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$2,495,000

Celebrating its 100th year, this beautifully updated Portland Heights classic seamlessly blends historic charm with modern convenience. Built in 1926 and thoughtfully enhanced for today's lifestyle, this special home offers the character and craftsmanship of a bygone era paired with the upgrades today's buyers seek.Breathtaking Mount Hood views take center stage, enjoyed from multiple balconies throughout the home where you can watch sunrises, changing seasons, and Portland's iconic landscape unfold. With undevelopable land located directly behind the property, this treasured vista is preserved, providing a rare sense of openness and privacy.Inside, abundant natural light fills inviting living spaces rich with architectural character and timeless appeal. A thoughtfully remodeled kitchen serves as the heart of the home, blending style and functionality for everyday living and entertaining. Modern upgrades include PEX plumbing, fiber optic internet service, and smart home features, ensuring comfort and connectivity while preserving the home's historic charm. The grounds are equally captivating, featuring a beautiful rose garden, multiple mature fruit trees, and thoughtfully landscaped outdoor spaces that create a private urban oasis. A fully remodeled guest house adds exceptional flexibility, offering ideal accommodations for guests, multigenerational living, a home office, or creative studio.Nestled in the coveted Portland Heights neighborhood, this special property offers a peaceful setting surrounded by mature trees and classic architecture, with convenient access to downtown Portland, parks, trails, and neighborhood amenities. As it reaches its centennial milestone, this Portland Heights treasure presents a rare opportunity to own a piece of the city's history—beautifully updated for the next 100 years.

5 Beds ⋅ 5 Baths ⋅ 605848521 MLS

Celebrating its 100th year, this beautifully updated Portland Heights classic seamlessly blends historic charm with modern convenience. Built in 1926 and thoughtfully enhanced for today's lifestyle, this special home offers the character and craftsmanship of a bygone era paired with the upgrades today's buyers seek.Breathtaking Mount Hood views take center stage, enjoyed from multiple balconies throughout the home where you can watch sunrises, changing seasons, and Portland's iconic landscape unfold. With undevelopable land located directly behind the property, this treasured vista is preserved, providing a rare sense of openness and privacy.Inside, abundant natural light fills inviting living spaces rich with architectural character and timeless appeal. A thoughtfully remodeled kitchen serves as the heart of the home, blending style and functionality for everyday living and entertaining. Modern upgrades include PEX plumbing, fiber optic internet service, and smart home features, ensuring comfort and connectivity while preserving the home's historic charm. The grounds are equally captivating, featuring a beautiful rose garden, multiple mature fruit trees, and thoughtfully landscaped outdoor spaces that create a private urban oasis. A fully remodeled guest house adds exceptional flexibility, offering ideal accommodations for guests, multigenerational living, a home office, or creative studio.Nestled in the coveted Portland Heights neighborhood, this special property offers a peaceful setting surrounded by mature trees and classic architecture, with convenient access to downtown Portland, parks, trails, and neighborhood amenities. As it reaches its centennial milestone, this Portland Heights treasure presents a rare opportunity to own a piece of the city's history—beautifully updated for the next 100 years.

1495 SW CLIFTON ST, Portland

$2,500,000

Built in 1938, this extraordinary 5-bedroom, 5.1-bath Brookman-inspired Portland Heights residence is a rare architectural jewel, rich in history, craftsmanship, and irreplaceable charm. Perfectly positioned to capture sweeping city and mountain views, the home is completed by a gorgeous patio and tiered yard, making this a truly exceptional offering in Portland Heights. The main level showcases stunning formal spaces designed for both grand entertaining and intimate gatherings. A den and elegant living room open seamlessly to the beautiful patio, creating effortless indoor-outdoor flow.Upstairs, the primary suite features its own private balcony and is joined by four additional bedrooms and a dedicated office, offering flexibility and space for modern living. The lower level is equally impressive, with a breathtaking library and an oversized bonus room perfect for media, play, or recreation. A timeless Portland classic, blending timeless design with livable luxury. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10245450]

5 Beds ⋅ 5 Baths ⋅ 613208236 MLS

Built in 1938, this extraordinary 5-bedroom, 5.1-bath Brookman-inspired Portland Heights residence is a rare architectural jewel, rich in history, craftsmanship, and irreplaceable charm. Perfectly positioned to capture sweeping city and mountain views, the home is completed by a gorgeous patio and tiered yard, making this a truly exceptional offering in Portland Heights. The main level showcases stunning formal spaces designed for both grand entertaining and intimate gatherings. A den and elegant living room open seamlessly to the beautiful patio, creating effortless indoor-outdoor flow.Upstairs, the primary suite features its own private balcony and is joined by four additional bedrooms and a dedicated office, offering flexibility and space for modern living. The lower level is equally impressive, with a breathtaking library and an oversized bonus room perfect for media, play, or recreation. A timeless Portland classic, blending timeless design with livable luxury. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10245450]

