A $31.5 million Greenwich waterfront estate that once belonged to Ivana Trump could become one of the town’s most ambitious residential redevelopments — but neighbors are already gearing up for a fight.
The private Indian Harbor Association has hired an attorney to oppose plans for 21 Vista Drive, a 5.9-acre peninsula property where the new owners want to replace the existing estate with a larger mansion, indoor and outdoor tennis courts, employee housing and a private beach.
During a July 7 pre-application meeting with the Greenwich Planning & Zoning Commission, attorney Steve Walko, representing the association and nearby residents, called the proposal’s scale “unprecedented” for the narrow waterfront site.
“The amount of fill that is going to be needed, and the disruption to this peninsula, these streets, is simply outstanding,” Walko said.
The property’s owner, 21 Vista Drive LLC, purchased the estate for $31.5 million in 2024, according to property records. The company’s principals have not been publicly identified.
The estate has a high-profile history. Donald and Ivana Trump purchased the property in 1982 for $4 million before Ivana sold it after their divorce in 1998 to financier Robert Steinberg and his wife, Suzanne, for $15 million.
What’s being proposed
The redevelopment plan would combine three lots and remove nearly everything currently on the property, including the roughly 19,000-square-foot main house, tennis court, pool, pavilion and accessory buildings.
The proposed replacement would include:
- A roughly 17,000-square-foot main residence designed by Robert A.M. Stern Architects
- A sunken indoor tennis court
- A new outdoor tennis court
- Two employee housing units
- An accessory dwelling unit
- A new sandy beach replacing existing shoreline riprap
The beach proposal requires approval from the Connecticut Department of Energy and Environmental Protection (DEEP). The project also requires a special permit from P&Z because the proposed building volume exceeds 150,000 cubic feet.
Flooding and construction concerns
The property sits in two flood zones, AE-14 and VE-15. The applicant is seeking a Letter of Map Revision that could alter the AE-14 flood zone boundary.
Walko questioned whether raising the property with imported fill could effectively change flood restrictions. He estimated the earthwork could require about 1,000 dump trucks bringing material onto the peninsula and another 1,000 leaving the site.
Neighbors also raised concerns about construction impacts.
Carolyn Weiner, whose property connects to Tweed Island, told commissioners that emergency access could become a problem if construction vehicles block the narrow roadway.
Commissioner Mary Jenkins questioned the removal of roughly 70 trees. Applicant attorney John Tesei acknowledged the project would remove “the majority of trees” but said new trees would be planted.
P&Z Chair Margarita Alban said the commission would expect strict compliance with coastal regulations, native and salt-tolerant landscaping, and protections for existing habitat. Commissioner Arn Welles also asked the applicant to confirm that the proposed beach fill would not extend into Long Island Sound.
Tuesday’s discussion was only an early review. No formal public hearing has been scheduled.
Before construction could begin, 21 Vista Drive LLC would need to submit a formal application to the Planning & Zoning Commission and obtain separate coastal approvals from DEEP.
