5-Bedroom Homes for Sale in Southwest Hills

An incredibly unique and extraordinarily functional floorplan is the highlight of this immaculate Allison Dean Designed & Built Home. Large Windows in every room embrace the serene, wooded setting that evokes the middle of a forest rather than the conveniently close ammenities such as desirable schools, Washington Park, Zoo and the downtown/nw 23rd/pearl districts. Super easy/quick access to OHSU

Dee Reddy The Group Real Estate Services

Exceptional modern luxury living in one of Portland’s most gated communities. Surrounded by lush greenspace, this former Street of Dreams showcase offers the perfect balance of privacy, elegance, and convenience. Ideally situated just minutes from downtown Portland, Nike, Intel, St. Vincent’s, and some of the city’s most sought-after public and private schools.This stunning home features soaring

Rachel Johnson LUXE Forbes Global Properties

Welcome to 1136 SW Davenport – one of the most desired streets in Portland heights. Originally designed in 1942 by renowned architect Herman Brookman, this is a rare architectural gem and a significant example of early Modernism in the Pacific Northwest. Brookman is celebrated for iconic Portland structures including the Fir Acres Frank estate, Menucha, and many more. In its 83-year history, this

Steve Odermann Windermere Realty Trust

Perched on over 3 private acres with sun-soaked southern views, this hidden retreat offers the rare luxury of space—just minutes from Portland’s best trails, schools, and amenities. Reimagined by award-winning architect Bob Thompson, the main level flows with modern warmth: a chef’s kitchen, open living areas, and walls of glass that bring the outdoors in.Play tennis under the stars, lounge by

Suzann Baricevic-Murphy Where, Inc.

Experience the epitome of timeless elegance and modern luxury in the heart of the Portland Heights ‘grid’ neighborhood. This distinguished residence, a modern interpretation of the classic Foursquare Craftsman, blends historic charm with state-of-the-art systems and unparalleled amenities. Originally designed by architect Emil Schacht in 1907, the home was meticulously rebuilt in 2017 under the

Macey Laurick Windermere Realty Trust

Step into a world of European craftsmanship and love with this custom-built gem, first time on the market. Crafted with a vision for family gatherings & heartfelt celebrations, this home showcases the owner-builder’s meticulous attention to detail. From the warm walnut cabinets to the rich hardwood floors spanning the main level, it shines with its soaring 10-foot ceilings with custom wood trim

Suzann Baricevic-Murphy Where, Inc.

Step into the rich history and luxury of the Joseph Gaston House, an architectural masterpiece built in 1911 by William C. Knighton in Portland's West Hills. This captivating estate offers a timeless allure with its elegant living spaces, and impeccable craftsmanship. Perched on 3/4 of an acre in The Grid, it commands panoramic views of the city skyline and mountains, creating an idyllic backdrop

Marcia Walsh Where, Inc

Seller's agent is related to Seller. Luxurious Portland Heights home tucked away on a private street on nearly half an acre. A private retreat inside & out w/ picturesque decks, patios & covered hot tub. Extensive mahogany millwork t/o, French doors & two gorgeous wood burning fireplaces. 2012 renovation w/ new heating/AC, roof, windows, electrical/plumbing, central vac. Updated kitchen,

Kate Hypes Windermere Realty Trust

Exceptional duplex in the heart of Portland Heights. 2417 features 2 bedrooms and 2 full bathrooms while 2419 enjoys 3 bedrooms and 1 full 1 half bathrooms. This residence offers the rare advantage of two separate spaces. The main level unit offers single level living with high-end finishes and incredible indoor outdoor flow. The lower level currently produces $36,000 in income and enjoys a

Macey Laurick Windermere Realty Trust

Stunningly updated—newly remodeled in 2024—this home sits on a tranquil 0.8-acre lot in a quiet cul-de-sac, offering rare privacy in unincorporated Multnomah County. Make living elegant and fun in this light, bright, open concept floor plan. Large kitchen, high ceilings, with a massive island that opens to the family room.The layout is ideal for entertaining, featuring refinished hardwood floors

Marcia Weiss Where, Inc

A Private Sanctuary in the Heart of Portland’s Prestigious SW Hills. Tucked privately off prestigious Hewett Boulevard, this exquisite estate in the coveted SW Hills offers an inspired blend of elegance, privacy, and playful luxury. Set on nearly an acre of lush grounds with a gracious circular drive, this home is a rare retreat, designed as much for sophisticated living as for unforgettable

Kendall Bergstrom-DeLancellotti Cascade Hasson Sotheby's International Realty

Designed in 1912 by Architect Josef Jacobberger, the Giesy/Failing House is a stunning blend of Craftsman and Arts and Crafts styles, offering an unparalleled sense of grandeur. Ideally located in the coveted West Hills on 1.55 acres, this property features steep intersecting gabled roofs, a cantilevered stucco second floor, and exquisite wrought-iron detailing. The distinguished arched glass and

Macey Laurick Windermere Realty Trust

Nestled on an incredibly rare eight private acres in Portland’s prestigious Southwest Hills, the historic Merlo Estate is a rare opportunity to enjoy timeless European sophistication in a stunning vineyard setting designed for epic entertaining. Built in 1939, this stately French Provincial residence was home to influential Portlanders whose business, civic and philanthropic legacies shaped the

Terry Sprague LUXE Forbes Global Properties

5 Plex with CITY VIEWS and close to PSU campus. Zoning is RM4 which accommodates a high density, multi-dwelling build up to 30 units in a fabulous, central city location. As an investment, this 1912 build has a consistent rental history with a blend of studio, 1,2 and 3 bedroom units. Both Roof and Boiler are newer. Main floor units have hardwood floors, period built-ins, large front porch and

Douglas Landers John L. Scott Portland Central

This iconic Tudor Revival estate in Portland’s West Hills has been reborn through a nearly $20 million renovation, blending historic charm with the ultimate in contemporary luxury. Originally crafted in 1930 by celebrated architect Roscoe D. Hemenway, the 25,568-square-foot residence has been meticulously transformed by JHL Design and Green Gables Restoration with a reimagined interior

Terry Sprague LUXE Forbes Global Properties