1490 SW CLIFTON ST, Portland

$1,475,000

OPEN Sat 7/18 FROM 1-3PM. Rare opportunity to own a mid-century modern classic with stunning city views and ideally situated in Portland Heights. Thoughtfully designed for privacy, enter through the gated front-entry atrium and experience the unmistakable feeling of home from the moment you step into the 5,000+ sq ft residence. The main level welcomes you with a spacious open floor plan, high ceilings, an abundance of windows and expansive hardwood flooring. The light-filled space flows from formal entry to living room to dining room and a very special sunroom, ideal for effortless entertaining year-round. The living room showcases built-ins, a wood-burning fireplace and captivating views of the City of Roses. A large chef’s eat-in kitchen with newly painted cabinetry throughout boasts ample storage. Completing the ease of one level living is a coveted and sought-after home office, laundry room, cozy den and two primary en-suite bedrooms; one complemented by an updated bathroom, and a large walk-in closet with custom vanity that’s both functional and elegant. The second primary bedroom with bath opens to a reading room, creating a comfortable and discrete retreat for overnight guests.Descend to the expansive lower level via elevator or staircase for more versatile living options including a third bedroom with adjoining bathroom, a fitness room equipped with sauna and shower, storage galore plus a sprawling en-suite guest quarters (or media/game room!) with its own city view and unique private entrance. Exterior features: An attached oversized two-car garage and a private driveway with plenty of additional parking. A greenhouse beckons for an urban garden, an artist studio or hobby haven.

4 Beds ⋅ 5 Baths ⋅ 278906550 MLS

OPEN Sat 7/18 FROM 1-3PM. Rare opportunity to own a mid-century modern classic with stunning city views and ideally situated in Portland Heights. Thoughtfully designed for privacy, enter through the gated front-entry atrium and experience the unmistakable feeling of home from the moment you step into the 5,000+ sq ft residence. The main level welcomes you with a spacious open floor plan, high ceilings, an abundance of windows and expansive hardwood flooring. The light-filled space flows from formal entry to living room to dining room and a very special sunroom, ideal for effortless entertaining year-round. The living room showcases built-ins, a wood-burning fireplace and captivating views of the City of Roses. A large chef’s eat-in kitchen with newly painted cabinetry throughout boasts ample storage. Completing the ease of one level living is a coveted and sought-after home office, laundry room, cozy den and two primary en-suite bedrooms; one complemented by an updated bathroom, and a large walk-in closet with custom vanity that’s both functional and elegant. The second primary bedroom with bath opens to a reading room, creating a comfortable and discrete retreat for overnight guests.Descend to the expansive lower level via elevator or staircase for more versatile living options including a third bedroom with adjoining bathroom, a fitness room equipped with sauna and shower, storage galore plus a sprawling en-suite guest quarters (or media/game room!) with its own city view and unique private entrance. Exterior features: An attached oversized two-car garage and a private driveway with plenty of additional parking. A greenhouse beckons for an urban garden, an artist studio or hobby haven.

1776 SW MONTGOMERY DR, Portland

$2,550,000

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 for everyday living. Features include intricate moldings, high ceilings, stunning primary bedroom with walk-in closet and spacious bathroom with steam shower, and remarkable cellar. Outside, a beautiful patio overlooks downtown Portland, providing a serene retreat to unwind and take in the scenery. Extensively remodeled in the early 2000s, including full replacement of plumbing, and electrical. From its historic charm to modern amenities, the Joseph Gaston House epitomizes sophistication and elegance, offering a rare opportunity to own a piece of Portland's architectural legacy. Option to included all furniture excluding all art and piano. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10227560]

5 Beds ⋅ 5 Baths ⋅ 733774792 MLS

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 for everyday living. Features include intricate moldings, high ceilings, stunning primary bedroom with walk-in closet and spacious bathroom with steam shower, and remarkable cellar. Outside, a beautiful patio overlooks downtown Portland, providing a serene retreat to unwind and take in the scenery. Extensively remodeled in the early 2000s, including full replacement of plumbing, and electrical. From its historic charm to modern amenities, the Joseph Gaston House epitomizes sophistication and elegance, offering a rare opportunity to own a piece of Portland's architectural legacy. Option to included all furniture excluding all art and piano. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10227560]

