Greenwich Waterfront Mediterranean Estate Renovation - Eastover

This Greenwich waterfront modern Mediterranean estate, known as Eastover, is a century-old coastal residence transformed through a comprehensive architectural restoration and modernization. Set high above the rocky shoreline of Long Island Sound, the home underwent a multi-phase design evolution that honors its 1916 origins while elevating it into a refined, contemporary retreat for a family with four children. The result is a meticulous blend of luxury residential renovation, architectural craftsmanship, and coastal elegance that redefines what it means to restore and reinvent a historic estate.

A Century of History, Reimagined for Modern Living

Originally designed for Henry Steers, a prominent New York construction engineer and devoted yachtsman, Eastover began as a stately stucco residence inspired by English and Irish country houses. When our firm first engaged with the property in the mid-2000s, the home still retained its low pitched asphalt roof, unadorned stucco, and interiors long untouched. Yet beneath the wear were exceptional proportions, masonry walls, and sweeping water views across Long Island Sound, features that made the home worthy of preservation.

During that initial phase, we replaced the failing exterior insulation system, added a higher pitched terracotta roof, introduced classical cornice detailing, restored water-damaged interior spaces, and upgraded windows and doors. These interventions established the architectural foundation that would guide the estate’s future transformation.

A decade later, under new ownership, we returned to fully realize the vision, this time with a more expansive scope, a bolder design language, and a client committed to honoring the home’s history while embracing the needs of contemporary family life.

A Modern Mediterranean Expression on the Connecticut Coast Begins with a Bold Exterior Transformation

The 18,000-square-foot residence underwent a dramatic exterior renovation that redefined its architectural character. The muted pink façade was replaced with a luminous white stucco finish, designed to harmonize with the bright maritime light and the rugged coastal setting. The terracotta roof added in the first phase of the renovations was meticulously stained a deep charcoal to anchor the composition and complement the home’s new modern Mediterranean architecture.

Trim and fenestration were finished in “Baby Seal,” a refined near-black tone that offers crisp contrast against the white stucco. The layered palette strikes a balance between coastal simplicity and formal elegance, an aesthetic direction developed collaboratively with interior designer Rob Rizzo of Cobble Court Interiors.

Comprehensive Site Enhancements

The estate’s hillside site presented opportunities for expanded outdoor living. Improvements include a new pool and pool house, as well as refreshed terraces, upgraded walkways, new iron and bronze railings, and an extensive drainage and coastal compliance system designed with the project’s civil engineers. Each intervention reinforces the property’s relationship with its dramatic waterfront while supporting long-term resilience.

Reimagining the Interior for Contemporary Family Life - Redesigned Floor Plan and New Programmatic Spaces

Like many historic homes, Eastover’s original planning no longer supported the rhythms of modern living. Our team restructured circulation and functionality throughout the main and lower levels, expanding the kitchen, creating a new mudroom, and adding two garage bays. New family and formal powder rooms replaced outdated layouts, and nearly all mechanical, electrical, and plumbing systems were modernized with efficiency and comfort in mind.

The lower level became a dynamic entertainment level, complete with a golf simulator room carved out literally from solid rock, a custom bar, gym, rec room, and staff quarters. These spaces introduce contemporary luxury while remaining carefully integrated within the historic architectural shell.

Craftsmanship, Millwork, and Architectural Detailing

Throughout the interior, we collaborated closely with Cobble Court Interiors on custom millwork, trim profiles, concealed lighting, and material selections. High ceilings and generous proportions offered a strong starting point, but the refinements brought the home to life: tailored paneling in the dining room, sculptural ceiling details in the living room, and a quiet yet powerful black-and-white palette that ties the architecture to the exterior expression.

The staircase, softened by arched openings, textural wall finishes, and a sculptural chandelier, embodies the project’s philosophy: classic bones refreshed with a modern sense of rhythm, craftsmanship, and light.

The Rewards of Thoughtful Historic Home Restoration

Restoring a home like Eastover requires more than replacing materials, it demands respect for the architectural lineage, a willingness to work within inherited constraints, and the imagination to bring forward something fresh and new. Though the roof, fenestration, and systems all required replacement, the underlying structure offered a rare opportunity: to preserve history while crafting a residence uniquely suited to contemporary coastal living.

Today, Eastover stands as a testament to the power of coastal estate renovation and the value of preserving homes that anchor the architectural fabric of Greenwich. As the ongoing pool and landscape master plan continues, the estate’s evolution remains rooted in its past while looking confidently toward its future.

For more examples of our historic home restoration work, explore our Waterfront Design blog https://www.hiltonarchitects.com/blog/the-allure-of-living-on-a-waterfront-property, or visit our residential Renovation portfolio page https://www.hiltonarchitects.com/renovations.