top of page

Room to Evolve

Expanding a home to create independent, connected space for multiple generations.

OLD HILL
WESTPORT, CONNECTICUT

THE PROJECT

MAKING ROOM FOR WHAT COMES NEXT

This ongoing project reimagines a 1960s Colonial for the next chapter of family life.

 

A 2,250-square-foot addition expands the home while creating greater flexibility for multiple generations to live together — and independently — under one roof.

 

At the same time, the existing house is being reconsidered so the old and new work as one, creating a home designed not just for how the family lives today, but for how their needs may change over time.

THE DETAILS

​SIZE:                      2,250+ SQ FT

​

SCOPE:                ADDITION​ 

PROJECTED TIMELINE:     6 - 8 MONTHS

BEHIND THE WORK

FINDING ROOM TO GROW

The first challenge was the property itself. With extensive wetlands and limited buildable area, there were few places the house could expand. Determining where to build meant working within the constraints of the site while creating enough new space to meaningfully change how the home could function.

​

Then came the challenge of adding onto an existing 1960s house. The addition couldn't feel like an appendage — it needed to become part of the house. That meant considering old and new together, inside and out, and creating a cohesive design while introducing the space, amenities and functionality the original home couldn't provide.

​

The new footprint was also planned with both independence and adaptability in mind. It provides the right degree of separation for someone aging in place today, while creating flexible spaces that can serve different purposes as the family's needs change over time.

​

The result isn't simply more square footage. It's an expansion designed to make the entire home work better — responding to a challenging site, integrating old and new, and creating greater flexibility for whatever comes next.

Old Hill Rendering - MelissaLevyResidential - Westport, CT

DESIGN DIRECTION

Old Hill Sketch - Melissa Levy Residential - Westport, CT

INITIAL DESIGN SKETCH

Melissa Levy | CT Licensed Real Estate Salesperson | 646.522.2252  

Compass Connecticut LLC Brokerage: 87 Post Road East, Westport, CT 06880 © 2026.

INSTAGRAM ↗: @melissalevyresidential

Select Project Photography:  BA Staging & Interiors, James Cooper Photography

bottom of page