luxury houses with pool for sale New Canaan, United States

119 Proprietors Crossing is a breathtaking estate by architect James E. Gearity. Set on four acres, this fully restored six-bedroom home blends timeless elegance with modern function.nnA private drive and grand fountain lead you in to a soaring foyer with a sweeping staircase beneath a dramatic Baccarat chandelier. The parlor, with one of seven fireplaces, flows to a serene terrace. The Blue Room offers a refined retreat, while the study, with a coffered ceiling and secret staircase, connects to the primary suite.nnThe formal dining room glows under another Baccarat chandelier. Adjacent is the chefs kitchen, now complemented by the extended family kitchen in the Great Room featuring an enormous leathered quartz island. This room, with a 35.5-ft vaulted ceiling, boasts integrated high-end speakers as part of a whole-home audio system.nnThe primary suite showcases an 800 sq. ft. dressing room and a gorgeous two level bathroom with freestanding tub. The lower level of the home offers a media room, gym and wine grotto. The outdoor space includes a dining pavilion, outdoor kitchen, and a brand-new pool with spa.nnBuilt for luxury and efficiency, the home has commercial-grade systems, SIP walls, a Welsh slate roof, radiant heat, and 14 temperature zones for your comfort. Additional features include a four car garage and an elevator accessing all levels of the home. This newly restored gem incorporates enhanced functionality for todays buyers, built to last for generations.

Enter a world of opulent privacy on nearly twenty-five acres of pristine countryside, boasting five acres of serene lakes, an elegant stone bridge, and expansive manicured lawns that cradle an entire valley just 45 miles from NYC. Discover a lavish retreat comprising of four distinct residences: a magnificent five-bedroom, four-bathroom main estate, a charming two-bedroom, two-bathroom guest cottage, a sophisticated two-bedroom, one-bathroom carriage house complete with a heated three-car garage, and a stylish one-bedroom, one-bathroom log cabin pool house overlooking a 20x50 heated saltwater pool. Additionally, luxuriate in a cozy writers cabin, with a majestic fireplace. The compound also has a versatile storage barn with separate private driveway access and a dog kennel. The property is artfully situated amidst majestic oak trees and vibrant flowering shrubs, adorned with professionally landscaped stone terraces, walls, and scenic viewpoints, featuring multiple rose and mixed flower gardens, an organic vegetable garden, and a host of other exquisite amenities. Stroll through this picturesque sanctuary of unmatched serenity - a truly enchanting haven of natural beauty and modern comforts.

This one-of-a-kind 5 bedroom, 5 full bathroom rustic Adirondack-style residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned by Ted Sorenson, JFK's speechwriter, the unique estate is ideal as a year-round home, weekend retreat or secluded hideaway with Belgian block and chestnut floors, stone columns (the stone of which was excavated from the site), tongue-in-groove cedar walls, soaring beamed ceilings, 22 skylights and custom windows. Custom stair railings designed by renowned rustic artist, Daniel Mack. Enjoy lavish entertaining in impressive living spaces with floor-to-ceiling fireplaces and windows. The stunning dining room seats 16, the masterful kitchen with copper counter tops, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite is joined by a home gym, media room sauna and office with custom desk made of one solid piece of hundreds of years old Boabab tree. The lower level en suite bunk room provides ample accommodations, with private entrance. Resort-like grounds and a bucolic location make this an exceptional country estate. Bespoke properties like this don't come up very often. This is truly a one-of-a-kind offering.

Hillandale is a once-in-a-lifetime offering—an extraordinary opportunity to own one of the most iconic and expansive estates in the region. Encompassing approximately 268.2 sylvan acres, this landmark property gracefully spans the New York/Connecticut border, offering stunning views over formal gardens, a private lake, and rolling woodlands. Total privacy, historic pedigree, and timeless elegance define every aspect of this extraordinary estate. At its heart stands a majestic European-style stone manor, originally constructed in 1900 and once owned by the Sulzberger family, publishers of The New York Times. The residence has since been expanded and masterfully restored by the current owners, now offering more than 15,000 square feet of refined living space. Exquisite materials—imported antique marble, limestone, onyx, mosaic tile, and stained glass—adorn the interiors, where craftsmanship of a bygone era meets the comforts of modern luxury. The stately manor features eight bedrooms and ten full and four half bathrooms, anchored by grand formal living and dining rooms with intricately carved wood paneling and elegant fireplaces. A gracious library, conservatory, cloakroom, and breakfast room add to the home’s refined flow and character. At the center of the home’s leisure offerings is a spectacular indoor Olympic-sized pool, clad in Italian mosaics, complemented by a second outdoor pool and adjacent pool house—ideal for warm-weather entertaining. The grounds are as captivating as the interiors, with private lakes, formal gardens, wooded trails, and a whimsical hedge maze designed for children. More than five miles of private roads wind through the estate, offering serene views and access to a variety of outdoor amenities, including a tennis court, greenhouse, two horse barns, and four additional guest or staff residences. With its clay-tiled roof, enduring stone construction, and unparalleled sense of scale and privacy, Hillandale is more than an estate—it is a generational legacy. Whether envisioned as a private retreat, equestrian compound, or world-class residence for entertaining on a grand scale, Hillandale stands as a rare jewel in the heart of the tri-state countryside.

