luxury houses with pool for sale New Canaan, United States

Set on over four and a half acres of private, level grounds in one of New Canaan's most sought after locations, this exceptional estate offers a rare combination of scale, privacy, and close to town convenience. Originally built in 1962 and thoughtfully expanded, the property unfolds as a true compound. The main residence features five bedrooms, seven baths, and beautifully proportioned living spaces anchored by three fireplaces. A seamless connection between the chef's kitchen and family room creates the heart of the home, designed for both everyday living and effortless entertaining. The kitchen is fully equipped with a six burner Wolf gas range, second Wolf oven, Miele dishwasher, Sub Zero refrigerator and freezer, wine cooler, beverage drawers, marble island, and double sinks. Beyond the main residence, the estate continues to impress. A separate antique guest house with full kitchen, 3 bedroom and 1-1/2 bath provides ideal accommodations for extended family or guests. The heated gunite pool and pool house, added in 1991, offer a true retreat setting, complete with a party room, kitchen, bedroom, bath, and sauna for a resort like experience. A rare opportunity to own a private New Canaan estate with exceptional grounds, flexibility of living, and proximity to town.

Private New Canaan Oasis: Bespoke Luxury can be found in this modern version of a traditional centerhall colonial in prestigious New Canaan's West School district. This custom-built Lukes Wood estate underwent a spectacular renovation by Award-winning RR Builders, updating the sophisticated main residence to over 7,000 square feet of turnkey luxury. The expansive floor plan boasts 6 generously appointed bedrooms - each featuring an ensuite bath and walk-in closet alongside elegant formal living and dining rooms, a private office, a wine cellar, a butler's pantry, and a finished walk-out lower level with a full bath. At the heart of the home, a fully appointed chef's kitchen with a double island and professional-grade appliances flows into a sun-drenched breakfast room and a magnificent great room, which showcases a floor-to-ceiling stone fireplace, cathedral ceilings, and rustic beams. French doors transition seamlessly to an outdoor sanctuary featuring a 45' x 22' heated gunite pool, an expansive terrace, a pavilion with a firepit, private walking trails, plus a custom-built barn that offers additional space for cars, equipment, a gym, art studio, or large office space delivering an unparalleled, ultra-private retreat close to New Canaan's top-tier schools and vibrant community.

Classic Colonial in sought-after Silvermine, set on four acres of protected natural surroundings that offer a rare combination of privacy, beauty, and enduring character. Mature trees, preserved wetlands, and seasonal views create a landscape that feels both expansive and intimately connected to nature, while a conservation easement helps ensure these surroundings remain protected for generations to come. Inside, elegant living spaces and thoughtful design create a home equally suited to quiet enjoyment and effortless entertaining. A two-story entry opens to an oversized formal living room, while the kitchen flows seamlessly into the family room. Two main-level offices offer flexibility for today's lifestyle. The primary bedroom features a spa-like bath with heated floors and dual walk-in closets. Three additional bedrooms include two en-suite baths. A private fifth bedroom with sitting room and full bath is ideal for in-law or au pair. Finished basement and full-house generator complete this exceptional offering.

Presenting the historic Landis Gores House, an architectural masterpiece epitomizing post-WWII Modernism. Designed in 1946 by Harvard Five architect Landis Gores for his own family, it stands proudly as one of New Canaan's first Modern homes. Gores was at that time working in association with Philip Johnson. He set his own home on a narrow granite ridge astride a majestic 4-acre wooded lot; the residence brilliantly leavens the glass-walled austerity of the International Style with the natural warmth of Wrightian organic architecture.The 130-foot long, single-story form is defined by sweeping horizontal planes, full-height plate glass walls, grey-stained cypress siding, and by natural stone fireplaces, walls and terracing. Its informal, open plan is divided into three distinct pavilions, anchored by the dramatic central living and dining area featuring a raised roof and tall ceilings. Original exterior lighting design by Richard Kelly enhances the seamless integration between the avant-garde interior and its environment. An expansive rear terrace, added by Gores himself in the 1980s, features circular seating areas and an elegant oval swimming pool.Listed on the National Register of Historic Places in 2002 and held by the Gores family since its inception. The Gores family granted a perpetual preservation easement to the National Trust for Historic Preservation. This iconic property offers a once-in-a-lifetime opportunity to own a foundational piece of architectural history

Prestigious Hoyt Farm Tudor: An Elegant Two-Acre Oasis Near the Village. Nestled on two beautifully landscaped, ultra-private acres in the highly coveted Hoyt Farm neighborhood, this exceptional Tudor offers over 7,400 square feet of sophisticated luxury and warmth. A grand, two-story foyer welcomes you into a seamless, light-filled layout featuring a formal living room with dramatic vaulted ceilings, a handsome wood-paneled library, and an open chef's kitchen that flows effortlessly into a spacious family room with a fireplace. The primary suite is a true sanctuary, boasting its own cozy fireplace, a private balcony overlooking the grounds, a generous dressing room, and a sun-drenched, spa-like bath. Four additional bedrooms and four-and-a-half baths ensure plenty of space and comfort for everyone. Outside, your personal resort awaits: host gatherings on the tranquil brick terrace by the outdoor fireplace, swim in the stunning heated pool, or simply enjoy the park-like property framed by mature specimen trees. Complete with a three-car garage, this magnificent estate offers unparalleled privacy and convenience, located just minutes from the train, vibrant village life, and top-rated New Canaan schools.

