Southwest Portland Hills Homes for Sale

The Southwest Portland hills are a green, wooded expanse of established neighborhoods between downtown and Beaverton - including West Slope, West Haven-Sylvan, and the areas around Sylvan and Raleigh Hills. Known for larger lots, mature trees, and quick freeway access, they offer space and privacy close to the city.

Living in the Southwest hills

Homes here range from mid-century ranches and splits to large contemporary houses on private, tree-lined lots. Residents value the central location - minutes to downtown, OHSU, Washington Park, and Beaverton via US-26 and Highway 217 - along with good schools and access to trails and parks. It appeals to buyers who want room to breathe without leaving the city's edge.

The Southwest hills market today

As of October 2026, there are roughly 65 to 70 homes for sale across the Southwest Portland hills (ZIP 97221), spanning a very wide range - from lots and smaller homes to multimillion-dollar estates - so the average is pulled upward by a handful of large properties. The live listings below are the best current picture. For how value is set here, see my West Slope guide and my West Haven-Sylvan guide.

Thinking of buying or selling in the SW hills?

Whether you are searching for a home here or weighing a sale, I would be glad to help. Browse the live listings below, set up instant listing alerts, or request a free, no-obligation home value estimate. I am Michael Smira of Smira Group - John L. Scott, among the top 1% of Portland-area brokers for the past twelve years.

Michael Smira, Realtor
Smira Group - John L. Scott
(503) 935-2560 | michael@smiragroup.com

$25,000,000

8 Beds ⋅ 11 Baths ⋅ 24631430 MLS

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 blending timeless elegance with top-of-the-line designer amenities, showcasing imported materials and handcrafted finishes. Perched on 3.26 stunning private acres, the property offers some of the best panoramic views of Portland’s skyline and four majestic mountains in the metropolitan area, creating an extraordinary setting for both grand entertaining and everyday living. This storied property, built as the estate of the day in 1930, is the estate of today with a winning combination of historic architecture and modern amenities to be enjoyed for generations to come.

4311 SW GREENLEAF DR, Portland

$4,310,000

3 Beds ⋅ 3 Baths ⋅ 213152639 MLS

Revived over two years by Green Gables and a detail-driven homeowner with an uncanny eye for form, flow, and finish—the home elevates mid-century architecture to meet the rhythm of modern life. Designed by renowned architect Roscoe Hemenway and tucked into Portland’s West Hills, the home unfolds in clean lines, warm materials, effortless one level living and wide-open views to the south. Inside and out move in sync, offering a quiet kind of luxury-for those who live artfully and expect their spaces to do the same. [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10249097]

4310 SW WARRENS WAY, Portland

$3,000,000

7 Beds ⋅ 4 Baths ⋅ 362104994 MLS

Mid-century modern masterpiece by renowned architect Walter Gordon, celebrated for seamlessly blending indoor and outdoor spaces. This architectural gemfeatures floor-to-ceiling glass walls, skylights, expansive rooms, travertine floors, accent walls, a sunken living room, built-in bookcases, and soaring ceilings.The primary ensuite will absolutely wow you with glass wall, fireplace, conversation pit, and a spa-like bath with dual suites and closets. The lower level offersa complete second living area.Recent updates include a new roof on the main house, a 5-zone HVAC system, new water heaters, new laundry-jet system &luxury carpeting. This home is expansive & full of surprises and delights, offering endless discoveries.Set on nearly an acre of flat property in the prestigiousSouthwest Hills of Portland, the lush grounds feature fountains, a sophisticated yet minimalist landscape design, and a gated entrance. The property alsoincludes a fully remodeled, private guest house with privacy & comfort in mind. Home is conveniently located near OES, French International, Catlin Gabel,Nike, Intel, Downtown Portland, top restaurants, nature trails, and shopping. This one-of-a-kind home is truly unforgettable. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10226724]

