As a leading real estate team, we enjoy providing our personal insight into the towns that we live, or have lived in. Our partner, Michael Mombello, shared this insight into Westport's Old Hill neighborhood:
One of the greatest pleasures of living in Westport’s Old Hill neighborhood is the ability to stroll into the vibrant, ever-evolving downtown. Restaurants, boutiques, the Westport Library, Levitt Pavilion, several schools, and places of worship are all within easy reach. Just as important is the Saugatuck River, the waterway that connects Old Hill’s current community to Westport’s rich, onion farming and sea-faring past.
Westport’s historic fabric—made up of lasting colonial homesteads, Victorian summer homes, gracious country estates and seaside escapes—remains remarkably intact. Historic homes, cherished for decades and in some cases more than a century, blend seamlessly with more private residences tucked down tree-lined driveways and thoughtful new developments.
Within the Kings Highway North Historic District, homeowners and preservationists have partnered with town officials to maintain architectural continuity, ensuring the past and present coexist harmoniously. The KMS Team, specialists in antique and vintage real estate, find the resulting landscape both authentic and aesthetically pleasing.
Some homes here date back to the American Revolution, when the land belonged to Fairfield and Norwalk. After Westport incorporated in 1835, town leaders worked diligently to protect the homes built during periods of growth and prosperity. The charm and elegance of the 1920s through the 1940s added a layer of gracious, welcoming, character-filled homes—perfect for entertaining, gathering, and community life.
Old Hill’s streets and lanes: Wright Street, Ludlow Road, Old Hill Road, Old Hill Farms Road, Winding Lane, and Broadview Road to name a few, all carry this “old Westport” allure and an understated elegance. The neighborhood surrounding Nash’s Pond—streets like Woodside Avenue, The Fenway, Sylvan Road North, and Partrick Road, and the community treasures of Earthplace, Lillian Wadsworth Arboretum and MoCA Westport further enhance the “hidden gem” quality of this sought-after part of town.
Here in the Old Hill neighborhood of Westport CT, historic preservation and a charming, mercantile-inspired downtown coexist with an abundance of green spaces. The resulting lifestyle has been shaped by generations raised in a community proud of its rich architectural heritage.
The Allure of Old Hill in Westport