1960 SW 16TH AVE, Portland

$4,250,000

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 showcases timeless craftsmanship and architectural distinction. The home has been exceptionally maintained over decades of ownership. Inside, experience approximately 10,000sf of living space that unfolds across four levels, featuring elaborate moldings, stained glass windows, rich wood floors, and multiple fireplaces. Grand formal rooms are complemented by a marble-clad chef’s kitchen with Thermador appliances, a butler’s pantry, and exquisite built-ins throughout.The upper-level grand ballroom represents architecture at its finest with maple wood floors, curved trusses, under-eave insulated storage, and finished with tongue and groove fir ceilings. The estate also includes two separate dwellings: a 2-bedroom, 1-bath guest house with fireplace and scenic views, and a 1-bedroom, 1-bath carriage house with full kitchen, office space, and a six-car garage. Outdoor amenities elevate the lifestyle with a full-size tennis court, in-ground pool surrounded by Italian porcelain patio, cobblestone driveway, and manicured gardens.Located minutes from NW 23rd, downtown Portland, top-rated schools including Ainsworth Elementary and Lincoln High, and major medical centers, this rare offering combines privacy, prestige, and convenience in one of the city’s most coveted settings. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10226736]

6 Beds ⋅ 5 Baths ⋅ 186005227 MLS

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 showcases timeless craftsmanship and architectural distinction. The home has been exceptionally maintained over decades of ownership. Inside, experience approximately 10,000sf of living space that unfolds across four levels, featuring elaborate moldings, stained glass windows, rich wood floors, and multiple fireplaces. Grand formal rooms are complemented by a marble-clad chef’s kitchen with Thermador appliances, a butler’s pantry, and exquisite built-ins throughout.The upper-level grand ballroom represents architecture at its finest with maple wood floors, curved trusses, under-eave insulated storage, and finished with tongue and groove fir ceilings. The estate also includes two separate dwellings: a 2-bedroom, 1-bath guest house with fireplace and scenic views, and a 1-bedroom, 1-bath carriage house with full kitchen, office space, and a six-car garage. Outdoor amenities elevate the lifestyle with a full-size tennis court, in-ground pool surrounded by Italian porcelain patio, cobblestone driveway, and manicured gardens.Located minutes from NW 23rd, downtown Portland, top-rated schools including Ainsworth Elementary and Lincoln High, and major medical centers, this rare offering combines privacy, prestige, and convenience in one of the city’s most coveted settings. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10226736]

1816 SW HAWTHORNE TER, Portland

$3,915,000

Built in 2004, this hidden jewel crowns Portland Heights at the top of the West Hills-rarely visible from the street yet unforgettable once discovered. Originally conceived as a NW estate with modern American ease, the home was thoughtfully redesigned with sleek, South American inspired interiors. Today, it presents as even more remarkable thanks to extensive updates by the current owners, who enhanced nearly every corner. The 6-bedroom, 5.1-bath layout spans nearly 7,000 square feet of elevated living. Multiple verandas, secret gardens, and outdoor fireplaces blur the line between indoor and outdoor life. Interiors are alive with texture-lime-washed walls, custom closets by California Closets, curated lighting, leathered wall finishes, and rich wood ceilings. Expansive entertaining spaces flow to a gourmet kitchen, while highlights include a custom wine cellar, soundproof theater with glitter carpet and projector, and a dedicated gym.Every detail has been addressed: new balcony doors and windows in the primary suite, new outdoor lighting, irrigation upgrades, fresh paint throughout, remote-control curtains, and a whole-house generator (2024). Three fireplaces-two gas and one wood-burning-anchor the gathering spaces, while Sonos sound enriches daily life. The 3-car garage, new security system, and a gated entry reinforce ease and privacy.Minutes from downtown yet worlds away, this home offers serenity, scale, and sophistication. For the next owner, the true luxury is inheriting a home that’s been elevated inside and out. [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10192482]

6 Beds ⋅ 5 Baths ⋅ 517376493 MLS

Built in 2004, this hidden jewel crowns Portland Heights at the top of the West Hills-rarely visible from the street yet unforgettable once discovered. Originally conceived as a NW estate with modern American ease, the home was thoughtfully redesigned with sleek, South American inspired interiors. Today, it presents as even more remarkable thanks to extensive updates by the current owners, who enhanced nearly every corner. The 6-bedroom, 5.1-bath layout spans nearly 7,000 square feet of elevated living. Multiple verandas, secret gardens, and outdoor fireplaces blur the line between indoor and outdoor life. Interiors are alive with texture-lime-washed walls, custom closets by California Closets, curated lighting, leathered wall finishes, and rich wood ceilings. Expansive entertaining spaces flow to a gourmet kitchen, while highlights include a custom wine cellar, soundproof theater with glitter carpet and projector, and a dedicated gym.Every detail has been addressed: new balcony doors and windows in the primary suite, new outdoor lighting, irrigation upgrades, fresh paint throughout, remote-control curtains, and a whole-house generator (2024). Three fireplaces-two gas and one wood-burning-anchor the gathering spaces, while Sonos sound enriches daily life. The 3-car garage, new security system, and a gated entry reinforce ease and privacy.Minutes from downtown yet worlds away, this home offers serenity, scale, and sophistication. For the next owner, the true luxury is inheriting a home that’s been elevated inside and out. [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10192482]

1948 SW TERRACE DR, Portland

Smira Group

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