Nestled in the heart of Silvermine, tucked away, yet close to it all, this Condo and complex are truly one of a kind. This 2 bed, 2.5 bath unit has been beautifully renovated. It's sophisticated with timeless style! The sun filled, open concept floor plan is designed for both everyday comfort and entertaining. The main floor features a generously sized Living Room with sliders to a private deck with skylines views of the well manicured grounds. This room anchors the Condo with its wood burning fireplace. The Dining Room is highlighted by a gorgeous, big window and opens to the completely renovated, modern and chic Kitchen. Granite counters, stainless appliances, elegant tile work and ample cabinetry make this space shine. Upstairs you'll find the oversized Primary Bedroom that is sophisticated and relaxing. The Primary Bath is well sized and updated with a large linen closet and gorgeous tub and shower. The Guest Room is private with a full bath, making it ideal for living or as a home office. The laundry is conveniently located on this floor and adds to the condo's smart functionality. Additional amenities include an attached one-car Garage and a Storage Room conveniently located just off the garage. Residents enjoy beautifully landscaped grounds, a sparkling swimming pool, and a pet-friendly community. Just moments from the Merritt 7 Metro-North station and close to and all that Norwalk has to offer. Asking for all offers by July 16th at 9pm. Please use the SMART MLS P&S.

'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.

This one-of-a-kind 5 bedroom, 5 full bathroom rustic California inspired 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 fireplace and windows. The rustic dining room seats 16, the masterful kitchen with original copper bar counter, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite, home gym, media room, sauna and office with custom desk made of one solid piece of hundreds of years old Baobab 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. Custom, high level properties like this don't come up very often.

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.

20 Cherry Lane is a rare Georgian Colonial estate set on nearly 2.5 flat, manicured acres bordering 50 acres of protected conservation land and hiking trails. Offering over 7200 sqft, with an additional 2100+ sqft lower level, this home combines exceptional scale, modern updates, and long-term value. Designed for entertaining and everyday living, the renovated chef's kitchen features double marble islands, double ovens, dual dishwashers, navy subway tile, and a custom coffee/wine bar, flowing into the oversized Great Room with a massive stone fireplace, full bar, and direct access to the resort style pool area. The flexible layout includes 6 bedrooms, a luxurious primary suite with private balcony and oversized walk-in closets, double office/conference spaces, library, homework zone, first floor guest suite, and a fully self contained in-law/au pair suite with private entrance, kitchen, and living area. The renovated lower level offers a gym space, wine cellar, oversized playroom with custom bunk beds. Outdoors enjoy a restored pool and spa, sports courts, playground, gazebo, fire pits, and multiple entertaining areas. Major upgrades include a new 2024 roof, updated HVAC, plumbing, electrical, and a renovated 4 car garage with smart-tech doors. Move in ready, this exceptional estate offers incredible space, infrastructure, and upside in a premier school district.

A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and well-proportioned spaces create an environment that feels both elevated and effortlessly comfortable. At the center of the home, a beautifully designed kitchen opens to expansive living and dining areas, creating a seamless flow for both everyday living and entertaining. The layout flows easily with ample room for work-from-home, multi-generational living, and evolving lifestyle needs. A main-level suite with a full bath provides privacy and versatility-ideal for guests, a dedicated office, or an extended family. Every detail accentuates comfort, function, and understated luxury. A back yard patio with pool abutting a nature preserve offers privacy with open space and the ease of in-town living. Positioned near Nash Pond and close to local nature trails and amenities, the home also offers exceptional convenience-walkable to the Post Road and just minutes to downtown Westport, shopping, dining, and Metro-North train service to New York City. Luxury new construction in Old Hill, Westport, CT-where location, design, and lifestyle align in one of the town's most desirable settings.

