luxury houses with terrace for sale Fairfield County, United States

Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside’s prestigious Indian Head Association, this storied property occupies the historic grounds of railroad magnate Henry Francis Shoemaker’s former compound—a Gilded Age legacy that later served as the backdrop for the iconic Cedar Cliff Beach Club of the 1920s. The estate bears the name Shoemaker originally gave his villa, ‘Cedar Cliff’—a designation that eventually defined the very road on which it stands today. Elevated high above the flood zone and offering 1,250 +/- feet of direct water frontage, the property unfolds with extraordinary scale and privacy. A sweeping, manicured lawn rolls gracefully toward the shoreline, creating a striking foreground to the panoramic coastal vistas and an exceptional setting for grand-scale entertaining. Each of the eight oversized bedrooms is oriented to capture breathtaking water views, while interiors blend the romance of pre-war craftsmanship with modern refinement—soaring ceilings, intricate millwork, antique wood floors, a three-level elevator and a professional recording studio. The East Wing, constructed in the early 2000s, introduces a new dimension of contemporary luxury, anchored by a sophisticated primary suite and complemented by a custom office, wine cellar, and private theater capable of accommodating up to twenty guests. The grounds rival those of a world-class private resort. A substantial stone pier and deep-water dock provide immediate access to open water, while a seaside tennis court with pergola and lighting offers championship-level play. At the water’s edge, a pool and spa are paired with a fully realized cabana featuring a fitness center, kitchenette, full bathroom and changing rooms. Sculpted into the eastern landscape, a series of stone terraces with a bluestone bar directly overlook Greenwich Cove and the vast protected expanse of Greenwich Point Park. Meticulously maintained and thoughtfully enhanced, the estate includes a newly installed Ludowici terra cotta roof, rebuilt sun decks, custom East Wing windows, and a full-property generator—ensuring seamless comfort and continuity. With access to a private beach and watercraft facilities, and located less than an hour from Manhattan and minutes from Westchester County Airport, the property offers a rare convergence of seclusion, scale, and global accessibility. Cedar Cliff is a singular offering for the most discerning buyer—an incomparable experience of refined luxury, inviting residents and their guests to revel in the natural beauty of one of the finest estates on the East Coast of the United States.

A Mid-Country luxury retreat combining classic architecture with a modern sensibility, set back on 2.36 impeccably landscaped acres. This exceptional 11,925-square-foot, six-bedroom home offers remarkable privacy and resort-style amenities. Expansive terraces span the rear of the home, overlooking sprawling level lawns and a heated pool and spa, while a separate carriage house for home office or guest quarters. The grand entrance, behind custom gates, has a sweeping driveway beautifully secluded by tall trees with an additional gated side driveway providing convenient access to a peaceful side lane and cul de sac.Inside, soaring 10-plus-foot ceilings, bespoke millwork, and grandly scaled rooms define this sun-filled residence. Designed with an exceptional flow for both everyday living and stately entertaining, the main level features magnificent formal living and dining rooms, a private study, and multiple fireplaces. The heart of the home is the customized gourmet kitchen, beautifully remodeled with brushed Taj Mahal quartzite and luxurious heated floors, which seamlessly opens to the dramatic, two-story breakfast and great rooms.A sweeping stairway leads to the second level, which hosts five impressive bedroom suites. The star of this floor is the luxurious primary featuring a private sitting room with balcony, vaulted tray ceilings, a romantic fireplace and dual walk-in closets. Four additional bedrooms provide luxurious space for family or guests. On the fully finished third floor, discover an incredible bonus level with another bedroom suite, a flexible play/lounge area and a show-stopping custom dressing room outfitted with a large island, shoe hall and additional storage.The finished lower level serves as the ultimate sanctuary for entertainment and wellness. Crafted for unforgettable gatherings and personal rejuvenation, this expansive space features a handsome full bar, a movie/family lounge, and a wood paneled billiards room. Wellness enthusiasts will appreciate the expansive fitness center complete with sauna, while connoisseurs can showcase their collection in the wine cellar and tasting room.Ideal for a car collector, the property has an attached three-car garage at the main residence and two additional bays at the carriage house.No detail has been overlooked, with significant recent improvements including a new DaVinci roof and six-inch copper gutters, 40kW quiet whole-house generator, DoorBird Wi-Fi gate system, Lutron lighting and newly paved driveway.A rare opportunity to own an architectural marvel that is impeccably maintained offering remarkable privacy, extensive amenities and a truly magical setting.

