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5 Oregon Luxury Homes from Portland Hills to Bend Acres

By Awais Manzoor

1 min read

Retreat living that still keeps downtowns, schools, and daily conveniences within easy reach. From a gated, garden-wrapped setting in Portland to five serene acres near Sisters, each home is positioned for privacy without isolation. Scenic outlooks shape the experience, spanning SW Hills perspectives, high-desert panoramas from Mt. Jefferson to Smith Rock, and Newport’s sunlit hillside setting. Throughout, design-forward architecture and adaptable layouts invite entertaining and modern, multiuse living.

Private Gated Garden Retreat | $1,795,000

1439 Sw Highland Road Portland OR 97221
1439 Sw Highland Road, Portland, OR 97221
Where Inc
LISTING AGENT:
Listing agents: Marcia Walsh & Catherine Kelley Petroff

Beyond a gated street in Portland, this residence blends city proximity with a notably private setting just minutes from downtown. Lush gardens frame thoughtfully designed outdoor spaces, including a gorgeous patio and an expansive deck made for easy entertaining. Inside, a modern floor plan keeps daily life fluid while still honoring more traditional moments: formal living and dining rooms bring timeless charm, and an open kitchen and family room create a natural hub that opens directly to the outdoors. Upstairs, four bedrooms include a spacious primary retreat with a fireplace, walk-in closet, and a large ensuite bath. The lower level expands the possibilities with a bonus room, plus an additional bedroom and full bath—ideal for guests or flexible routines. It’s a home that lets Portland living feel quietly removed, without losing connection to the city.

Price:
$1,795,000
Size:
5,312 sq ft
Contact:
Marcia Walsh & Catherine Kelley Petroff, Where, Inc, 503.781.5714 , 503.545.2905
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Serene Ranch Retreat | $1,750,000

67554 Trout Lane Bend OR 97703
67554 Trout Lane, Bend, OR 97703
Trista Deane
LISTING AGENT:
Trista Deane

Surrounded by 5 serene acres just 5 miles from downtown Sisters, this single-level ranch-style residence balances everyday ease with a sense of retreat. Inside, hardwood floors run through a thoughtful layout that includes three bedrooms, three full baths, and a dedicated office for quiet work or creative projects. The kitchen is designed for real life, with generous space and a walk-in pantry that keeps essentials organized and close at hand. Out back, the view opens to a large yard framed by mature juniper trees, inviting unhurried mornings and long, peaceful evenings. A substantial 2,500-square-foot shop adds remarkable flexibility, finished with epoxy flooring and warmed by a pellet stove—ideal for hobbies, storage, or work. It’s a setting made for privacy, functionality, and simple daily comfort.

Price:
$1,750,000
Size:
2,520 sq ft
Contact:
Trista Deane, Harcourts The Garner Group Real Estate, 541.815.3688
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1255 NW Constellation | $1,495,000

220215926 1
1255 Nw Constellation, Bend, Oregon 97703
colleenpeterson
LISTING AGENT:
Colleen Peterson

On a residential street in Bend, this 4-bedroom, 4.5-bath custom home frames high desert living with views stretching from Mt. Jefferson to Smith Rock. Thoughtfully curated finishes and a generous three-level layout create a sense of ease and intention throughout. Arrival is streamlined with a fully heated, spacious 3-car garage and driveway tucked along the alley, offering easy access to the main floor. Inside, the flow centers on a gourmet kitchen, a large dining room with built-in cabinetry, a sunlit living room, and a main-level primary suite. Upstairs, three additional bedrooms are joined by a versatile bonus room. The lower level expands daily options with a dedicated office, home gym, cozy family room, and two large storage rooms. Mature landscaping and low-maintenance grounds complete the setting, with convenient access to schools, Northwest Crossing, downtown, and the new Costco.

Price:
$1,495,000
Size:
4,221 sq ft
Contact:
Colleen Peterson, Engel & Völkers, 541.213.9810
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Classic 1925 Mediterranean With Modern Luxury Updates | $1,490,000

4323 SW Hamilton Ter Portland OR 97239
4323 SW Hamilton Ter, Portland, OR 97239
shelleylucas
LISTING AGENT:
Shelley Lucas

From its elevated setting in Portland’s coveted SW Hills, this 1925 Mediterranean / Spanish Revival residence pairs historic character with a complete restoration. Rejuvenation fixtures and beautiful millwork set a refined tone, while the main level’s refinished oak hardwood floors run through the kitchen, dining and living rooms, den, plus an additional bedroom and full bathroom for main-level living. French doors open to a romantic arched loggia that frames sweeping Mt. Hood and Willamette River views, flowing out to a generous IPE deck designed for indoor-outdoor entertaining. Upstairs, a nearly 800-square-foot owner’s suite spans the entire floor with a private upper terrace, sitting room, walk-in closet with laundry, and an ensuite bath with heated floors, walk-in shower, and soaking tub. A lower-level guest retreat and detached ADU extend the flexibility, with landscaped terraces completing the setting.

Price:
$1,490,000
Size:
3,424 sq ft
Contact:
Shelley Lucas, The Agency, 503.989.9930
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1025 NE 7th Drive | $1,395,000

1025 NE 7th Drive Newport OR 97365
1025 NE 7th Drive, Newport, OR 97365
Geoff Groener Emerald Coast Realty
LISTING AGENT:
Geoff Groener

From its elevated hillside setting in Newport, this brand-new, custom-designed modern residence is slated for completion in late spring 2026. Updated as Phase 3 of 4, the design by Capri Architecture leans into architectural precision with a distinctly coastal sensibility. Inside, a dramatic floor-to-ceiling fireplace wrapped in custom tile anchors the living experience, while an expansive custom window package by Innotech Windows and Doors brings light through the home. Three-level elevator service creates an easy daily flow, connecting the oversized two-car garage level to the upper living areas without missing a beat. In the chef’s kitchen, two Sub-Zero refrigerators join a Wolf range alongside a wall oven and steam oven, setting the stage for everything from quiet mornings to effortless entertaining. Life here is defined by light, elevation, and considered design.

Price:
$1,395,000
Size:
4,211 sq ft
Contact:
Geoff Groener, Emerald Coast Realty, 541.390.4488
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