-4511
85 Total Sales
1 in Hillside
$720,000 Price
| 1 - Low Crime, 10 - High Crime | Hillside | US |
|---|---|---|
| Homicide | 5 | 4 |
| Sexual Assault | 5 | 4 |
| Assault with Weapon | 4 | 4 |
| Robbery | 4 | 4 |
| Burglary | 6 | 4 |
| Motor Vehicle Theft | 6 | 4 |
| Larceny | 6 | 4 |
| Crime Score | 5 | 4 |
Source: WhatIsMyCrimeRisk.com
On average, homes in Hillside, Portland sell after 94 days on the market compared to the national average of 55 days. The median sale price for homes in Hillside, Portland over the last 12 months is $1,067,000, up 16% from the median home sale price over the previous 12 months.
$289,900
Perched high above the city on a scenic hillside bluff, this private end-unit condo captures sweeping views of Portland’s skyline, surrounding mountains, winding rivers, and lush valley below. Few homes offer this combination of breathtaking scenery, peaceful privacy, and unbeatable access to the heart of Northwest Portland.Inside, the home features engineered hardwood floors, granite
$1,350,000
*TWILIGHT OPEN HOUSE FRIDAY 4/3 5:30PM TO 7:30PM, COME EXPERIENCE THE SUNSET VIEWS & CITY LIGHTS* City and mountain views from nearly every room, including Mt. Hood and Mt. St. Helens, set on a quiet Kings Heights street above the city. Just blocks from NW 23rd, with an attached garage, driveway parking, and additional street parking, this home has been fully remodeled inside and out with a high
Stephen Malfa Real Broker
$895,000
Welcome to 2724 NW Imperial Terrace, a beautifully situated home nestled in one of Portland’s most desirable neighborhoods. Perched in the scenic West Hills, this property offers the perfect blend of tranquility, character, and city convenience. This architecturally significant English Tudor home features beamed & barrel-vaulted ceilings trimmed in natural woodwork, arched doors and wrought iron
Greg Messick RealtyNET, LLC
$350,000
Located in the coveted West Hills of Portland, this rare .24-acre parcel is a blank canvas waiting for the right vision. Whether you're a buyer dreaming of a custom forever home, a developer eyeing a high-value build, or an investor seeking a foothold in one of Portland's most desirable enclaves, this lot delivers the location and the land to make it real. You will have easy access to Forest
$1,695,000
Welcome to one of Portland's popular, premier neighborhoods Kings Heights! Gracious 1920's Traditional proudly nestled into the hillside overlooking the City, offering the homeowner amazing 4 Mountain View's, Willamette River, Cascade Foothills, and City's from almost every room w/amazing "ever changing" Vistas Day & Night. Period architecture greets you featuring spacious entry, higher ceilings,
Libby Benz Windermere Realty Trust
$1,477,500
Sweeping mountain and city views, perched above the city in NW Portland, this light filled home blends striking Art Deco influences with the essence of Pacific Northwest living where forested hills, mountain vistas, and city lights come together in perfect balance.From soft sunrises over the mountains to evenings illuminated by the Portland skyline, the ever changing views create a daily backdrop
Sara Jones Graham Cascade Hasson Sotheby's International Realty
$1,395,000
**OPEN HOUSE 3/29 from 11-1pm!** Experience elevated city living with spectacular views at The Westerly! This beautifully remodeled SE facing residence offers refined comfort, thoughtful elevated design, and sweeping vistas of downtown Portland, Mt. Hood, and Mount Adams through dramatic floor-to-ceiling windows that fill the home with natural light. The extensive remodel features new wood
Christy MacColl Windermere Realty Trust
$519,000
Quite possibly the best views in the complex - maybe even all of Portland! Enjoy this spacious and refreshing townhome style condo that includes two bedrooms and an oversized tandem garage. Remodeled kitchen, wood flooring, absolutely BREATHTAKING views of four mountains, downtown Portland and the trees of Washington Park. Minutes to all that Northwest 23rd / the Alphabet District has to offer
Kelly Fitzmaurice Harnish Company Realtors
$1,575,000
This beautifully restored Art Deco executive home is nestled on a desirable corner lot in the prestigious NW Heights neighborhood, offering unmatched curb appeal and a south-facing flat yard. With its thoughtfully curated design, the home boasts 5 sets of French doors that open to an exquisite backyard, boasting mature landscaping, premium hardscaped entertaining areas, and a turf yard—perfectly
Paige Stefani Where, Inc
$275,000
Urban living at its best in a bright and spacious one-bedroom condo high up on the hilltop. Open kitchen/dining room/ living room plan with large windows and private deck overlooking the City skyline, with breathtaking views of Mt Adams and Mt St Helens. This remodeled condo features quartz countertop, wood floor, stainless appliances, in-unit laundry, fresh paint in 2025, low HOAs and additional
Fangfei Yang Oregon First
$425,000
Rare opportunity to reside in this light, bright condo in desirable Hillside community above vibrant NW 23rd Ave. This large 1 bed, 1 bath features a wall of windows and expansive deck that takes in views of Mt. Hood and city lights. Remodeled Kitchen and Bath. New Windows and Heat Pump. Utilities: Water/Sewer $124. Garbage $47. Cable $91.
Dianne Hagan Premiere Property Group, LLC
$1,425,000
Exquisite 1932 English Tudor in pristine condition, offering views of the Portland skyline, Mt. Hood and Mt. St. Helens from its setting in one of the city's most sought-after historic neighborhoods. Forest Park's trail system is just outside your door, while the boutiques, cafés, and cultural destinations of NW 23rd Avenue and the Pearl District are only minutes away. Classic architectural
Cindy Johnson John L. Scott Portland Central
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Walk Score®
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Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Suburban enclave overlooking Washington Park, 3 miles from downtown Portland
Bohemian hub with boutiques, historic homes and converted industrial buildings
A hip district known for its bustling art, shopping and dining scenes
A lush, hilly neighborhood full of charming homes and trendy retail and dining
Charming, pseudo-suburban neighborhood with ample greenery southwest of Downtown
Reclusive, mountainous corner of Portland with top-tier parks and schools