luxury houses with terrace for sale Old Greenwich, 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 rare waterfront estate of true scale and presence, this reimagined coastal masterpiece commands 1.6 acres on the Long Island Sound with sweeping, unobstructed horizon views. Rebuilt from the foundation up, the home delivers level beachfront living with powerful architectural lines, floor-to-ceiling glass, and a seamless connection to the water at every turn. The approach opens to a 19-foot entry and a 21-foot great room that presents the Sound as a moving canvas of light and color. Terraces, manicured grounds, and a heated Gunite pool extend the living space outdoors, creating a private resort environment ideal for year-round enjoyment. Six ensuite bedrooms and two half baths include a serene primary wing with balcony, steam shower, and sauna. Savant smart-home systems geothermal efficiency, and refined materials anchor the residence in modern comfort and longevity. A sandy private beach, deep-water dock, and protected cove support boating, paddleboarding, kayaking, swimming, and quiet waterfront mornings. This is coastal living without compromise. Infinity by the Sea. A legacy property where luxury meets the horizon.

A unique opportunity awaits the new owner to put their own footprint on this lovely 1911 home. This house is beautifully sited on 2.27 acres in one acre zoning and cannot be subdivided. One can make a family compound here. High ceilings throughout, lovely sunroom which opens to the terrace and spacious yard with mature gardens. Magnificent alee of the most spectacular sycamore trees. Truly special property just a short distance to Greenwich High, YWCA and downtown. Two additional rooms on the third floor are presently used for storage.

Stunning and Stylish , Mid-City Stamford This beautifully renovated 1-bedroom, 11/2-bath condo delivers modern design and everyday comfort in one of Stamford's most convenient locations. The open-concept layout is bright and spacious, with an updated kitchen featuring stainless steel appliances, stone countertops, and plenty of room to cook and entertain. Both bathrooms are freshly renovated with clean finishes. A full-size in-unit laundry room rounds out the practical side nicely. The living area is sun-filled and opens directly onto a private balcony. The primary bedroom is generously sized with a walk-in closet and its own balcony access via glass doors. Two assigned parking spaces - one covered, one open - are included. Minutes to Metro-North and steps from Stamford's dining, shopping, and entertainment scene. An easy commute and a great place to come home to.

Modern Sophistication Meets Suburban Serenity in Westover - Tucked away on a tranquil cul-de-sac, this recently built architectural gem offers a masterclass in modern living, blending refined elegance with the vibrant energy of nearby downtown Stamford. The residence unfolds through a dramatic two-story foyer into a sun-drenched, open-concept sanctuary, where a chef-inspired kitchen-adorned with pristine white cabinetry and expansive granite surfaces-flows effortlessly into a fireside living room and adjacent sunroom with French doors leading outside. The outdoor experience is truly peerless, featuring a resort-style saltwater pool with waterfall, a professional-grade basketball/sports court, and a sprawling bluestone patio framed by artisanal rock walls and secure perimeter fencing. With a high-efficiency infrastructure, vast expansion potential in the walk-out basement, and a commute to Manhattan in under an hour, this property represents a rare opportunity to enjoy like-new luxury and a private backyard oasis without the wait.

Beyond the classic white picket fence you will find a tastefully updated 1930's colonial in the heart of Stamford. The main level features an expansive living room with oak flooring and a wood-burning fireplace. The open floor plan has the dining room adjacent to the living room. The star of the home is the newly remodeled sleek designer kitchen with custom cabinets, quartz tops, and stainless appliances. A sparkling new powder room and mudroom complete the first floor and lead to the oversized deck in the back yard. Upstairs there are three bedrooms. The hall bath has been remodeled as has the primary bedroom, en-suite. The lower level has a home office, a playroom with a laundry nook, and a powder room. The sunny back yard has a detached 2-car garage and is completely fenced in. The home is in the desirable Hubbard Heights area, only steps to the vibrant Scalzi Park and shopping & dining at Ridgeway Plaza. Minutes to downtown Stamford, Metro North Train, and public beaches. Welcome Home!

