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
111 Total Sales
2 in Hillside
$322K - $768K Price Range
Maureen Swan
Portland Proper Real Estate
(877) 525-3678
101 Total Sales
1 in Hillside
$595,000 Price
Victoria Buck
Coldwell Banker Bain
(971) 351-0278
212 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
1,288 Total Sales
1 in Hillside
$1,147,500 Price
John Powers
Real Broker
(855) 879-2931
50 Total Sales
1 in Hillside
$795,000 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 97 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 $1,067,000, up 16% from the median home sale price over the previous 12 months.
$1,295,000
-Classic Northwest home, which offers a unique opportunity to enjoy beautiful morning sunrises and expansive east-facing views. Situated in a tranquil neighborhood, this 3,506-square-foot home features four bedrooms and three and a half bathrooms.-The interior is highlighted by a "Dream Kitchen Magazine"-featured kitchen, complete with premium "Pyrolave" (enameled lava) countertops and a
Stacy Niedermeyer Where, Inc
$1,799,900
Located in sought-after King’s Heights, this NW Contemporary home offers sweeping views of the city, river, and mountains, just minutes from Portland’s most vibrant cultural destinations. Designed by the Paolo Design Group, the home has been extensively reimagined since 2012 with a focus on quality construction, thoughtful design, and long-term performance. The exterior features custom clear
Marc Fox Keller Williams Realty Portland Premiere
$1,150,000
A home offering a beautiful combination of design and nature. Set in complete privacy with spectacular views of the city and Portland landscape. Relax and see Mt Hood perfectly framed in the window. Light abounds with walls of windows and vaulted beamed ceilings. The primary ensuite on the main, hardwood floors, new carpeting, custom cabinetry, a spacious kitchen with an incredible amount of
Thomas Patterson Belrose Realty, LLC
$1,474,900
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
$1,575,000
Experience timeless elegance reimagined. Perched in Portland’s coveted Kings Heights, this 1939 traditional has been meticulously restored by Maison Inc. to the highest modern design standards while fulfilling the owners mission in honoring its original character. Sweeping city vistas frame Mt. St. Helens and Mt. Adams, setting the stage for refined living. Every detail has been considered:
Steve Odermann LUXE Forbes Global Properties
$199,000
Great opportunity to build your dream house in the West Hills on a quarter acre view lot. Zoned R7. Buyer to do due diligence.
Devyn Stearns Works Real Estate
$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
$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
$1,050,000
Behind The Gated Entry This Westover Square View Condo Has It All. One Level Living Beautifully Maintained with Meticulous Detail. Wood Floors, Fireplace, Custom Bookcases Throughout. Entertainment Size 19'X12' View Terrace Off Living Room. Gracious Dining Room with Built-Ins and Bookcases, Den/Office Adjoins the Newly Refurbished Kitchen with Marble Basket Weave Backsplash. Open Picture Windows
Patricia Miller Where, Inc
$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
$290,000
Breathtaking views! Come sit above the clouds from this bright and spacious Hilltop condo, perfectly positioned for both privacy and convenience. Tucked away in a tranquil setting yet just minutes from Washington Park trails and the bustling shops and restaurants of NW 23rd and 21st Avenues. This home offers the best of both worlds. With one of the most coveted viewpoints in the community, take
Atika Hagen Living Room Realty
Bike Score®
Walk Score®
Transit Score®
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
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