4414 SW SEMLER WAY, Portland

$2,900,000

5 Beds ⋅ 3 Baths ⋅ 508062474 MLS

Built in 1929 and offered for only the second time in more than 80 years, 4061 SW Greenleaf Drive is a rare English-style residence whose history has been preserved while every element has been thoughtfully reimagined for modern life. Set on one-third of an acre in Portland’s coveted Greenleaf Hills, the 5,151-square-foot home underwent a comprehensive 15-month transformation led by GEN Architects, Amanda Klash Interiors, and Mooney Construction. A new primary wing and garage were added, while the interiors, plumbing, electrical, and mechanical systems were completely renewed. The vision was exacting: to open and modernize the home without compromising the warmth, craftsmanship, or integrity of its original architecture. That attention to detail is beautifully woven throughout. Custom inset cabinetry, Waterworks fixtures, a Lacanche range with a custom metal hood, and Carrara marble create a refined yet welcoming kitchen. Two interior wood-burning fireplaces, integrated Sonos audio, dual-zone climate systems, and carefully selected finishes bring comfort and ease to every room. Outside, the grounds were fully redesigned with layered landscaping, irrigation, a fountain, outdoor lighting, and a private rear patio anchored by a third wood-burning fireplace. Greenleaf is known for its peaceful, low-traffic streets and long-term homeowners, offering exceptional privacy just minutes from downtown and Northwest 23rd. From the front door, walk toward the zoo, accessed by nearby trailheads, or set out for a run along the beloved Fairmount Loop. This is more than a beautifully renovated home. The English-style residence possesses the character that can only be acquired over time: a gracious silhouette, enduring craftsmanship, substantial rooms, and an unmistakable sense of permanence. It is a storied Portland residence, thoughtfully transformed for its next generation!

4061 SW GREENLEAF DR, Portland

$2,600,000

5 Beds ⋅ 4 Baths ⋅ 538555918 MLS

Architectural distinction, privacy, and an exceptional West Hills location converge in this fully remodeled residence. Set on beautifully curated grounds, the home offers rare seclusion with effortless access to downtown Portland, OHSU, Beaverton, and Hwy 26. Designed by internationally acclaimed designer Andee Hess of Osmose Design, the interiors thoughtfully blend Mediterranean, French, and Mid-Century influences with a contemporary focus on light, flow, and connection to the landscape. Expansive Fleetwood windows bring natural light deep into the home—an uncommon feature in this serene, forested setting. The main level is equally suited to everyday living and sophisticated entertaining, with terrazzo floors, multiple fireplaces, generous formal spaces, and a beautifully appointed chef’s kitchen featuring quartz and marble surfaces, Wolf and Sub-Zero appliances, and an intuitive layout. A richly layered lounge wrapped in warm wood paneling and custom millwork includes integrated sound, creating an inviting retreat for work, music, or intimate gatherings. Upstairs, the private quarters offer exceptional flexibility. The primary suite features a fireplace, tranquil outlooks, and a spa-like bath with custom Ann Sacks tile and soaking tub. A separate guest wing with its own living area and full bath provides an ideal setting for extended guests or multigenerational living. Outside, mature landscaping originally designed by renowned Japanese landscape designer Nagao Sakurai creates a sense of serenity and structure throughout the grounds. An L-shaped wraparound patio extends the living spaces outdoors, offering effortless indoor-outdoor living within a private, Japanese-influenced setting. Situated in one of Portland’s most tightly held West Hills neighborhoods, this distinctive property offers architectural integrity, exceptional privacy, natural beauty. A rare opportunity to own a thoughtfully re-designed residence in one of Portland’s enduring premier locations. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10242289]

4855 SW HEWETT BLVD, Portland

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 397531358 MLS

Come for the architecture, stay for the lifestyle! A stately Portland classic with a wonderfully relaxed side. Designed by renowned architect Herman Brookman, this distinctive Highlands home pairs gracious proportions and elegant architectural detail with spaces made for modern life. The charming turret entry opens to generous rooms equally suited to quiet mornings and lively gatherings. At the heart of the home, the dining room is framed by gorgeous arched passages to the kitchen, sunroom/office and grand living room. With its tall ceilings, dramatic bay window and French doors, the living room opens naturally to the terrace and gardens beyond. The renovated kitchen, sunny nook and welcoming family room create an easy hub for everyday life. And then there is the garden. The backyard has been transformed into an inviting outdoor retreat, with a generous new patio, raised garden beds, fruit trees, berries and a custom English-style greenhouse. A place to linger, grow something, gather around the table and enjoy summer at home.Thoughtful improvements include foundation bolting, a whole-house generator, tankless water heater, new patio and greenhouse, invisible fence and numerous additional updates. Set in coveted Sylvan Highlands, the home is within walking distance of the Hoyt Arboretum and the Racquet Club, with easy access to Washington Park, Highway 26 and downtown. A home with architectural pedigree, a wonderful sense of scale and, importantly, plenty of room for life to happen.

