Portland NW/ SW/ S, Raleigh Hills Homes with English Style

Welcome to the charming neighborhoods of Portland, specifically the picturesque areas of Northwest, Southwest, and Raleigh Hills. Nestled in the heart of Multnomah County, these vibrant communities offer a unique blend of urban convenience and serene suburban living, making them a coveted destination for homebuyers seeking both comfort and style.

In these regions, you’ll find a delightful selection of homes, many of which showcase the timeless elegance of English-style architecture. These homes often feature steeply pitched roofs, intricate brickwork, and charming leaded glass windows that evoke a sense of history and sophistication. With their cozy nooks and inviting gardens, these residences create a warm atmosphere perfect for both entertaining and quiet evenings at home.

Portland's NW and SW neighborhoods are known for their eclectic mix of boutiques, cafes, and parks, providing residents with a vibrant lifestyle right at their doorstep. Meanwhile, Raleigh Hills offers a more tranquil setting, characterized by its lush greenery and stunning views of the surrounding hills. This area is perfect for those who enjoy outdoor activities, with ample hiking trails and parks just a stone's throw away.

Whether you’re drawn to the lively urban scene or the peaceful suburban charm, the homes in Portland’s NW, SW, and Raleigh Hills neighborhoods promise a lifestyle of comfort, beauty, and community. Explore the possibilities and discover your dream home in this enchanting part of Oregon, where every day feels like a charming retreat.

Newest Portland NW/ SW/ S, Raleigh Hills Homes with English Style

$1,349,000

2 Beds ⋅ 2 Baths ⋅ 475094460 MLS

Tucked away in Portland’s dreamy Dunthorpe neighborhood, this flawlessly reimagined English-style cottage is an extremely rare blend of storybook character and chic modern refinement. With every fine detail met, its high-design, top-to-bottom remodel leaves no surface or system untouched, creating a home that lives like new while preserving the property’s architectural grace. Inside, classic features meet contemporary polish with exquisitely restored windows and custom window treatments, period built-ins, Rejuvenation lighting/hardware, refinished hardwoods, pristine finishes, and all immaculately tailored to high sophistication. The generous great room with marble gas fireplace opens to the dining room and patio overlooking the expansive fenced back lawns. The fully remodeled kitchen is both pristine and functional, pairing elevated design with JennAir commercial-line appliances, full height backsplash, and a coffee bar. Main level living option bedroom and remodeled full bathroom with heated floors, along with a swanky main level study with 2nd marble gas fireplace and custom screen window treatment. Upstairs, the primary suite is an absolute haven with multiple custom closets, a serene remodeled spa-inspired bathroom with heated floors, and a dressing room that could be reconfigured as a den or 3rd bedroom. You’ll find meticulously planned Closets by Design storage solutions throughout and many key upgrades including a whole-home generator, EV charger, new boosted hot water heater, Penntek floor garage with wine refrigerator and 2nd home refrigerator, and beautifully repainted interiors/exterior. Outside, the transformation is equally impressive with newly sculpted trees and plantings plus landscape lighting for Zen-inspired outdoor living across this private 1/3 acre parcel. At mere minutes to Portland and Lake Oswego’s key amenities, and with miles of PNW trails at nearby Tryon Creek, this treasure blends heritage character and the ultimate in turnkey ease!

