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$5,250,000
4 Beds 4 Baths 338843522 MLS
Stillwater Vista by TimberRidge Development - A Private Lake Oswego Retreat Above the Water Commanding a premier vantage above Oswego Lake. Stillwater Vista is a rare expression of architectural elegance and effortless lakefront living. Selected for the 2026 Street of Dreams Home Builder Showcase, this residence showcases an exceptional level of design, craftsmanship, and innovation in one of Lake Oswego’s most coveted settings. A dramatic great room features 20-foot vaulted ceilings, statement lighting, and a sculptural fireplace, while walls of glass frame serene lake views and open to a vaulted, covered upper terrace with a striking stone fireplace, integrated heating, and outdoor entertaining spaces. The kitchen is both a showpiece and a professional workspace, defined by exposed beam ceilings, a 12-foot island, side-by-side Sub-Zero refrigeration, and a 60-inch Wolf range, complemented by custom inset cabinetry and a fully equipped scullery. An indoor-outdoor bar enhances seamless entertaining. The main-level primary suite offers 17-foot vaulted ceilings, tranquil water views, and a spa-inspired bath with heated floors, slab marble, a soaking tub, and a custom dressing room with island and integrated laundry. The lower level is designed for leisure, featuring a lounge with fireplace, glass-enclosed wine cellar, fitness studio with sauna, and access to a covered lakeside terrace with hot tub and media setup. Residents enjoy access to Oswego Lake via a private neighborhood tram to a dedicated boat slip—an increasingly rare amenity completing this exceptional offering. Stillwater Vista is a showcase, a retreat, and a legacy property designed to be experienced.

843 TERRACE DR, Lake Oswego

$5,900,000
5 Beds 5 Baths 454331616 MLS
Set within Lake Oswego’s coveted Village on the Lake neighborhood, this extraordinary Hamptons-inspired Modern Craftsman estate captures spectacular east-facing views of Oswego Lake and Mt. Hood from every level. Spanning approximately 9,027 square feet with elevator access throughout, the residence blends timeless craftsmanship with exceptional luxury amenities, including a resort-style pool and jacuzzi. Designed for both grand-scale entertaining and everyday enjoyment, the residence offers an exceptional collection of lifestyle amenities, including a tiered theater room, fitness center, wine cellar, private sauna, and expansive gathering spaces throughout. Chef’s kitchen with Wolf, Sub-Zero, and Miele appliances; more than 1,000 square feet of beautifully finished, flexible-use penthouse space further elevates the experience, offering endless possibilities for a game lounge, a golf simulator, a fitness retreat, a studio, home office, or a creative workspace. Rich custom millwork and beautifully appointed interiors open seamlessly to expansive covered decks and patios, thoughtfully designed to embrace the breathtaking lake and mountain views while creating an effortless connection to indoor-outdoor living. Enjoy access to the Village on the Lake easement along with close proximity to Oswego Lake Country Club, downtown Lake Oswego’s boutiques, acclaimed restaurants, the Farmers’ Market, and year-round community events, creating an unparalleled lifestyle opportunity in one of the city’s most sought-after neighborhoods.

15599 VILLAGE DR, Lake Oswego

$5,495,000
6 Beds 5 Baths 540798156 MLS
Introducing a truly exceptional rare retreat in the heart of Lake Oswego set on 1.88 private acres in unincorporated Clackamas County, this gated estate offers an extraordinary blend of luxury, comfort & seclusion.The outdoor setting is a showpiece, centered around a resort-style pool & an impressive vaulted pool/guest house designed for unforgettable entertaining.The 7,773sf grand primary residence is ideal for both large-scale gatherings as well as everyday living.The main level is highlighted by a vaulted primary suite, privately positioned complete with a generous custom dressing room & convenient laundry. The center of the home offers a chef's kitchen with high end finishings, dramatic great room, grand scale formal dining room with custom buffet, a refined library complete with a custom rolling ladder, 2nd main level bedroom, office & a fully equipped lower-level theater. Throughout, soaring ceilings with rich wood beam accents & expansive windows create a bright, airy atmosphere while maintaining a strong sense of privacy. Upstairs, a distinctive split layout separates a spacious guest suite—featuring its own laundry & storage/bonus space—from the separate upper level offering three bedrooms, playroom & a dedicated fitness room. Additional amenities include outdoor fireplace, an oversized three-car attached garage, RV parking and picturesque gardens with expansive lawns, meandering walking paths, huge verandah & custom lighting. Versatile 1390 sf pool/guest house features a stage, fireplace, stylish bar & kitchenette, dedicated office or studio, 1 1/2 baths, plethora of storage, plus an additional oversized two-car garage/shop suitable for a lift. Bordering the 6.8-acre Woodmont Park & near Tryon Creek State Park with miles of scenic trails, this property is located in the highly desirable Forest Highlands neighborhood, just minutes from top-rated schools, charming Lake Oswego Village & Lake Grove restaurants, cafes, shops, golf, gourmet markets and more!

