luxury houses with pool for sale Cos Cob, 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.

Stunning property, with landscape lighting and pool in the sought after Willowmere Assoc with deeded access to private beach, dock and kayak storage. This fabulously renovated and lovingly cared for home has a DaVinci roof, copper gutters, wonderful light from huge windows, doors and skylights soaring ceilings, gourmet kitchen and sumptuous primary suite. Quality finishes and thoughtful design elements throughout. SMART primary bath with spectacular shower featuring rain head and 4 alternating programmable body sprays, soaking tub, and Kohler Konnect system with speakers in the lighted medicine cabinets. Glass lit cabinets are finished with electric outlets and personal items. Gourmet kitchen with quartz counter tops, waterfall tile backsplash, great appliances and sunny 10 p banquet.

Set back from the road on 1.56 manicured acres in the coveted Golden Triangle overlooking a stream, this beautifully updated colonial with a pool offers privacy, charm, and timeless style. The home includes a light-filled chef's kitchen with breakfast room and adjacent family room, 5 fireplaces, a sunny library, formal dining and formal living room. Luxurious 2nd floor primary suite features a walk-in closet, fireplace, balcony and renovated bathroom. There are 4 more en-suite bedrooms on this floor. The 3rd floor has a full bath and two spacious rooms. Walk-out lower level with playroom, powder room and mirrored exercise room. The peaceful backyard terrace with pool overlooks mature trees and a stream with a small waterfall, complemented by a delightful treehouse at the front of the home.

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+/-

Bellavista is a 16,000+sf estate designed by Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus LI Sound views from the 2nd and 3rd floors,A truly sophisticated modern lifestyle.The residence is distinguished by its extensive integration of advanced technology systems, seamlessly embedded throughout the home. Smart-home infrastructure (lighting,climate,security, and entertainment). State-of-the-art environmental and wellness technologies(air,water,energy efficiency,and comfort).Features also include: 2 car attached garage and carriage house with lifts for 5 cars.45'x20' pool. Full house generator

This timeless estate, situated in an exclusive private association moments from town, masterfully blends turn-of-the-century grandeur with 21st-century luxury. The main house was extensively renovated and expanded in 2006 by award-winning architects Austin Patterson Disston. It showcases grand-scale rooms, soaring ceilings, and impeccable millwork. In 2016 the current owners made it their own by adding a wine cellar and renovating the master suite to the same outstanding standards. The main house features six ensuite bedrooms and 7.3 baths. The expansive primary suite is a true sanctuary, complete with private office, custom walk-in dressing room, and a large balcony overlooking the grounds. Outside, the property is an entertainer's dream, featuring lush gardens, mature flowering trees, stunning 2019 Shoreline over-sized pool with an integrated spa and automatic cover, extensive landscape lighting and built-in grill. Further updates in 2024 include repaved driveway, new roof on main house, and a chip and putt area. A charming carriage house adds nearly 800 square feet of versatile space, offering four-car garaging and a private one-bedroom apartment--perfect for guests or staff.

You don't look at your home...you look out from it. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering and execution where every material, finish and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a faade clad in premium Thermory wood siding beneath a Spanish slate roof an exterior that feels both grounded and enduring..Walls of Aluprof glass dissolve the boundary between interior and Long Island Sound, drawing light deep into nearly every principal room. The result is a seamless connection to the water, with unobstructed views that are impossible to replicate. Inside, large-scale radiant-heated Porcelanosa tiles grace the main and lower levels, setting a warm, modern foundation. At the heart of the home, a statement kitchen delivers both performance and presence; featuring custom Vimora cabinetry, top-of-the-line Gaggenau appliances and a fully equipped secondary prep kitchen designed for effortless entertaining at scale.Upstairs, European white oak introduce warmth, while radiant heat continues throughout all main spaces and baths reinforcing a consistent commitment to comfort and precision. The primary suite is conceived as a private retreat, oriented entirely toward the water. A fireplace anchors the space, while a private deck leads directly to the heated pool below. The bath offers a spa-like experience, featuring a sculptural soaking tub positioned toward the view and a separate steam shower. Custom Italian wardrobes complete the suite, incorporating bespoke detailing, opaque glass, and integrated features throughout. Additional bedrooms on this level are all ensuite, each perfectly positioned to capture water views.nThe lower level opens into a fully realized entertaining environment featuring a wine room, fitness center with sauna, guest accommodations, and a dramatic lounge anchored by an illuminated marble bar and a 162-inch screen.nA concealed underground car gallery, accessed by hydraulic lift, offers a discreet and highly engineered space designed for discerning collectors. Outdoors, an expansive terrace and heated waterfront pool overlook the cove, creating a setting defined by privacy and open water. Minutes from Tod's Point, Metro North, and the village of Old Greenwich, the property occupies that rare overlap of seclusion and convenience. With five bedrooms, five baths, and two powder rooms, every element has been resolved with intention. This is a rare chance to own a crown jewel waterfront property that stands in a league of its own. A defining waterfront residence where design, setting, and permanence align at the highest level.

