In the heart of Portland’s most prestigious neighborhoods, five extraordinary homes redefine luxury living with their architectural significance and modern sophistication. From a sleek, contemporary marvel with a resort-inspired backyard in Lake Oswego to the historic grandeur of the 1911 Joseph Gaston House and a mid-century gem with Japanese-inspired gardens in the West Hills, these properties share stunning views, bespoke amenities, and unparalleled privacy. Each offers a unique story—whether through innovative design or timeless legacy—while promising an exclusive lifestyle connected to nature, history, and the city’s iconic vistas.
Contemporary Luxury | $2,999,900


Dennis Laird

Dennis Laird
Positioned along a serene waterfront, this modern masterpiece, reimagined by architect Leon Miller Trice III alongside builder Don Tankersley, embodies refined craftsmanship and contemporary elegance. A striking linear water feature guides you to sun-drenched, open-concept living spaces framed by designer windows. The chef’s kitchen, a haven for culinary enthusiasts, boasts custom oak cabinetry, premium appliances, a wet bar, and waterfall-edge quartzite countertops, seamlessly connecting to expansive outdoor entertaining areas. Thoughtful touches elevate every corner, from four custom steel fireplaces to smart home technology and adjustable art lighting. The primary suite offers a spa-like escape with a Bain Ultra soaking tub and oversized steam shower, while two additional suites ensure comfort. A resort-inspired backyard awaits with a saltwater pool, custom spa, and lush landscaping, complemented by territorial views and deeded access to Palisades Park Community Club’s lakefront amenities.
- Price:
- $2,999,900
- Size:
- 4,556 sq ft
- Contact:
- Dennis Laird, Windermere Realty Trust, 503.317.7972
Timeless Elegance | $2,999,000


Listing agents: Marcia Walsh & Catherine Kelley Petroff

Listing agents: Marcia Walsh & Catherine Kelley Petroff
Rising above Portland’s West Hills, the Joseph Gaston House stands as a testament to timeless elegance and architectural brilliance. Built in 1911 by William C. Knighton, this historic estate in The Grid spans nearly three-quarters of an acre, offering breathtaking panoramic views of the city skyline and surrounding mountains. Inside, intricate moldings and soaring ceilings define the sophisticated living spaces, while a stunning primary bedroom boasts a walk-in closet and a luxurious bathroom with a steam shower. A remarkable 5,000-bottle cellar adds a unique touch for wine enthusiasts. Outside, a beautifully designed patio overlooks downtown Portland, creating a peaceful haven to relax and soak in the scenery. Extensively remodeled in the early 2000s with updated plumbing and electrical systems, this estate seamlessly blends historic charm with modern comforts, embodying the pinnacle of refined mountain living.
- Price:
- $2,999,000
- Size:
- 8,752 sq ft
- Contact:
- Marcia Walsh & Catherine Kelley Petroff, Where, Inc, 503.781.5714 , 503.545.2905
Mid-Century Masterpiece | $2,750,000


Listing agents: Marcia Walsh & Catherine Kelley Petroff

Listing agents: Marcia Walsh & Catherine Kelley Petroff
Rising above the vibrant heart of Portland, this mid-century masterpiece offers an elevated escape with breathtaking, panoramic views of the city skyline and surrounding mountains. Meticulously remodeled with impeccable attention to detail, the home marries timeless design with modern luxury, creating a sophisticated yet serene retreat. A long, private driveway leads to an oversized deck, ideal for soaking in 180-degree vistas, while below, tranquil Japanese-inspired gardens by Kurisu provide a peaceful sanctuary. The expansive primary suite on the main floor serves as a true haven, boasting a walk-in closet and a spa-like bathroom with heated floors. Downstairs, a beautifully appointed secondary bedroom suite, sauna, wine cellar, family room, and workout space await. With a 4-car garage, generator, and sleek finishes throughout, this residence in one of Portland’s most coveted neighborhoods redefines urban luxury and comfort.
- Price:
- $2,750,000
- Size:
- 4,880 sq ft
- Contact:
- Marcia Walsh & Catherine Kelley Petroff, (w)here, 503.781.5714 , 503.545.2905
Modern Luxury In The Heart Of Bend | $2,590,000


David Gilmore

David Gilmore
Situated in the heart of a coveted Westside neighborhood, this remarkable home, rebuilt in 2025, effortlessly marries timeless design with modern sophistication. The showstopping kitchen steals the spotlight, boasting a 48-inch range, a built-in refrigerator seamlessly integrated with matching cabinet panels, and an impressive 9.5-foot island perfect for gatherings. With four spacious bedrooms and four well-appointed bathrooms, the layout prioritizes both space and functionality, catering to a variety of lifestyles. Every detail reflects the meticulous care of a new build, while the storied locale adds a layer of charm and character. Imagine hosting friends in the open, inviting spaces or unwinding in the comfort of thoughtfully designed rooms. This property offers a rare opportunity to enjoy contemporary living in a neighborhood steeped in history, where convenience and elegance converge effortlessly.
- Price:
- $2,590,000
- Size:
- 3,540 sq ft
- Contact:
- David Gilmore, Cascade Hasson SIR, 619.203.1749
5720-5724 Sw Barnes Rd | $2,500,000


Listing agents: Craig Weston & Macey Laurick

Listing agents: Craig Weston & Macey Laurick
Tucked away just beyond the city’s edge, this remarkable rural estate offers a serene escape with the convenience of urban proximity. Spanning two tax lots, the property blends timeless architecture with modern comforts, creating a haven for both relaxation and recreation. The traditional main house, enveloped by meticulously landscaped gardens, serves as the heart of this compound, while a collection of versatile structures enhances its appeal. A sparkling pool and spa, accompanied by a charming pool house, invite leisurely afternoons, while a tennis court and gazebo provide spaces for active pursuits and quiet reflection. Multiple outdoor gathering areas encourage memorable entertaining. A separate ADU offers flexibility for multi-generational living or guest accommodations. With additional storage buildings and a thoughtfully designed floor plan, this estate effortlessly supports diverse lifestyles, all just moments from hospitals, high-tech hubs, and Northwest Portland.
- Price:
- $2,500,000
- Size:
- 5,570 sq ft
- Contact:
- Craig Weston & Macey Laurick, Windermere Realty Trust, 503.738.2838 , 503.730.4576




















