luxury houses with pool for sale Fairfield County, United States (page 4)

Some homes are built for the market. Others are built for a legacy. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering, and execution, where every material, finish, and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a façade clad in premium Thermory wood siding beneath a Spanish slate roof, an exterior that feels both grounded and enduring. Walls of Aluprof glass dissolve the boundary between interior and Long Island Sound, drawing light deep into nearly every principal room. The result is a seamless connection to the water, with unobstructed views that are impossible to replicate. Inside, large-scale radiant-heated Porcelanosa tiles grace the main and lower levels, setting a warm, modern foundation. At the heart of the home, a statement kitchen delivers both performance and presence, featuring custom Vimora cabinetry, top-of-the-line Gaggenau appliances, and a fully equipped secondary prep kitchen designed for effortless entertaining at scale. Upstairs, European white oak introduces warmth, while radiant heat continues throughout all main spaces and baths, reinforcing a consistent commitment to comfort and precision. The primary suite is conceived as a private retreat, oriented entirely toward the water. A fireplace anchors the space, while a private deck leads directly to the heated pool below. The bath offers a spa-like experience, featuring a sculptural soaking tub positioned toward the view and a separate steam shower. Custom Italian wardrobes complete the suite, incorporating bespoke detailing, opaque glass, and integrated features throughout. Additional bedrooms on this level are all en suite, each perfectly positioned to capture water views. The lower level opens into a fully realized entertaining environment featuring a wine room, fitness center with sauna, guest accommodations, and a dramatic lounge anchored by an illuminated marble bar and a 162-inch screen. A concealed underground car gallery, accessed by hydraulic lift, offers a discreet and highly engineered space designed for discerning collectors. Outdoors, an expansive terrace and heated waterfront pool overlook the cove, creating a setting defined by privacy and open water. Minutes from Tod's Point, Metro North, and the village of Old Greenwich, the property occupies that rare overlap of seclusion and convenience. With five bedrooms, five baths, and two powder rooms, every element has been resolved with intention. This is a rare chance to own a crown jewel waterfront property that stands in a league of its own. A defining waterfront residence where design, setting, and permanence align at the highest level.

Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with apartment, and converted barn, largely by architect Jack Franzen. The main residence offers over 11,000 square feet with 7 bedrooms, 6 full and 2 half baths. The two-story media wing includes a home theater, library, office, and billiard room. The conservatory overlooks stone terraces, a waterfall and pond, and gardens. The primary suite and office have private balconies. The estate is further distinguished by multiple auxiliary structures: a carriage house with guest accommodations, a separate guest residence, and a heated party barn dating to circa 1850. A pool with spa, pergola, and outdoor kitchen complete the grounds. Original architectural details such as leaded glass windows, rich hardwood paneling and window seats and doors, five stone and brick fireplaces, and other features have been preserved. Modern additions introduce light-filled living spaces. New appliances and updated mechanicals service the buildings. Rock Ledge offers luxury and privacy rare in this area, and promises a lifetime of enjoyment for a buyer who appreciates its beauty.

Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected open space with no immediate neighbors, the property offers a rare sense of peace and privacy-reminiscent of the Lowcountry, the Hamptons, or Nantucket, a scale and atmosphere seldom found in Westport. Beautiful in every season, the setting also offers extraordinary birdlife and nature watching. Yet it remains moments to the Post Road, train, and town centers, and just one hour from Manhattan. A collection of residences and outbuildings is thoughtfully positioned across the land, including two circa 1940s three-bedroom guesthouses with sweeping water views, creating a true family compound where generations can come together while maintaining a sense of independence. Other structures offer flexibility for staff or future use. The grounds invite a lifestyle centered around the outdoors, with a tennis court, indoor pool, pool house, and formal gardens set within expansive lawns that stretch toward the water. Whether preserved, enhanced, or reimagined, this is a once-in-a-generation opportunity to shape a legacy estate-one that will be experienced and remembered for years to come.

