Greenwich's Premier Luxury Condominium Development Unveiled

July 29, 2026

Greenwich, Connecticut, a locale long synonymous with sprawling estates and vast properties, is undergoing a significant transformation in its luxury housing market. A new condominium development, Chilston Court, is emerging as a compelling option for affluent residents who desire a more flexible, maintenance-free lifestyle without departing from their cherished community. This shift reflects a growing trend among long-term homeowners seeking to downsize while retaining the comforts and prestige associated with their previous residences.

Embrace the Future of Luxury Living in Greenwich

Addressing a Shifting Demographic in Affluent Communities

For many decades, Greenwich has been the preferred destination for wealthy individuals looking for grand estates with considerable land. However, an evolving demographic is leading many established residents to seek alternatives that offer convenience and reduced upkeep. This demand has created a gap in the market for sophisticated, urban-style luxury homes, a need that Chilston Court aims to fulfill.

Introducing Chilston Court: A Landmark Development

Developer Josh Caspi has introduced Chilston Court, a prestigious condominium project featuring 78 upscale residences scheduled for completion by 2028. This development is strategically positioned to cater to homeowners from Greenwich's extensive estates, as well as nearby Fairfield and Westchester counties, who wish to transition to a modern, lock-and-leave lifestyle. Caspi notes the strong desire among these buyers to remain connected to their community, family, and social networks in Greenwich.

Architectural Excellence by Robert A.M. Stern Architects

To realize this vision, Caspi enlisted the renowned Robert A.M. Stern Architects (RAMSA), celebrated for their expertise in designing both high-end private residences and exceptional multi-family complexes. RAMSA's involvement ensures that Chilston Court embodies a blend of traditional elegance and contemporary functionality, making it a perfect fit for Greenwich's discerning clientele.

Strategic Location and Community Integration

RAMSA partner Sarge Gardiner was particularly drawn to the project's prime location at 275 and 290 Mason Street. Situated just moments from the Metro-North station and the vibrant Greenwich Avenue, the development seamlessly connects the town's commercial heart with its residential areas. Gardiner emphasizes the opportunity to create a harmonious transition within the urban landscape, fostering a walkable lifestyle that is increasingly sought after by affluent commuters.

Modern Traditionalism: Design Philosophy

The architectural design of Chilston Court, termed 'modern traditionalism,' skillfully marries classically inspired facades with advanced construction techniques. The buildings draw inspiration from Greenwich's historic civic structures, such as its post office and fire headquarters, incorporating elements like cornices, stone details, and arched entrances. This approach results in a design that respects the town's heritage while offering expansive windows, open floor plans, and recessed loggias that serve as elegant outdoor living spaces.

Unparalleled Interior Comfort and Amenities

Designed to exceed the expectations of those accustomed to spacious estates, the residences at Chilston Court range from generous two-bedroom units to luxurious penthouses, with even the smallest homes spanning over 2,000 square feet. Interiors by London's Bryan O’Sullivan Studio provide a sophisticated touch, complementing the development's extensive amenities. These include a lap pool, wellness facilities, a 20-person private dining room, a speakeasy, concierge services, and dedicated delivery closets, all aimed at enhancing convenience and luxury. Units are priced from approximately $4.5 million to over $10 million, reflecting the premium quality and exclusive lifestyle offered by Chilston Court.