Milwaukee

Old Olympia Ski Hill Trade-Up: Oconomowoc Signs Off On 93 New Homes At Olde Highlander

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Published on June 18, 2026
Old Olympia Ski Hill Trade-Up: Oconomowoc Signs Off On 93 New Homes At Olde HighlanderSource: City of Oconomowoc

Oconomowoc’s former Olympia golf course and ski hill are getting yet another batch of front doors and mailboxes. On Thursday, city leaders signed off on a fourth residential phase of the Olde Highlander neighborhood, clearing the way for roughly 93 new homes along the western edge of the Pabst Farms corridor. Neumann Developments, the master developer, has already been stitching together new streets, townhomes, condos and single-family lots as builders move parcels from grading to framing.

As reported by the Milwaukee Business Journal, the council’s vote greenlit about 93 units in this latest phase and noted that nearly half of the development’s planned homes are already under construction. The outlet described the approval as the newest milestone in a multi-phase redevelopment of the former resort lands.

Where the new streets and lots land

The city’s Plan Commission packet details a certified survey map and new right-of-way dedications tied to the approval, mapping the property at Pabst Road, Olde Highlander Drive and the proposed extension of Snyder Way. The documents describe dedicating nearly an acre of land along Olde Highlander Drive to accommodate the street connection and to widen turning radiuses for fire apparatus, according to the City of Oconomowoc.

Developer plans and partners

Neumann’s own project materials describe Olde Highlander as a mix of single-family lots, townhomes and condominiums. A 2023 release from the company put the master plan at roughly 352 home sites and highlighted partnerships with Tim O’Brien Homes and Harbor Homes, along with neighborhood amenities such as walking trails, a clubhouse and a pool, per Neumann Developments.

Why this matters for Oconomowoc

The Olde Highlander buildout is part of a broader push to reactivate the former Olympia Resort and nearby parcels that have sat underused since the golf course and ski hill closed more than a decade ago. Local reporting and city planning talks have tied this neighborhood to other redevelopment in the Pabst Farms corridor, including mixed-use work at Olympia Fields and nearby commercial projects, according to TMJ4.

City housing records show Olde Highlander has advanced through multiple additions in recent years, with final plats and condominium filings already recorded for earlier phases. The new 93-unit tranche will add to that count. Public documents and the city’s housing tracker indicate the project has been brought forward in staged plats and certified survey maps as infrastructure extends into the site, per the City of Oconomowoc.

With the council’s sign-off now in hand, developers can move ahead with certified survey map recordings, utility work and street construction that come before lot-by-lot building permits. City packets lay out the procedural timelines and deadlines that will steer the next rounds of engineering, inspections and plat approvals as the property shifts from graded dirt to framed houses this summer.