4422 SW FAIRVIEW BLVD, Portland

$2,495,000

4 Beds ⋅ 4 Baths ⋅ 125546007 MLS

This newly built NW Modern marvel has been crafted to a meticulous standard with gorgeous designer finishes throughout and offering rare main level living on a private almost half acre parcel. A versatile and contemporary floor plan, soaring ceilings, plank flooring, floor-to-ceiling Milgard windows, and walls of sliding doors opening to an atrium-style sculpted courtyard create oasis living in the heart of Portland's elegant Bridlemile neighborhood. The statement living room features a quartz fireplace, vast picture windows and chic paneling accents, and the stylish dining room includes a built-in buffet with two Thermador beverage refrigerators, quartz countertops, sink, and glass rinser. Dream up your next dinner party in the sleek chef’s kitchen featuring built-in Thermador appliances with overlay paneling, double ovens, a dramatic waterfall island, incredible storage, and access to both decks. The private primary suite is situated at the north side of the home with its own private deck, adjustable recessed lighting, a spa-inspired bathroom with pedestal soaking tub, vast walk-in shower with rainfall head, dual vanities, and heated floor with a nearby walk-in closet featuring custom built-in features and adjacent executive office. Enjoy 3 bedrooms and 2 full bathrooms upstairs, a generous family room, mudroom complete with generous sauna and built-in storage, and well-equipped laundry room. No fine detail has been overlooked from the home’s solid core wood doors, under cabinet lighting, illuminated shower niches, pre-wiring for electric window treatments, plumbing for a central vacuum system and wired for a backup generator. The 2 car oversized garage and large crawlspace offers additional storage solutions. Situated very near Portland Golf Club, top private schools, the Portland Metro’s tech corridor, and St. Vincent's Medical Center, this is modern living as it was meant to be! [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10244691]

6233 SW HAMILTON WAY, Portland

$2,444,000

5 Beds ⋅ 5 Baths ⋅ 605390746 MLS

A private Northwest sanctuary in Portland's Southwest Hills. Nestled among distinguished estate homes, this extraordinary Northwest contemporary offers remarkable privacy on over half an acre of Japanese-inspired gardens. Winding paths, cascading waterfall, koi pond, tea house, stone patios and fire pit create a setting unlike any other. Inside, nearly 7,100 sq ft blends architectural sophistication with everyday comfort. Soaring ceilings, Brazilian cherry floors and expansive windows connect the home to its natural surroundings. Chef's kitchen with quartz counters and 6-burner Thermador gas range. Main-level primary and guest suites, covered decks, outdoor kitchen and fireplace make entertaining effortless. The ultimate luxury awaits downstairs: a private indoor spa with swimming pool, hot tub, sauna and lounge, plus glass-enclosed fitness room. Five bedrooms, 5.5 baths and a four-car tandem garage. Minutes to downtown Portland and Nike, yet wonderfully secluded. An exceptional estate where architecture, nature and wellness come together. A home to experience, not simply admire.

5702 SW GROVER CT, Portland

$2,295,000

5 Beds ⋅ 5 Baths ⋅ 327006766 MLS

Discover an exceptional opportunity to own a Street of Dreams builder’s personal residence. Tucked back from the main street on an expansive .61-acre lot with enviable privacy, superb craftsmanship and remarkable livability. The light-filled great room features soaring ceilings, engineered wood floors, custom wood cabinetry, abundant natural light through expansive windows, which flows seamlessly to a covered outdoor living area with a built-in kitchen, heater and firepit—perfect for entertaining. The gourmet kitchen is beautifully appointed with high-end appliances, granite counters, two sinks, two ovens, built-in refrigerator, gas range, eating bar and walk-in pantry. The main level offers a bedroom and full bath plus a private office with French doors and built ins. The stunning primary suite features a spacious walk-in closet, fireplace, and a spa-inspired bathroom. Two additional en-suite bedrooms with walk-in closets provide flexible living space. A spacious bonus room offers another place to gather or escape. The lower level reveals a beautiful 800 SF, 1 bedroom, 1 bathroom ADU, generating over $21K in annual revenue, with laundry, parking, step-free exterior access and an interior connection to the main house—ideal for guests, extended living or rental income. A detached studio, 393-square-foot shop and 3-car garage with pet bathtub, and lower-level storage spaces add versatility. Outside, enjoy a level lawn, mature, low-maintenance landscaping, raised garden beds and a private orchard with apples, peaches, pears, plums, figs, cherries, persimmons, mulberries and berries. $83,200 in recent improvements include new exterior paint, carpet, epoxy garage floor, and HVAC upgrades. Just minutes to Downtown Portland, the Oregon Zoo, OHSU, local employers, shopping, restaurants, parks and everyday essentials. Come see why this exceptional home is truly one of a kind. Schedule your private tour today! [Home Energy Score = 2. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10250277]