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.

Direct Waterfront , Greens Farms: An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island Sound through dramatic walls of glass designed to flood the interiors with natural light. The home will feature 8 bedrooms, 8 full baths, and 2 half baths, with expansive living and entertaining spaces that seamlessly connect indoors and out. The architecture embraces a clean contemporary design that maximizes the stunning waterfront setting while creating an atmosphere of warmth, elegance, and effortless coastal living. Resort-inspired amenities include two pools, a cold plunge, a spa, an infrared sauna, and a fully equipped fitness center, offering a private retreat for wellness and relaxation. For the automotive enthusiast or collector, the property also includes garage space for up to 10 cars, a rare feature for a waterfront estate. Ideally located walking distance to the Greens Farms train station and Greens Farms Academy, and just minutes to the town centers of Westport, Fairfield, and Southport. Just 55 miles to Manhattan. Completion anticipated mid-2027, with the opportunity to collaborate with the builder to customize finishes and create a home that reflects your personal lifestyle

This exceptional contemporary home on a quiet cul-de-sac has been transformed with a complete meticulous custom renovation. The dramatic yet highly functional home is being offered fully furnished with Roche Bobois furniture in addition to Barovier and Toso Venetian light fixtures throughout the home. The beautiful parklike grounds encompass 4 acres including a tennis court, pool with spa and large yard area. The border to the north abuts the 300-acre Babcock Preserve with 7 miles of trails. The interior space extends to 7,700 sq.ft. on 3 levels with 6 ensuite bedrooms all with custom walk-in closets. The luxurious primary suite is highlighted by a limestone fireplace, an office loft, private balcony and glistening bathroom featuring Blue Macuba marble. Truly a peaceful and private oasis.

Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room offers a stone fireplace, coffered ceilings with French doors leading to a bluestone terrace, overlooking the gorgeous landscaped property. Gather in the sophisticated formal dining room w/yet another fireplace. The main level graciously accommodates a guest bedroom suite with a full bath, walk-in closet, as well as a study adorned w/Cherrywood & built-ins, leading to a serene blue stone screened-in porch. The main level also has the convenience of 2 powder rooms & a mudroom, as you enter from the 3 car garage. Upstairs, discover the luxurious primary bedroom w/a sitting room, 2 walk-in closets, changing room, & spa-like bathroom w/a claw hydro tub, shower & private balcony access. Additionally, there are 3 more bedrooms each w/a custom full bathroom, along w/a generous bonus room. The fully finished 3rd floor offers versatility with a half bath. Entertain on the lower level, featuring a theater room, gym w/sauna, family room, wine room & powder room. Outside, the meticulously landscaped grounds showcase an inground gunite pool, hot tub, pool house w/a full bathroom overlooking 2 acres.

PRICE REDUCED. MOTIVATED SELLERS. Experience premier Candlewood Lake living in this family-friendly 3-level waterfront home. Play or entertain in the expansive backyard or enjoy the no stairs access to the two private docks with ample boat and jet ski space. Relax on a 1,000 sq. ft. two-story deck with outdoor fireplace, hot tub, and private shower, plus two sheds and western sunset views. The open-concept main level features cathedral ceilings and a primary suite with walk-in closet, en suite bath, and deck access. Upstairs offers a lakeview bedroom, full bath, and remodeled skylit loft. The walkout lower level includes a guest suite with bedroom, full bath, laundry, and large bonus room. Highlights of the extensive upgrades include high-efficiency dual-fuel heat pump, central air, solar-equipped roof with generator hookup with battery backup. (Solar contract to be paid by sellers at closing.) Become a part of the highly sought-after Candlewood Shores community and enjoy access to the private beach and updated Club House, as well as the private park that includes volleyball, basketball and a playground. This isn't just a home. It's a lifestyle, a retreat, and a rare chance to own one of Candlewood Lake's most versatile waterfront properties.

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.

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.

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 6 acres on a cul-de-sac, offering a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

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.