Check Out Some of the 2018 HOBI Award-Winning Homes

This 34,000-square-foot home is spread over five levels—three above ground and two below—which were created by carving into the sloping hillside. Guests cross a blue-bottomed moat to reach a two-story front door, which pivots open to a dramatic foyer and an unobstructed view to the lawn, lake, pool and pool house.

Floor-to-ceiling windows are the perfect backdrop for the living room that can be transformed by opening or closing hidden doors to a pair of offices on one side, and a dining room that seats 20 on the other. The second floor has five family suites and a master suite, while the top floor is a rooftop den surrounded by glass on all sides.

The basement boasts an indoor pool and spa with a green wall, a game room, gym, media room, wine cellar and guest suites. The lowest level includes a squash and basketball court, a locker room and a recreation area. (Architecture: Marchese Gashi)

This more than 8,000-square-foot home was built for a busy family of five. The kitchen anchors the home and is open to the mother’s office/command center, the living room, mudroom and a butler’s pantry painted in a high-gloss blue lacquer. The dining room is located in the center of the home and abuts the foyer with a modern glass-railed staircase. A large office is located in the back of the house with a floor-to-ceiling, blackened-steel fireplace. A finished lower level includes a custom bunkroom that sleeps eight, a media room and a gym. An outdoor kitchen and patio are complete with an outdoor fireplace, grilling area and professional pizza oven.

Classic Nantucket shingle style blends with sleek modern finishes for this contemporary beach home. Privately set in Westport’s Compo Beach area, this new home has 7,650 square feet of handcrafted elegance on four finished levels, with five ensuite bedrooms, plus the option to convert a first floor study to a first floor guest or master bedroom. The foyer area is separated from the formal areas of the house by a gallery created by floor-to-ceiling white rift oak built-ins with glass inset shelves. Interiors offer four finished levels with handcrafted millwork, paneling and built-ins. Polished chrome fixtures, white painted cabinetry, white Glassos counters and a cool color palette of light grays combine to evoke a transitional and contemporary mood. (Architecture: Anthony J. Tartaglia Associates)

European architecture. Bright white stucco with black windows creates a crisp, clean look, while black metal and glass railings coupled with floating treads speak to the contemporary architecture of the structure. Inside the open-floor-plan home, the kitchen’s modern minimalist design of sleek black cabinets maximizes function and storage. To balance the bold kitchen, a large fireplace makes an equally powerful statement in the family room. Four bedrooms include a master suite with a wall of white-oak accent panels and water views. Topping it off: a rooftop deck overlooking Westport’s Compo Beach. (Architecture: Donald William Fairbanks)

This renovation project began with an existing midcentury modern structure built in 1964 by architect Gray Taylor for his personal use. The original house was a rectangular bar built entirely out of CMU block and pre-stressed concrete planks. Between 1964 and 1994, the house underwent four major additions/renovations. In the mid-’70s, a dramatic large-scale addition added a living space on a concrete pier and pre-cast deck out over a stream adjacent to the home. The current owner, who had lived in the home growing up, hired Joeb Moore & Partners Architects to refresh the home and provide a modern addition. While the interior finishes were immaculately maintained, during demolition several structural issues emerged. Eventually, all the exterior walls and roof decks above the original concrete plank foundation, save the ’94 addition, were removed and rebuilt. This removal triggered the reconfiguration of the floor plan and allowed for the mechanical systems to be properly reconfigured for the demands of a contemporary home. (Architecture: Joeb Moore & Partners Architects)

The 2018 project of the year was awarded to Cole Harris Homes for a pair of homes built on Brush Island in Darien. Designed and built to be quintessential waterfront homes with sweeping lawns and natural indigenous tree and plants, the overriding focus for this property was about lifestyle. This pair of homes also won Best Spec Home Over $7 million and Best Home Staging (LTW Design); and Outstanding Spec Home Over $7 million.

The first home was built with a strong, rich and rustic sense, which was realized through many high-caliber finishes, materials and amenities.

It is also very contemporary, as seen in simplified details in cabinetry, millwork and steel rails, plus a one-of-a-kind sculptural chandelier built of found driftwood, moss and steel specifically for the home’s two-story family room.

Outdoor amenities include perennial gardens, covered entertaining and grilling areas, pools and boat docks.

For the second home (opposite page), approval from the planning and zoning commission was conditioned on saving a 96-inch-diameter European Beech, which became a focal point, and the house was designed around it.

To create Windover, an enclave of eight bespoke homes in Norwalk, Silver Heights Development worked with the contours of the land, the pond, the mature perimeter hardscape and wetlands. The residences are nestled into 12 acres and surrounded by private fencing, stone walls, mature trees and specimen plantings, plus have access to the private four-acre pond and Cranbury Park. Designs include four Saltbox and four Courtyard style homes. The traditional facade gives way to spacious interiors with luxury features, branded fixtures and modern aesthetics. All have first-floor master suites, open floor plans and high ceilings. A homeowner’s association fee includes snow plowing, landscaping, irrigation, water, maintenance of wood roofing and siding, common grounds and more. (Architecture: Beinfield Architecture)

This sun-drenched, first-floor master bathroom exudes a sense of grandeur with exceptional attention to contemporary amenities, such as Fleetwood windows with electric window solar shades, a floating teak vanity topped with Danby marble and a spacious, frameless glass-paneled shower equipped with a showerhead and a rain head. The highlight of the room is an interior soaking tub married by a wall of glass to an exterior soaking hot tub. A ceiling sky window and a rectangular window above the vanities between Robern medicine cabinets deliver views and sunlight to the space. Floors are in a large-scale Atlantic bluestone with radiant heat. The walls are plaster skim-coated then covered in marble mosaic tile.