10950 S AVENTINE AVE, Portland

$3,795,000

5 Beds ⋅ 3 Baths ⋅ 437974535 MLS

Tucked behind lush gardens in the heart of Dunthorpe, this extraordinary estate carries historic character, thoughtful design, and modern livability in equal measure. A recent remodel touched the home with exceptional care, preserving original architectural details while introducing designer lighting, hand-selected wallpaper, and refined finishes that honor its timeless spirit. Four fireplaces warm the home, from the gas fireplace in the living room to a wood-burning hearth in an upstairs bedroom. Multiple sets of main level French doors open directly to the gardens, dissolving the boundary between indoor and outdoor living. At the heart of the home, the remodeled kitchen pairs crisp white cabinetry and quartz countertops with high-end appliances and a generous island with bar seating, made for both quiet mornings and lively gatherings. Upstairs, the serene primary suite opens to an enclosed sun porch and private second-story patio. Three sunny additional bedrooms are just down the hall, while third floor bonus space is your fifth bedroom, office, or gym. The basement level adds a dedicated home theater and an adjoining bonus room with kitchenette. Outside, nearly an acre of beautifully manicured grounds unfold with a sparkling swimming pool, emerald lawns, outdoor dining room under a wisteria-covered pergola, covered patio, and a charming greenhouse. Located within the top-rated Riverdale School District with easy access to Portland and Lake Oswego, this is Dunthorpe at its best.

1546 S MILITARY RD, 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 La Cornue 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

$1,245,000

4 Beds ⋅ 2 Baths ⋅ 571874754 MLS

Storybook character and effortless modern living come together in this beautifully restored Kings Heights home. Thoughtfully refined by its architect-owner, the residence honors its 1928 heritage while creating a warm, comfortable flow for everyday life and entertaining. Rich hardwoods, wrought-iron details, natural finishes, and carefully preserved architectural elements give each room a distinct sense of character. The main level moves easily from gracious living and dining spaces to an updated kitchen designed for both function and connection. Throughout the home, windows frame greenery, seasonal views and mountain vistas, while inviting rooms, remodeled baths, and flexible spaces make the layout as practical as it is beautiful. Outside, the home unfolds from beautiful french doors into a series of private garden spaces. A walled front courtyard with lush landscaping and a fountain creates a peaceful buffer from the street, allowing the home to feel remarkably secluded. In back, an expansive mahogany deck, stone terraces, mature plantings, and a charming garden house create a magical setting for dining, relaxing, and gathering.One of the property’s most special features is its gated rear access to secret Quimby Street, offering a hidden back-door connection to the heart of Northwest Portland. From here, Forest Park trails, NW 23rd shops and restaurants, Wallace Park, Chapman School, and neighborhood cafés are all close at hand. Meticulously cared for and extensively improved, this is a rare home where historic soul, thoughtful design, privacy, and city convenience live beautifully together. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10239917]

2939 NW CORNELL RD, Portland

$875,000

3 Beds ⋅ 2 Baths ⋅ 390665064 MLS

Peace and serenity await in this private hillside retreat, where breathtaking valley views meet the convenience of city living. Nestled on a rare double lot, this one-of-a-kind property is just moments from everything Portland has to offer. Walk to Council Crest Park and Marquam Nature Park, where over 40 miles of wooded hiking trails await, or enjoy being just minutes from Fairmount Boulevard, OHSU, Washington Square, the Oregon Zoo, the Japanese Garden, and the vibrant shops, restaurants, and entertainment along NW 23rd.Inside, abundant south-facing windows fill the home with incredible natural light, creating a bright and welcoming atmosphere even on Portland's grayest days. The beautifully remodeled kitchen features quartz countertops, stainless steel appliances, and thoughtful finishes that blend seamlessly with the home's warm, inviting character.Designed for both relaxation and entertaining, the property features three expansive decks that capture the stunning valley views, along with a finished garage currently used as a home gym that offers endless potential as a studio, workshop, creative space, or additional living area—all while enjoying the same spectacular scenery.Outside, the grounds are a true gardener's paradise, complete with raised garden beds, mature fruit trees, berry bushes, herbs, and beautifully landscaped spaces that make the most of this exceptional setting. Additional highlights include a private sauna, a separate office/studio with potential for a third bedroom or ADU, a cozy loft perfect for curling up with a good book, and a luxurious primary suite featuring a beautiful soaking tub.With breathtaking views, incredible versatility, thoughtful updates, and an unbeatable location that perfectly balances nature with city convenience, this is a truly special place to call home. [Home Energy Score = 4. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10201811]

