ROADSIDE - A Storied 53-Acre Private Estate in Fairfield County, CT
Escape to your own private nature retreat at ROADSIDE, an extraordinary 53.44-acre country estate blending historic charm and modern luxury, just 90 minutes from Manhattan and 1.5 miles from the Redding train station. This rare legacy property offers unparalleled privacy, provenance, and polish-ideal for equestrians, creatives, collectors, and those seeking an exceptional lifestyle sanctuary where inner peace meets outer glow.
Originally built in 1710 and masterfully reimagined in the early 1900s, the meticulously maintained 5,200+ sq ft Colonial farmhouse features 4 bedrooms, 4 full bathrooms, and 3 half baths across three levels of living space. Period details including wide plank floors, six fireplaces, and custom millwork pair beautifully with modern comforts.
The heart of the home is the expansive chef's kitchen with a dramatic double-sided fireplace that flows into sun-drenched gathering rooms and a glass-wrapped solarium. The luxurious primary suite offers dual spa-like bathrooms, a dressing room, and a private sitting area overlooking the grounds.
One of the most striking spaces is the dream library, complete with a cozy fireplace, intricate built-ins, and a stunning mezzanine loft above-perfect for book lovers, creatives, or remote professionals seeking a peaceful and inspiring work-from-home haven.
The partially finished walk-out lower level includes a media/game room, fitness space, and an impressive 500-bottle wine room. Every corner of the home is designed for comfort, sophistication, and timeless entertaining.
Surrounded by fencing, gated entries, and professional landscaping, the estate is a fully self-contained world. Wander through 2+ miles of groomed trails with electricity throughout-ideal for future equestrian lighting or nature-inspired enhancements. A scenic aerated lily pond, stone bridge, and gentle brook accentuate the estate's park-like setting.
Outdoor living is elevated with a heated Gunite pool, pergola, gazebo, and a fully equipped outdoor kitchen. Enjoy vibrant fruit orchards, cutting gardens, vegetable beds, and expansive lawns-ideal for recreation, events, or simply reconnecting with nature.
A detached 3-car garage, 3-stall barn with electric and water, and open land provide exceptional lifestyle flexibility: add a tennis court, solar field, guest house, or equestrian amenities. Zoned RA40 and buffered by woodlands, this is a canvas for self-sustaining living or visionary development.
Located on Long Ridge Road, a designated scenic country road with a rich cultural history, this peaceful haven is moments from Candlewood Lake, Waubeeka Lake, Moses Mountain, Tarrywile Park, downtown Danbury, and I-84.
Whether you're a New Yorker seeking a weekend escape, a West Coast buyer craving Northeast charm, or a collector of legacy estates, ROADSIDE is a one-of-a-kind opportunity to own a premier estate in Fairfield County.
Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of December 5, 2025 3:22 AM EST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.
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