NEW CANAAN — If trees could talk the centuries old towering maples and a graceful sycamore on a 3.68-acre level property at the corner West Road and Hemlock Hill Road would tell the stories of the families that have lived there.

They would talk about the Pennoyers, one of Canaan Parish’s early families who, according to old deeds, probably built a homestead on the site shortly after purchasing the land in 1753. That house was razed, perhaps by a fire, and the current structure that stands at 183 West Road was built in 1790. Several construction projects in the 1920s, 1940s, 1960s and 1990s gave the house additions and updates that bring it to its current 6,111 square feet.

If trees could talk they would say the past was in good hands when a present-day interior designer took on the Pennoyer-Raymond-Smith House, an antique colonial, and that he updated and restored it to perfection. The designer, who is also the owner, took special care to preserve the home’s architectural and historic integrity while imbuing it with every modern convenience today’s homeowners expect. It is a modern home and yet maintains its classic New England style, or as the homeowner describes it, the house is “an antique that doesn’t creak.”

The finest materials and finishes were used to create this elegant mélange of classic and modern elements. There are unpredictable textures, patterns and colors that are pleasing throughout the house and serve to bridge old and new. The house has custom interior woodwork throughout. The artistry continues to every portion of this property including the landscaping, the formal sunken garden, the magnificent pool house, and the guest house. Nothing was overlooked.

The house is so appealing and comfortable, even in its elegance, that one might not want to venture outside, and yet this property lends itself to outdoor living as well. There is a generous covered wraparound porch, a bluestone patio around the heated in-ground swimming pool and spa, and a red brick breakfast terrace.

This is a true center hall colonial with sidelights at the front door and a Dutch door that leads into the rear yard. The office off the foyer has built-in bookshelves and a full bath with a water closet in one space and a sink and shower in another. The formal living room has the first of the home’s four fireplaces and a recessed area with a built-in window seat.

In the formal dining room there are built-in china cabinets that flank its fireplace. A pocket door separates it from the gourmet kitchen, where there is a two-inch thick slab of Carrera marble on the long center island and counters, and a pale gray elongated subway tile backsplash. Appliances include a Viking six-burner range with a pot-filler. Off the kitchen is a breakfast room that doubles as a mudroom. It has a long cupola which brings in ample amounts of natural light.

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There is a morning coffee bar and a separate cocktail bar on either side of the steps down to the family room, which features a coffered ceiling with a bit of a twist, a fireplace, and two separate doors to the porch and yard.

Upstairs there are five bedrooms, one with a fireplace. The master suite has front and back entrances, wall-to-wall carpeting, a marble bath, and large walk-in closet. The attention to detail in this house even extends to secondary bedrooms. The bath in one bedroom has a honed stone vanity, cloth wallcovering in a herringbone pattern and dark gray subway tiles as the backsplash. While monochromatic in its coloration it is eye-catching and pleasing.

In the finished walk-out lower level there are exposed ceiling beams, a wine cellar, reading nook, and a gym.

More Information


STYLE: Updated Antique Colonial

ADDRESS: 183 West Road

PRICE: $6,995,000


FEATURES: guest house, barn, 3.68-acre level property, corner lot, heated in-ground swimming pool and spa, pool house, bluestone terraces and patios, wine cellar, generator, wrap-around porch, front and rear staircases, semi-circular driveway, service driveway, outdoor kitchen, four fireplaces, fire pit, thermal windows, sound system, lawn sprinkler system, only minutes from downtown New Canaan and train station, skylights, professionally landscaped, formal garden, exterior lighting, full partially finished walk-out basement, finished walk-up attic, two laundry rooms, wood roof, well water, detached three-car garage, six bedrooms, five full and one half baths

SCHOOLS: West Elementary, Saxe Middle, New Canaan High School

ASSESSMENT: $2,377,900

MILL RATE: 16.312 mills

TAXES: $38,784

The guest house has a cathedral ceiling, bedroom, living room with a stone fireplace, kitchen, and its own patio.

It’ll be difficult to get guests to leave the pool house, where there is a slate floor, service bar/island, a tall beverage refrigerator, two dishwashers, and skylight. Other features include a changing room, full bath and laundry room.

For more information or to make an appointment to see the house contact Kathy Tanner of Houlihan Lawrence at 203-856-6265 or