SKYLANDS Homes for Sale

Welcome to Skylands, an enchanting subdivision nestled in the heart of Lake Oswego, Oregon, within the picturesque Clackamas County. This charming community is renowned for its breathtaking natural beauty, lush landscapes, and a serene atmosphere that perfectly complements the Pacific Northwest lifestyle. Skylands offers a unique blend of tranquility and accessibility, making it an ideal choice for families, professionals, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

The homes for sale in Skylands are a testament to modern living, featuring a variety of architectural styles that cater to diverse tastes. From contemporary designs to classic craftsman homes, each property boasts spacious layouts, high-end finishes, and expansive outdoor spaces that invite you to enjoy the stunning surroundings. Many residences are positioned to take full advantage of the area’s natural beauty, offering picturesque views and easy access to nearby parks and trails.

Living in Skylands means embracing a lifestyle that prioritizes community and connection. Residents enjoy access to top-rated schools, vibrant local shops, and an array of recreational opportunities, including boating and hiking. The close-knit community hosts regular events that foster neighborly bonds and a sense of belonging.

If you’re searching for your dream home in a serene yet vibrant setting, look no further than Skylands. With a range of homes for sale, this subdivision is not just a place to live; it’s a place to thrive. Discover the perfect blend of comfort, style, and community in Skylands—your new 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.