Five bedroom, six bathroom estate on 2.09 private acres in Redding, CT | Over 5,300 square feet of living space plus detached guest house and pool house | Heated gunite pool surrounded by expansive entertaining deck | Separate lower-level guest suite with private entrance | Library, home office, and multiple gathering spaces | More than $500,000 in recent improvements | Minutes to Ridgefield, Westport, Wilton, and Easton | Approximately 90 minutes from NYC | Asking $1,695,000

Set on just over two private acres in Redding, CT, this updated Fairfield County estate offers more than 5,300 square feet of living space designed for both everyday living and effortless entertaining. Centered around a heated gunite pool, detached guest house, and beautifully landscaped grounds, the property balances the scale of a full-time family home with the atmosphere of a private countryside retreat.

Inside, a traditional layout unfolds across multiple gathering spaces, including a library, home office, formal dining room, and a soaring family room filled with natural light. The eat-in kitchen sits at the heart of the home, while a finished lower level with its own entrance provides additional flexibility for guests, extended family, or work-from-home needs.

Just beyond the pool, a detached guest house offers a living area, kitchenette, bedroom, and loft—creating a rare opportunity for hosting visitors, accommodating long-term guests, or establishing a private studio or workspace separate from the main residence.

A newly constructed Trex deck surrounds the heated gunite pool, offering multiple spaces for lounging, dining, and gathering throughout the warmer months.

The grounds are equally inviting, with mature trees, flowering gardens, and multiple outdoor spaces designed for gathering throughout the seasons. A newly constructed Trex deck surrounds the heated pool, creating an ideal setting for summer afternoons, outdoor dining, and entertaining.

Since 2021, the property has undergone more than $500,000 in improvements, creating a turnkey opportunity in one of Fairfield County’s most desirable communities. Though the setting feels remarkably secluded, Westport, Ridgefield, Wilton, and Easton are all just minutes away, offering easy access to acclaimed restaurants, farmers markets, cultural attractions, and some of the region’s most beloved farms and open spaces.

Equal parts private retreat and year-round family home, the property offers a rare combination of space, flexibility, and thoughtful updates just 90 minutes from New York City.

Listed by Tara Hawley of Coldwell Banker Realty. For showings and inquiries, contact Tara at 203-331-5939 or tara.hawley@cbrealty.com.

The Neighborhood: In + Around Redding, CT

Though the property feels remarkably secluded, some of Fairfield County’s most beloved destinations are just a short drive away. Nearby Westport offers one of the region’s best farmers markets, along with a lively downtown filled with restaurants, boutiques, and waterfront dining. Ridgefield’s charming Main Street is lined with independent shops, galleries, and cultural venues, while neighboring Wilton and Easton offer their own mix of small-town character, open space, and local favorites.

Redding itself is known for its commitment to preserving nature, with miles of hiking trails, protected woodlands, and working farms woven throughout the community. Local institutions like Sport Hill Farm, Silverman’s Farm, and Shaggy Coos Farm make it easy to embrace the area’s agricultural roots, whether you’re picking up seasonal produce, fresh flowers, or one of Silverman’s famously abundant pie selections. For those balancing city and country life, Metro-North service from nearby Westport and Branchville provides easy access to New York City.

Our Favorite Detail: A Guest House That Functions Like a Home

Many properties advertise a guest house, but few offer one that feels truly independent. Set just beyond the pool, the detached guest house includes its own living room, kitchenette, bedroom, and loft, creating a flexible space that can easily accommodate visiting friends and family, long-term guests, a private home office, or creative studio.

Rather than functioning as an occasional overflow space, it creates a second, self-contained living environment that feels both connected to and separate from the main house—a rare feature that immediately distinguishes this property from the many traditional Colonials found throughout Fairfield County.