Cannondale Homes for Sale

Welcome to Cannondale, a picturesque neighborhood nestled within the charming town of Wilton, Connecticut. Known for its serene ambiance and tight-knit community, Cannondale offers a unique blend of suburban tranquility and vibrant local culture. With its tree-lined streets, historic architecture, and lush green spaces, this neighborhood is a haven for those seeking a peaceful retreat from the hustle and bustle of city life.

Cannondale boasts an array of amenities that cater to both families and professionals alike. Residents can enjoy easy access to top-rated schools, delightful parks, and a charming local shopping scene. The area is also well-connected to major highways and public transportation, making commutes to nearby cities like Stamford and Norwalk a breeze. For nature enthusiasts, the nearby Wilton Nature Preserve and the scenic trails of the Norwalk River Valley are perfect for hiking, biking, and leisurely strolls.

When it comes to homes for sale in Cannondale, you’ll find a diverse selection that caters to various lifestyles and preferences. From quaint cottages to spacious family homes, each property exudes character and charm. Many homes feature beautifully landscaped yards, modern amenities, and inviting interiors that make them perfect for both entertaining and relaxation.

Whether you are a first-time homebuyer or looking to settle into a forever home, Cannondale offers a welcoming community and a vibrant lifestyle. Explore the available homes for sale, and discover why so many have chosen to call this enchanting neighborhood their home. Your dream home awaits in Cannondale!

Newest Cannondale Homes for Sale

$2,399,000

5 Beds ⋅ 6 Baths ⋅ 24194109 MLS

Set on a private, beautifully landscaped two-acre property, 14 Powder Horn Hill Road offers exceptional space, privacy and convenience just minutes from Wilton town center, shopping and the train. A stunning front porch creates a memorable first impression and opens to a grand entry foyer with a sweeping staircase. Inside, rich hardwood floors, generous room sizes, high ceilings and thoughtful architectural details create an elegant yet comfortable atmosphere. The spacious chef's kitchen features a large center island, Sub-Zero refrigeration and abundant workspace, flowing seamlessly into the inviting family room with coffered ceilings, a fireplace and French doors leading to the deck. Formal living and dining rooms provide ideal entertaining spaces, while a private library offers the perfect home office or quiet retreat. Upstairs, the expansive primary suite features a fireplace, luxurious bath and two exceptionally large walk-in closets. Four additional bedrooms and an oversized playroom room with a full bath offer outstanding flexibility for guests, recreation or media. The walk-out lower level is a true blank canvas, featuring impressive 9-foot ceilings, plumbing already in place for a future bathroom and endless potential to create a gym, home theater, game room, guest suite or additional living space. Outside, the flat, fenced backyard offers an ideal setting for entertaining, play and pets, with ample room for a future pool.

14 Powder Horn Hill Rd, Wilton

$1,190,000

3 Beds ⋅ 2 Baths ⋅ 24193149 MLS

Beautifully renovated and impeccably maintained, this sun-filled 3-4 bedroom home offers timeless style, quality craftsmanship, and exceptional indoor-outdoor living on a picturesque, meadow-like property. Soaring ceilings, walls of windows, and an open, inviting layout create the perfect setting for everyday living and entertaining. The chef's kitchen features premium cabinetry, quartz countertops, a large center island, Wolf six-burner cooktop, Bosch wall ovens, and a walk-in pantry, flowing seamlessly into the beamed family room with wide-board floors, wood-burning fireplace, and French doors to an expansive stone patio complete with multiple seating areas, a custom outdoor fireplace, and spa. The main level includes two bedrooms, a renovated full bath, and a flexible den with fireplace and built-ins that can serve as a fourth bedroom or home office. Upstairs, the private primary suite features vaulted ceilings, a walk-in closet, and a beautifully appointed ensuite bath. Recent improvements include a new 50-year roof, high-efficiency propane boiler, sump pump system, renovated basement, CarbonArmor garage wall stabilization, polyaspartic garage floor coating, and fresh interior paint. Central air, whole-house generator, two-car garage, and a level driveway complete this move-in ready home, ideally located just minutes from Wilton's town center, top-rated schools, and commuting routes.

130 Blue Ridge Rd, Wilton

$999,000

3 Beds ⋅ 3 Baths ⋅ 24169226 MLS

This iconic mid-century modern home offers a rare blend of architectural character and natural beauty, situated on two private acres along Olmstead Hill-one of Wilton's designated scenic roads. Designed in 1958 by architect Robert Van Summern (whose work has been featured in The New York Times) as his first family residence, the home thoughtfully integrates timeless design with its serene, wooded surroundings to create a distinctive treehouse-like feel. Original architectural elements remain beautifully intact, including a striking floor-to-ceiling stone fireplace and a dramatic wall of glass that fills the home with natural light throughout the day. The main level features an open layout that seamlessly connects the dining and living areas to a remodeled kitchen featuring custom cabinetry with seeded glass accents, a 9-foot quartz center island, and a dedicated prep sink. A brand-new powder room and freshly painted interiors add a crisp, updated feel, while the vaulted three-season porch and multiple sliding glass doors extend the living space onto the wraparound deck and wooded grounds. Upstairs, the primary suite offers cathedral ceilings, a private balcony overlooking the wooded grounds, and an oversized walk-in closet and dressing area. The en-suite bath showcases striking artisan glass vessel sinks that complement the home's mid-century modern aesthetic. The upper landing features floor-to-ceiling built-in bookcases and a cascading glass chandelier.

305 Olmstead Hill Rd, Wilton

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