Timeless curb appeal blends with a tastefully updated and renovated interior designed foreffortless everyday living and entertaining in this stylish four-bedroom Colonial with Trex deck, quiet backyard and seasonal second floor River views on a cul-de-sac near schools, shops, park, trains and highway. Sundrenched interior features chef's kitchen with Quartz clad center island offering seating for four which opens into the dining room office/playroom or possible bedroom, living room with fireplace flanked by built-in bookcases and powder room. Primary suite with walk in closet, sumptuous bath, two bedrooms with Jack and Jill bath and laundry comprise second floor. Lower level adds substantial additional living space with homework station, family room, gym and/or office and storage.

Tucked at the end of a private road in Cos Cob, this newly built (2025) Louis Contadino-designed home offers a layout rarely available in central Greenwich at this price point: sophisticated single-level main-floor living over a fully finished walk-out lower level, all on a private 0.34-acre setting. The main floor delivers four bedrooms -- three with private en-suite full baths, including a primary suite with soaking tub, double vanity, and heated floors. The chef's kitchen features Sub-Zero and Wolf appliances, custom cabinetry, marble counters and backsplash, a white oak island, and a walk-in pantry, all opening to a light-filled great room and formal dining. Wide-plank white oak flooring runs throughout. Below, a generous family room with full bath and direct yard access expands the home for guests, entertaining, or future flexibility. Approximately 3,500 square feet of finished living space in total, with available FAR for roughly 1,000 square feet of additional expansion if desired. Outside, extensive stonework frames the entry, terrace, and grounds, with four-zone HVAC and EV charging completing a thoughtful modern build. Set high above a quiet private road yet minutes from the village, train, and I-95, the property offers the privacy of an estate in a location that keeps you fully connected to Greenwich. Vision, design, and execution complete -- a finished home, ready to move into.

Set on 4.1 beautifully landscaped acres at the corner of Locust Road and Carpenters Brook, this exceptional Greenwich estate blends timeless elegance, privacy, and resort-style living. A sweeping circular driveway leads to the approximately 8,300-square-foot main residence, surrounded by mature trees, flowering gardens, stone walls, and expansive lawns designed by Wesley Stout Landscape Architects. Sun-filled formal and informal spaces feature coffered ceilings, antique oak floors, a dramatic double-height family room, chef's kitchen, and four fireplaces. The home offers six bedrooms, including a luxurious primary suite with spa-like bath, gym, walk-in closet, and private balcony. The finished lower level includes a wine cellar, home theater, recreation room, craft room, and cabana area. Outdoors, enjoy a heated gunite pool, vine-covered pergola, stone fireplace, multiple entertaining terraces, and a private par-three golf hole. A separate guest house with full bath and private driveway provides flexibility for guests, extended family, or a home office, all conveniently located to town, schools, dining, and transportation.

Set on 1.21 acres, this beautifully maintained home has exceptional indoor and outdoor living designed for entertaining. Home was completely taken down to the studs in 2017. The freshly painted interior offers top-of-the-line finishes and a flexible floor plan. The main level features a private office with Murphy bed, dining room with soaring ceilings, and a cozy living room with wet bar and fireplace. Open-plan gourmet kitchen, breakfast area, and family room flow seamlessly to an expansive terrace with multiple seating areas, an outdoor kitchen, and fire pit, creating an ideal setting for gatherings throughout the year. The gorgeous primary suite features a spa bath with sauna, walk-in closet, and floor-to-ceiling windows overlooking the property. Two additional bedrooms share a full bath, while two versatile bonus rooms can be customized to fit your needs. They would make a great nursery, playroom, second office, or gym. Other highlights include an outdoor shower, space for a climbing frame and golf net, and an attached two-car garage. This property provides privacy and convenience to everything Greenwich has to offer.

Brand new construction in Cos Cob features four finished levels and an abundance of natural light. The main level offers an inviting open-concept kitchen, breakfast area, and family room, leading to a private deck and backyard, extending the living space outdoors. Glass walls along the staircase create a striking architectural detail while allowing light to flow through the home. The luxurious primary suite features a spa-like bath and custom walk-in closet with beautifully designed built-ins. Two additional bedrooms and a full bath complete the second level, with an optional connection for a stackable washer and dryer in the hall closet. The third floor offers a spacious bedroom, full bath, and versatile bonus space ideal for a playroom or office. The finished lower level provides a private office with custom cabinetry, second family room with wet bar, and full bath. Finished carport accommodates one car and would make a great party room. Set on a residential street, the property offers an ideal balance of privacy and convenience, with an easy route to North Mianus and Eastern schools, local shops, restaurants, parks, and the train station.