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Shelly Simms Tretter of Sotheby's International Realty in Greenwich (203-618-3103) has this listing along with a new-construction manse, also within the gated Old Round Hill enclave. The hand-cut stone Georgian on more than three acres measures almost 16,000 square feet and offers seven bedrooms and nine bathrooms (plus two half-bathrooms). The price: $13,995,000.
The Ridge of Greenfield Hill, Fairfield
You say you want a gated community with all the fixings? The Ridge rivals the area's country clubs, and that's saying a lot—if the state of Connecticut does one thing well, it's a country club. To ensure privacy, each of the 97 luxury homes is sited on at least two acres. Conviviality is also guaranteed at the recreation center, which features a clubhouse with locker rooms and saunas, a pool with life guards and swimming instruction, lighted tennis courts, jogging paths and bridal trails, a 24-hour guarded entry and a shuttle service to and from the local train stations.
Two homes are currently on the market, starting with a newly constructed, 10,000-square-foot manse on three acres at 33 Merry Meet Circle, which includes a wine cellar and home theater. It's offered for $3.2 million by Michelle & Company of Westport (203-454-HOME). Also listed is number 1555 Fence Row. Inspired by an English country manor, it features six bedrooms, seven fireplaces and a little more than two landscaped acres on the market for $2.9 million with Jaclyn and Debra Gailhard of Waterfront & Estate Properties at Prudential CT Realty in Westport (203-981-5012).
Wilson Point, Norwalk
A hilly, wooded peninsula with a family-friendly beach club, Wilson Point is a laid-back, anti-snob kind of place—no mean feat when most of the homes are sprawling antique compounds, including Tudors, Victorians and shingle-style "cottages." Number 2 Woodland Road is a circa-1920 Tudor on almost two waterfront acres. The 3,900-square-foot home has retained its vintage details: massive stone fireplaces, built-in cabinetry and, best of all, broad covered porches and porticos overlooking the Sound. It's listed with Russell Ashcroft of Kelly Real Estate in Darien (203-621-0971).