Set on 5+ private acres at the end of a coveted cul-de-sac, this distinctive family compound is minutes to town and top-rated schools. Classic New England architecture opens to a striking, loft-inspired interior defined by soaring three-story ceilings, hand-hewn antique beams from the late 1800s, wide-plank floors, and walls of glass that fill the home with natural light. Generous living spaces are designed for both connection and comfort, featuring elegant gathering rooms, a beautifully appointed chef's kitchen, a year-round sunroom, expansive play loft, and a lower-level fitness studio. The open layout creates seamless flow while offering distinct, flexible spaces for everyday living and entertaining. Three fireplaces add warmth and a natural sense of gathering. A private guest suite with a professionally designed recording studio is thoughtfully set apart, ideal for extended stays, creative pursuits, or a refined work-from-home setting. Outside, a freeform pool, private lake for canoeing and fishing, firepits, cutting gardens, flowering trees, and rolling lawns create a resort-like setting with access to Westport's beaches. With exceptional privacy and the ease of a whole-house generator, this is a home where light, nature, and everyday living come together in a setting designed for both retreat and connection.
Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with apartment, and converted barn, largely by architect Jack Franzen. The main residence offers over 11,000 square feet with 7 bedrooms, 6 full and 2 half baths. The two-story media wing includes a home theater, library, office, and billiard room. The conservatory overlooks stone terraces, a waterfall and pond, and gardens. The primary suite and office have private balconies. The estate is further distinguished by multiple auxiliary structures: a carriage house with guest accommodations, a separate guest residence, and a heated party barn dating to circa 1850. A pool with spa, pergola, and outdoor kitchen complete the grounds. Original architectural details such as leaded glass windows, rich hardwood paneling and window seats and doors, five stone and brick fireplaces, and other features have been preserved. Modern additions introduce light-filled living spaces. New appliances and updated mechanicals service the buildings. Rock Ledge offers luxury and privacy rare in this area, and promises a lifetime of enjoyment for a buyer who appreciates its beauty.
Set on three private acres of serene woodland along the banks of the Saugatuck River, this extraordinary Riverfront Retreat offers a rare opportunity to live immersed in nature in a modern masterpiece. Creating a seamless connection between the stunning interiors and the tranquil beauty of the surrounding landscape, experience breathtaking river views from the rooftop deck with succulent gardens, from the heated gunite pool surrounded by an oversized terrace and through the walls of glass throughout the home. From the moment you enter, prepared to be wowed by this concrete, glass and bamboo structure, as you flow through the stunning open living spaces into the private first floor Primary Bedroom, then up to the well thought out second floor. Rare and remarkable, this noteworthy home was designed by Specht Harpman and artfully built in 2010 by Michael Greenberg in the bucolic setting of Weston, CT. Enjoy best of both worlds- living in secluded waterfront serenity with effortless access to the areas shopping, restaurants and beaches in Westport and neighboring communities.
This restored, 6,100 sf-expanded 18th century antique commands a view of its 1.24 ac, brook-fed lake; expansive lawn; raised beds; and 450 ft. bleached stone driveway. Your vision--Big Tented Celebrations,Fabulous Local Tomatoes--is correct. The former NYC chef's professional kitchen, wet bar, and 2 eat-in dining areas are open to the 5 rooms that circle around this heartbeat, making large gatherings feel and taste delicious. The antique's original entrance to a home office + fireplace (cozy, authentic) complete the floor. The 2nd floor offers 4 secondary beds/baths, a superior primary suite, and has a 600-sf bonus room with its own entrance and full kitchen. Generous third-level space fronted by a viewing balcony becomes the game/exercise/screening room you choose. Windows are featured everywhere, in particular note the sunroom array and the sitting room's 28ft of windowed walls. The separate 1,100 sf, 1-2 BR COTTAGE has had just 4 long-term tenants in the owners' 28 years. The COTTAGE rental income and tax/financial advantages make your net purchase price and occupancy exceedingly comfortable. The owner has prepared for final approvals a survey,building plans, and rendering package of a pool and surrounding deck connected to the home's 500sf front terrace. The buyer wishing the design can move forward with confidence in the sellers' careful efforts. A 2025, 95% efficient,state-of-the art, Navien natural gas boiler and HW installation has proven to be a gas bill slayer.
In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every turn, including a coffered ceiling living room, a banquet sized dining room with a curved wall of windows, and an octagonal office. French doors create a natural flow to two stone patios and sweeping lawns. The gourmet kitchen, appointed with four Wolf ovens, dual Sub Zeros and dishwashers, and extensive custom cabinetry, is designed for both comfortable daily living and memorable entertaining. The serene primary suite offers a private sitting room, balcony, barrel-ceiling dressing room, and an inspiring octagonal bathroom, while additional en-suite bedrooms and a full in-law suite provide exceptional comfort. The finished lower level includes a custom cherry wet bar, gym, and flexible space for a media room or wine cellar. Two full-size laundry rooms and a pool bath w/exterior access offer flexibility. Outdoors, a heated Gunite pool with auto cover and spa create a private resort experience. Convenient to the Merritt Parkway and Westport, this rare offering blends timeless sophistication with modern livability in one of Fairfield County's most sought-after settings.
Reminiscent of an European Estate this 4420 square-foot home features, four bedrooms, two full bathrooms and two half bathrooms on an open acre of land. It's extensive outdoor patio and entertainment areas wrap around the rear of the property, a cobblestone lined driveway, and specimen landscaping are all situated on a cul-de-sac in an easy to get to everything location. The gourmet kitchen features high end appliances, and the house is served by radiant heat as well as central air.
Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.

Weston is located in Connecticut. Weston, Connecticut has a population of 10,339. Weston is more family-centric than the surrounding county with 44.69% of the households containing married families with children. The county average for households married with children is 34.39%.
The median household income in Weston, Connecticut is $204,792. The median household income for the surrounding county is $101,194 compared to the national median of $69,021. The median age of people living in Weston is 46.9 years.
The average high temperature in July is 84.2 degrees, with an average low temperature in January of 18.8 degrees. The average rainfall is approximately 52.4 inches per year, with 35 inches of snow per year.