5716 SW HAMILTON ST, Portland

$2,250,000

4 Beds ⋅ 3 Baths ⋅ 775449704 MLS

Driving along one of the Southwest Hills most coveted lanes, a story begins to unfold. It starts with the drive itself, past a collection of architecturally significant homes, before opening to a sun drenched 1.59 acre clearing where this charming residence sits with quiet confidence. It's easy to understand the draw: privacy, character, and a setting that feels tucked away from the world. And then there are the gardens. Love at first sight. Originally designed by Wade Pipes, the home captures his English Country style in a way that feels effortless rather than formal. It's less about making a statement and more about how the home makes you feel. The current owners enlisted Jeff Miller, one of Portland's most respected architects for historic and legacy homes, to thoughtfully expand and modernize the property. His addition feels like it has always been here, preserving the original charm and character while making the home work beautifully for the way we live today. Brought to life by Olson & Jones, known for their craftsmanship, the quality and attention to detail are evident throughout. A comprehensive renovation ties it together, creating a home that feels both timeless and current across 5,398 square feet. What truly makes this property special, beyond its undeniable charm, is the relationship between the house and the gardens. The landscape, originally designed by Craig Keist, isn't a backdrop, it's part of daily life here. Stone paths, layered gardens, and sweeping lawns wrap around the home, creating spaces to wander, gather, and enjoy. Windows frame greenery in every direction, and rooms open naturally to the outdoors. A striking oversized chess set anchors the front garden, while beyond, an open field offers room for a sport court, tennis, pickleball, or whatever comes next. Close in, but completely in its own lane, minutes from downtown, shops, freeways, and the airport, connected when you want to be and private when you don't. The next chapter is waiting.

5050 SW HILLTOP LN, Portland

$2,150,000

4 Beds ⋅ 3 Baths ⋅ 313392154 MLS

Welcome home to a West Hills retreat in unincorporated Multnomah County, designed by Ellis F. Lawrence, one of Oregon’s most esteemed architects. This enchanting French Normandy residence offers a rare blend of timeless architecture, privacy, and modern luxury in a tranquil setting. Situated on a level 1.24-acre lot, the property is perfectly suited for family, small gatherings, & grand entertaining. A generous driveway provides ample guest parking and welcomes you to this meticulously maintained and thoughtfully updated home. Inside, soaring ceilings, spacious rooms, & oversized windows fill the interiors with natural light. The updated kitchen features top-of-the-line appliances, custom wood cabinetry, expansive island, and a casual dining area. The kitchen flows into a spacious sunroom. The formal dining room overlooks the extraordinary Craig Kiest English garden, where mature laurel hedges and established trees create a private, elegant setting. Beyond the garden is a lighted, full-size tennis/pickleball court. A 700-square-foot covered veranda extends the living space outdoors, with a glass ceiling, gas fireplace, infrared heaters, and spa, creating a space for year-round enjoyment. The Benjamin Silver Design updated owner’s suite is a private sanctuary, with Carrara marble throughout the spa-like bathroom with a walk-in shower and soaking tub. A generously sized dressing room with custom built-ins completes the suite. The spacious second bedroom offers exceptional flexibility, accommodating a king, queen, or twin-beds and includes its own private bath. The lower level provides an additional bedroom suite with a wall of windows overlooking the beautiful grounds, a full hallway bathroom, versatile media room, and large exercise room that could also function as a wine cellar or generous storage space. A whole-home generator completes this thoughtfully designed residence. Enjoy access to Highway 26, OHSU, Good Samaritan, St. Vincent, Nike, and downtown Portland.

5020 SW HUMPHREY BLVD, Portland

$1,995,000

6 Beds ⋅ 3 Baths ⋅ 545523169 MLS

Tucked away on a spacious tiered lot in the highly coveted Bridlemile neighborhood, this beautifully remodeled daylight ranch pairs expansive living spaces with elegant contemporary finishes. Mahogany walls in the entry and newly installed solid maple hardwood floors lead to a vaulted living room with a Malm fireplace and floor-to-ceiling windows that bring abundant natural light and territorial views. Exquisite artisan tile accents can be found throughout the house along with stylish custom fixtures. The thoughtfully designed open concept dining room and kitchen with sleek high-end appliances, cherrywood cabinetry, quartzite countertops and an eating bar allow for easy entertaining. Follow the wide hallways to a luxurious primary suite with a soundproof walnut wall, a walk-in closet, a lavish custom wet room with dual showerheads, a freestanding acrylic tub, tile flooring and double vanity with quartz countertops. Main level living is made complete with two additional large bedrooms with closets, a full bathroom with enclosed tile shower and soaking tub, additional powder room with terra cotta tiled floors, laundry room with extra cabinets and storage as well as a newly fully insulated two-car oversized garage. The lower level has waterproof luxury rubber tile flooring, a second living area with exposed beams, an additional kitchen with quartz counters, a wood-burning fireplace and three additional large bedrooms offering flexibility for guests, multigenerational living or workspace. A micro-cemented bonus room on the lower level serves as the perfect home gym. Outside, enjoy a custom multilevel waterproof deck, covered patio, garden space on 2 levels, new exterior paint and custom woodwork. With newly updated electrical and plumbing systems including an automatic shut-off, new windows, a new roof, a preventative radon system installed and room to spread out, this home offers a distinctive blend of comfort, peace of mind, style and versatility.

