luxury houses with pool for sale Stamford, 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.

Welcome to this quintessential Greenwich home, fabulously refurbished and sited on a generous and private .91 acre in central Greenwich. Within an easy reach to schools, train stations and all of the amenities the town has to offer, this 4 bedroom home is move-in ready. The formality of the living and dining room is complemented by the open eat-in kitchen and family room. There are several home ''offices'' from which to chose! Perfect for the summer months, the heated pool is naturally shaped and acts as the centerpiece to the mature and landscaped garden. Two car garage is a benefit.

GREAT INVESTMENT OPPORTUNITY-Bellavista is a 16,000+sf estate designed by architect 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 Long Island 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). Attached 2 car garage + 5 car carriage house w lifts. 45'x20' pool. Features: Full house generator. Venetian plaster walls, bleached white oak and porcelain floors throughout, radiant heated floors (including garage), self cleaning glass beaded stucco exterior with composite slate roof, imported windows/doors and stone, and expansive property for sports and entertaining. Pet grooming room with separate laundry. Chef's kitchen and additional family kitchen. Separate staff quarters. Plans available for an additional indoor pool and underground parking garage for 8 more vehicles with a car elevator.

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.

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.

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.

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+/-

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.

Hidden away at the end of a coveted West Side cul-de-sac, 48 Driftway Lane is a private estate tucked among the winding back roads of New Canaan. Perched atop 1.62 beautifully landscaped acres and surrounded by nature, the setting offers a rare sense of peace and privacy, yet remains just minutes from downtown New Canaan and approximately one hour from New York City. Newly constructed from the ground up in 2017 and offering over 10,000 square feet of thoughtfully curated living space, the home unfolds through a series of light-filled rooms where architectural detail, craftsmanship, and connection take center stage. A grand central foyer showcases a statement staircase framed by glass railings, creating a stunning focal point from the moment you enter. At the heart of the home, a sunlit gathering space serves as the natural connection point between the designer kitchen, soaring two-story family room, and outdoor living spaces beyond. Anchored by a stunning 10-foot quartzite waterfall island and matching custom quartzite hood, the kitchen balances beauty and function with Thermador appliances, Sub-Zero refrigeration and wine storage, custom cabinetry, and a walk-in pantry. The dramatic family room draws the eye upward with soaring ceilings, extensive architectural detailing, automated Lutron shades, and walls of windows that flood the space with natural light.

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.

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.

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

One level living at its best! A gated drive introduces this beautifully appointed stone residence, gracefully set on over two exquisitely landscaped Mid-Country acres. Light-filled interiors offer a rare combination of scale and comfort, and are defined by dramatic ceiling heights, expansive windows, and beautifully proportioned spaces. A generous entry flows to the formal dining and living rooms, as well as the eat-in kitchen. French doors are showcased throughout the main level to create a seamless connection to the surrounding grounds and deck. The main-floor primary suite is thoughtfully positioned for privacy and features dual walk-in closets, a sumptuous bathroom that has just been renovated with spa-like finishes, and direct access to the terrace and gardens beyond. Three additional bedrooms on the main level, each with their own bathroom, provide exceptional flexibility for family and guests. Upstairs, a versatile suite with extensive built-ins, full bathroom, and adjoining exercise room offers ideal space for a home office or private guest space. A walk-out lower level includes a generous family room, anchored by a gas fireplace, and a full pool bathroom. A recently installed cedar shingle roof with copper flashing underscores the property's enduring quality and attention to detail. Outside, mature landscaping, a pool with spa, and a waterfall provide a tranquil backdrop for this one-of-a-kind offering.

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!

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.

Timeless 1925 Colonial reimagined for modern living. Set on oversized, stunning 3.43 private acres in a coveted Mid-Country Greenwich location, this exceptional estate offers over 7,000 square feet of beautifully updated living space. Thoughtfully transformed, the home seamlessly blends the architectural character and craftsmanship of a bygone era with sleek contemporary design and today's most sought-after amenities. Elegant formal rooms, inviting gathering spaces, and 6 spacious bedrooms are complemented by 7 full baths, while 4 fireplaces add warmth and character throughout. The stunning grounds provide a true retreat, featuring a sparkling pool, expansive lawns, and exceptional privacy. A rare opportunity to enjoy historic charm and modern luxury!

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.

'La Gentilhommière' is a unique property in North Stamford, inspired by Château de Givenchy-le-Noble in France. Built 20 years ago, this property exudes an authentic French charm with imported materials gracing its construction. From the stately Pierre de Bourgogne limestone that adorns its exterior to the exquisite 18th-century French elements found within, every detail evokes a sense of timeless elegance. Inside, you'll discover the beauty of Versailles wood parquet flooring and the comfort of double-paned insulated windows, each adorned with brass European-style handles that enhance the estate's allure. The heart of the home showcases a Smallbone kitchen, complete with a La Cornue Château range, while radiant-heated floors and numerous other exceptional features elevate this property to a class of its own. Bordering the Helene Altschul Land Trust, ensuring no adjacent construction, the privacy in this estate is second to none. The property includes 2 newly built guest houses, one pool house featuring a kitchen with a private bathroom, and a studio house with an inspiring view to stimulate the mind. The newly built 12 meter pool is surrounded by amazing landscapes, as the large schist boulders are reminiscent of Central Park. Combining historical aspects that cannot be duplicated, in addition to the modernized renovations, this property will appeal to anybody with its unprecedented versatility. Conveniently close to the Merritt Parkway and Manhattan, it offers a rare opportunity for discerning buyers looking for quick access to the city.

Set on over two acres of exquisitely manicured grounds, this exceptional six-bedroom Georgian estate offers approximately 8,500 square feet of elegant living space, including the finished lower level. Beautifully proportioned interiors feature refined formal rooms, a chef's kitchen with premium appliances and marble island, an inviting family room, library, and a luxurious primary suite with sitting room and spa-inspired bath. Designed for effortless indoor-outdoor living, the resort-style grounds showcase a spectacular pool and spa, expansive terraces, outdoor kitchen with pizza oven and grills, fire pit, greenhouse, and organic gardens. Complete with a heated three-car garage and approved seven-bedroom replacement area, this is a rare Greenwich offering.

Handsome brick Georgian just off Round Hill Road, renovated and expanded in 2010 with pool and spa, set on 2.41 landscaped and private acres. Custom built with exceptional attention to detail, this 5 bedroom, 6,200 +/-sq ft home embodies timeless architecture paired with a floor plan for modern living. A grand double-height reception hall creates a striking first impression, unveiling sun-drenched interiors and beautifully proportioned formal and informal spaces ideal for both entertaining and comfortable everyday living. The eat-in kitchen, accompanied by a butler's pantry, is designed to satisfy the most discerning chef. Paneled library with fireplace for work at home, or relaxation. Primary suite with fireplace and two walk in closets is complemented by four additional ensuite bedrooms. Third floor is flexible space in use as a large gym with spa bathroom. The lower level is fully finished and ready for customization. Completing this exceptional offering is a four-car garage, mudroom and laundry room. Enjoy resort-style outdoor living with pool and spa surrounded by mature plantings and exceptional landscaping providing a true sense of privacy and tranquility.