'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.

Discover this distinctive Colonial, gracefully positioned on a quiet cul-de-sac with 2 acres of stunning natural beauty. From the moment you arrive, timeless elegance and thoughtful design welcome you home. Sun-filled grand rooms flow seamlessly throughout. The impressive living room captivates with a fireplace, gleaming hardwood floors, and a wall of windows. The gourmet kitchen is a true showpiece - granite counters, premium stainless appliances, and an oversized island perfect for entertaining. Step through French doors to your private deck and sparkling heated in-ground pool - outdoor living at its absolute finest. The primary suite is a sanctuary of its own - a private wing complete with a fireplace, personal gym, steam shower, jetted tub, and two oversized walk-in closets. Four generous upstairs bedrooms, including an en-suite second primary, accommodate family and guests beautifully. A main-level office and two powder rooms add everyday convenience. The finished lower level offers a mud room playroom, cedar closet, and exceptional storage - ideal for hobbies or a private workspace. A whole-house generator and EV charging hookup deliver the ultimate in modern luxury and peace of mind. Exceptional space. Exquisite details. Extraordinary value. This is the one you've been waiting for.

A rare offering where extraordinary craftsmanship, uncompromising luxury, and complete privacy converge to create a residence without equal. Hidden behind a gated entrance and framed by magnificent stone walls in prestigious Bedford, this exceptional estate makes an unforgettable first impression long before you arrive at the front door. Step inside and discover a world designed to elevate everyday living-where soaring ceilings, dramatic open spaces, and walls of glass create a breathtaking interplay of natural light and architectural beauty. Every inch of this remarkable home has been masterfully crafted with an unwavering commitment to quality, seamlessly blending timeless sophistication with modern comfort. The main level is designed for both grand-scale entertaining and effortless daily living, featuring expansive gathering spaces, a beautifully renovated chef's kitchen, and a private guest or in-law suite offering comfort and flexibility for extended stays. Outside, a resort-caliber setting awaits. A spectacular covered terrace is anchored by a grand outdoor fireplace on one end and a built-in grilling station on the other, with generous spaces in between for elegant entertaining or quiet evenings under the stars. Beyond, an extraordinary custom stone infinity-edge pool, separate stone spa, and sweeping terraces create a private sanctuary that feels more like a five-star resort than a private residence. Return indoors to enjoy the private steam sauna and Finnish spa on the main level-bringing a true wellness experience into your daily life. The second floor is dedicated to luxurious private living, highlighted by an exquisite primary suite designed as a personal sanctuary, along with three additional en-suite bedrooms that offer exceptional comfort and privacy for guests. The lower level redefines home entertainment with an experience rivaling premier private clubs-featuring a custom-designed full bar, a state-of-the-art home theater, fitness studio, and expansive recreation spaces ideal for billiards, celebrations, or unforgettable gatherings. For the automobile enthusiast, the heated garage comfortably accommodates six vehicles. Perfectly positioned in Bedford, New York-renowned for its historic charm, estate properties, and timeless appeal-this extraordinary residence offers the ultimate escape from the demands of everyday life while remaining close to exceptional dining, boutique shopping, and equestrian pursuits. This is more than a home-it is a destination, a retreat, and a once-in-a-lifetime opportunity for buyers seeking nothing less than perfection.

Exceptional custom-built 4 to 5 bedroom Colonial in desirable North Stamford! This impressive 4,644-square-foot residence welcomes you with a dramatic two-story entry hall and offers sophisticated living on a beautifully landscaped 1.1-acre lot. Four generous bedrooms and four full baths plus one half bath provide ample space for family and guests. A versatile bonus in-law suite over the three-car garage features convenient back stair access, perfect for multi-generational living or au pair accommodations. Plus 2200 square foot lower level with high ceilings is just waiting to be finished. Outdoor living is a dream with a level yard, expansive wood deck and patio with a heated in-ground pool-ideal for entertaining throughout the seasons. The prime North Stamford location offers tranquility and privacy while remaining just minutes from the Merritt Parkway for easy commuting. Experience the perfect balance of luxury, functionality, and location in this distinguished home.

Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridges most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence.nnThe grounds are thoughtfully designed to enhance both beauty and livability. The three ponds are supported by aerator systems that maintain water quality, circulation, and ecological balance, allowing them to remain vibrant and visually striking year-round. A wireless deer fence system, along with perimeter fencing, helps preserve the integrity of the landscape and plantings, ensuring the setting remains peaceful, natural, and undisturbed. The result is an environment that feels both curated and effortless, offering a true sense of calm and connection to nature.nnOutdoor living is elevated with an infinity-edge saltwater pool and spa positioned to overlook the property, a full tennis court, and multiple outdoor spaces designed for both entertaining and quiet relaxation.nnThe residence, a meticulously maintained stone and shingle Country House, offers over 5,500 square feet of light-filled living space. A two-story entrance hall introduces the home, leading into a series of elegant yet comfortable interiors defined by high ceilings, custom millwork, and walls of windows that bring the outdoors in.nnAt the center of the home, a dramatic great room with a soaring ceiling and fireplace anchors the main living level, flowing seamlessly into a chefs kitchen with a large center island and adjoining breakfast area. Formal living and dining rooms provide a more classic setting, while the overall layout remains open and adaptable for modern living.nnThe home offers four bedrooms, including a first-floor primary suite designed as a true private retreat. The suite features a double-sided fireplace, a spa-like en-suite bath, and custom walk-in closets, along with direct access to the grounds, creating a seamless connection between indoor comfort and the surrounding landscape. Additional spaces include a large playroom, multiple offices, and flexible bonus rooms suited for todays lifestyle.nnA screened porch and expansive rear terrace extend the living spaces outdoors, creating a natural flow for entertaining or quiet evenings overlooking the property.nComplete with a three-car garage and surrounded by preserved land and natural beauty, this is a home that offers both substance and ease.nJust minutes to Katonah, Bedford Village, Ridgefield CT and Metro-North, yet entirely removed, this is Pound Ridge at its best: understated, private, and enduring.

Exquisite custom Georgian manor perfectly situated on over 2 acres of park-like grounds in a gated Association. The manor boasts beautifully proportioned, light-filled rooms with high ceilings, stunning architectural details, and impeccable craftsmanship. Residence offers both sophisticated formal areas and comfortable family spaces, striking a unique balance for easy enjoyment. Magnificently scaled rooms include a mahogany library, and a spectacular Christopher Peacock kitchen with Calcutta marble double islands and an oversized breakfast room. Features include seven en-suite bedrooms, lounge & bar, wine cellar, gym and home theater. Property features stunning verandas overlooking gardens, fountains, terraces, and a pool with spa and waterfall. Square Footage is for 1st and 2nd levels. Lower Level: 2,262.58

HOMEWOOD – This remarkable country compound is one of the precious few eighteenth and nineteenth century shingle style Colonial Revival estates remaining in Fairfield County. Dating back to 1750, the original pre-Revolutionary War home captivated the attention of prominent New York City banker, George Haven, who purchased the home in 1890 and expanded it significantly including a glorious 50 foot ballroom designed by Elsie de Wolfe, nineteenth century designer, rivaling the best of her work in New York City. Today, after two million dollars of extensive and thoughtful updates over the past decade, Homewood is unparalleled in its historical detail and state of the art features. Total 12,853 square feet on three levels with more than 20 rooms, 13 original fireplaces, eight or more bedrooms, seven full and two half bathrooms; pool house with kitchen, full bathroom, and changing rooms; heated gunite pool and spa; three carriage style garages with porte-cochere; multiple porches and terraces; set on 3.22 manicured and level acres. Highest attention to detail: front to back Great Hall with ingenious ceremonial mahogany staircases; expansive chef's kitchen and butler's pantry; oversized formal dining room with breakfast alcove; plus primary suite with private balcony, multiple closets and two sumptuous bathrooms offering radiant heated floor, steam shower, and jetted tub. Vast third floor with additional bedrooms, artist studios, even a cookbook library, plus elevator to all levels in the home. Additional: nine zones of HVAC; three zones of radiant heating; generator; irrigation system; Glen Gate designed stone terraces, flowering gardens and orchard; all in premier Silver Spring location, just moments to the New York border.

