Downtown Greenwich is getting its first major luxury condo
Downtown Greenwich is getting its first major luxury condo development in years: Chilston Court, a Robert A.M. Stern Architects project with 78 residences priced from about $4.5 million to more than $10 million, aimed at lock-and-leave living near Greenwich Avenue and Metro-North.
Key Takeaways
- Chilston Court will deliver 78 luxury residences and penthouses in downtown Greenwich, with completion targeted for 2028.
- Homes are priced from roughly $4.5 million to upward of $10 million, with even the smallest layouts topping 2,000 square feet.
- Developer Josh Caspi is aiming the project at local downsizers, not only Manhattan weekenders.
- Robert A.M. Stern Architects designed the twin buildings at 275 and 290 Mason Street; Bryan O'Sullivan Studio is handling interiors.
- Shared amenities total about 10,000 square feet, including a lap pool, wellness spaces, private dining, and a residents-only speakeasy.
For decades, Greenwich, Connecticut, drew affluent buyers seeking sprawling estates. That preference is shifting as longtime residents look for lock-and-leave living without leaving the town's country clubs and family ties behind.
Developer Josh Caspi has unveiled Chilston Court as that missing option of scale. In comments to Robb Report, he said many owners want out of large homes but have had nowhere comparable to go in town.
What is Chilston Court and who is behind it?
Chilston Court is a condominium development of two buildings planned for 275 and 290 Mason Street, steps from the Metro-North station and busy Greenwich Avenue. Caspi tapped Robert A.M. Stern Architects (RAMSA) for the design, citing the firm's mix of high-end houses and thoughtful multifamily work.
RAMSA partner Sarge Gardiner described the site as a chance to link the commercial core with nearby residential streets. The firm looked to local civic landmarks—the historic post office, YMCA, and fire headquarters—for cornices, stone detailing, and arched entrances, then folded those cues into what it calls "modern traditionalism."
London's Bryan O'Sullivan Studio is designing the interiors. Residences will range from two-bedroom homes to penthouses, with oversized primary suites, generous closets, wide hallways, and ceilings exceeding nine feet.
Why is downtown Greenwich getting its first major condo now?
Caspi expects many buyers to come from Greenwich's backcountry estates and from neighboring Fairfield and Westchester counties. The pitch is optionality: walk, drive, take the train, or lock the door and leave—without giving up community ties.
That story fits a broader appetite for polished urban living among luxury audiences, a theme we track across luxury real estate and dream homes. Chilston Court is framed as hospitality-inspired condo living rather than a miniature suburban estate.
What amenities and pricing should buyers expect?
Beyond the residences, the development plans roughly 10,000 square feet of shared amenities. Those include a lap pool, wellness facilities, a 20-person private dining room, a speakeasy, concierge services, and dedicated delivery closets for packages, groceries, and laundry while owners are away.
Pricing starts around $4.5 million and climbs past $10 million. If the 2028 delivery holds, downtown Greenwich will finally have a large-scale luxury condo alternative in one of the country's wealthiest enclaves—and the lifestyle many longtime residents say they have been waiting for.