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.
Amy McMahon
Windermere Realty Trust
(503) 447-4403
95 Total Sales
2 in Hillside
$1.1M - $1.5M Price Range
Regina Very-Modesto
Keller Williams Realty Professionals
(573) 691-5440
25 Total Sales
1 in Hillside
$918,000 Price
Shawn Watson
RE/MAX NORTHWEST - BRANCH OFFICE
(971) 308-4511
82 Total Sales
1 in Hillside
$720,000 Price
Aimee Virnig
Windermere Realty Trust
(971) 245-2598
193 Total Sales
4 in Hillside
$770K - $2M Price Range
Zak Meaut
Premiere Property Group, LLC
(971) 273-1766
69 Total Sales
1 in Hillside
$1,100,000 Price
Sasha Welford
Windermere Realty Trust
(971) 703-5371
117 Total Sales
9 in Hillside
$460K - $1.5M Price Range
| 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 75 days on the market compared to the national average of 56 days. The median sale price for homes in Hillside, Portland over the last 12 months is $1,033,500, up 6% from the median home sale price over the previous 12 months.
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Median List Price
$1,125,000
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Median Sale Price
$1,033,500
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Median Single Family Sale Price
$1,320,000
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Median Townhouse Sale Price
$850,000
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Median 2 Bedroom Sale Price
$789,000
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Median Change From 1st List Price
3%
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Last 12 months Home Sales
72
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Median Home Sale Price YoY Change
6%
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Average Price Per Sq Ft
$406
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Number of Homes
1,087
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Number of Homes for Sale
32
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Median Year Built
1969
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Months of Supply
5.30
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Average Single Family Home Size Sq Ft
3,414
Significantly above the national average
1,934
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Average Townhouse Size Sq Ft
1,885
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Average 2 Bedroom Size Sq Ft
1,693
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Average 1 Bedroom Size Sq Ft
1,070
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Median Lot Size Sq Ft
8,712
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$999,900
Check out the night photos! —. Perched high above the city in Portland's prestigious Kings Heights neighborhood, this exceptional mid-century modern home showcases sweeping panoramic views of the city skyline, Willamette River, and surrounding mountains. Thoughtfully positioned to maximize natural light, privacy, and scenery, the home blends timeless architecture with modern comfort.A dramatic
Jesse Richter Knipe Realty ERA Powered
$284,900
Perched high above the city on a gorgeous hillside bluff, over looking the city. 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
$1,595,000
Welcome to #601 at The Westerly, where you open the door, and the city unfolds before you. The Portland skyline stretching wide, beautiful mountains standing watch on the horizon and breathtaking floor-to-ceiling windows turning every sunrise and sunset into a private show. This is what luxury living in Nob Hill feels like. The open floor plan has a sense of ease from the living room to dining
$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
$1,499,000
Experience modern living with this stunning new construction by Creekside Homes. This beautifully designed home offers 3 spacious bedrooms, 3 full bathrooms, and approximately 2,700 sqft of thoughtfully crafted living space. Featuring an open-concept floor plan, high-end finishes, designer touches, and abundant natural light throughout. The gourmet kitchen flows seamlessly into the living and
$1,995,000
Bold architecture. Thoughtful design. Exceptional execution. This custom NW modern residence in Kings Heights offers nearly 4,000 square feet of refined living space where every detail has been carefully considered. Walls of glass flood the home with natural light, while the open main level flows effortlessly between the kitchen, dining, living, and outdoor gathering spaces. Designer finishes,
Todd Talcott Windermere Realty Trust
$1,598,000
OPEN Sun 8/2 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
$875,000
Outstanding example of a Midcentury Daylight Ranch home with stunning views to the NE featuring Mt. St. Helens and Mt. Adams, Willamette river, the waterfront and forest. Decks on 3 levels provide plentiful opportunities to entertain and relax. Hardwood floors, 3 fireplaces, spacious + practical kitchen with pantry, eating nook and access to the decks. Primary suite upstairs features a wall of
Chris Bonner Neighbors Realty
$455,000
Premier condo living at the Westerly. Rare garden-level residence with a private front patio overlooking the west-facing garden commons, offering the feel of courtyard living rather than a traditional condo. Impeccably maintained with soaring ceilings and warm engineered hardwood floors. Cooks will love the gourmet kitchen featuring gas appliances, a built in oven, pantry, and island. The
Karoline Ashley Windermere Realty Trust
$1,250,000
Outstanding $95K Price Improvement!! OPEN Sunday, 8/2 from 11-1PM! Luxury city living with spectacular views at The Westerly just got even more compelling! 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
Christy MacColl Windermere Realty Trust
$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
$1,050,000
NEW PRICE FOR A RARE NOB HILL LIFESTYLE: ENJOY EURO-STYLE WALKABILITY, NOW OFFERED AT $1,050,000.European-style luxury meets West Hills tranquility. Perched on the second floor, this stunning Hillside residence offers seamless SINGLE-LEVEL LIVING. Two elegant sets of French doors—from the living/dining area and the kitchen—plus a bedroom glass door open to nearly 500 SQ FT OF PRIVATE TERRACE
Kimberly Brenner Berkshire Hathaway HomeServices NW Real Estate
$925,000
Beautifully maintained, this lovely traditional home in the Hillside neighborhood stands tall above downtown Portland, overlooking gorgeous trees and territorial views. Spend time gazing out from your warm and inviting kitchen and breakfast nook featuring custom hand-painted tiles, a gorgeous terracotta tile floor and warm family room; you'll feel like you're in a villa in the hills of France!
Barbara Mount Premiere Property Group, LLC
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Number of Homes for Rent
1
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Median Rent
$7,000
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Median Single Family Home Rent
$7,000
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Total Population
2,348
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Median Age
52
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Population Density
6 ppl/acre
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Population under 18
17%
Below the national average
23.8%
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Population over 65
30.4%
Above the national average
19.1%
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Median Household Income
$203,065
Significantly above the national average
$79,597
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Average Household Income
$208,612
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High School Graduates
98.9%
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College Graduates
84.7%
Significantly above the national average
34.1%
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Advanced Degrees
44.3%
Significantly above the national average
13.3%
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% Population in Labor Force
66.6%
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Annual Precipitation
41''
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Average Winter Low Temperature
34°F
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Average Summer High Temperature
82°F
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Annual Snowfall
1''
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Bikeability
Walkability
Transit
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