Welcome to Vermont in Wilton! 1.5+ acres + I/G SW Pool! 3 Bedroom New England Cape sanctuary tucked away in a peaceful pocket of North Wilton. One meticulous owner since built in 1973, this rare find offers a charmingly rustic, soul-warming lifestyle combined with the refined convenience of Wilton living. A true testament to quality craftsmanship and generations of pride of ownership. Now, freshly painted and prepared for the next chapter. Warm hardwood floors on Main level and 4 panel sliders invite the outside in and create a panoramic view of the natural surroundings and parade of wildlife. Primary first floor Bedroom continues with hardwood, walk in closet and en suite Full bathroom. With 2 Bedrooms upstairs and 2nd Full Bath, there is no shortage of closet space with hidden closet storage! The exceptional grounds offer an incredible level of privacy on your own secret park. The in ground heated salt water pool is perfect to beat the summer heat or for outdoor poolside gatherings, framed by nature's bounty.Properties with this level of soul, history and privacy are a rare find in Wilton. If you've been dreaming of a serene escape without sacrificing proximity to town, this cherished single owned property is ready to welcome you home. Award winning schools, seconds to Rt. 7, shopping, trains, restaurants and the up and coming Georgetown revivial with fun night life, this home offers a singular, affordable lifestyle. Awaiting your updates! Property is an Estate, sold AS IS

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

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.

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.

Panoramic vistas of Long Island Sound extend from this gated, resort-style estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawn, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Secluded outdoor shower with exterior access powder room. Separate 2-bedroom guest cottage with kitchen, laundry and one-car attached garage. Full house generator.

Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over 6,500sf of thoughtfully designed living space, including 6 bedrooms and 9 baths. Expansive panoramic windows capture serene water views and fill the home with natural light. A dramatic two-story entry foyer and soaring ceilings create an impressive sense of space. The open-concept kitchen/living room is a true centerpiece, featuring a massive 12-foot island with seating for 6, high-end appliances, dual dishwashers, a wine fridge, an ice maker - ideal for both everyday living and entertaining. Designed for effortless indoor-outdoor living, the home seamlessly connects its interior to exceptional outdoor entertaining areas. The spacious family room features sliders that open directly to the expansive covered patio with retractable screens, an outdoor kitchen, and a relaxing pool and spa. The 3rd floor great room has amazing water views, and features a 1/2 bath and wet bar. Additional highlights include a private office, whole house generator, 2 laundry rooms, sauna, a mudroom, and a charming 'hidden' playroom. A truly turnkey offering, this home embodies the very best of the Stony Point

Cosseted within the gates of the exclusive Conyers Farm association with 24hr security, this baronial French Normandy chateau is poised on more than thirteen park-like acres. Hospitality sets the tone from the entrance through the grand foyer to the dual living rooms, an impressive formal dining room for large-scale entertaining and a warmly paneled library. The heart of the home is the luxurious kitchen with butler's pantry, breakfast room and adjoining family room with fireplace. French doors open to the immense terrace, perfect for outdoor dining. A true sanctuary, the primary suite features two bathrooms, two sizable walk-in closets, a dressing room and a romantic sitting room with balcony overlooking the naturally secluded, private backyard. Six additional bedrooms offer abundant space for guests or family. Creating captivating vignettes of multifunctional living, the lower level features a home theater, sitting room with fireplace, full bar with kitchenette, gym, indoor resistance pool and a hot tub. Outside the terrace overlooks beautiful, level lawns and a pool with spa. Peace of mind is the directive for this characterful estate, with its reassuring security in a guard-gated enclave and its luxury leisure amenities.

Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft ceilings, custom paneling, character grade oak floors, refined millwork, and expansive windows. Sun-filled living and dining rooms complement the great room with a sleek 60inch fireplace and reclaimed beams. The chef's kitchen includes full size SubZero refrigerator and freezer, Wolf cooktop and double ovens, quartzite waterfall island, custom cabinetry, and walk-in pantry. A private office with built ins enhances work from home convenience. Outdoor living shines with a covered porch, granite patio, outdoor kitchen, and direct access to the 20x40 saltwater pool. The luxurious primary suite offers vaulted ceilings with antique beams, oversized walk ins, and a spa bath with custom vanities and textured tile. All five second floor bedrooms are ensuite. The finished third floor adds a full bath, office/craft room, and playroom. The walkout lower level includes a bedroom and bath, gym, wet bar, media room with raised platform, and large recreation area. **Images with exterior are AI Altered. House is complete inside. Exteriors complete 6/15/26.** **See Addendum**

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.

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.

A truly exceptional Greenwich estate combining privacy, sophistication in a coveted backcountry setting. Set on four secluded acres, this classic European-inspired residence offers timeless elegance and exceptional living spaces. The main level features a gourmet chef's kitchen,charming family room with fireplace, formal dining room, dramatic beamed living room with stone fireplace,and double bedroom with full bath. Upstairs are a primary suite and three additional bedrooms. French doors open to wonderful outdoor entertaining space which is adorned by a gunite pool and spa. Formal gardens and expansive grounds complete this spectacular outdoor space. The finished lower level offers a spacious game room with a stone fireplace, extensive office space, with a private entrance.