Cannondale Homes for Sale

Welcome to Cannondale, a charming neighborhood nestled in the heart of Wilton, Connecticut, within the picturesque Fairfield County. Known for its serene landscapes and tight-knit community, Cannondale offers a perfect blend of suburban tranquility and convenient access to urban amenities. With its tree-lined streets and beautifully maintained homes, this area is an idyllic setting for families, professionals, and retirees alike.

Residents of Cannondale enjoy the best of both worlds—peaceful living with a vibrant community spirit. The neighborhood is home to a variety of local shops, quaint cafés, and delightful eateries, making it easy to enjoy a leisurely afternoon exploring the area. Nature enthusiasts will appreciate the nearby parks and trails, perfect for hiking, jogging, or simply enjoying a picnic on a sunny day.

For those considering a move to this enchanting neighborhood, there are a variety of homes for sale that cater to different lifestyles and preferences. From charming historic properties to modern family homes, Cannondale boasts a diverse real estate market that reflects the area’s unique character. Each residence is designed to offer comfort and style, with many featuring spacious yards, updated interiors, and proximity to top-rated schools.

With its strong sense of community, excellent amenities, and beautiful surroundings, Cannondale is not just a place to live—it's a place to thrive. Explore the homes for sale and discover the possibilities that await you in this delightful neighborhood. Your dream home in Cannondale is just a click away!

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 bonus 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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