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.
Becky Jackson
Corcoran Prime
(855) 920-3084
48 Total Sales
2 in Hillside
$1.3M - $2.3M Price Range
Maureen Swan
Portland Proper Real Estate
(877) 525-3678
100 Total Sales
1 in Hillside
$595,000 Price
Victoria Buck
Coldwell Banker Bain
(971) 351-0278
213 Total Sales
1 in Hillside
$925,000 Price
Jeff Birndorf
Cascade Hasson Sotheby's International Realty
(971) 307-9410
78 Total Sales
8 in Hillside
$440K - $1.3M Price Range
Nick Shivers
eXp Realty, LLC
(971) 232-4415
1,284 Total Sales
1 in Hillside
$1,147,500 Price
Chris Eden
eXp Realty, LLC
(888) 558-6087
117 Total Sales
1 in Hillside
$850,000 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 91 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 $1,033,500, up 12% from the median home sale price over the previous 12 months.
$850,000
Open House Sat 3/21 and Sun 3/22 1-3pm. Nestled in the serene Northwest hills, this stunning English cottage is a true gem. Presenting breathtaking views and walkable distance to the heart of the city, you will enjoy privacy and accessibility. Step inside to newly refinished hardwood floors that add warmth and elegance to the living space. This home marries vintage aesthetics with modern
Carolyn Hoty Keller Williams Realty Professionals
$1,099,000
This Kings Heights cottage style home is truly one of a kind. Timeliness character combined with tasteful upgrades in a highly desirable neighborhood. The main floor features real hardwoods, a tuscan style kitchen with high end appliances and granite countertops, a cozy den with wood accents and wood burning fireplace, a huge dining space with exposed beams, and a spacious great room with
Tracy Hasson Cascade Hasson Sotheby's International Realty
$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
$1,695,000
OPEN 3/8 SUN FROM 1 TO 3PM. 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
Libby Benz Windermere Realty Trust
$1,395,000
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 floors, fresh paint throughout, new
Christy MacColl Windermere Realty Trust
$1,424,900
VIEWS Galore! Prepare to be wowed as you step into this newly renovated Modern Craftsman in the heart of Kings Heights! Taken down to the studs and brought back with extensive thought on design and detail. Basque in the comforts of this home, while enjoying the stunning City and Mountain views. Open-concept main-floor living features retractable doors off the great room, showcasing downtown
Alicia Liberty MORE Realty
$285,000
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
$450,000
Refined Urban Living in the Heart of NW Portland.Experience the perfect blend of luxury, comfort, and modern design in this one-level condominium. Offered fully furnished (optional). Enter through the lobby or your private courtyard entrance into a serene and secure retreat that feels worlds away, yet sits just steps from vibrant NW 23rd Avenue — Portland’s premier shopping and dining district.A
Dennis Haggar Coldwell Banker Bain
$129,000
An exceptional opportunity to build in one of Portland’s most coveted West Hills locations. This 7,000–9,999 sq ft lot on NW Macleay Blvd sits directly across from 140 NW Macleay Blvd and offers the rare combination of privacy, proximity, and potential—ideal for a custom luxury residence or long-term investment hold.Located in the prestigious Kings Heights neighborhood, the site offers
Dori Olmsted Cascade Hasson Sotheby's International Realty
$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
$140,000
PRIME LOCATION right off Burnside Rd in Kings Heights. Hillside lot with 2 underlying plotted lots, could possibly be converted into 2 separate tax lots with lot confirmation (per BDS). Build options include Single family home, SF Home w/ ADU, or Duplex on each lot (per BDS). Can access the property from Santanita Ter or Burnside Rd. Lots undeveloped. *Adjacent lot w/ home and additional vacant
Brian Migliaccio Premiere Property Group, LLC
$150,000
Build your dream home on this private view lot in the coveted King's Heights neighborhood. Located on a private dead end culdesac adjacent to Forest Park the potential is endless. Enjoy unobstructed views of the city and mountains. With an 81' wide lot the design options are abundant. Don't miss this great opportunity!
Dori Olmsted Cascade Hasson Sotheby's International Realty
$299,000
Enjoy breathtaking views, peaceful living, and unbeatable walkability in this beautifully updated condo tucked away in a serene, wooded setting- just steps from the vibrant shops, dining, and energy of NW 23rd. Perfectly positioned up one flight of stairs, this home truly lives large, offering privacy, quiet, and exceptional natural light.The bright and inviting living room flows seamlessly into
Katie Ransom MORE Realty
Bike Score®
Walk Score®
Transit Score®
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