Homes for Sale in Portland, OR with 5-Bedrooms & a Private Pool

Set on an impeccably landscaped lot in the heart of Dunthorpe and deeply rooted in Frank Lloyd Wright's Prairie tradition, this custom home is a study in thoughtful architecture and material integrity. Cherry millwork, exposed vertical grain timber trusses, and natural stone showcase meticulous craftsmanship, while expansive glass draws Dunthorpe's lush greenery inside. Artisan leaded glass

Kristen Kohnstamm Cascade Hasson Sotheby's International Realty

Cedarhurst is more than a residence. It is a turn-key lifestyle rooted in heritage and enriched by thoughtful design. Originally built in 1895 and masterfully reimagined through an extensive 2023 renovation, the estate is tucked atop a graceful circular driveway. The manicured grounds feature an incredible 6-car underground garage plus an adjacent 2-car bay. The outdoor oasis is designed for

Matthew Tercek Real Broker

Mediterranean Retreat in Portland’s Coveted West Hills – Private, Versatile & Full of Character. Situated on a peaceful 1.31-acres in the prestigious West Hills, this extraordinary Mediterranean-style estate offers a rare combination of timeless elegance, modern updates, and incredible versatility—ideal for multigenerational living, entertaining, or generating income through a private guest space

Mimi Mccaslin LUXE Forbes Global Properties

Set on an incredibly rare eight private acres in Portland’s prestigious Southwest Hills, the historic Merlo Estate offers a once-in-a-generation opportunity to experience timeless Pacific Northwest elegance in a breathtaking vineyard setting designed for unforgettable entertaining. Built in 1939, this stately residence was home to influential Portlanders whose business, civic, and philanthropic

Andrew Pienovi Christie's International Real Estate Evergreen

One-of-a-Kind luxury home celebrating the pacific NW lifestyle over looking Forest Park, Columbia river gorge, city and partial Mt. Hood and Mt St Helens views. An architectural masterpiece with circular driveway and hand chosen selected NW materials and design features. The magnificent, quietly elegant updated and renovated lodge home is ideal for the most discerning buyer in search of the full

Libby Benz Windermere Realty Trust

Tucked away in the desirable Greenhills enclave, this gracious home set on approximately 1 acre is an architectural masterpiece designed by Joseph Jacobberger, offering a rare blend of privacy, elegance, and livability. Set amidst lush, meticulously curated gardens, the property feels like a private retreat—yet remains just moments from the best of Portland. Designed for both everyday comfort and

Macey Laurick Windermere Realty Trust

Set on a private 0.23-acre corner lot in the coveted Alameda neighborhood, this Japanese-modern inspired residence blends thoughtful design with elevated amenities, including a pool, spa, and a detached pool house/ADU with an additional 1,000 sq. ft. The main home showcases rich walnut built-ins, honed stone surfaces, and expansive windows that fill the interiors with natural light. The main

Macey Laurick Windermere Realty Trust

Beautifully updated estate on nearly one acre of private grounds with a separate pool house and studio or guest quarters. Tucked discreetly off prestigious Hewett Boulevard, this exquisite SW Hills retreat offers a refined blend of elegance, tranquility, and playful luxury. Set amid lush landscaping with a gracious circular drive, the property is designed for sophisticated living, memorable

Wendy Martin Cascade Hasson Sotheby's International Realty

Welcome to your Southwest Portland staycation dream home — a timeless traditional residence designed for comfort, entertaining, and everyday luxury.Step through the grand entry into a spacious, light-filled interior featuring six bedrooms and four bathrooms, with thoughtfully designed living spaces throughout. Multiple entertaining areas provide the perfect setting for hosting gatherings,

Xan Gale Premiere Property Group, LLC

Wake each day to filtered sunlight through towering firs, stroll manicured lawns framed by mature gardens, and enjoy a setting that feels both secluded and effortlessly connected. Set on more than two acres in prestigious Dunthorpe bordering Lake Oswego, this remarkable estate offers a rare blend of privacy, scale, and refined living. The 11,000+ square-foot residence, designed in 1924 by