Nestled within the sought-after Putnam Park community in the heart Greenwich, this sun-drenched 2-bedroom, 2-bathroom co-op offers effortless, single-level living in a serene, park-like setting. Spanning over 1,200 square feet, the residence features three exposures, filling the home with natural light throughout the day. The open floor plan creates a seamless flow between living and dining spaces, complemented by an updated kitchen outfitted with stainless steel appliances--ideal for both everyday living and entertaining. Thoughtfully renovated bathrooms add a modern touch, while an oversized in-unit washer and dryer provide everyday convenience. Step outside to a private bluestone terrace--perfect for morning coffee or evening relaxation. Set on 13 beautifully landscaped acres, Putnam Park is a 194-unit community just moments from Greenwich Avenue's shops, dining, and transportation, with Manhattan approximately 45 minutes away. With no stairs and true one-floor living, this home offers the perfect blend of comfort, style, and convenience in one of Greenwich's most desirable locations.

Nestled within the Putnam Park community in the heart Greenwich, this sun-drenched 2-bedroom, 2-bathroom co-op offers effortless, single-level living in a serene, park-like setting. Spanning over 1,200 square feet, the residence features three exposures, filling the home with natural light throughout the day. The open floor plan creates a seamless flow between living and dining spaces, complemented by an updated kitchen outfitted with stainless steel appliances--ideal for both everyday living and entertaining. Thoughtfully renovated bathrooms add a modern touch, while an oversized in-unit washer and dryer provide everyday convenience. Step outside to a private bluestone terrace--perfect for morning coffee or evening relaxation.

Welcome to Chesterfield, one of the area's most sought-after gated communities, where comfort, privacy, and convenience come together beautifully. Tucked in a quiet enclave on a residential street. This home delivers the perfect blend of style, space and location. This spacious multi-level end-unit townhouse offers the breathing room of a single-family home with the ease of truly carefree living. The main level is made for both entertaining and everyday enjoyment. A dramatic, light-filled living room with a cozy fireplace and custom built-ins flows naturally into the dining area, with sliding glass doors opening onto a private balcony - your ideal spot for morning coffee or a quiet evening wind-down. The custom kitchen is a genuine showstopper: rich granite countertops, top-tier stainless steel appliances, abundant cabinetry, and a charming built-in casual dining nook that makes every meal feel special. Upstairs, the primary suite is a true retreat - unwind in the jetted tub, refresh in the separate shower, and enjoy the luxury of dual fitted walk-in closets. A large second bedroom with its own en-suite bath offers wonderful flexibility, while the upper loft is perfect as a home office or creative space. The walk-out lower level adds even more room to spread out, with a generous rec room, half bath, and a private patio. Outside your door, two sparkling pools, a pool house, and a clubhouse await - and with lawn care and snow removal handled for you, weekends are entirely your

An extraordinary newly constructed residence in the heart of Greenwich, Seven Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously designed living space. Inside, soaring ceilings and stylish lighting illuminate refined interiors, including a dramatic great room with vaulted ceiling and fireplace, formal living and dining rooms. The chef’s kitchen appointed with custom cabinetry with walnut interiors and Sub-Zero Designer Series appliances is complimented by a Butler’s Pantry with wet bar. A generous mudroom with washer and dryer in addition to informal and formal powder rooms complete this level. A floating glass staircase rises through the home, connecting to the upper levels where the primary suite dazzles with a fireplace, coffee bar, spa-like marble bathroom with radiant heated floor, steam shower, soaking tub and two water closets plus two boutique-style dressing rooms. Three additional ensuite bedrooms on this level, each with custom closets and rich hardwood floors- as well as an oversized laundry room with built in drying racks. A second-floor covered deck overlooks the rear of the property for easy enjoyment. The third floor houses a fifth ensuite bedroom, a flexible room for an office or sixth bedroom, large walk-in cedar closet, and a coffee bar with refrigerator. Lower-level amenities include high ceilings with a floor plan designed for entertaining. A gym prewired for a golf simulator with 11-foot ceilings, custom humidity-controlled wine room, home office with built-ins, full bathroom with heated floor, and a lower-level great room with full bar are complimented by ample storage spaces. Outdoor living is equally impressive with a new heated 20x40 pool with auto cover with 2 ft coping and smart controls. Two covered terraces with infrared heaters plus the second-floor covered deck overlook the manicured grounds with 100 14-16 ft Arborvitae Trees enclosed by a 300-ft stone wall and motorized gates. A permeable paver motor court accommodates 12+ vehicles behind the gates plus a 3-car heated garage. Whole-house generator and property wide sprinkler system. Every detail—from the slab marble finishes to integrated smart home systems—has been thoughtfully curated for the most discerning buyer. A rare opportunity for luxury, privacy, and proximity to downtown Greenwich.