4110 SW JERALD CT, Portland

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 384723811 MLS

The Swan House / Designed for Dr. Kenneth and Virginia Swan by John Yeon in 1953, this rare Northwest Regional Modern residence is located within one of Portland's most remarkable architectural enclaves, neighboring Pietro Belluschi's Sutor House and adjacent to Yeon's celebrated Watzek and Cottrell houses. Sited on 3.95 acres of mature forest in Sylvan Highlands and abutting the Hoyt Arboretum, the home exemplifies Yeon's belief that architecture should be a response to nature rather than an object placed upon it. A sheltering roof superstructure unifies the home, covered walkways & outdoor spaces while creating what Yeon described as a distinctly "northern sense of shelter." Original board-and-batten siding, slate roofing, copper gutters, stone walls, and expansive walls of glass reflect a restrained palette of authentic Northwest materials. Inside, cedar-clad living spaces, soaring ceilings, skylights, integrated architectural lighting, trademark louvered ventilation panels, and carefully framed forest views demonstrate Yeon's mastery of light, materiality & spatial planning. At the heart of the home, the living & dining rooms serve as the architectural and social center, connecting the surrounding spaces while welcoming the landscape and forest in. Throughout, the house balances movement & repose, shelter & openness, creating an experience that feels as compelling, warm and inviting today as it did seventy years ago. Thoughtfully updated for contemporary living, the home pairs its architectural pedigree with modern comforts, including a gourmet kitchen, updated baths, a cinema room, and outdoor amenities that enhance everyday living while respecting the home's original design intent. One of the Pacific Northwest's most influential architects, Yeon helped define NW Regional Modernism. The Swan House stands among the clearest expressions of his philosophy and is a rare opportunity to own an important piece of Oregon's architectural history. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10248754]

4645 SW FAIRVIEW BLVD, Portland

$1,995,000

4 Beds ⋅ 4 Baths ⋅ 589748201 MLS

New in 2023 and sited at the end of a quiet cul-de-sac in Honey Hill Farms, this Northwest contemporary backs to greenbelt. Treetop and territorial views, and Bridlemile Elementary attendance. The vaulted great room opens to a Wolf kitchen with quartz counters, double ovens, butler's pantry, and an oversized island. A main-floor bedroom with full bath allows for single-level living or multigenerational use. The primary suite offers a soaking tub, walk-in shower, and generous walk-in closet. Downstairs, the daylight lower level is built for gathering: media room, gym, sauna, wet bar, and wine wall with integrated sound. Covered and open decks extend the living space into the trees. Three car garage, heated tile floors, and a small turf backyard. HOA includes exterior maintenance. Newer construction quality without the weekend upkeep. Minutes to Beaverton, OHSU, and downtown.

4560 SW 59th AVE, Portland

$1,975,000

5 Beds ⋅ 4 Baths ⋅ 294851103 MLS

Distinctive architecture, remarkable versatility and a setting made for entertaining come together in a home that reveals something unexpected at every turn. Thoughtful design and craftsmanship carry throughout, from curved architectural elements and custom wood detailing to extensive brick and stonework, all complemented by expansive windows that draw natural light and the surrounding landscape into the home. Beautifully connected living and dining areas create an easy rhythm for both everyday life and memorable gatherings. At the heart of the home, the kitchen pairs rich wood cabinetry and granite surfaces with built-in appliances and a dramatic brick hearth and masonry centerpiece that makes an immediate impression. Seven fireplace settings add warmth and character, including both gas and wood-burning. Three bedrooms on the main level include an ensuite bedroom with a walk-in closet, offering an ideal arrangement for guests or multigenerational living. Upstairs, the primary suite feels distinctly its own with high ceilings, a double-sided gas fireplace shared with the ensuite bath, generous walk-in closet and built-in cabinetry with marble accents. The ensuite bath features a marble dual vanity, tiled walk-in shower and soaking tub. An additional bedroom and spacious bonus room with wet bar, fireplace and balcony round out the upper level. A resort-inspired setting unfolds around the in-ground pool, with an expansive patio, mature landscaping and a waterfall and pond designed to be seen and heard from multiple areas of the property. Three attached garage bays, additional covered parking and abundant storage complete the picture. What sets this home apart is not any one feature, but the way every element comes together.