3810 SW GROVER ST, Portland

$824,900

3 Beds ⋅ 1 Baths ⋅ 677221903 MLS

A lovely classic English cottage welcomes you in the sought-after neighborhood of Hillsdale and Terwilliger. Sitting on a beautiful level lot backing to an open greenspace, this 1928 home preserves its original and timeless charm with modern updates and today’s comfort. Ideal floor plan to meet your everyday carefree and convenient living style. Inviting dining and living area is a perfect place for family and friends to gather for cheers. A cozy breakfast nook awaits to be enjoyed in the morning with a fresh cup of coffee. Handsome den with the fireplace is where you can sit for hours reading your favorite book. Generous sized rooms to create space for your hobbies, arts/crafts, or flex area for yoga/exercise. Surrounded with year round greenery and landscape, the yard and deck are a perfect place for fun and relaxation. Ideal location to trails, eateries, library, and more. Come and love living here at 1035 SW Westwood Drive! [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10249091]

1035 SW WESTWOOD DR, Portland

$2,495,000

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

$5,395,000

6 Beds ⋅ 7 Baths ⋅ 138611139 MLS

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 renowned architect Ellis Lawrence, pairs timeless Tudor Revival, Arts and Crafts, Spanish Renaissance, and Mediterranean influences with thoughtful modern enhancements, including a chef’s kitchen reimagined in 2025, a resort-style pool & guest house, a detached private fitness center, and professional-grade turf and basketball sport courts. Meticulously preserved and beautifully refreshed, with extensive renovations by the current owners, the home features restored Garry oak floors, leaded glass windows, elegant archways, and light-filled living spaces designed for both grand entertaining and everyday comfort. Surrounded by sweeping lawns, mature trees, and curated gardens, this landmark property offers a truly exceptional retreat just minutes from Lake Oswego and downtown Portland.

1905 S GREENWOOD RD, Portland

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 560490076 MLS

Restored and rocking in the heart of Portland, this beautifully reimagined 1932 English Tudor in Burlingame blends timeless character with bold craftsmanship and creative energy. Set on a spacious, tree-lined lot, the home offers versatile living across three levels with a rare mix of historic charm and thoughtful modern upgrades. Inside, you’ll find restored mahogany trim, built-ins, and hardwood floors paired with curated lighting and elevated finishes throughout. Multiple fireplaces and a light-filled sunroom create inviting spaces for both quiet moments and lively gatherings. The kitchen features granite countertops, gas appliances, an island, and pantry, flowing seamlessly into formal and casual living areas designed for entertaining. The primary suite offers a private retreat with soaking tub, walk-in shower, dual sinks, and direct deck access. A standout feature is the fully permitted (2021) attached ADU, showcasing incredible craftsmanship with reclaimed wood cabinetry, concrete countertops, copper accents, hardwood flooring, and its own heating and cooling system—ideal for guests, rental income, or a private creative studio. The finished lower level adds flexibility for extended living, guest quarters, or additional entertaining space—perfect for movie nights, creative pursuits, or simply spreading out. Extensive exterior upgrades include a refreshed stucco façade with cedar accents, copper details, an updated deck with outdoor kitchen and sauna, and beautifully curated landscaping. The property also offers RV/boat parking, multiple outbuildings, and added privacy. A rare opportunity—this sale includes two additional lots totaling just under an acre, complete with a seasonal creek, offering a peaceful, natural setting with room to expand or simply enjoy.Conveniently located near OHSU & downtown Portland, this one-of-a-kind property blends history & livability—a home with soul & style.Sellers will contribute towards buyer's closing costs. [Home Energy Score = 2. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10248297]

