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.

ROADSIDE - A Storied 53-Acre Private Estate in Fairfield County CT Escape to your own private nature retreat at ROADSIDE, a rare 53-acre country estate just 90 minutes from Manhattan. This legacy property blends historic charm with modern luxury in a setting that feels worlds away-yet is 1.5M from the Redding train station and the cultural vibrancy of Fairfield County. Set within a fully fenced, surveillance and professionally manicured landscape, this estate offers: A Private Natural Sanctuary: Meandering trails, a stone bridge, an aerated lily pond, a stream wind through your own personal private woodland reserve plus 2 M of groomed trails. Electricity is available throughout the trail system-ideal for future enhancements such as equestrian trail lighting. A Modernized Historic Home: Originally built in 1710 and reimagined in the early 1900s, the farmhouse-colonial has been meticulously updated with six fireplaces, a double-sided chef's kitchen, and a luxurious primary suite with dual baths and a sunroom. 500 bottle Wine Room. Outdoor Living at Its Finest: A heated gunite pool, outdoor kitchen, pergola & gazebo overlook sweeping vistas. The four-season landscape includes fruit orchards, cutting gardens, and vegetable beds. Flexible Lifestyle Potential: With a detached barn, three-car garage, and ample space for a guest house, tennis court, or livestock, this is a dream property for equestrians, hobby farmers, or those seeking a self-sustaining lifestyle.

Privately set, Sail Harbour Waterfront offers enticing south exposure, multi-level decks w/ glass rails for unobstructed views, terraced gardens w/intimate seating in an idyllic 1.43 acre lakefront setting! A unique plan showcases a 2 story great room w/central fireplace, open to a vaulted sunroom w/long lake views & lots of light. The designated dining room, now used as a den, offers an extended entertaining area. or quiet media viewing. The center island kitchen w/stainless appliances, Subzero, wet bar, wine fridge & turreted dining area offers captivating, long lake views. A wall of bookcases, 14ft ceilings & French doors for privacy highlight the main level office. A first floor primary suite w/fireplace & full tiled bath offers glass shower, double sinks, WIC & dressing area. Upstairs, a balcony encircles the great room. A private guest suite w/full bath & balcony offers an idyllic retreat for guests. Two bedrooms w/Jack & Jill baths adjoin a large vaulted area to be used as a recreation room or second master retreat w/private loft & window seating. A main level mudroom, 3 car att. garage, professional landscape & more! Be enraptured by southerly water views & a sun lit yard. This quiet cove setting encourages slower boat traffic & 2 private docks afford multiple seating areas to enjoy the relaxing vistas. Indulge in tennis, pickleball, beach activities & clubhouse events in this sought after lake community. Discover the beauty of Sail Harbour Club on Candlewood Lake

Exceptional Waterfront Estate in Candlewood Shores w/ 115 ft frontage, renovated Main House & Guest House (completed 2024) showcases the ultimate in Lake Front Living on Candlewood Lake. This gated property, surrounded by stone walls, paths, patios, gardens & terraces is in the middle of it all, yet exudes extreme privacy & serenity. A lakefront oasis, the main house hosts main level living w/vaulted great room, floor to ceiling stone fireplace & hardwood floors plus an adjacent dining room w/slate floors. Expansive picture windows capture the western exposed, views & dramatic sunsets. The updated kitchen offers an island bar, Subzero and induction cooking. It opens to the dining room which leads through sliders to the stone terrace for dining indoors to out. Two main level bedrooms with full bath & an additional bedroom & bath in the lower level, allow privacy for family & guests, alike. The expansive family room w/wood floors, 2nd fireplace, wet bar & lots of built-in cabinets, is ideal for entertaining. A 100 ft sand beach w/scenic vignettes allow you to enjoy summer in full glory.A few steps lead to your private dock, covered deck lakeside & all encompassing lake views! The guest house hosts a grand vaulted bedroom w/fully enclosed glass bath, beadboard ceiling & private balcony. A gourmet kitchen with quartz counters leads to a covered Trex deck. Gym w/coffered ceiling & media room,2 car garage, putting green on sod lawn, basketball court & more! A True Lakefront Oasis!

