SKYLANDS Real Estate

Welcome to Skylands, a breathtaking subdivision nestled in the heart of Lake Oswego, Oregon. This enchanting community is a hidden gem in Clackamas County, where nature's beauty meets modern living. Skylands offers a serene retreat, surrounded by lush landscapes, tranquil lakes, and scenic views that will take your breath away.

The homes in Skylands are a perfect blend of elegance and comfort, featuring contemporary designs that cater to various lifestyles. Each property is thoughtfully crafted to provide ample space, natural light, and high-end finishes, making it an ideal choice for families, professionals, and retirees alike. With spacious yards and beautifully landscaped gardens, residents can enjoy outdoor living at its finest.

Skylands is more than just a collection of homes; it’s a vibrant community where neighbors become friends. Residents benefit from a tight-knit atmosphere, with community events and gatherings that foster connections and create lasting memories. The nearby parks and recreational areas offer endless opportunities for outdoor activities, from hiking and biking to kayaking and fishing in the pristine waters of Oswego Lake.

Conveniently located, Skylands provides easy access to Lake Oswego's charming downtown area, filled with boutique shops, delightful cafes, and gourmet restaurants. With excellent schools and a strong sense of community, this subdivision is perfect for families seeking a nurturing environment.

Discover the magic of Skylands, where your dream home awaits amidst the beauty of Oregon's landscape. Come experience a lifestyle that perfectly balances tranquility and convenience in one of Lake Oswego's most sought-after neighborhoods. Your new beginning starts here!

Newest Listings in SKYLANDS

$4,950,000

4 Beds ⋅ 6 Baths ⋅ 243699933 MLS

A private-club lifestyle unfolds across nearly two acres at the peak of Lake Oswego, where panoramic views of the Willamette River, Mt. St. Helens and Mt. Adams provide a spectacular backdrop for everyday living. The approximately 6,600-square-foot modern Northwest residence features a main-level primary retreat, three additional en suite bedrooms, beautifully crafted mahogany millwork, expansive entertaining spaces and a 1,200-bottle wine cellar, while the extraordinary grounds transform the property into a destination of its own. A lagoon-style pool and spa, lighted regulation tennis court, expansive lawns, view decks, fire pit terrace and established gardens are joined by a detached clubhouse with a regulation racquetball court, indoor climbing wall, full kitchen, billiards area, locker room and extensive garage/RV space. Exceptionally private yet minutes from downtown Lake Oswego, this rare Skylands estate offers the space, amenities and enduring craftsmanship to bring family and friends together for generations.

17849 UPPER CHERRY LN, Lake Oswego

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The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.