A fresh development plan in Greenwich would level the Georgian waterfront mansion that once housed Donald and Ivana Trump, trading the nearly 20,000 square foot structure for a slightly smaller main residence and a clutch of high end recreation buildings. The roughly 5.8 acre spread at the tip of Indian Harbor is slated in the application for a new main house of about 17,150 square feet, with courts, a pool and staff housing filling out the rest of the peninsula.
What’s proposed
The application, filed by 21 Vista Drive LLC, asks the town to merge three separate parcels, clear every existing structure and rebuild the site around a new estate layout. The proposal calls for a main house, an indoor sunken tennis court, an outdoor tennis court, a pavilion, an accessory dwelling unit, employee housing and new beach areas, according to documents filed with the Town of Greenwich Planning & Zoning Department. Local coverage that walked through the same filing has broken out the building footprints and landscaping changes in greater detail, as reported by Patch.
A storied ownership history
The house, long identified in real estate listings as 21 Vista Drive, was built in 1939 and purchased by Donald and Ivana Trump in 1982. After their 1992 divorce, Ivana kept the property, according to local reporting. Financier Robert Steinberg bought the estate in the late 1990s, and the site most recently changed hands in October 2024. Public records list the current owner as 21 Vista Drive LLC, and local reports put the sale price at about $31.5 million, according to Greenwich Time.
The architect and the design
The new construction plans credit Robert A.M. Stern Architects with the overall design of the buildings and the reworked site layout. Presentation images included in the filing show the proposed look of the main house and the surrounding landscape. Both Patch and the town submission identify RAMSA as the design firm. The company’s founder, Robert A.M. Stern, died in 2025, according to an obituary published by The Washington Post.
Permits and what comes next
The owners are seeking a special permit because the total proposed building volume would exceed Greenwich’s usual cap and the indoor athletic facility would be larger than allowed without extra scrutiny. Those thresholds automatically send the file to the Planning & Zoning Commission for a formal review, according to the Town of Greenwich Planning & Zoning Department. The paperwork, submitted through the owners’ attorney, is expected to be taken up first at a preliminary hearing, and any demolition or new construction will need Planning & Zoning sign off before work can start, as outlined by Greenwich Time.
Why it matters locally
The filing drops this property squarely into Greenwich’s ongoing debate over waterfront tear downs and just how far owners can go in remaking prized shoreline parcels. It is also almost guaranteed to attract attention far beyond Indian Harbor thanks to its Trump history. National outlets picked up on the local filings after the application hit the town system this week, with Page Six among those covering the proposal.
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