951 ATWATER RD, Lake Oswego

$5,998,000
3 Beds 4 Baths 774213430 MLS
A one-of-one Architectural Offering with Panoramic Mountain & Willamette River Views. Perched high in Lake Oswego’s coveted Skylands neighborhood this extraordinary mid-century modern estate represents a rare opportunity to own a true legacy property in the Pacific Northwest. Set on a private & manicured .92-acre parcel, the residence captures breathtaking panoramic vistas that stretch across the region’s most iconic landscapes. From its expansive living spaces, sweeping views unfold across the Willamette River & surrounding valleys to the majestic peaks of Mt. Hood, Mt. St. Helens, and Mt. Adams, a constantly shifting canvas of river, sky, and mountains. Originally constructed in 1966, the home has been thoughtfully reimagined through a meticulous multi-million-dollar renovation that honors its Mid-Century Modern and Northwest Regional architectural heritage while seamlessly integrating the comforts and sophistication of contemporary luxury living. Spanning 4,755 square feet of primarily single-level living, the residence offers three bedrooms and four-and-a-half baths, with interiors designed to frame the extraordinary natural surroundings at every turn. Walls of glass invite natural light throughout the home while creating an effortless connection between indoor living and the dramatic landscape beyond. The exterior is wrapped in St. Helens stone grounding the home in its Pacific Northwest setting while making a bold architectural statement. Gently angled walls appear to reach toward the horizon, complemented by distinctive copper roof flashing with a diamond motif, a subtle yet remarkable detail that speaks to the home’s craftsmanship and thoughtful design. More than a residence, this is a property defined by place, provenance, and permanence, a home that celebrates its architectural legacy while offering an extraordinary setting for the next chapter of ownership.In a neighborhood known for its prestige and privacy, opportunities like this rarely come to market.

777 CHERRY CIR, Lake Oswego

$5,695,000
5 Beds 4 Baths 104151261 MLS
Experience luxury vacation-like living in this extensively remodeled home on the main shores of the quiet water portion of Oswego Lake. With five bedrooms, an office, a gym and four and a half bathrooms, this inviting home was mindfully designed around extensive entertaining and everyday ease. At every turn, there is a harmonious blend of upscale finishes and light bouncing off of water outside into serene spaces inside. The expansive walls of glass dissolve the boundary between indoors and out, opening to panoramic waterscapes in every direction and a rare large, flat yard. The gourmet kitchen centers around an impressive island with beautiful surfaces, custom cabinetry, highest end appliances and a generous butlers pantry designed to house all the necessary kitchen accoutrements. The main level also boasts a large ensuite bedroom, an office, a stunning design forward powder bath, a bespoke bar and a cleverly customized wine cellar. Upstairs, the primary suite is a peaceful retreat with impressive scale and features that include lake views, automated blinds and absolute privacy. Its spa-inspired flow embodies relaxing extravagance with a freestanding tub, heated floors, a steam and rain shower, dual sinks with illuminated mirrors and a custom walk-in closet tailored for curated wardrobes. On this level, you'll also find two additional bedrooms, two full bathrooms, an expansive and inviting family room with another wet bar and a dedicated fitness area with breathtaking lake views. The third floor flexible space, currently a bedroom, showcases that this residence offers beautifully designed options for every need. Outside, a spacious deck cascades through custom low-maintenance, natural landscaping to your private 72 feet of waterfront. The boat house is equipped with a hydraulic lift sized for the maximum length boat allowed on the lake and there is an additional dock. Lake life has never been so beautiful or so easy!

16840 ALDER CIR, Lake Oswego

$5,195,000
4 Beds 4 Baths 679565322 MLS
THE SHAW HOUSE-John Yeon designed true Mid Century Modern. The quality per square inch in this home cannot be matched. Masterfully restored/renovated as part of the 2015 Street of Dreams. This home is an inspiration with it's 1950's design and style coupled with all of today's amenities including single level living, wine cellar, media room, pool and pool house/party room, 25,000 square foot private lot with three outdoor fire places, covered outdoor living area and protected commanding Mt. Hood and valley views. A "forever home" in the sought after Forest Highlands neighborhood. This home is special, the lot is spectacular, the location is a 10 and the quality is unmatched. This is one that must be experienced in person to be fully appreciated. Truly a special package.