Sail Harbour Club, on Candlewood Lake, presents this grand colonial on 1.13 acs hosting 5 BRS, 6 Baths, 4 car garage plus an expansive yard w/seasonal lake views. Spacious rooms, hardwood floors throughout, center isle kitchen w/coffee bar & breakfast nook topped with granite adjacent to a formal dining room plus a separate living room that can be used as a library, den or second office. The stone fireplace is the focal pt of the spacious family room with adjacent bar room; great entertaining space with French doors to access the oversized deck. Discover an owner sanctuary in the private primary suite w/whirlpool bath, 2 WICs w/built-ins plus 4 other grand bedrooms with access to full baths. Enjoy fun times in the 1800+ SF lower level w/playroom with gym & full bath that walks out to the private yard surrounded by lush greenery. The expansive deck offers many seating options & relaxation areas. Grand spaces for all to enjoy, from large extended family to overnight guests. Play set for children in yard will remain. Enjoy sunbathing at the white sand beach, boating from your private dock at the community marina, tournament caliber fishing all over the lake, tennis and pickleball plus festivities at the community clubhouse. Many recent updates include furnace, hot water heater, roof, deck, appliances & more! Just 10 minutes to local shops & less than 70 min to NY city! A true find in this sought after lake community! Most furniture & water toys are an option! Don't Miss It!

Welcome to 76 Old Trolley Rd, a gracious Bennington Colonial located in Ridgefield's coveted Stone Ridge Estates. This elegant 4-bedroom, 3.5-bath home offers over 4,300 square feet of beautifully appointed living space, plus an expansive 1,852 sq. ft. unfinished basement-perfect for future customization as a media room, gym, or guest suite. The main level features a two-story foyer with a Palladian window, gleaming hardwood floors, and spacious rooms ideal for entertaining. The expansive kitchen boasts granite countertops, stainless steel appliances, and a sunlit dining area that opens to a large deck with a hot tub. The family room includes a cozy fireplace and custom built-ins, while a private office and formal dining and living rooms add versatility. Upstairs, the luxurious primary suite includes two walk-in closets, a spa-like bath, a separate sitting area along with an adjacent bonus space ideal for a nursery, home gym, or quiet workspace. Additional bedrooms include an en suite and a Jack-and-Jill layout. Set on 1.1 professionally landscaped acres with stone walls and mature plantings, this home also features central air, natural gas heat, a whole-house generator, and a three-car garage. Located just minutes from downtown Ridgefield and the Brewster Train Station and is an easy commute to NYC. This property offers the perfect blend of suburban tranquility and commuter convenience in one of the areas most desireable neighborhoods. Come see for yourself and Welcome Home!

Step into the grand two-story foyer of this inviting Colonial, setting a warm, timeless tone. Freshly painted interiors, gleaming hardwood floors throughout, new exterior lights, a new front storm door, and premium architectural shingles enhance the home's classic charm in a serene Connecticut setting. The kitchen, the heart of this home, is a welcoming space for solo meal prep or collaborative cooking, blending function and comfort with double ovens, an induction cooktop, stainless steel appliances, granite countertops, and a spacious island with room for seating. An eat-in area in the kitchen has sliders that open to a deck overlooking the private backyard, ideal for daily meals or gatherings. The adjacent sunken family room, adorned with Palladian windows and French doors, invites cozy fireside gatherings bathed in natural light. Transom windows above select doorways add an airy, elegant touch. The dining and living rooms offer ample space for entertaining, while a versatile office doubles as a den, study, or craft room. The lower level features a flexible bedroom with a full bath, perfect for an au pair, in-law suite, plus rec room, with walkout access to the backyard. A newly paved road ensures smooth access to this tranquil haven. Don't miss this gem, where classic Colonial style meets modern comfort in a peaceful setting. 5BR per health department

Nestled in the desirable Candlewood Lake Shores community, 31 Longview Drive offers a harmonious blend of modern comfort and lakeside charm. This Colonial-style home boasts a spacious layout on a generous 0.35-acre lot. The residence features three well-appointed bedrooms and two and a half bathrooms, providing ample space for both relaxation and entertainment. Enjoy serene lake views from the front porch and access to private community amenities including a beach and playground. Perfect blend of comfort and lakeside living!

NEW PRICE**** Fantastic opportunity to make Redding your home! This spacious 5-bedroom, 3-bath Cape Cod offers the perfect blend of classic charm and modern updates. Enjoy an updated kitchen and two stylishly renovated bathrooms, gleaming hardwood floors, and a newer high-efficiency boiler for comfort and savings. Stay cool with central air, and bring your vision to life in the full walk-out basement-flooded with natural light and ready for transformation. New vinyl siding provides excellent insulation and curb appeal. Set on nearly 3 private acres, this serene retreat is just minutes from Redding Center . Close to train and great restaurants. Welcome Home!