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.
Shawn Watson
RE/MAX NORTHWEST - BRANCH OFFICE
(971) 308-4511
79 Total Sales
1 in Hillside
$720,000 Price
Zak Meaut
Premiere Property Group, LLC
(971) 273-1766
58 Total Sales
1 in Hillside
$1,100,000 Price
Kevin Caplener
Windermere Realty Trust
(971) 256-8125
169 Total Sales
1 in Hillside
$500,000 Price
Michael Green
Coldwell Banker Bain
(360) 803-1735
141 Total Sales
1 in Hillside
$925,000 Price
Katie Sengstake
Windermere Realty Trust
(971) 270-4414
118 Total Sales
2 in Hillside
$322K - $768K Price Range
Maureen Swan
Portland Proper Real Estate
(877) 525-3678
102 Total Sales
1 in Hillside
$595,000 Price
On average, homes in Hillside, Portland sell after 100 days on the market compared to the national average of 53 days. The median sale price for homes in Hillside, Portland over the last 12 months is $1,135,000, up 21% from the median home sale price over the previous 12 months.
$995,000
Perched on a picturesque Portland hillside with sweeping views, this modernized Tudor Revival home perfectly blends timeless charm with refined updates. A welcoming foyer opens to a gracious living room featuring a classic fireplace and elegant arched pass-throughs, highlighting the home’s character and craftsmanship. The updated kitchen is a showpiece with stainless steel appliances, an island
Sindos Searty Opt
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Perched above Portland’s beloved Alphabet District, 2677 NW Westover Road is a rare fusion of architectural pedigree, timeless elegance, and sweeping city views. This estate home offers over 4,100sf of refined living—where classic symmetry meets modern sophistication. Step into a foyer that sets the tone with graceful millwork and balanced proportions. The formal living is anchored by a fireplace
Patrick Clark Christie's International Real Estate Evergreen
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OPEN HOUSE 11/1 12-2PM. Refined Urban Living in the Heart of NW Portland. /Experience the perfect blend of luxury, comfort, and modern d 12-2PMesign 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
Dennis Haggar Coldwell Banker Bain
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Rarely available end-unit at the Joann’s Place Rowhomes in NW Portland’s Nob Hill and just blocks from vibrant NW 23rd Avenue. This exceptional home features expansive walls of windows, a fully fenced private backyard with easy care Trex deck and an extra deep garage that accommodates two tandem cars in addition to driveway parking. With its brick and cedar façade, these townhomes pay homage to
Dan Volkmer Windermere Realty Trust
$800,000
Spectacular view of city and Mount Hood from house perching on hill in Kings Heights. Wall of windows in living room faces east for unobstructed view! Large living room has fireplace, it is a living dining room combo, and has slider out to long deck facing city, you feel like you are in a treehouse, high above the world, looking out at the city and mountain! kitchen has eating area that also
Helen Hoyt Portland Creative Realtors
$495,000
Exceptional courtyard home in the heart of NW Portland in the coveted Westerly. With over 250 sqft of outdoor space and direct access to the scenic private courtyard, this home offers unparalleled outdoor condo living. Meticulously maintained and updated with modern luxury finishes including walnut storage built-ins and paneling. The spacious floor plan features a generous primary suite, 2nd
Sean Becker Sean Z Becker Real Estate
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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
