luxury houses with pool for sale Westport, United States

Grand and gracious, this impressive custom Colonial on estate property with a gorgeous gunite pool is ideally set in convenient Lower Weston. Just 2.3 +/- miles to the Merritt Parkway & 1.6 +/- mi to the convenient school campus & town Center, this home blends the appeal of a tranquil setting with immediate access to all amenities. Introduced from a paved circular drive, this architecturally striking residence makes a memorable impression. The foyer welcomes you to the airy, grand-scale interior which is filled w/sunlight. Upon entering, you will be drawn to the spectacular Great Room w/a 2+ story ceiling & incredible windows that span the full height, bringing exquisite vistas into the home and creating an exceptional backdrop for memorable moments. The octagonal DR is lined w/windows and built-ins. The custom kitchen was recently remodeled w/excellent taste & quality, incl double islands, dual ovens, warming drawer & a lrg breakfast rm w/bar, all opening to the fam rm w/1 of 5 fpls. Incredible office/library w/ herringbone wood floor & fpl. Nearly all main level rooms have French doors to the deck & patio. The flexible layout incl an attached pool house/extra BR w/full bth on the main floor. Upstairs, find 5 exceptional BR suites, beginning with the vast primary that incl an ofc/sitting rm w/fpl, vltd ceil BR w/3 walk-in clsts & lrg marble bth. Finished walk-out LL w/ rec/play rm, full bth & storage. Stunning pool & waterfall spa, level lawns, gardens. 3 car garage.

This commanding estate has extraordinary 240% views of the Long Island Sound Archipelago. The custom renovation by the esteemed firm S.R. Gambrel, Inc. was created with an intention for comfortable, gracious living, with a woven theme of health and wellness providing seamless indoor/outdoor living and entertaining spaces. The combination of stunning finishes, high ceilings, breathtaking views, and natural light makes this offering one of a kind and irreplaceable.The two-story entry hall reflects interior spaces that are both grand and intimate. The great room, expansive dining room, and chef's kitchen with its massive marble island are designed for entertaining. The breakfast room, den, and two private offices provide intimate spaces. The primary suite, with breathtaking views, has two dressing rooms and a marble bathroom.Three additional bedrooms are on the east wing. A hidden gym,wine room, and laundry room are all located on the entry floor. with a tandem 4-car garage.The property has 265 feet of private shoreline with a deepwater pier, gangway, and 30'x15' floating dock,low-tide sandy beach and a separate mooring. Designed as a private waterfront oasis, the sound view pool and pool pavilion are tucked under an ancient ledge.The outdoor living room with fireplace, jaccuzzi, infrared sauna and cold plunge are connected by a wide terrace across the entire house. A private association beach club with two tennis courts and tennis pro is just moments away.

Experience refined luxury in this custom new construction offering 3,200 sqft. of thoughtfully designed living space, situated on a cul-de-sac just moments from downtown Fairfield, premier dining, boutique shopping & beautiful beaches. Step inside to discover exceptional millwork & upscale finishes. The main level features a spacious dining room complemented by a wet bar, perfect for entertaining. The heart of the home is the spectacular eat-in chef's kitchen boasting Thermador appliances, quartz countertops, white custom cabinetry, a white oak center island & an area for a charming breakfast nook. The kitchen flows seamlessly into the family room highlighted by a gas fireplace & sliders leading to a bluestone patio overlooking the private backyard & potential pool site. A mudroom and powder room complete the 1sr floor. The 2nd level offers four generously sized bedrooms, including a luxurious primary suite featuring a spa-like bathroom with a soaking tub, double-sink vanity & a glass enclosed shower. A secondary bedroom enjoys the convenience of a private en-suite bath, while the 3rd & 4th bedrooms share a Jack-and-Jill bathroom with a double vanity and tub/shower combination. A 2nd floor laundry room adds everyday convenience. Additional highlights include a walk-up third level offering the opportunity to create 850 additional sqft. of future finished living space, a lower level with 9 ft. ceilings providing storage or future finishing potential, and a two-car garage.

