luxury houses with pool for sale New Canaan, United States

119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere. Spacious entertaining areas flow seamlessly to a tranquil terrace. The heart of the home includes a chef's kitchen that opens to a Great Room with a remarkable 35.5-foot vaulted ceiling, centered around a large quartz island with integrated audio. A formal dining room beneath another Baccarat chandelier sets the stage for memorable gatherings. The West wing hosts the primary suite, featuring a cozy retreat and a study with a hidden staircase leading to a gym and an 800-square-foot dressing room. An adjacent Junior Primary Suite has its own entrance and living area. Upstairs, four additional bedrooms include two ensuite and two with a jack-and-jill bath. The finished lower level boasts a media room, fitness center, and wine cellar. Outdoors, curated grounds offer a dining pavilion, outdoor kitchen, and a newly constructed pool and spa, with space for a tennis/pickle-ball court. Engineered for efficiency, the estate features commercial-grade systems, radiant heat, and a rare Welsh slate roof. A four-car garage and an elevator service complete this exceptional offering.

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.

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.

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

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.

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.

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.

61 High Ridge Ave is an extraordinary estate in the heart of Ridgefield's Historic District, set atop one of the town's highest elevations with sweeping skies, radiant sunsets, and far-reaching views beyond the Hudson River. Custom built in 1997, this distinguished Stone Manor blends timeless elegance with exceptional craftsmanship. Encompassing more than 8,000 square feet across three levels, the residence showcases a stone facade, slate shingle roof, five generously sized bedrooms, and 6.1 baths. A dramatic two-story foyer opens to refined formal rooms and a handsome library, enriched by mahogany windows and doors, hardwood floors, and exquisite millwork. The expansive eat-in kitchen flows seamlessly into the inviting family room with fireplace, creating an effortless setting for everyday living and gracious entertaining. Upstairs, the serene primary suite offers two walk-in closets, a fireplace, and a private balcony, while additional ensuite bedrooms provide comfort and privacy. A finished third floor adds versatile space for wellness, work, or leisure. Beyond the main house, a separate studio cottage with full bath and fireplace offers elegant guest or flexible accommodations. Set on 2.61 landscaped acres, the estate is further enhanced by a pool, tennis court, and four garage bays, completing this rare and luxurious retreat.

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, infrared sauna, indoor hot tub, wine cellar, spa lounge, oversized playroom, and custom bunk room. 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 with the option to be sold fully furnished, this exceptional estate offers incredible space, infrastructure, and upside in a premier school district.

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.

Overlooking Wilshire Pond, 35 Wilshire Road is a rare modern backcountry compound set on 5.29 private acres with a true resort-like feel. Designed by noted architect Gerald Schiff, the home offers approx. 7,884 sq ft, 8 total beds & baths, bold entertaining spaces, and dramatic architectural details throughout. Amenities include a natural pool with waterfall and 15+ ft deep diving well, stone pool house with guest suite, tennis court with stadium lighting, expansive sports lawn, renovated gym with floor-to-ceiling windows, 3-car garage and generator. Substantially improved by the current owners, with reimagined landscaping, enhanced living spaces & upgraded systems, this is a one-of-a-kind Greenwich retreat is designed for privacy, recreation and effortless entertaining.

Vacation at home in this exceptional five bedroom residence, where refined design, resort inspired amenities and the flexibility of optional single level living create an extraordinary lifestyle. Tucked at the end of a quiet cul de sac on a spectacular 3.2 acre private parcel, property abuts conservation land with direct access to scenic walking trails offering tranquility and natural beauty. Designed for both elegant entertaining and everyday comfort, the outdoor living experience is highlighted by a new saltwater pool and spa. The breathtaking new main level primary suite serves as a private sanctuary complete with custom closets. Upstairs four additional bedrooms - including an optional second primary, accompany updated full baths. LL boasts wine lit wine closet, sauna and media room.

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.

Nestled on 4.09 acres in Greenwich, CT, this breathtaking 8-bedroom Georgian Colonial estate offers unparalleled elegance and privacy. Commanding spectacular big sky views from its perch 560' above sea level, the property features exquisite formal gardens, and pool. Inside, grand-scale rooms with soaring ceilings, masterful stonework, elegant millwork, and arches create a luxurious atmosphere. Highlights include a Beverly Ellsley gourmet kitchen, cherry library, solarium, and expansive living areas. The primary suite boasts two dressing rooms, spa baths, and a sitting room. A true modern-day ''Great Estate,'' just an hour from NYC.

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 one of Round Hill's most treasured historic properties. Originally established in 1795 as the community's first schoolhouse and later transformed into a picturesque mid-19th century center hall Colonial, this remarkable home is located within the Round Hill Historic District. Perched high on 4.6 fully fenced acres, the property enjoys broad western exposures and magnificent sunsets. The 5-bedroom main residence blends period character with modern comfort and is complemented by a separate garage cottage. Wide plank floors, sweeping lawns, mature landscaping, vegetable and flower gardens, a swimming pool, and enduring architectural details create a quintessential Greenwich country setting and a rare opportunity to own an authentic piece of local history.

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.

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!

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.

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.