6155 SW SEYMOUR ST, Portland

$1,899,900

4 Beds ⋅ 4 Baths ⋅ 399393088 MLS

An exceptional estate that seamlessly blends luxury, comfort, and functionality. Encompassing approximately 7,111 square feet, this distinguished residence offers thoughtfully designed spaces for entertaining, relaxation, recreation, and everyday living. From its elegant architectural presence to its professionally landscaped grounds, every aspect of the property reflects quality craftsmanship and meticulous attention to detail. The home's intelligent floor plan creates a natural flow between formal and informal living spaces, offering room to gather, celebrate, and unwind. At the heart of the residence is a gourmet chef's kitchen designed to inspire culinary excellence. Premium appliances, generous workspace, and abundant storage make the kitchen equally suited for intimate family dinners and large-scale entertaining. The home's extensive amenities elevate it far beyond the ordinary. A private wine room with dedicated tasting area provides the perfect setting for collectors and enthusiasts to showcase and enjoy their favorite vintages. For recreation and entertainment, the residence features a spacious game room and a dedicated media room, creating exceptional spaces for gatherings, movie nights, and hosting guests. Wellness and relaxation are central to the property's design. A private indoor saltwater lap pool and adjoining hot tub create a year-round wellness retreat rarely found in Portland residences. The saltwater system provides a more comfortable and enjoyable swimming experience while supporting an active lifestyle and resort-quality relaxation within the comfort of home. Outdoor living is equally impressive. Professionally designed landscaping enhances both the front and rear grounds, creating a beautiful and private setting. A covered patio extends the living space outdoors, while the inviting fire pit gathering area serves as a natural focal point for entertaining.

4221 SW SELLING CT, Portland

$1,792,000

5 Beds ⋅ 4 Baths ⋅ 546295689 MLS

Beautifully situated on a private lane in SW Portland's coveted Raleigh Hills neighborhood, this lovely executive home offers comfort and spaciousness and plenty of room to roam both inside and out. Main-level living areas with mid-century ambiance, large windows with tons of natural daylight, and an impressive stone fireplace. Formal & casual dining, family room with wet bar, gourmet kitchen. Open layout for easy living and effortless entertaining. Thoughtfully designed with relaxation and rest in mind, the elegant main-floor primary suite and spa-like bathroom also has an impressive walk-in closet with custom built-ins. Comfortable and private, this home is a refined retreat blending everyday luxury and tranquil living. Entertainers' delight with large game areas and for hosting movie nights, plus versatile bonus spaces including home-gym, sauna, reading room, and an art studio suitable for every lifestyle. One level living, with multi-generational living options, and in-home office/business space or ADU with its own separate lower-level entrance. Just under one acre level lot, surrounded by nature. Spacious driveway + 3-car garage perfect for the car enthusiast in you and your RV parking. Come inside to feel the happiness.

6200 SW ROUND HILL WAY, Portland

$1,675,000

3 Beds ⋅ 2 Baths ⋅ 427344862 MLS

Originally designed in 1939 by noted Portland architect Roscoe Hemenway, this home has been reinvented by local designer Benjamin Silver who transformed it into a breathtaking modern interpretation of Hemenway's original vision. The living spaces are defined by a bright, light,airy ambiance beneath vaulted open beamed ceilings while natural wood flooring flows throughout. The living room with its centered picture window that bathes the space in natural light and connects the inhabitants with the forested lot beyond while two sets of French doors open to outdoor lounge areas.The adjacent dining room is open to the kitchen and features glass doors that connect to a covered patio. A bright and spacious chef's kitchen is filled with high-end touches and appliances including a Wolf gas range and Sub-Zero refrigerator. A central quartz wrapped island provides prep workspace and seating for casual meals.The main floor primary suite features vaulted ceilings and French doors leading out to an outdoor patio.The luxe ensuite bathroom has a custom vanity,heated tile flooring and the suite is complete with a large walk-in closet. A modern wood staircase leads to the lower level featuring a second living room with a gas fireplace and large windows. This level also includes two bedrooms with a full bathroom,laundry room,office/flex space&custom wine storage.Throughout the home,high-end details combine with detailed craftsmanship,designer lighting,tankless toilets&wood flooring. Beautiful natural wood built-in cabinetry provides ample storage, and the main level powder room features marble tile and a custom concrete counter.The exterior is wrapped in beautiful cedar and a durable metal roof.Custom hardscaping blends seamlessly into the natural contours of the property in a forested setting with open yard space, providing a private oasis. This property is a rare find in its celebrated architectural history while offering modern Dwell-worthy, elevated living. [Home Energy Score = 9. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10098292]