The former home of Richard Rodgers, composer of The Sound of Music, this 10.92 acre estate with a stunning modern residence was recently fully renovated and expanded and offers curated one floor living. Generous main rooms are enhanced by lofty ceilings,skylights and walls of glass. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. Separate residential wings include 7 bedrooms and 7 full baths, each with a unique design. All property systems have been upgraded and integrated to work seamlessly .The barn pool house includes a full eat-in kitchen and lounge, bath ,and full gym steps from the pool. An office pavilion is set privately in a quiet garden area. The park like property is surrounded by high stone walls, a nature preserve, open land, a heated paddle tennis court, and an orchard. Live in ultimate style and easy elegance just a quick commute to NYC and airports. This private haven surrounded by a 155 acre nature preserve is minutes to Fairfield,Westport and Greenwich dining and shopping.

Nestled at the end of a peaceful cul-de-sac, in the highly sought-after Greenfield Hill neighborhood, 220 Stonewall Lane offers a rare opportunity to own a beautifully situated home on 2.07 acres. The expansive outdoor setting provides an inviting space perfect for entertaining or relaxing while enjoying the tranquil surroundings. When entering the thoughtfully planned main level, you are drawn to the large open space with a renovated modern eat-in kitchen, a sitting area with a wood-burning pizza oven, a Great Room with cathedral ceilings, a wood-burning fireplace, and an additional family room with views of the in-ground pool and lush landscaped grounds. Natural light flows throughout. Additional highlights include hardwood floors throughout, large decorative tiles, a formal living room with fireplace, a dining room, walk-up bonus room, laundry and access to the two-car garage. Upstairs, five well-appointed bedrooms include a private primary suite, creating a comfortable and functional area. The unfinished basement offers ample space for utilities, storage and possible recreational activities. Ideally located near Fairfield's beaches, Metro-North, recognized restaurants, and the Fairfield Theatre Company, this private property blends lifestyle, location, and appeal in one of Fairfield's most desirable areas.

Framed by classic stone walls, fruit trees, and lush grounds, this masterfully renovated Colonial blends timeless curb appeal with top-tier modern luxury. The expansive layout flows seamlessly from a sunlit living room, stunning formal dining room and massive 24'x23' family room with a modern woodburning fireplace, dual home offices and a lower-level playroom with large mudroom. Designed as the ultimate heart of the home, the gourmet kitchen is a chef's dream-featuring a custom Raging River wood island, honed granite countertops, dual sinks, and a magnificent CornueFe 110 gas range. Upstairs, four peaceful bedrooms include a lavish primary suite with a marble shower, BainUltra soaking tub, and radiant heated floors. French doors lead to a private outdoor oasis, where a wisteria-draped pergola, covered deck, expansive terrace, sparkling pool, and spa set the stage for effortless summer entertaining-all just minutes from town and an easy walk to local schools.

The first time on the market, this custom-built Easton Colonial has been lovingly maintained by its original owner and offers approximately 3 private acres, generous living space, and a highly adaptable floor plan designed to suit a variety of lifestyles. With numerous rooms that can easily serve as a home office, playroom, gym, guest quarters, or additional living space, this home offers exceptional flexibility. A standout feature is the first-floor bedroom with its own private entrance, handicap access, and ensuite bath suitable for a wheelchair. This also could be an ideal setup for extended family, an au pair, guests, or anyone seeking the convenience of a private suite. Adding to the home's appeal is a natural-gas-powered whole-house generator, providing year-round peace of mind. Surrounded by nature and adjacent to protected watershed land, the setting offers an exceptional sense of privacy. During the warmer months, enjoy the heated in-ground pool, perfect for relaxing, entertaining, and making the most of your private outdoor retreat. Ideally located with convenient access to Easton, Westport, and Fairfield, this property offers the best of both worlds: a peaceful, private setting with easy access to local schools, shopping, dining, beaches, recreation, and commuter routes. Part of an estate, the property is being sold in its present as-is condition. No seller property disclosures are available. Please note: This is an estate sale. The property is being sold as-is, and no property disclosures are available.

New Construction by noted developer Ritzzo Development. This striking Contemporary Colonial offers 10,000 SF of elevated living on three finished floors. Set on two manicured acres with a heated saltwater pool and built-in BBQ, this house boasts extensive 2026 improvements - including new paint, refinished wide-plank white oak floors, new trim, updated AV, a whole-house generator, and a fully reimagined lower level. Inside, extra high ceilings, custom millwork, and luxurious finishes define every room. The open-plan chef's kitchen features a marble waterfall island and flows into a sun-filled breakfast room + formal living room. A dramatic great room boasts a wet bar, a vaulted beamed ceiling and double-height fireplace. Stylish formal rooms, a butler's pantry, pool cabana room and a private office with powder complete the main level. The primary suite is a true retreat - featuring a fireplace, private deck, and lavish bath. The fun filled lower level offers a bar and sitting room, media room, gym, sauna, full bath and steam room. A rare offering.

