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 offers a serene and idyllic setting, perfect for families, retirees, and anyone seeking a tranquil lifestyle surrounded by nature’s beauty.

Skylands boasts a variety of elegant homes for sale, each designed with modern living in mind. From spacious single-family residences to cozy townhomes, there’s something for everyone in this vibrant neighborhood. Many of the homes feature open floor plans, gourmet kitchens, and lush outdoor spaces, ideal for entertaining or enjoying quiet evenings under the stars. With an array of architectural styles, you’ll find a home that perfectly complements your taste and lifestyle.

Living in Skylands means embracing the best of both worlds—peaceful suburban living with easy access to the bustling amenities of Lake Oswego. Residents can enjoy nearby parks, scenic walking trails, and pristine lakes, perfect for outdoor enthusiasts and families alike. The community is also conveniently located near top-rated schools, shopping centers, and charming local eateries, making it an ideal place to call home.

Whether you’re looking for a place to settle down, raise a family, or simply enjoy a slower pace of life, Skylands offers the perfect backdrop for your next chapter. Explore the homes for sale in this delightful subdivision and discover the unmatched charm and community spirit that Skylands has to offer. 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

Start Your Search

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.