Olde Highlander

Welcome to Olde Highlander. Set at the base of the former Olympia ski hill, Olde Highlander is one of Waukesha County’s most exciting master-planned communities, thoughtfully designed to offer a variety of home styles and a truly elevated lifestyle in the heart of Oconomowoc.

Olde Highlander features three distinct living opportunities to fit every stage of life:

• The Towns include 106 thoughtfully designed townhomes from both our Signature and Classic collections, with floor plans ranging from 1,479 to 1,996 square feet — perfect for easy living without compromising space or style.
• The Villas offer 120 single-family homesites with over 20 unique floor plans and multiple elevations, providing flexibility and personalization for homeowners seeking a traditional single-family experience.
• The Reserve features 58 well-appointed condominiums designed for easy, low-maintenance living, including snow removal and landscape care, so you can spend more time enjoying your home and community.

Residents can enjoy miles of scenic paved walking trails, two pools, pickleball courts, a playground, and a community fire pit. The beautifully designed clubhouse offers gathering and entertainment space complete with a golf simulator, billiards, arcade games, darts, a kitchenette, and a party room.

Located in one of the area’s fastest-growing communities, Olde Highlander provides convenient access to everything Oconomowoc has to offer — from its vibrant downtown filled with shops and restaurants to nearby parks and highly rated schools. Whether you're enjoying an active lifestyle, relaxing with neighbors, or exploring the surrounding area, Olde Highlander brings together community, convenience, and comfort.