luxury houses with pool for sale Ridgefield, United States

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.

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.

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.

Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush landscape inside. At the heart of the home, a newly updated gourmet kitchen serves as a culinary showpiece. The primary suite is a true retreat, offering a private balcony, fireplace, and the rare luxury of dual bathrooms. Each of the six bedrooms in the main house features an ensuite bath, ensuring absolute privacy for family and guests alike. The amenities rival the world's finest resorts: a walk-out lower level equipped with a theater and wine room, and a 30x50 lagoon-style pool. The 2020-built pool house (700+ sq. ft.) provides a full guest experience with its own kitchen, bath, and flexible sleeping quarters-all just five minutes from the boutiques and bistros of New Canaan's vibrant village center.

Timeless character and thoughtful, recent updates come together beautifully at this classic 1930s Colonial set on over three private acres in one of New Canaan's most serene settings. Lovingly maintained and enhanced over time, you'll find a rare combination of architectural charm, graceful living spaces, and a sense of quiet retreat surrounded by protected land. The gracious foyer introduces interiors filled with warmth and personality, where rich finishes and curated details create a home that feels both refined and deeply comfortable. The living room, anchored by a fireplace, opens seamlessly to a terrace, inviting an easy connection between indoor and outdoor living. A very generous dining room and a cozy, wood-paneled family room offer intimate spaces for gathering or unwinding, while the recently renovated kitchen is both functional and beautifully designed, with custom cabinetry, high-end appliances, and beautiful western sunlight with views across the property. Upstairs, four well-proportioned bedrooms include a serene primary suite with a newly designed bath and custom closet. Each additional bedroom offers its own sense of privacy and comfort. A separate studio complete with its own full bath and walk-in closet, provides exceptional flexibility for guests, extended family, or a private work-from-home suite. The grounds are as special as the home itself.

Nestled at the end of a quiet, tree-lined cul-de-sac, this exceptional home offers one of the best locations in the community. Enjoy abundant natural sunlight, privacy, and serene wooded views that create a peaceful retreat right at home while remaining conveniently close to everything. Inside, the home features numerous upgrades and custom details. The expanded and upgraded kitchen is bright and highly functional, perfect for both everyday living and entertaining. Upgraded hardwood flooring flows throughout the house, complemented by high-end lighting and beautiful custom finishes, including a striking fireplace that adds warmth and character. The primary bedroom is a true retreat, boasting a gorgeous bath and a custom walk-in closet. Custom closets throughout the home provide exceptional organization and storage. Additional garage storage offers further convenience for hobbies or seasonal items. The finished lower level provides valuable extra square footage, ideal for a home theater, gym, office, or guest space. This home is nestled in a beautiful community offering vacation-like amenities, including pools, clubhouse, gym, tennis courts, trails, and more. Perfectly situated near shopping, restaurants, and easy access to I-84. A standout combination of privacy, luxury finishes, and everyday convenience.

Enchanting country estate located on a rare private lane. Sophistication Grace and Style are the hallmarks of the residence. Entire house has been exquisitely renovated - designer kitchen with bespoke cabinetry, deluxe appliances, stunning new Primary suite bath, newly transformed lower level Garden Room Salon. And as a bonus - a world class barn offering additional 3 car parking; entire 2nd floor entertainment/exercise room; and 2 workrooms for your Vintage or Contemporary cars. All of this sited on 4+ acres of rolling lawns, perennial gardens, pool, pergola, PERFECTION! All located in the charming New England town of New Canaan with outstanding shopping, delightful restaurant choices, beautiful parks, numerous recreational facilities, highly-rated schools, and convenient access to the Metro-North Railroad.

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.

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.

Once in a lifetime, a home of this caliber becomes available. Sited on a cul-de-sac in a coveted neighborhood close to town, this exceptional residence pairs custom design with luxurious indoor-outdoor living areas enhanced with smart technology and supported by upgraded mechanicals. A gracious front-to-back foyer showcases elegant living and dining rooms. Everyday living and elevated entertaining are effortless with a new custom kitchen designed by Deane appointed with Simon Pearce pendants, premium appliances, wine frig, and a Zip tap for still and sparkling water. A sun filled eat-in area flows seamlessly into a coffered ceiling family room with fireplace and a covered porch-with flat screen TV, stone fireplace and Bromic heating. A richly paneled office, mudroom and second staircase complete the main level. Upstairs, five bedrooms include a serene primary suite with fireplace and sitting room, a private guest suite and an additional office. The outdoor experience is nothing short of a 5-star resort-with a saltwater Glengate pool, sun shelf, spa and a new outdoor kitchen fully equipped with a built-in grill, pizza oven, Traeger smoker, and refrigeration-all surrounded by stone terraces, lush landscaping, audio system and curated lighting. The lower level boasts a chalet-inspired retreat with recreation, fitness rooms, an infrared sauna, and bedroom suite with a flexible private entry. An exceptional offering for those seeking outstanding craftsmanship and luxury!

Looking for a turn key home that is both sophisticated and spacious? Look no further.... this townhouse is for you! Located in the Hills at Rivington, this home has stunning hardwood floors throughout the main level . Crown molding and wainscoting offer an elegant feel as you entertain in the spacious living room and dinning room areas. The stunning kitchen has granite countertops, newer stainless steel appliances, generous island sitting and a custom hutch with a wine refrigerator. Sliding doors allow you to enjoy the outdoor patio for a BBQ or just to relax. The upper level bedrooms all offer vaulted ceilings with ceiling fans for your comfort. The primary bedroom has an impressive walk in closet with custom built in shelving and a luxurious full bathroom. If you need more storage, there is plenty right off the tandem 2 car garage. This Hills-unique home also includes access to a private pool, pool house and playground within walking distance! The Main Clubhouse offers both indoor & outdoor pools, fitness center, yoga studio, movie theater, arts & crafts room, bocce, tennis, pickleball, basketball courts, walking trail and more. All this and the convenience to highways, shopping and restaurants make this the ideal place to live!