7 Kingdom Ridge is an architectural marvel epitomizing modern luxury and showcasing bold, avant-garde design with an open concept that seamlessly merges style and functionality. The approach alone sets the tone. Set behind gates and approached by a long, axial drive, the residence unfolds to a grand courtyard anchored by a central fountain. A stately arrival framed by symmetry and scale, the home makes an immediate impression. Inside, a breathtaking double-height atrium crowned by a barrel-vaulted glass ceiling floods the interiors with natural light. A dramatic twin staircase frames the entry, with oversized gallery walls, leading to expansive living spaces designed for both large-scale entertaining and refined everyday living. The great room, with soaring ceilings and walls of glass, opens directly to the resort-style pool terrace, creating effortless indoor-outdoor flow. The chef’s kitchen is both sleek and functional, featuring custom cabinetry, professional-grade appliances, and an oversized island that seats six . Adjacent dining and lounge spaces offer a sophisticated yet inviting atmosphere, enhanced by rich finishes and curated design elements throughout. Upstairs, the primary suite offers a private retreat of exceptional scale and design. Its spa-like bath centers around a sculptural soaking tub with ceiling-mounted water features and set against an exquisite floral Sicis Italian mosaic backdrop. A spacious dressing room with a center island completes the suite. Three additional bedrooms and two full baths are thoughtfully positioned to provide comfort and privacy. The cabana room and movie theater addition enhances the property’s lifestyle offerings. From the theater, a spiral staircase leads to a dedicated gallery space, complete with its own climate control, ideal for displaying art or collectibles. The outdoor setting is equally impressive, designed as a true extension of the home. A heated vanishing edge pool with integrated spa and waterslide serves as the focal point, surrounded by expansive terraces, a covered dining area, and an outdoor kitchen equipped for effortless entertaining. Other outdoor highlights include a sports court and firepit . The manicured grounds and sculpted pond are framed by mature trees, creating a sense of privacy and tranquility throughout. An exceptional blend of architectural precision, modern luxury, and resort-style amenities, this residence delivers a rare opportunity for elevated living in a truly distinctive setting. All within close proximity to Byram Hills schools, dining, shopping, and convenient access to major commuter routes.

Welcome to 103 Cedar Lane, Ridgefield! Nestled on a picturesque one acre property in prime south Ridgefield, this classic New England Colonial home offers a wonderful lifestyle. With summer fast approaching, enjoy the glorious level property with mature landscaping, heated pool, beautiful decking and a pergola with free standing firepit. Inside the home, the entry foyer leads to a spacious living room complete with a wood burning fireplace, custom built-ins and an oversized picture window bringing the outdoors in. A newly renovated custom kitchen offers granite counters, upscale appliances and beautiful center island. Opening to the kitchen, the dining room features a custom-designed built-in hutch and sliders leading to the inviting deck and pool oasis. The main floor is complete with a separate family room (that could be used as a main floor bedroom) and full bath. The second level offers four bedrooms along with an updated full bath. Hardwood floors throughout. This home also offers tremendous expansion potential. Come discover the possibilities waiting for you in this timeless Colonial home! Cedar Lane is ideally located just minutes to train stations and to vibrant downtown Ridgefield - CT's first Cultural District- offering exceptional dining, shopping, galleries and entertainment. Approx one Hour to NYC.

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.

*H/B by 5:00 Tues 5/19* Set on a beautiful, professionally landscaped acre in one of Ridgefield's most coveted neighborhoods, this meticulously renovated 5bed/3.5bath Colonial offers timeless elegance & modern luxury. The heart of this home is the stunning chef's kitchen, thoughtfully expanded w/ walls of windows, premium custom cabinetry, quartz countertop in Calacatta Romanao ,& professional appliances which include an 8 burner Wolf range, Miele coffee station, an oversized GE Cafe refrigerator & radiant heated flooring. The butler's pantry adds convenience w/extra storage, a new GE Cafe wine chiller & a built in ice maker which flows into the family room, featuring a built-in electric fireplace, for perfect ambiance. For outdoor living, the screened porch opens to a deck w/views of the heated salt water gunite pool & lush professionally landscaped backyard. The main level also boasts an oversized foyer w/new tile, a formal dining room, & a large living room w/wood burning fireplace. Throughout the home the newly refinished hardwood floors are gleaming. Upstairs, the primary suite is a private sanctuary w/a spa inspired bath, soaking tub and oversized shower plus walk in closet. 4 additional bedrooms & a brand new hall bath complete the upstairs level. The finished lower level includes a recreation space, wine cellar, full bath and laundry room. Through the double french doors, discover a resort style backyard w/ a stunning stone patio & total privacy out to the pool