SKYLANDS Homes for Sale

Welcome to Skylands, a picturesque subdivision nestled in the heart of Lake Oswego, Oregon, within the charming Clackamas County. This serene community is renowned for its stunning natural landscapes, friendly neighbors, and a strong sense of community spirit. Whether you’re a first-time homebuyer or looking to upgrade, Skylands offers a variety of homes for sale that cater to diverse tastes and lifestyles.

As you explore this enchanting neighborhood, you’ll be captivated by the lush greenery and beautifully manicured gardens that define the area. Skylands is designed for those who appreciate the perfect blend of tranquility and convenience. With easy access to local parks, hiking trails, and the pristine waters of Lake Oswego, outdoor enthusiasts will find themselves right at home. Families will appreciate the proximity to highly-rated schools, ensuring a bright future for the little ones.

The homes for sale in Skylands range from charming single-family residences to modern architectural masterpieces, each offering unique features and finishes. Many properties boast spacious layouts, contemporary kitchens, and expansive backyards, perfect for entertaining or simply enjoying the serene surroundings.

Living in Skylands means embracing a lifestyle filled with community events, local shops, and dining options that reflect the vibrant culture of Lake Oswego. With its ideal location, stunning homes, and welcoming atmosphere, Skylands is truly a hidden gem waiting to be discovered. Don’t miss your chance to become part of this delightful community – your dream home awaits!

Newest SKYLANDS Homes for Sale

$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.