Some homes are built for the market. Others are built for a legacy. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering, and execution, where every material, finish, and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a façade clad in premium Thermory wood siding beneath a Spanish slate roof, an exterior that feels both grounded and enduring. Walls of Aluprof glass dissolve the boundary between interior and Long Island Sound, drawing light deep into nearly every principal room. The result is a seamless connection to the water, with unobstructed views that are impossible to replicate. Inside, large-scale radiant-heated Porcelanosa tiles grace the main and lower levels, setting a warm, modern foundation. At the heart of the home, a statement kitchen delivers both performance and presence, featuring custom Vimora cabinetry, top-of-the-line Gaggenau appliances, and a fully equipped secondary prep kitchen designed for effortless entertaining at scale. Upstairs, European white oak introduces warmth, while radiant heat continues throughout all main spaces and baths, reinforcing a consistent commitment to comfort and precision. The primary suite is conceived as a private retreat, oriented entirely toward the water. A fireplace anchors the space, while a private deck leads directly to the heated pool below. The bath offers a spa-like experience, featuring a sculptural soaking tub positioned toward the view and a separate steam shower. Custom Italian wardrobes complete the suite, incorporating bespoke detailing, opaque glass, and integrated features throughout. Additional bedrooms on this level are all en suite, each perfectly positioned to capture water views. The lower level opens into a fully realized entertaining environment featuring a wine room, fitness center with sauna, guest accommodations, and a dramatic lounge anchored by an illuminated marble bar and a 162-inch screen. A concealed underground car gallery, accessed by hydraulic lift, offers a discreet and highly engineered space designed for discerning collectors. Outdoors, an expansive terrace and heated waterfront pool overlook the cove, creating a setting defined by privacy and open water. Minutes from Tod's Point, Metro North, and the village of Old Greenwich, the property occupies that rare overlap of seclusion and convenience. With five bedrooms, five baths, and two powder rooms, every element has been resolved with intention. This is a rare chance to own a crown jewel waterfront property that stands in a league of its own. A defining waterfront residence where design, setting, and permanence align at the highest level.

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.

A gated drive opens to this elegant six-bedroom Mid-Country Manor overlooking tranquil views of Horseneck Brook. A stone courtyard introduces the dramatic four-story residence with elegant foyer, where sweeping butterfly staircases and limestone floors create a striking architectural welcome. From the gracious gallery hall, beautifully proportioned formal and informal rooms unfold-including generous living and dining rooms, a family room, chef's kitchen with breakfast room and a private paneled library-all distinguished by hardwood floors, bespoke detailing, and soaring ceilings. A gracious ground floor guest suite completes this level. The serene primary suite offers a spacious retreat with fireplace, luxurious bathrooms, generous dressing rooms and complemented by an elegant sitting room with its own fireplace. Four additional en-suite bedrooms are located on the second floor. The third level offers versatile living space, including a custom home office, playroom, and full bathroom. The walk-out lower level is thoughtfully designed with a pool cabana, sauna and pool bathroom, wine cellar, gym, game room, mudroom, and direct access to the three-car garage. Outdoors, a pool, spa, and outdoor kitchen overlook the gently flowing brook and beautifully landscaped grounds. Ideally situated in the heart of Greenwich, this exceptional residence seamlessly blends privacy, architectural character, and convenience.

Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated and expanded, this warmly inviting residence offers 10,664± square feet with six bedrooms, six full and two half baths, plus eight fireplaces. Above the three-bay detached garage is a renovated two-bedroom, 903-square-foot apartment with full kitchen and laundry. Leafy views from every room overlook the enchanting landscape. There is a pool with spa, fenced vegetable garden and fenced chicken coop. With so many aspects of special distinction, this is a wonderfully unique compound that captures the feel of the English countryside in a tranquil mid-country location. Includes legally permitted medical office.

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.

LOCATION ,LOCATION, LOCATION! Striking, sophisticated, & contemporary w/a true WOW factor. This exceptional residence is tucked within the celebrated Golden Triangle, surrounded by some of Greenwich's most prominent estates. A rare blend of timeless modern sensibility, the home showcases stunning interiors, refined elegance, & impeccable craftmanship. Designed for today's lifestyle, the layout balances grand entertaining spaces w/ intimate, inviting rms. High ceilings, sun-filled interiors, & seamless indoor/outdoor flow create an atmosphere of effortless luxury. Every detail has curated to elevate daily living. Sited on 3 pvt acres across 2 sep. deeded lots, framed by lush landscaping, specimen trees, & vibrant seasonal gardens creating a one-of-a-kind paradise. Do not miss the apiary! Summer magic is unmatched. A delightful screeded porch ideal for lingering with the Sunday paper, a sparking pool, and al fresco dining at its best. A charming cottage offers exceptional flexibility for a guest retreat, home office, art studio, or fitness space. Capture your future memories in this dream that can come true!

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

Rare opportunity to own one of the sprawling combined residences at the prestigious Park Tower. This wonderful unit features a complete top-to-bottom renovation, highlighted by a brand-new gourmet kitchen with a center island and exquisitely renovated bathrooms, including a primary spa-bath with a soaking tub and separate shower. The flexible layout offers 3 bedrooms plus a dedicated office, a private sitting room, and a massive walk-in closet, all complemented by breathtaking views from two private balconies. Residents enjoy world-class building amenities including 24-hour security, full concierge service, a year-round indoor pool, and a stunning rooftop deck with panoramic skyline views. For ultimate commuting ease, the building provides a private weekday shuttle service directly to the Stamford train station. Perfectly situated just steps from Stamford's premier dining, shopping, and Metro-North, this home offers the absolute peak of luxury and convenience.

Privately set on more than 6 extraordinary acres within the prestigious Khakum Wood Association, this award-winning estate offers distinction, privacy, and architectural excellence in an A+ location. Clad in limestone, fieldstone, and stucco and crowned by a graduated slate roof, the residence is defined by timeless elegance and exceptional quality. Bright interiors feature soaring ceilings, imported natural materials, and superb craftsmanship throughout, while a modern floor plan is designed for both entertaining and daily living. Stone terraces on every level overlook sweeping level lawns. Complete with a separate apartment for guests or staff, 7 garage bays, pool, and bocce court, this is unlike anything else on the market.

Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage with sleeping loft, kitchenette, and full bath -the only remaining structure from one of Greenwich's Great Estates. Tremendous potential to build new 10,584 sq.ft. house offering unparalleled waterfront living. Close proximity to Byram Park with a public pool, beach, marina and boat launch for Greenwich residents. Easy access to downtown Greenwich as well as Manhattan.

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

A coveted Mid-Country cul-de-sac address sets the stage for this distinguished Connecticut Colonial, poised on two level acres of manicured grounds. High ceilings and gracious formal rooms give way to an expansive eat-in kitchen, fireside family room, and sun-drenched solarium -- spaces designed for both elegant entertaining and relaxed daily living. A handsome library with fireplace offers refined privacy, perfectly suited as a home office of distinction. Six bedrooms include a primary suite, four additional upper-level rooms, and a first-floor guest suite with sitting room and private bathroom -- thoughtfully appointed for family and guests alike. Outside, a heated pool and spa invite warm-weather leisure, while a three-car garage and verdant level lawn complete this remarkable offering.