Terry Sprague LUXE Forbes Global Properties

One-of-a-kind custom estate on a rare .80-acre lot, perfectly positioned to capture sweeping Mt. Hood and valley views framed by mature trees. From the moment you step inside, vaulted open-beam ceilings and a floor-to-ceiling basalt fireplace set an unforgettable tone, while walls of windows in the living room flood the space with natural light. The updated kitchen is a chef’s dream with

Benson Bui Real Broker

Fewer than 30 homes rest on the bank of the Willamette River in Dunthorpe, one of the most coveted neighborhoods on the West Coast. What sets this estate apart from all others: a pool at the river's edge, framed by a half acre of immaculate terraced gardens, a grand lawn, & rose gardens behind a gated, private entrance. Originally built in 1960 and essentially newly rebuilt in 2006, this home was

Kendall Bergstrom-DeLancellotti Cascade Hasson Sotheby's International Realty

Scandinavian Modern Farmhouse - Perched atop the neighborhood and tucked into a private lot, the best views in the neighborhood in this custom contemporary modern estate with unparalleled exclusivity bordering the breathtaking Amaterra Winery vineyards. Enjoy Southwest facing views and incredible sunsets from this thoughtfully renovated home that boasts a Euro-inspired elegance and its very own

Rachel Smith Modern Homes Collective

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 seamlessly

Terry Sprague LUXE Forbes Global Properties

Custom crafted and exceptionally appointed to capture sweeping Mt. St. Helens and Portland city vistas, this 6,062 SF quality built residence sits on .79 private, park-like acres backing to a peaceful conservation zone. This rare gated estate blends refined craftsmanship with everyday livability with 5 bedroom suites and 5 full plus 1 half bathrooms, featuring rich Brazilian cherry, maple, and

Kevin Hall Cascade Hasson Sotheby's International Realty

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 reimagined since 2012 with a focus on quality construction, thoughtful design, and long-term performance. The exterior features custom clear cedar

Marc Fox Keller Williams Realty Portland Premiere

Located within an established community, this extensively updated home offers exceptional flexibility, generous living spaces, and meaningful capital improvements—alongside access to neighborhood amenities including a community pool, tennis court, and miles of trails at nearby Tryon Creek State Park. Vaulted ceilings and expansive windows fill the interior with natural light while maintaining a

Ruth Maher Opt

Tucked at the quiet end of coveted Greenwood Rd, this extraordinary Dunthorpe Riverdale estate evokes the romance of a European retreat. Set behind lush landscaping on two parcels totaling .81 acres, the property offers exceptional privacy, manicured gardens, and resort-inspired living with a sparkling pool and private cabana/guest suite.Inside, dramatic 19-foot ceilings and a sweeping mezzanine

Andrew Galler Realty Works Group

Rare opportunity to own one of Portland’s most extraordinary private estates. Perched atop 25 breathtaking acres bordering Forest Park, this nearly 7,000 SF luxury residence captures sweeping panoramic views of Mt. Hood, Mt. Adams, surrounding valleys, and unforgettable sunsets — creating a true “top of the world” living experience just minutes from downtown Portland.Designed for both grand

Gary Donovan Call it Closed International, Inc

Nestled in Portland’s prestigious West Hills, this extraordinary estate offers sweeping views of the city skyline, Willamette River, and Cascade Mountains. Set on 1.17 acres of gated, park-like grounds, the property blends historic elegance with modern luxury.Originally built in 1887 by JJ McCaffrey and thoughtfully updated in 1928 by renowned architects Jacobberger and Smith, the residence

Patrick Clark Christie's International Real Estate Evergreen

Welcome to this beautiful home in the desirable Bull Mountain neighborhood, offering spacious living, flexible spaces, privacy, and an incredible backyard with pool and hot tub - perfect for entertaining or relaxing year-round. This well-maintained home features multiple living areas plus versatile bonus spaces ideal for a home office, media room, fitness area, hobby space, or potential 6th

Richard Susnjara Windermere Heritage

Honey, this is it.Quiet cul-de-sac. Backs to the Kerr Conservation. Mountain Park. Beautifully renovated top to bottom and tons of personality. Vaulted ceilings, walls of windows, and trees outside every room. When your backyard is a nature perserve the view only changes with the seasons — and each one is amazing. Open gathering spaces on the main floor flow straight to an enormous, sun-drenched

Rebecca Green Real Broker