5202 SW BURTON DR, Portland

$1,599,000

3 Beds ⋅ 3 Baths ⋅ 324855077 MLS

Mid-century architecture meets sophisticated modern living in this extensively remodeled 1960s home. Thoughtful design elements—including beamed and vaulted ceilings, rich hickory hardwood floors, and walls of windows—blend seamlessly with today’s amenities, creating a warm, light-filled home with effortless indoor-outdoor flow and flexible one-level living. At the heart of the home, the chef’s kitchen features custom walnut cabinetry, top-of-the-line Asko, Miele, and Sub-Zero appliances, induction cooking, and an impressive quartz island. The open dining area flows into the spacious family room, while the living room overlooks the lush grounds and southwest views. A well-appointed mudroom offers laundry, extensive storage, and direct patio access. The redesigned hall bath features floor-to-ceiling tile, a walk-in shower, and soaking tub. The king-size primary suite includes a walk-in closet, built-in bureau, dual sinks, heated floors, and walk-in shower. An adjoining office with ample built-ins provides a quiet workspace, while another spacious bedroom completes the main level. The lower level adds flexibility with a second family/bonus room ideal for movies, games, or fitness, plus a private bedroom and bath. Set on a private .34-acre lot, the exceptional outdoor spaces include a covered deck with built-in heaters, expansive back deck, stone outdoor fireplace, and secluded upper firepit area. Mature trees, native plantings, lush landscaping, and meandering paths create a peaceful garden setting. Excellent storage, a large garage with EV charging, tool shed, and backup generator add convenience. This property combines architectural character, modern updates, flexible living spaces, and exceptional indoor-outdoor living, along with top-rated schools and unincorporated Multnomah County taxes. Located in sought-after Wilcox Estates with wonderful community pool, tennis and basketball courts.

3646 SW 50TH AVE, Portland

$1,595,000

5 Beds ⋅ 4 Baths ⋅ 368169762 MLS

Set on just under two private acres in Portland's coveted Bridlemile neighborhood, this exceptional mid-century estate offers a rare combination of privacy, recreation, and land in one of Southwest Portland's most desirable close-in locations. Thoughtfully positioned among mature trees and established landscaping, the property feels worlds away while remaining just minutes from downtown Portland, OHSU, parks, shopping, dining, and top schools.The residence features 5 bedrooms, 4 full bathrooms, and 1 powder room, with expansive living spaces designed for both everyday comfort and memorable entertaining. Walls of glass invite natural light throughout and create a seamless connection to the surrounding landscape, bringing the outdoors in and enhancing the home's timeless Northwest character.Rare lifestyle amenities distinguish this property from anything else on the market. Enjoy year-round recreation in the indoor swimming pool, host friendly competition on the private sport court, and experience the freedom and flexibility that nearly two acres of usable land provide. Whether entertaining on a grand scale, pursuing hobbies and wellness, or simply enjoying the peace and privacy of the setting, the property offers a lifestyle seldom found so close to the city center.Over the decades, this home has been carefully stewarded and thoughtfully evolved while maintaining the enduring qualities that make classic mid-century architecture so compelling. The result is a residence that balances character, scale, and functionality in a way that feels both authentic and inviting.Mature grounds, exceptional privacy, and a truly unique collection of amenities create an uncommon opportunity in today's market. Whether you're seeking a private retreat, a recreational estate, or a gathering place for generations to come, this remarkable Bridlemile property offers the perfect blend of history, architecture, and lifestyle in one of Portland's most sought-after neighborhoods.