Welcome to effortless one-level living at Manor North Condominium! This inviting ground-floor ranch-style unit offers the perfect blend of comfort and convenience. Featuring two generous bedrooms and one full bath, the primary suite boasts a large walk-in closet for ample storage. The open-concept kitchen, family room, and dining area create an ideal space for both everyday living and entertaining, with slider doors opening to your private patio overlooking the expansive lawn. Enjoy the convenience of in-unit laundry and the unbeatable location just moments from downtown shopping and train service for easy commuting. Experience low-maintenance condo living at its finest!

Originally a turn of the century horse racing track named Field Point Park, the prestigious Field Point Circle Association is now one of Greenwich’s most coveted guard-gated enclaves. Distinguished by its exclusive address, this grandly proportioned French-inspired manor of 9,565 +/- square feet combines stately elegance on a level 2.2 acres with exquisite privacy and a pool with spa. Clad in limestone with a slate roof, the six bedroom, seven full and two bathroom residence is is distinguished by a flexible floor plan, offering a primary suite option on both the first and second floors. Principal entertaining spaces—an elegant living room, gracious dining room, and refined library—are enhanced by high ceilings and oversized windows that flood the home with natural light. Opening to a grand rotunda with a double-height curved staircase, the marble foyer is the intersection between the east and west wings of the house. On the east side, an elegant formal dining room adjoins the butler’s pantry and opens to the generously sized kitchen with pantry, breakfast area and powder room. There is an attached 3-car garage in this wing, with a laundry room. Formal rooms in the west wing include an airy living room with fireplace and cozy library with fireplace and concealed wet bar which opens through French doors to the private backyard terrace. The ground floor primary suite with dressing room and full bathroom also overlooks the peaceful backyard. There is another first floor en-suite bedroom across the hall. A great room that is perfect for entertaining adjoins the full pool bathroom, kitchenette, bar and dining area which serves as a “pool house” and opens to the main terrace and pool with spa. The great room was originally an indoor pool and the pool is intact below the floor and can be put back into use. Screened by greenery for ultimate privacy, the secluded backyard with verdant level lawn and pool with spa completes this idyllic retreat perfect for all lifestyles. The Field Point Circle Association consists of only 27 homes and offers 24-hour security, while its wide, tree-lined boulevards maintain its glamorous, Gilded Age legacy. In a treasured coastal location, this historic neighborhood offers a compelling mix of proximity to downtown Greenwich, as well as easy access to New York City vis Interstate 95 or the Metro North train.

DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive, manicured lawns with desirable western exposure, framed by stone walls, mature trees, and a pool. Completing the estate is a three-bedroom cottage, providing additional flexibility. Ideally serviced by public gas, water, and sewer allowing for ease of development. Perfectly positioned near schools, clubs, houses of worship, and Greenwich Avenue. Lot is 2.02 acres in RA-1. FAR = 11,878+/-

Classic 6/7 bedroom 1925 colonial on a picturesque lane minutes to downtown Greenwich. The oversized 1.5 acre lot features verdant level lawn with all town utilities. Inside embrace the modern floor plan seamlessly tied in with classic architectural details and high ceilings. Front to back living room opens to the solarium with terrace access. A handsome library with flows to the oversized formal dining room for seamless entertaining. The kitchen with breakfast room and ample storage steps down to the family room with access to the terrace, yard, mudroom, and 2 car garage. Upstairs find a generous primary suite with dressing room and bathroom. Five additional bedrooms, four full bathrooms, playroom and laundry room on 2nd and 3rd floor. Bonus staff apartment over garage. One of a kind!

LIVE THE PERPETUAL VACATION LIFE IN NOROTON BAY - Experience this chic, sun-drenched Beach Colonial, perfectly situated on an open double lot. Extensively remodeled, the home's bright, open configuration is designed for effortless year-round family living and entertaining. Enjoy seamless indoor-outdoor living with expansive terraces, professionally landscaped grounds, and a charming signature front porch. Retreat to the primary suite or the home office to enjoy serene water views. As part of The Bay community, you are steps away from a private beach, pier, and a private yacht club. Association amenities include boat moorings, a seasonal snack bar, and a vibrant year-round social calendar. All of this with Darien's award winning schools and an easy commute to NYC. A true gem on Fairfield County's Gold Coast - this is a MUST-SEE!!!

