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.
Do you have other availabilities? Add up to two additional timeframes.
Please select a valid date
Please select a valid time
Please select a valid date
Please select a valid time
How would you like to tour?
Select your preferred video platform(s).
Zoom
FaceTime
Facebook Messenger
Google Meet
WhatsApp
Other
Your health and safety are our top priority. That`s why we’ve added the option to tour properties you are interested in through a live video chat.
Additional info
Enter a valid phone number.
Any additional questions or comments?
Message (optional)
Additional Terms of Use
Before you continue, please review the VOW Terms of Use:
(a) the Registrant has received, read and understood the brochure published by the British Columbia Real Estate Association entitled "Privacy Notice and Consent";
(b) the Registrant acknowledges entering into a lawful REALTOR®/ consumer or REALTOR®/client relationship with the Member;
(c) all data obtained from the MLS® VOW is intended for and may only be used for the Registrant’s personal, non-commercial use;
(d) the Registrant has a bona fide interest in the purchase, sale or lease of real estate of the type being offered through the MLS® VOW;
(e) the Registrant will not himself, and will not permit or assist others to, directly or indirectly:
(i) copy, redistribute or retransmit any of the MLS® VOW Data or information provided;
(ii) display, post, disseminate, distribute, publish, broadcast, transfer, sell or sublicense any of the MLS® VOW Data to another person.
(iii) engage in Scraping (including "screen scraping" and "database scraping"), "data mining" or any other activity intended to collect, store, re-organize, summarize or manipulate any MLS® VOW Data or any related data;
(f) the Registrant acknowledges the Board’s ownership of, and the validity of the Board’s proprietary rights and copyright in the MLS® VOW Data, and listing information; and
(g) the Registrant expressly authorizes the Board or their duly authorized representatives, to access the MLS® VOW and Registrant’s information provided to the MLS® VOW Participant, for the purposes of verifying compliance with and pursuing enforcement of the Terms of Use and all applicable rules, regulations, bylaws, policies, and laws.
This website uses cookies to improve your experience. For more info, read our
Cookie Policy.
By clicking “Accept” or continuing to use this site, you agree to our use of cookies
Terms of Use
and
Privacy Policy.
You have access to 1 more listing!You have access to {value} more listings!
Sign up to view unlimited properties and connect with an agent.
Get connected and never miss another property
Create your free account today!
Receive timely updates on your searches
Get meaningful market data and price trends
Access the world’s largest off-market property network through your KW Agent
KW Concierge
KW Concierge
Concierge
You’re on your way!
Our concierge team will reach out shortly to learn more about your home goals and connect you to a local real estate professional.
KW Concierge
Concierge
You’re on your way!
Our concierge team will reach out shortly to learn more about your home goals and connect you to a local real estate professional.
Did you know that by creating an account, you’ll also gain access to your very own dashboard, market insights and exclusive listings? Create an account today to gain access to these benefits & much more!
KW Concierge
Something went wrong
An error occurred while submitting your information. Please try again, and if the error persists you may also browse local agents here.