Set on 2.93 private acres along coveted Long Neck Point, this extraordinary waterfront Colonial offers a rare combination of sweeping water views, privacy, and direct access to the water. Spanning more than 10,000 square feet, the residence is designed to embrace its spectacular setting, with expansive living spaces and breathtaking vistas from nearly every room. The eight-bedroom main residence features seven full and three half baths, eight fireplaces, and an effortless flow between gracious entertaining spaces and comfortable everyday living. A pool and private dock extend the experience outdoors, creating an idyllic setting for waterfront living and entertaining. A charming two-bedroom, two-bath guest cottage offers additional space and privacy for family and guests. Distinguished by its scale, setting, and direct water access, this remarkable Long Neck Point estate offers a rare opportunity to experience the quintessential coastal lifestyle.

Set on 2.19 private acres in a prime Darien location, 222 Brookside Road offers exceptional space, privacy, and opportunity just minutes from town and Cherry Lawn Park. With more than 7,000 square feet above grade, plus an additional 3,000 square feet on the lower level, this expansive 4-bedroom, 5.5-bath residence provides an incredible canvas to create a home tailored to your vision. Generously proportioned rooms and tall ceilings create a wonderful sense of scale throughout, while a flexible floor plan offers endless possibilities, including the potential for a first-floor in-law or guest suite. The exceptionally spacious lower level provides abundant room for entertaining, relaxing, and recreation. Outdoors, the expansive property is highlighted by a pool and well-appointed pool house featuring a full bath, laundry hookups, and full kitchen with a range and space for a refrigerator-creating a private setting for summer gatherings and relaxation. An attached four-car garage, plus an additional detached two-car garage, provides parking for six cars and even more flexibility. A rare opportunity to enjoy significant acreage, remarkable space, and endless potential in an incredibly convenient Darien location.

Set high 4.5 + private acres, this impressive six-bedroom home offers space, privacy and resort-style amenities, with beautiful views from its elevated setting. Designed for both everyday living and entertaining, the home features four finished levels with flexible spaces for family, guests, work and recreation. Generously proportioned living areas flow throughout the main level, with an expansive property and outdoor entertaining spaces. The bedroom accommodations are exceptionally versatile. In addition to the main bedroom level, a private bedroom and full bath above the three-car garage creates an ideal guest, au pair or extended-family suite. A fully finished walk-up third floor provides additional space for a home office, playroom, studio or recreation area. The finished walk-out lower level adds yet another dimension to the home, with a bedroom, full bath, wine cellar and direct access to a screened porch and the grounds beyond. Outside, the property becomes a private retreat. A free-form swimming pool, expansive garden and tennis court are surrounded by 4.5+ acres of beautiful grounds, while the home's hilltop position captures views and light from morning through evening. With six bedrooms, four finished levels, a three-car garage, pool, tennis court and an extraordinary elevated setting, this is a home that offers exceptional space and the opportunity to enjoy a true country lifestyle.

Nestled on over 3 breathtaking acres with over 500 feet of riverfront on the West Branch of the Saugatuck, 6 Old Orchard Drive offers an unparalleled setting, abundant natural light, and a rare opportunity for its next owner. Featuring solid bones, a sprawling open layout, and unbeatable water views, this home is move-in ready today, yet holds incredible potential for custom aesthetic updates to make it your ultimate forever home. Whether you choose to simply update a few finishes over time or embark on a complete design transformation, the foundation here is exceptional. The main level has numerous formal and informal spaces, featuring a sunlit kitchen, a family room, an elegant dining room, and two separate living spaces-each with its own fireplace and tranquil river views. There are four spacious ensuite bedrooms, plus a soaring second-story great room with cathedral ceilings, oversized windows, and a full bath (easily converted to a 5th bedroom suite or primary retreat). Outside, the property is pure magic: lush lawns, mature trees, an expansive deck, and a stone patio surrounding a pristine gunite pool-all set against the serene backdrop of the river. If you've been searching for a setting you can't replicate and a home you can tailor to your own taste, this Weston paradise is ready for its next chapter.

