Spread out homes on the wooded hills of Cannondale neighborhood, in Wilton, CT

Cannondale Neighborhood - Wilton, CT

Verdant luxury, privacy, serenity

Homes for Sale

3 active homes for sale

About the Neighborhood

Verdant luxury, privacy, serenity
Old and new homes in the heart of nature

In the embrace of a scenic river valley carved by the Norwalk River, Wilton's Cannondale neighborhood offers an escape into a world imbued with historical allure. This idyllic enclave, conveniently situated within walking distance of Wilton's main town area, is distinguished by its immersion in nature, with protective preserves and open green lands forming its periphery.

The soul of the area, Cannondale Village, acts as a living museum, transporting visitors to the agrarian New England lifestyle of the mid-1800s. This carefully preserved Historic District, a significant area covering roughly 202 acres and featuring around 60 structures, also boasts a unique commercial charm where 19th-century edifices, thoughtfully revitalized by actress June Havoc in the late 1970s, now serve as inviting boutiques and restaurants.

The homes

The homes in Cannondale present a charming blend of history and modern comfort, with many older residences beautifully maintained and thoughtfully updated to meet contemporary standards. These properties are typically situated on large, almost rural lots, now predominantly wooded, creating a sense of secluded tranquility. Professional landscape design and meticulously kept gardens are common sights, enhancing the natural beauty of the surroundings. While the classic Colonial architectural style is a hallmark of the neighborhood, prospective residents will also discover a variety of Contemporary homes showcasing modern design, alongside appealing Cape Cod and practical Ranch-style houses. This diversity extends to home sizes, with living spaces ranging significantly from approximately 1,300 to over 7,500 square feet. Most homes offer between three and five bedrooms, though the larger, stately Colonial residences frequently provide five to six bedrooms to accommodate more extensive needs.

Inside these Cannondale homes, a host of desirable features contribute to their appeal. It's common to find interiors graced with multiple fireplaces, gleaming hardwood floors, and updated kitchens equipped with high-end finishes and modern appliances. Luxurious primary suites offer private retreats, and many homes include finished basements, providing versatile additional living or recreational areas. Externally, convenience and outdoor enjoyment are emphasized, with most properties featuring two- to three-car attached garages, expansive decks, and patios perfect for alfresco dining or relaxation. Many residences are tucked away on quiet cul-de-sacs or are enveloped by woods, ensuring privacy, ample space for outdoor activities, and a tangible connection with the natural environment. Furthermore, a significant number of homes boast in-ground swimming pools, often complemented by pool houses or cabanas, creating ideal settings for private leisure and entertaining.

Cannondale Lifestyle

Recreation and relaxation embraced by nature!

Life in Cannondale offers a tranquil and private retreat, deeply immersed in a bucolic setting that prioritizes serenity and a close connection with nature. Surrounded by extensive nature preserves and verdant open spaces, the neighborhood is an idyllic haven for those who cherish peace and seek ample opportunities for outdoor recreation.

The renowned Norwalk River Valley Trail, a significant local asset, conveniently passes directly through Cannondale, providing residents with many miles of scenic trails that extend across five different towns.

For enthusiasts of hiking and nature exploration, the options are further expanded by vast nearby preserves such as the Belknap Preserve, Gregg Preserve, and Honey Hill Nature Preserve, each offering unique landscapes to discover.

Beyond the embrace of nature, Cannondale residents benefit from access to premium recreational facilities and convenient amenities.

The nearby Rolling Hills Country Club provides a resort-like atmosphere, featuring an impressive 18-hole championship golf course, a six-lane swimming pool, and comprehensive racquet facilities including eight tennis courts, four pickleball courts, and a paddle tennis setup complete with three courts and a comfortable warming hut, ensuring year-round entertainment for all ages and interests.

Despite its peaceful, secluded feel, Cannondale remains just a stroll away from Wilton's town center, placing luxury shopping, fine dining and diverse arts and cultural attractions within easy reach.


Recently Sold Homes

17 homes sold / past 12 months

Because we love Fairfield County!

© Copyright 1999 - 2025 Dagny's LLC. - 20 Windy Ridge Place Wilton, CT 06897 - Terms & Conditions