Experience the pinnacle of sophisticated living in this impeccably upgraded Portman model at The Ridge at Rivington. Overlooking a serene wooded nature trail for ultimate privacy, this residence offers the ease of condo living with the scale and refined feel of a private home. Truly turnkey and lightly lived-in, the open-concept layout impresses with 9' ceilings, hardwood floors, crown molding, and a cozy gas fireplace. The heart of the home is the chef's kitchen, featuring an expansive quartz center island with seating, custom cabinetry, premium stainless steel appliances, and a beautiful tile backsplash. Upstairs, the vaulted primary suite serves as a true sanctuary, boasting a spa-like bath with an intricate floor-to-ceiling tile shower and frameless glass enclosure. Two additional spacious bedrooms, a dedicated laundry room, and a full bath complete this level. For future expansion, the massive walk-out lower level is already plumbed for a full bathroom. Complete with an attached two-car garage, you'll enjoy the ultimate convenience and security year-round. Beyond the home, enjoy amenities at The Rivington Club, featuring a state-of-the-art fitness center, indoor/outdoor pools, tennis courts, and a stylish clubhouse for social gatherings. Conveniently located near I-84 and Metro-North, this home offers a maintenance-free lifestyle without compromise. Luxury awaits in Danbury's premier community!

In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every turn, including a coffered ceiling living room, a banquet sized dining room with a curved wall of windows, and an octagonal office. French doors create a natural flow to two stone patios and sweeping lawns. The gourmet kitchen, appointed with four Wolf ovens, dual Sub Zeros and dishwashers, and extensive custom cabinetry, is designed for both comfortable daily living and memorable entertaining. The serene primary suite offers a private sitting room, balcony, barrel-ceiling dressing room, and an inspiring octagonal bathroom, while additional en-suite bedrooms and a full in-law suite provide exceptional comfort. The finished lower level includes a custom cherry wet bar, gym, and flexible space for a media room or wine cellar. Two full-size laundry rooms and a pool bath w/exterior access offer flexibility. Outdoors, a heated Gunite pool with auto cover and spa create a private resort experience. Convenient to the Merritt Parkway and Westport, this rare offering blends timeless sophistication with modern livability in one of Fairfield County's most sought-after settings.

Artisan Craftsmanship Meets Modern Autonomy - Your Private Oasis Awaits! Nestled on four idyllic, professionally landscaped acres at the end of a quiet cul-de-sac, this spectacular 2002 post-and-beam is a perfect blend of artisan craftsmanship and modern design. Built to exacting standards, this one-of-a-kind residence presents a dramatic, flexible open floor plan bathed in natural light through walls of windows highlighting exposed beams, soaring ceilings, and rich hardwoods. The chef's kitchen gleams with cherry cabinetry, upscale appliances, and quartz and limestone finishes. The home features a much-desired bedroom suite on the main floor as well as a primary suite upstairs, two additional bedrooms and a sleeping loft! Outdoor living is unrivaled: a heated Gunite salt-water pool, an expansive stone patio and fireplace, a wrap-around porch with panoramic views of the lush landscape, gardens, and a private stream-fed pond with a fountain. Beyond the beauty lies incredible efficiency. This home boasts high-efficiency mechanicals, seamed metal and arch shingle roofing (2021), a whole-house generator, on-demand hot water system, propane/HW system, pond-fed irrigation system, electric car charger, and a 1000-gallon propane tank for up to two weeks of off-grid autonomy. Sophisticated, secure, loaded with character, immaculate and artfully designed. This is the dream lifestyle realized - a mini-resort in the Summer, a wonderland in the Winter and very, very special.

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.

Pristinely maintained and completed in 2020, this exceptional Toll Brothers home perfectly blends sophisticated architectural design with extensive premium upgrades that far elevate it beyond the standard base model. Boasting 4 spacious bedrooms and 2.5 beautifully appointed baths, the home features an ideal layout for both daily living & elegant entertaining. The inviting main level flows seamlessly, highlighted by a cozy gas fireplace in the living room and a significantly expanded family room that offers abundant extra space to relax. The expanded gourmet Palladian kitchen is a true chef's dream, meticulously outfitted with rich quartz countertops, upgraded cabinetry, a dynamic glass tile backsplash, an extra light fixture, & an upgraded exterior vented stove hood. A highly functional laundry room doubles as a custom drop zone with built in cabinetry and additional storage. Upstairs, the primary suite offers a private oasis complete with a luxury jet tub, premium quartz double vanity, and elegant diagonally laid floor tile and custom closet organizers.. The lower level features an impressive footprint with daylight window, a pre plumbed rough in for a future bath. Notable infrastructure upgrades include a high efficiency tankless water heater, a whole house humidifier, & many storage cabinets in the garage. The premium exterior offers an architectural lighting package & a fully fenced backyard. Enjoy the community pool and club house with low monthly maintenance charges.

Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a 2014 transformation. The volume of the rooms, soaring ceilings, proportion of the windows and quality of light create a sense of serenity and openness. Stately yet modern, this is a house that can be lived in with comfort and ease. Adjacent to the dining room gallery is a walled garden with a custom pavilion for entertaining. The 52 acres were transformed in collaboration with noted landscape architect Perry Guillot into a private park with a dramatic meandering approach, a great lawn, and woodland trails amongst streams and waterfalls. A 60 x 22 pool and tennis court were also added. At the discrete entrance to the property are twin cottages; a caretaker residence and a gym. Privacy and proximity to NYC and airports along with this caliber of property make this a world class offering and a rarity by any standards.