There are homes that sit on land… and then there are those that seem to emerge from it. Set at the end of a hushed cul-de-sac, tucked into 2 acres of forested serenity, The Oasis at Richmond Hill offers a quiet, deliberate take on mid-century modernism, where geometry and nature enter into a serene partnership. Originally built in 1956 and thoughtfully refined over time, the residence pays homage to the design language of the Harvard Five.. clean lines, natural materials and a reverence for light and landscape. Anchoring the main living space is a monolithic stone fireplace, its texture and scale creating a sculptural centerpiece. Walls of glass invite the outside in, dissolving all boundaries between the surrounding canopy, tiered lush lawns and interior. From the sundrenched kitchen, detailed with granite countertops, contemporary appliances, and a fluid indoor-outdoor flow... French doors open onto a natural stone terrace, cantilevered just above a natural stone ledge. Below, a winding stone path leads through the mature gardens to a heated gunite pool and cabana, where cocktails and conversation unfold beneath the shade of mature elms and rhododendrons. Inside, three bedrooms and two full baths unfold with thoughtful simplicity. The primary suite features a private deck, an en-suite bath, and sightlines framed by towering rhododendrons and spruce. Two additional rooms, both with custom built-ins, serve equally well as guest quarters, creative studios, or remote work sanctuaries. Throughout the home, subtle nods to the era remain: built-in shelving, breezeways that frame views like paintings, and the soft glow of afternoon sun reflecting off hardwood floors. Central air and modern systems ensure year-round comfort, while a detached garage, previously reimagined as an artist's workspace, offers yet another dimension of possibility. Set on a property defined by elevation shifts and native Connecticut flora, this home exists not just as shelter, but as retreat. Moments from nature preserves, walking trails, and the town's beloved dog park, The Oasis at Richmond Hill is as much an invitation as it is a destination: to slow down, to breathe deeply, and to experience design not as decoration - but as a way of life.

Hidden away at the end of a coveted West Side cul-de-sac, 48 Driftway Lane is a private estate tucked among the winding back roads of New Canaan. Perched atop 1.62 beautifully landscaped acres and surrounded by nature, the setting offers a rare sense of peace and privacy, yet remains just minutes from downtown New Canaan and approximately one hour from New York City. Newly constructed from the ground up in 2017 and offering over 10,000 square feet of thoughtfully curated living space, the home unfolds through a series of light-filled rooms where architectural detail, craftsmanship, and connection take center stage. A grand central foyer showcases a statement staircase framed by glass railings, creating a stunning focal point from the moment you enter. At the heart of the home, a sunlit gathering space serves as the natural connection point between the designer kitchen, soaring two-story family room, and outdoor living spaces beyond. Anchored by a stunning 10-foot quartzite waterfall island and matching custom quartzite hood, the kitchen balances beauty and function with Thermador appliances, Sub-Zero refrigeration and wine storage, custom cabinetry, and a walk-in pantry. The dramatic family room draws the eye upward with soaring ceilings, extensive architectural detailing, automated Lutron shades, and walls of windows that flood the space with natural light.

PLEASE SUBMIT ALL OFFERS BY 5PM TUESSStep into a seamless blend of historic charm and modern luxury, ideally located in the heart of New Canaan. Nestled on 1.46 lush, private acres, this beautifully maintained Farmhouse Colonial offers the quintessential New England lifestyle. Spanning 3,383 square feet, this unique home has been thoughtfully updated to feature 5 spacious bedrooms and 5 full bathrooms. From the moment you step inside, you are greeted by pristine interiors and gleaming refinished floors. The inviting, sun-drenched layout is tailor-made for both relaxed everyday living and elegant entertainment. Outside, a true sanctuary awaits. Spend your summers enjoying the sparkling pool, running across the expansive play space, or picking fruit from your very own apple trees. Attached is a year-round pool house featuring a full bath and a gym room. A standout feature of this property is the spectacular detached guest house. Complete with a kitchenette, a spacious great room, and a beautifully appointed bathroom, it offers unmatched versatility. Whether you envision a welcoming suite for extended family and au pairs, a quiet home office away from the main house, or a creative studio for music and art, this space easily adapts to your imagination. Ideally located just minutes from the train, the Merritt Parkway, and award-winning schools, this move-in-ready gem delivers absolute convenience without sacrificing tranquility.