1933 HIGHLANDS LOOP, Lake Oswego

$5,990,000
6 Beds 4 Baths 307744421 MLS
Rare Lake Oswego riverfront legacy estate offering more than one acre of private Willamette River frontage. This once in a lifetime opportunity presents an irreplaceable architectural masterpiece blending timeless craftsmanship, exceptional privacy, and resort inspired living. A tree lined drive winds past your own pond and dramatic bamboo grove to a striking residence featuring authentic Wyoming stone, a DaVinci slate roof, Pella windows, an Iron Lion front door, and custom architectural lighting. Inside, soaring 18 foot ceilings, Level 4 smooth finish walls, expansive walls of glass, dual gas fireplaces, and a temperature controlled glass wine cellar frame breathtaking river views. The chef's kitchen showcases an 11 foot leathered granite island, premium appliances, custom cabinetry, and a walk in pantry. The luxurious main level primary suite offers vaulted beam ceilings, automated blinds, river views, a spa inspired bath with a microbubble soaking tub, heated floors, a computer controlled rain shower, and a custom walk in closet with laundry. Upstairs features four additional bedrooms, walk in closets, and a loft. Hidden media/family room with additional storage area. A temperature controlled 10 car garage with three lifts and guest quarters creates the ultimate collector's residence. Professionally designed grounds lead to a private dock with a solar boat lift and two WaveRunner ports, delivering an unparalleled Willamette River lifestyle. Rarely does a waterfront estate of this caliber come to market.

18418 OLD RIVER LNDG, Lake Oswego

$5,500,000
4 Beds 4 Baths 321077367 MLS
Extremely rare, highest quality updated classic 1930’s gem on the Westpoint Road peninsula. Located just out of half-moon bay and a short boat ride or paddle, or reasonable walk to the farmers market, shopping, restaurants, coffee shops, theatre and more. Westpoint is a small cul-de-sac road jutting out into the main lake of Lake Oswego and contains some of the top locations anywhere in Oregon. This property features a style and craftsmanship that would be hard to duplicate today. From the boxwood hedges and brick pathways to the heavy use of copper, gables, balconies and Henry Jaegler ironwork, this home is unmatched. With a remodel in 2022, the original lines and feel have been preserved, but upgraded with modern amenities. Updates include a new kitchen and bathroom, featuring upgrades such as heated tile flooring, sound system, security, connectivity and a new dock. As you walk down the quiet lane and into the property, you will notice the split shake roof with copper gutters and beautiful mature gardens. On the waterfront is a pool & hot tub with automatic covers, a large balcony with a built-in gas barbecue, refrigerated drawers for drinks and an outdoor fireplace. Next to the water is a Paris inspired dining area, and a brand new dock with a boat lift and room for mooring for guest boats. The home features 4 bedrooms and an office (which may easily be used as a 5th bedroom), multiple fireplaces, vaulted ceilings and many recent upgrades. There are amazing entertaining areas and even a theatre in the bonus room. Step out onto your bedroom balcony to look onto the water or take a swim in the pool after a ski or wake surf session, this is an unbeatable blend of timeless elegance and resort lifestyle.

919 WESTPOINT RD, Lake Oswego

$5,500,000
603017664 MLS
An increasingly rare opportunity, this 3.24-acre dividable property in Lake Oswego offers one of the last remaining large-acreage sites in one of Oregon’s most prestigious neighborhoods. Set along picturesque Knaus Road, the land provides exceptional privacy, natural beauty, and a premier address within a coveted community. Spanning multiple tax lots, the parcel offers remarkable flexibility—ideal for a private estate, a luxury multi-residence compound, or a thoughtfully planned development. The gently sloped, wooded landscape creates a serene retreat just minutes from downtown Lake Oswego, award-winning schools, boutique shopping, fine dining, parks, and recreation. Architectural plans by Green Gables Design & Restoration are included, offering a ready-to-build vision backed by one of the region’s most respected firms, or you may bring your own design team to craft a fully custom estate. Acreage of this scale and quality seldom becomes available. Refined, private, and abundant in potential.

13501 KNAUS RD, Lake Oswego

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