Portland Real Estate Experts

Skyline Real Estate Neighborhood Guide


Skyline is one of the leafiest areas in Portland, striped with winding roads and stately homes to please all tastes. While not an officially designated neighborhood, Skyline Boulevard is recognized as one of the most picturesque areas of the city, attracting day trippers and photographers to its stunning views and curving streets. Homes for sale along Skyline are nestled into the lush greenery of Forest Park and the trees of the West Hills of Portland, where life is good and the views are even better. We love the West Hills because they offer a quiet, secluded, park-like atmosphere with views and a sophistication that reminds you how close you are to the best that Portland has to offer. You can literally glance down at the lights of the city skyline, complete with world-class dining, outstanding music venues, picturesque farmers markets, and the sparkling Willamette river, all while appreciating the privacy of your own piece of Northwest forest. How could it get better than that? At its peak height, the Skyline Neighborhood’s elevation tops 1100 feet, making it one of the first Portland neighborhoods to experience snow in the winter months. Miles of trails traverse the West Hills, offering a haven for active families and happy pets. Skyline definitely has an upscale, luxury feel, and you'll feel pampered by the welcoming environment of beautiful homes, outstanding schools, and amazing views of the best city in America.


The Skyline area was first plotted out to accommodate the Great Plank Road, an 1850's-era dirt and mud road that was created to connect the rich agriculture of the Tualatin Valley to the deep water ports of the Willamette and Columbia Rivers. The Great Plank Road traversed the distance between Goose Hollow and followed a path very similar to what is now Highway 26. Its route commenced in Goose Hollow and wound its way up modern-day Hwy 26. When you're driving up to explore the Skyline area, imagine all of the hard work and labor that it took to complete a road through such thickly forested and hilly terrain. Amazing!


Skyline Boulevard is located on the west slope of Portland's West Hills, adjacent to the natural wonderlands of Forest Park and Washington Park. For the next ten miles Skyline Boulevard meanders above Tualatin Valley through horse ranches, farmhouses and million dollar mansions. The views are breathtaking and though you are just a few miles from Downtown Portland, you'll feel miles away. Some of the official neighborhoods along Skyline are the Forest Park, Arlington Heights, Northwest Heights, Nob Hill, Linnton, and Southwest Hills neighborhoods. Skyline is located near some of the best schools in Portland, including Chapman Elementary School (2425 SW Vista Dr.), West Sylvan Middle School (8111 SW West Slope Dr.), and Lincoln High School (1600 SW Salmon St.).


Skyline is near the attraction-packed Washington Park, home to the Oregon Zoo (home to more than 1000 animals), the International Rose Test Garden (the oldest official rose test garden in the US), the World Forestry Center, the Oregon Vietnam Veterans Memorial, Hoyt Arboretum (home to over 10,000 trees of 1,100 species), the Portland Japanese Garden, the Oregon Children's Museum, and easy access to the Washington Park underground station to take advantage of MAX Light Rail transit into the heart of Downtown Portland.

During the summer months, the Washington Park and Zoo Railroad takes visitors on a peaceful trip around the park, including the Rose Garden and the Oregon Zoo. The train was built in the 1950's and is a charming way to enjoy the scenery and history of the area.

The Pittock Mansion: 3229 NW Pittock Drive, (off NW Burnside) The grounds provide lovely walks and picnic areas, and those who wish can hike to the mansion from nearby parks. The sweeping views from the mansion and grounds overlook Portland's downtown and Willamette River.

Forest Park Wildwood Trail: The 30-mile Wildwood Trail in Forest Park is part of the region’s 40-Mile Loop system that links Forest Park to pedestrian and trail routes along the Columbia River to Gresham, through southeast Portland, along the Willamette Greenway, and back to the Marquam Trail in southwest Portland. A landmark on the trail is the Stone House. This structure was built in the mid-1930s by the Works Progress Administration (WPA) as a public restroom. The infamous Columbus Day storm on October 12, 1962, took out the water line. Because the structure had been heavily vandalized over the years, the decision was made to gut the building rather than embark on costly repairs. It remains as a favorite spot to rest along the trail.


The Skyline area boasts a diverse selection of architectural styles, ranging from classic Northwest, to Colonial, to Mediterranean (and a lot of custom design in between). Homes for sale in Forest Park, Linnton, Arlington Heights, and Skyline Real Estate are often higher-end luxury homes with amazing views and custom details. 

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Residents of the West Hills have immediate access to the dining and shopping opportunities of Downtown Portland, the Pearl District, and the best of Nob Hill. Some of Portland's best restaurants are within an easy 10 minute drive from your hilltop home. In 2005, the Forest Heights Village Center opened its doors as the area's first shopping center with dining, coffee shops, dry cleaning, a hair studio and even a spa.

Skyline Restaurant - 1313 Northwest Skyline Boulevard - This classic diner serves up great burgers, fries, and milkshakes, perfect for a rest stop on an afternoon drive along Skyline Boulevard. They also serve up a mean breakfast. One of the last standing drive-ins in Portland, this historic spot features 1950's decor and menus, as well as summer car hops.

Skyline Tavern - 8031 Northwest Skyline Boulevard - A portland landmark, Skyline Tavern has sat upon the hill overlooking Beaverton and Hillsboro for over 50 years. Here you can watch the sun set over the city while playing horse shoes, pool, ping pong or darts. Music inside and out and a great beer selection. Come up the hill and view this extraordinary "Saloon" from the 40's and all it's antiques, atmosphere, and unsurpassed beauty.

Anna Bannanas - NW Portland's oldest independent coffee house has lots of perks: great coffee and staff, wifi, subtle music, laid back atmosphere with the "aged in a good way" feel, and they're dog friendly. Hours are open early, close late for whenever you have your coffee craving, and they serve some of the best chocolate milkshakes around. The menu is made up of pastries, breakfast choices, sandwiches, smoothies and shakes; there's also lots of comfortable seating to enjoy your coffee and book.

23Hoyt - This comfortable, sophisticated restaurant is where the resident food community feels at home. 23Hoyt's philosphy is "A New American Tavern" which combines bar menu favorites, like grilled burgers and fish & chips, with comforting Pacific Northwest classics such as grilled wild salmon, and a double cut pork chop with sweet corn and chanterelle succotash. The café, bar and dining room feature several seating areas, (including outdoor seating on NW 23rd Avenue) simultaneously providing warmth, comfort and refinement to customers while they dine on delicious "wow" food.

Papa Haydn - For 24 years Papa Haydn has been the popular stop for desserts thanks to the family-owned restaurant's focus on high quality foods, beverages, and service. But they don't just offer amazing desserts like Triple Chocolate Torte, Raspberry Gateau and Banana Cream Pie. The duck duck salad, is a delicious and modest dish of heaping fancy greens, two types of prepared duck and topped with an egg. Their menus change frequently, allowing them to take advantage of seasonal fare and keep their prices wonderfully modest.


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