Escape to your own private waterfront sanctuary at this hidden gem on Holly Pond, where relaxing on a back porch with a gentle breeze as the sun sinks into the water is your daily reality. Seamlessly designed for effortless entertaining and coastal living, the main level features a formal dining room and a fully renovated chef's kitchen (2021). The spacious living room, anchored by a cozy fireplace, and a light-filled three-season sunroom offer breathtaking water views, spilling out onto the updated porches (2023)-the perfect vantage point to look out over the beautiful yard and gardens leading to the water. Upstairs, you will find three bedrooms and a dedicated home office, highlighted by a primary bedroom that serves as a private oasis with an expansive second-floor porch and unforgettable, panoramic vistas. Outdoor living is truly unmatched here, boasting 65 feet of direct, prime waterfrontage on Holly Pond complete with a private dock (2021) and a brand-new roof (2026), making this home as turn-key as it is beautiful. Whether you are taking a boat cruise, launching a kayak, or enjoying an evening by the water, this property offers a seamless lifestyle. As part of the coveted Noroton Manor association, you'll enjoy exclusive amenities including tennis courts and private beach access, all paired with unbeatable proximity to downtown Darien, local beaches, the YMCA, Metro-North, and top-rated schools. Welcome home to the ultimate coastal lifestyle!

Exceptional NEW construction in a coveted mid-city location offers the perfect blend of refined comfortable living. This sensational 5-bedroom, 4.5 bathroom home with well proportioned rooms throughout, showcases sophisticated design together with an open-concept. The gourmet kitchen serves as the heart of the home, boasting a large center island, walk-in pantry, and abundant cabinet and counter space for the discerning chef. A fireplace and wet bar enhance the space with seamless access to an oversized deck. Four second floor bedrooms, 3 full baths and a full sized laundry room add to the comfort of this level. Thoughtful details include a fabulous mudroom with built ins for everyday convenience. The finished lower level expands living space with the fifth bedroom, full bathroom, and generous rec room, all enhanced by full-sized windows that flood the space with natural light throughout the day. Hardwood flooring, 9-foot ceilings and energy-efficient LED recessed lighting. City water and sewer, natural gas for heating and cooking plus underground utilities compliment the location. Traveling distance from Walnut Ridge Court to the Stamford Train Station is a mere 2.5 miles and CT Transit has a stop practically at the front door. A grand opportunity for NEW construction in this limited NEW construction market.

Rare and exceptional side-by-side two-family is being offered for the first time since being built!! Boasting true one-floor living in both residences. The front unit is a showstopper that was completely renovated and expanded with stylish finishes and modern comfort throughout in 2019 with 3-bedrooms and 2. full baths, family room with vaulted ceilings and gas FP. Gas heat and cooking. The second unit offers a flexible 2/3-bedroom layout with good space and great potential and could benefit from some updating. The private deck overlooks serene conservation land, creating a peaceful retreat which is not found in multi-families. A separate barn is ideal for a gym, studio, workshop, or additional storage. A unique opportunity for owner-occupants, investors, or multigenerational living.

Interior recently painted and WOW what a transformation!! Tucked at the end of a peaceful cul-de-sac in Cos Cob, within the coveted North Street School district, this serene 5-bedroom home (featuring a main-level en-suite) offers a tranquil escape. Contemporary design shines through vaulted ceilings, skylights, and sun-drenched interiors that flow seamlessly to a large screened-in porch and an expansive 900 sq ft wraparound deck with private wooded views, with direct access to Mianus Park trails. The open layout includes a formal dining room, bright kitchen, generous laundry/mudroom, and a living area centered around a stone fireplace. Interior recently fully painted with new landscaping installed, this home offers over 4,000 sq ft of living space (3283 above grade, 741 finished basement) in an exceptional location for those seeking tranquility and a true sense of escape from the hustle and bustle.