4004 SW SCHOLLS FERRY RD, Portland

$1,550,000

5 Beds ⋅ 3 Baths ⋅ 270300769 MLS

Nestled among the trees in Portland's coveted Southwest Hills, this exceptional, modern residence offers a rare combination of bold architecture, sophisticated design and effortless connection to nature. With five bedrooms, 3.5 baths, soaring ceilings and beautifully updated interiors, the home delivers an elevated yet livable approach to modern luxury. A dramatic two-story living room anchors the home, with expansive windows drawing the wooded landscape indoors. The sleek fireplace creates a quiet focal point while the open arrangement provides an effortless flow between living, dining and kitchen spaces. At the center of the main level, the gourmet kitchen pairs clean-lined cabinetry and premium finishes with an oversized quartz island, built-in appliances and a Miele refrigerator. Designed with privacy in mind, the primary suite occupies its own level, providing an intimate retreat removed from the main living areas. A dedicated office or dressing area, dual closets and a beautifully appointed luxury bath with soaking tub and walk in shower- an ideal private sanctuary at the end of the day. The flexible lower level features a spacious family room, four additional bedrooms, and two full baths. Perfectly suited for family, guests, private offices, creative pursuits, or multigenerational living, this level adapts effortlessly to a variety of lifestyles. Multiple patios and decks extend the living space outdoors, creating a series of modern, low-maintenance areas to dine, entertain or simply enjoy the peaceful canopy of surrounding trees. The expansive frontage combines ample off-street parking with a beautifully landscaped outdoor space. A two-car garage, dedicated parking pad and additional capacity for vehicles offers convenience while garden beds, patio w/bench and layered plantings create an inviting connection between the home and street. Fantastic location served by sought after schools and minutes to the amenities and energy of the city! [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10251085]

5144 SW HEWETT BLVD, Portland

$1,545,000

4 Beds ⋅ 3 Baths ⋅ 23344132 MLS

Gorgeous contemporary custom designed plan with 420 square foot deck off master bedroom and covered deck off great room. Top of the line modern finishes and appliances. Meet with the builder's designer to select yours. Very private setting at end of street in a great neighborhood with quick downtown/Council Crest/Hillsdale access. You may also customize your home by adjusting the floor plan or exterior elevation.

4453 SW Melville, Portland

$1,500,000

5 Beds ⋅ 4 Baths ⋅ 522268062 MLS

Lovingly remodeled, this five-bedroom, four-bathroom home offers an unusual combination of space, flexibility, privacy, and outdoor living, with convenient access to both downtown Portland and Beaverton via Highway 26. The generous floor plan provides plenty of room for everyday living, guests, home offices, or multigenerational living. Additional bonus space sits just outside the main home and is connected by a covered walkway, creating separation without sacrificing convenience. Equipped with a gas fireplace, it is ideal for a private home office, creative studio, gym, game room, workshop, or flexible space that can evolve with the next owner's needs.The property is fenced with an electric gate at the driveway, adding an extra layer of privacy and security. Outside, the flat backyard feels private and expansive, with plenty of room to relax, play, garden, and entertain. The pool, featuring solar hot water, and the outdoor kitchen cabana create a natural gathering place for summer afternoons, dinners with friends, and larger celebrations. Supported by 70% solar coverage, the main 0.42-acre grounds balance privacy with entertaining capacity. It is a rare functional combination of updated living space, private grounds, and distinct real estate potential.Optional to purchase adjacent .26 acre flag lot with shed, cement pad and flexible space for office with electricity/internet

1334 SW 57TH AVE, Portland

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 209394243 MLS

An ideal central location and a glamorous remodel headline this pristine Bridlemile transitional, positioned on a quiet no-through road very near the peaceful West side's top-rated private and public schools. Enter to a striking great room with incredible soaring 16' ceilings and wall of windows, a sleek chef’s kitchen with generous breakfast room and deck access, and picture perfect dining with butler’s pantry and adjoining European-inspired patio. Revel in showcase interiors that create an exceptional backdrop for entertaining with smart-home features, automated shades, designer lighting, fine finishes, and plank flooring for a refined contemporary ambiance throughout. Versatile main-level office with separate entrance and nearby full bathroom could double as a main level bedroom. Vast upper level primary retreat with luxurious spa bath, double-sided fireplace, expansive walk-in closet, and a private viewing deck. Enjoy 2 additional bedrooms upstairs sharing a remodeled bathroom and a fourth bedroom/flex room for even more options. Step outside to the fenced private yard and multiple decks that invite relaxed outdoor enjoyment. Minutes in any direction to OES, Jesuit, and Catlin Gabel schools, as well as New Seasons and several golf courses. Convenient access to nearby thoroughfares makes it easy to reach downtown Portland and Beaverton, while miles of nearby Forest Park trails and the Oregon Coast beckon within easy reach for weekend escapes. Beautifully reimagined and designed for the way you want to live, this is Bridlemile at its best! [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10036331]

4411 SW 63RD AVE, Portland

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The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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