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.
Katie Sengstake
Windermere Realty Trust
(971) 270-4414
120 Total Sales
2 in Hillside
$322K - $768K Price Range
Maureen Swan
Portland Proper Real Estate
(877) 525-3678
105 Total Sales
1 in Hillside
$595,000 Price
Victoria Buck
Coldwell Banker Bain
(971) 351-0278
223 Total Sales
1 in Hillside
$925,000 Price
Jeff Birndorf
Cascade Hasson Sotheby's International Realty
(971) 307-9410
75 Total Sales
6 in Hillside
$440K - $1.3M Price Range
Nick Shivers
Keller Williams PDX Central
(971) 232-4415
1,272 Total Sales
1 in Hillside
$1,147,500 Price
John Powers
Real Broker
(855) 879-2931
47 Total Sales
1 in Hillside
$795,000 Price
Interested in learning more about homes in this area? Reach out to , an experienced agent in this neighborhood.
On average, homes in Hillside, Portland sell after 26 days on the market compared to the national average of 70 days. The median sale price for homes in Hillside, Portland over the last 12 months is $342,500, down 24% from the median home sale price over the previous 12 months.
$1,425,000
This contemporary NW modern home, designed by architect Jon R. Jurgen in 1982, has been beautifully updated with modern fixtures and designer finishes. Enter into a soul lifting space intentionally designed to utilize the sun's light to its advantage. The open kitchen to dining room with vaulted ceilings and natural light pouring in from the clerestory windows has been updated with Pedini
Marisa Swenson Modern Homes Collective
$398,800
When no cookie cutter condos will do, check out this unique, cozy-condo, masterfully tucked into a classic, NW Alphabet District, stately mansion. Only 6 units in this tight knit community, just a quick stroll from NW Portland's world-famous shops, restaurants and nightlife. City and territorial views this true one-bedroom-layout home with lots of vintage details including an enclosed sun porch.
William Gilliland Windermere Realty Trust
$1,249,900
This 4 bedroom (three en-suite!), 5.5 bathroom home has it all: stunning panoramic views of the city and landscapes from every room, open layout, gourmet kitchen, low maintenance yard, A++ location in the prestigious King's Heights neighborhood and SO MUCH MORE! Tons of light in this beautifully renovated English Tudor. Features include integrated audio, lighting, and security systems throughout,
Andrew Galler Realty Works Group
$899,000
Welcome to 2802 NW Ariel Terrace, a stunning NW Contemporary home, perched high above the street in Portland's coveted Kings Heights neighborhood. This custom-built residence offers refined living amongst the trees, featuring three bedrooms and three bathrooms. The home is designed to maximize natural light and offers breathtaking views of the Willamette River, Mt. St. Helens, Mt. Adams, and Mt.
Brett Fischer Corcoran Prime
$1,385,000
NW Classic: This inviting 4-bedroom, 3.5-bath, 3506 sq.ft. home sits in a quiet NW neighborhood with city and mountain views. Highlights include a Dream Kitchen Magazine-featured kitchen with Pyrolave countertops, breakfast nook with fireplace, primary suite with two walk-in closets and remodeled bathroom, and a lower-level family room with theater setup, fireplace, wine cellar, and separate
Stacy Niedermeyer Where, Inc
$1,795,000
Where timeless architecture meets a once-in-a-decade price - this Kings Heights Tudor is ready to steal the spotlight. Just up the hill from NW 23rd and moments to Forest Park’s 5,000 acres of trails, this 1927 Tudor offers over 6000+ square feet of rich architectural detail, leaded glass windows, grand rooms, and timeless character. Five bedrooms, six baths, and space to live, host, or just
Suzann Baricevic-Murphy Where, Inc.
Interested in learning more about homes in this area? Reach out to , an experienced agent in this neighborhood.
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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