MULTIPLE OFFERS - Highest & Best Offers Due Tuesday MAY 19th by 5pm. Move-in ready 3-bedroom ranch in the highly desirable Springdale neighborhood, offering a bright, open layout and exceptional updates throughout. Filled with natural light and hardwood floors, the main level features a spacious living room with gas fireplace that flows seamlessly into the dining area with access to a private deck, ideal for entertaining. The updated kitchen is finished with quartz countertops, stainless steel appliances, and a classic subway tile backsplash. All three bedrooms are well sized and located on the main level, along with a renovated full bathroom. The finished lower level adds valuable living space with new LVP flooring, a second full bath, mudroom, and direct access to the attached one-car garage, plus excellent storage. Recent upgrades include a new roof and gutters, full interior and exterior painting, newer A/C wall unit, and a new hot water and heating combination system. City water, sewer, and natural gas. Set on a large backyard and ideally located near restaurants, shopping, Metro North, and local parks. New playground coming soon at Haig Park.

Experience refined luxury in this expansive Westover home, discreetly nestled at the end of a tranquil driveway just moments from schools, highways, transportation, and Stamford and Greenwich amenities. The property is enveloped by lush mature landscaping and offers access to the sprawling beauty of Mianus River Park. Designed for both grand entertaining and effortless everyday living, this move-in ready home exudes timeless sophistication. The gourmet chef's kitchen, complete with an elegant butler's pantry, flows seamlessly into gracious open-concept living spaces. French doors throughout the main level open onto an expansive west-facing deck, perfectly positioned to capture breathtaking sunset views, while a sun-drenched patio just off the kitchen creates an exceptional indoor-outdoor lifestyle. The serene main-level primary suite is a luxurious and expansive, featuring dual walk-in closets and a spa-inspired bath with a Jacuzzi tub. The second level offers four generously proportioned bedrooms, including two en-suite bedrooms and two with a shared bath. Bathed in natural light, the home also features an extraordinary walk-out lower level with a private en-suite guest suite, spacious office, and an expansive recreation room anchored by a dramatic stone fireplace. Every detail of this exceptional residence has been thoughtfully curated to offer unparalleled comfort, elegance, and privacy.

An approximately 8,000 SF Connecticut Colonial on more than seven acres in mid-country Greenwich, on one of the town's most established addresses. Seven bedrooms, eight fireplaces, a formal dining room, and a slate-tile roof -- a 1923 residence with period character on a scale of grounds increasingly rare in mid-country. A long private drive rises from the road, with the land revealing itself gradually: a nearly one-acre pond at the back of the property, a swimming pool, tennis court, two-bedroom guest cottage, and a detached three-car garage. The amenity stack -- pond, pool, tennis, cottage, garage -- is essentially irreplaceable on a single Greenwich parcel and reflects six decades of stewardship by one family. This is part of the four-parcel Spring Farms at Round Hill assemblage, brought to market for the after sixty years in one family. For buyers also considering renovation, expansion, or longer-term redevelopment, Workshop/APD -- leading architecture and interior design firm -- and Davis Chase Homes are available to design and build on the buyer's timeline. See the full Spring Farms at Round Hill brochure for context on the broader collection: https://issuu.com/workshopapd/docs/rhg_marketing_brochure

Offering a warm blend of 19th-cent character & modern updts, this 1860 Greek Revival Col showcases truly distinctive features. Despite its expansive 5,358sf, the home feels inviting & intimate, highlighted by rustic design elements incl brick hallways & accents. Orig rich random width pumpkin pine plank flrs recently refin 10' clgs thru-out & 5FPs. Set on 1.22 lvl acres w/specimen trees, this special property offers a peaceful, prvt setting in desirable Westover-just moments from city amenities. The orig residence, believed to be the orig area farmhse, feat a gracious LR & DR both w/FPs, Kit w/access to charming Bkfst Rm, Full Bth & unique brick hallway w/sunlit nooks ideal for reading, gardening & relaxing. An award-winning late 1960s addition recognized for architectural accuracy of design & craftsmnshp, enhances the home w/stunning FR feat a wall of blt-ins & spacious Den-both w/FPs & wonderful windows flooding the space w/natural light. Upstairs you'll find a priv & spacious PBR w/FP & en-suite Full Bth. 4 add'l BRs, 3rd Full Bth w/Laundry, & a framed space ready for an add'l bth, +a bright, airy Bonus Rm. Dramatic walls of floor-to-clg windows overlook the brick patio & beautifully landscaped grounds. The lvl, fenced yard w/mature plantings provides a serene outdoor retreat perfect for relaxation and entertaining. This wonderful home features brand new mech sys incl C/A, Furnace, Wtr Htr, Boiler & Well Purification sys.