$4,500,000

Set across 53 gated acres in Northern Fairfield County, this exceptional estate offers a rare combination of privacy, scale, and natural beauty, just minutes from Ridgefield, approximately 10 minutes from Danbury Airport, and within practical reach of New York City. Originally conceived as a country retreat, the property blends historic character with modern comfort in a setting that feels private and serene, yet fully suited to year-round living. Beyond the gates, the grounds unfold across woodland trails, a stone bridge, pond, brook, orchards, gardens, and approximately two miles of groomed paths through the estate's own natural preserve. The landscape has been carefully maintained and offers both beauty and utility, with room for recreation, agriculture, and future enhancements. The residence is rich in character and thoughtfully updated, with six fireplaces, a double-sided chef's kitchen, wine cellar, and a 1,055 SF primary suite with dual baths, dressing room, walk-in closet, private sitting room, and sunroom. Outdoor living is centered around a heated gunite pool, outdoor kitchen, pergola, and gazebo, all positioned to take in sweeping views of the surrounding landscape. A detached barn, detached garage, and expansive acreage create unusual flexibility for equestrian pursuits, agriculture, a guest house, tennis or paddle court, and other future improvements, subject to local approvals. A detached barn, detached garage, and expansive acreage create unusual flexibility for equestrian pursuits, agriculture, a guest house, tennis or paddle court, and other future improvements, subject to local approvals. Historically known as "Roadside," the estate takes its name from its early 20th-century identity as a distinguished country retreat connected to the Broadway and social circles of the period. Rachel Crothers, who reshaped the property during her ownership, described it as "the house the plays built," a phrase that speaks both to its cultural significance and to its enduring character as a private sanctuary. Estate highlights include a private 1,055 SF primary suite wing with 357 SF bedroom, 210 SF sitting room, 128 SF dressing room, 40 SF walk-in closet, dual baths, fireplace, and sunroom; approximately two miles of groomed trails with electrical service throughout the trail system; a lower-level wine cellar with approximately 500-bottle capacity; extensive updates, including an 80-gallon propane hot water system and multi-zone climate control; and fully fenced and gated grounds with surveillance systems in place.