6164 SW CAPITOL HWY, Portland

$1,050,000

4 Beds ⋅ 4 Baths ⋅ 536103724 MLS

Historic English 1931 clinker brick masterpiece located on the edge of Tryon Creek State Natural Area. This home features 4 bedrooms, 4 full baths, an office, and a media room. Hardwood floors throughout highlight the home’s classic English charm, complemented by coved ceilings, leaded windows, and a Juliet balcony—just a few of the standout architectural details. Surrounded by nature, the backyard offers a private, forested setting with a peaceful, wooded feel. The gourmet kitchen features stainless steel appliances, a gas cooktop, double ovens, and a cozy eating area. The family room includes a wood-burning fireplace and a large picture window that frames the natural landscape surrounding the home. The primary suite offers double walk-in closets and an ensuite bath with tasteful updates, including a walk-in shower. The lower level features a spacious media room with a wet bar and exterior access to the fully fenced backyard, complete with landscaping and a saltwater spa—perfect for relaxing in a serene, forest-like environment. Additional features include a natural gas-powered whole-house generator, offering reliable backup power and added peace of mind year-round. An oversized garage offers ample storage and includes a pull-down ladder for additional access. Blending timeless character with modern amenities, this exceptional home is ready to welcome its next owner. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10144666]

626 SW COMUS CT, Portland

$699,000

3 Beds ⋅ 2 Baths ⋅ 734529176 MLS

Situated in Portland Heights on Montgomery Dr. Noted by the Oregonian, One of the Most Prestigious Addresses in Portland. Built by Jamieson Parker. Master on Main with Large Sliding Glass Doors Overlooking the Private Wooded Area. Living Room Features Hardwood Floors, Fireplace and Wood Beamed Ceilings Adding a Touch of Old World Charm and Warmth. Kitchen Provides Separate Eating Area. Low Maintenance petite Fenced Front Yard, no backyard, side yard ready for creativity. Full Basement provides ample storage. 8 Minutes to OHSU, 5 Minutes to Hwy 26. Moments Away from the Rose Gardens, Tennis Courts, Arboretum Walking Trails, NW 23rd, Fine Dining and Shops. A Great Opportunity to Own in Portland Heights! [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10227084]

2271 SW MONTGOMERY DR, Portland

$4,250,000

4 Beds ⋅ 3 Baths ⋅ 786715699 MLS

There is no other setting like Penridge in Portland.Sited on 1.36 level acres in the West Hills, 7307 NW Penridge delivers a level of finish more familiar to the Hollywood Hills than the Pacific Northwest: absolute privacy, mature gardens cultivated over seventy years, and grand lawn that opens to the vast skyline. The privacy & scale of the grounds this close to the city, is rare.Effectively rebuilt in 2021, the estate lives like new. All new systems, completely reimagined. Daily life happens on the main floor, with the lower level holding an expansive gym, glass-enclosed wine cellar, sauna, private office, and guest suite: spaces you use when you want them, not rooms you maintain. The kitchen and family room are anchored by bookmatched Nero Marquina marble, a floating hood, and a fireplace running the full length of the room, paired with seamless walnut slab cabinetry and Kelly Wearstler leather accents. Original wide plank oak floors with wood plug nails, refinished in 2025. Custom Venetian plaster fireplace surrounds. Hand-stitched leather stair rail. Iron and glass throughout.The primary suite is exceptional: walk-in closet, slab marble head wall, custom lined wood walls, and a bath finished floor to ceiling in Eros Gray marble slab with a solid stone soaking tub and radiant heated floors.The outdoors flows across two levels. Off the main floor, a newly added covered living room with outdoor kitchen and gas grill, lounge seating, and fire pit opens onto the grand lawn, with the hot tub just off the primary and seventy years of gardens enveloping it all. Below, a saltwater pool with auto cover, private bar, turf lawn for games, and a sunbathing terrace.The privacy reads as remote. The location is anything but. NW 23rd Avenue is minutes down the hill, with OHSU, Nike, and Intel all within an easy commute. For those arriving in Portland for the first time, or returning to be near family- Welcome Home to Penridge!

7307 NW PENRIDGE RD, Portland

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