1386 Hillside Road
Fairfield, Connecticut, United States


This majestic estate has 3.68 private acres with panoramic distant views of the Long Island Sound, sweeping emerald lawns, lush gardens, a wildflower meadow, a sparkling pool and a two bedroom carriage house - all of which provide the backdrop for this exceptional six bedroom Greek Revival in the heart of Greenfield Hill. Perfectly located just minutes from the schools, trains, beaches and shopping of vibrant Fairfield, with an easy hour commute to NYC, makes this an excellent choice for a main residence or second home.This home, built in 1834, has a glamorous and storied past. In the roaring 1920's it had a fabulous bar that recalls the Great Gatsby era for its fashionable owners to spend weekends away from Manhattan. Today, thanks to the thoughtful expansions and updates by noted local architects Cameron Clark in the 1920's-1950's and David Parker in the 2000's this home captures this exuberance with great indoor/outdoor living spaces. Well-designed from the outside in, beautifully scaled rooms boast wonderful flow in the light-filled interior that blends contemporary touches with original and restored symmetrical architectural detailing resulting in a fresh modern aesthetic. An alluring veranda unfolds into a welcoming entry hall with high ceilings. Captivating views over the meadow take center stage in the elegant living room through bay windows and tall French doors leading to the south facing veranda, gardens and pool. Floor to ceiling glass doors open onto this extensive wraparound veranda in both the formal dining room and living room, both complemented by stately fireplaces, allowing for enjoyable indoor/outdoor entertaining. A stylish gallery connects the living room and veranda with the casual wing of the home. The chef's kitchen expands into an inviting breakfast room enhanced by a fireplace and into the adjacent family room with access to the sundrenched breezeway. The glass enclosed curvilinear breezeway overlooks the garden and accesses both the side gardens and attached garage. A study with glass pocket door, cozy reading nook with custom bookcases and powder room sits just off the main living area.On the second floor, a master suite provides a quiet respite for relaxation with a generous bedroom showcasing mesmerizing sunrises and verdant garden views; dressing room; his and hers well appointed bathrooms, abundant closet space and a comfortable sitting room overlooking the woodland garden. Two en-suite bedrooms, one of which accesses the veranda facing the charming green; two additional bedrooms, one with an enticing sleeping loft; shared full bath and laundry room complete this level.The third floor has a sixth bedroom with a skylight and original exposed chestnut beams; full bath; two cedar closets; a secret nook and an extraordinary recreational wing with built in bookcases and views of the Sound in the distance. This versatile space well suited for use as a game/playroom, is flanked by additional rooms, which are perfect for yoga, reading, homework and hobbies. The lower level features a 100 case, temperature controlled wine cellar; tasting room; workbench; full bath with a sauna, changing room and lockers with access to the pool; as well as an inspired gardener/potting room.The peaceful, sprawling property is bordered by a stone wall with an iron estate gate and includes a handsome two bedroom carriage house with an eat-in kitchen, family room with a fireplace and attached two car garage; gravel courtyard, private bluestone dining terrace surrounded by stone walls. Historic beech trees are combined with a splendid variety of specimen trees; formal boxwood, rose and vegetables gardens; and hidden moments of pure pleasure throughout the estate. A conveniently located private oasis to call home.

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Houlihan Lawrence

Houlihan Lawrence
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Main: +1 914 273 2800
Toll Free: +1 888 454 7356
Fax: +1 914 273 0100



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