Coming Soon - Privately tucked away at the end of a tranquil lane in prestigious Mid-Country Greenwich, this custom-built stone manor is a rare offering of timeless architecture, exceptional craftsmanship, and resort-like amenities. Encompassing more than 11,373 square feet and set upon 3.2 exquisitely landscaped level acres, the estate is surrounded by sweeping lawns, mature specimen plantings, and beautifully curated gardens that create an atmosphere of complete serenity and privacy. Designed for both grand-scale entertaining and comfortable family living, the residence features six bedrooms, eight bathrooms, and elegant interiors defined by high ceilings, abundant natural light, and refined architectural detailing. The main level boasts impressive 11-foot ceilings, gracious formal and informal rooms, a gourmet kitchen and oversized windows framing picturesque views of the grounds, pool, pool house and cottage with kitchen. The second floor, with 10-foot ceilings, is highlighted by an extraordinary primary suite offering a private sitting room, dual spa-inspired bathrooms, and two generous walk-in dressing rooms and a home office. Four additional en-suite bedrooms and a spacious laundry room complete this level. The thoughtfully designed lower level provides exceptional recreational and lifestyle spaces, including a guest bedroom and bathroom, family room, media room, fitness center, powder room, and additional space perfectly suited for the creation of a world-class wine cellar. The estate's outdoor amenities rival those of a private resort. A charming stone pool house with soaring ceilings, a fireplace, inviting living and dining areas, a kitchenette, changing room, and a full bathroom overlooks the spectacular 30' x 60' swimming pool and spa. Completing the compound is a beautifully appointed 1,500-square-foot guest house with two bedrooms, one full and one half bathroom, living room with fireplace, dining area, kitchen, office and an attached two-car garage, providing luxurious accommodations for extended family and guests. Offering an unparalleled combination of privacy, scale, and sophistication in one of Greenwich's most coveted locations, this exceptional estate represents the very best of country estate living just moments from town, schools, and commuter access.

Nature lovers look no more! Welcome to this very quiet private home nestled comfortably within its surrounding. Enjoy tranquility, mature trees and landscape from every room including a special screened-in patio with fireplace. Additionally, this well maintained and spacious 4 bed, 3 1/2 bath offers multiple floor plan uses for your very own enjoyment.

Serene living in this bright, turnkey 5-bedroom, 4.5-bath Colonial set on two private acres with a pool and entertaining terrace. Designed for comfort and flow, the home features abundant natural light and an open floor plan. The sun-filled family room opens to a newly renovated chef's kitchen, while a private study with fireplace offers a quiet retreat. Upstairs includes a spacious primary suite with spa-like bath, plus four additional bedrooms and two baths. The finished lower level with fireplace and full bath adds versatile living space. Mature landscaping, specimen trees, whole-house generator, and numerous upgrades complete this move-in-ready home.

Welcome to Manursing Island, an idyllic coastal year around resort-like community. Offering Rye City's only 24hr guard-gated security, experience one of Rye's most exclusive neighborhoods yet only 5 minutes to beach clubs, train, town, schools and major highways. Masterfully designed and meticulously constructed by a well known local architect, Paul Benowitz, this breathtaking waterfront property is situated as to take advantage of almost 270 degrees of expansive waterfront vistas. This custom redesigned home was designed to enjoy waterfront views from almost every room. Enjoy sunrise and sunset right outside your door. With over 5400 square feet of multilevel living there is privacy for all . Existing floor plan offers optionality for upsizers and downsizers alike. Additional potential square footage allowable for the next homeowner to make it their own. With stunning water views in all directions and high ceilings, sunlight pours through the home. Pool and expansive patio setting seamlessly blends with serene waterfront for endless entertaining opportunites. Take your morning walk along your own private peninsula before a morning swim in your heated waterfront pool. Enjoy your favorite cocktail where spectacular sunsets abound. Experience tranquil waterfront living like no other. Fun, airy, sun-filled home for everyone to enjoy !