luxury houses with pool for sale Weston, United States

Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the open, landscaped property. Lofty ceilings and walls of glass create magical interior spaces, a perfect setting for an art collector. Private wings radiating off the house center accommodate guests comfortably. A hidden theater and a stunning Moroccan lounge with bar are some of the special features of this extraordinary property. The barn-style pool house with full kitchen, bath and spacious gym, the pool, and a heated paddle tennis court are all easily accessible from the main residence. The updated stone gatehouse accommodates guests or staff. A two story office pavilion is tucked in a private garden area. The landscape offers open vistas, meadows and an orchard. There is potential for equestrian use. Live in ultimate style and easy elegance at this private retreat just a quick commute to NYC and airports. Fairfield and Westport town centers are in close vicinity. Enclosed behind a stone wall and surrounded by a 155 acre nature preserve, this is a uniquely private haven. Main residence 9129 sq ft. Barn 2400 sq ft., Guest House 2800 approx. Total 14,329 sq ft. Whole property generator. Solar and geothermal systems. Water filtration system. Two laundries. Slate roof. Heated parking. Dog washing station. Wine room. Orchard. This offering encompasses three lots: 4800 Congress St consists of main residence, 10.92 acres, office pavilion, pool/barn pool house and heated paddle court. 4900 Congress St consists of stone guesthouse on 25.87 acres with fields, meadows and pond. 5010 Congress St is open land: 2.12 acres with potential for barn or tennis courts and tennis pavilion. Equestrian use potential for entire property. All measurements approximate.

Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury homes on manicured grounds. This sun-drenched five-bedroom, six-bathroom home has been freshly painted inside and out and features extensive millwork, gleaming hardwood floors, and floor-to-ceiling windows that flood the home with natural light. The open-concept layout is ideal for entertaining, centered around a fully renovated gourmet kitchen with high-end appliances, custom cabinetry, and a large island, flowing seamlessly into the great room and out to a spacious patio. Upstairs, generous bedrooms include a luxurious primary suite, while flexible living spaces throughout the home cater to modern lifestyles-perfect for hosting or working from home. The flat, private yard offers multiple outdoor entertaining areas and is complemented by a three-car garage. Enjoy privacy and elegance while being just minutes from the vibrant downtowns of Fairfield and Westport, as well as local beaches and train stations. This is luxury living with everyday convenience-completely turnkey and ready for it's new homeowners.

Imagine a residence where every element has been considered for gracious living in stylish surroundings. This newly completed home by awardwinning Able Construction is set on a peaceful Coleytown estatearea street, framed by scenic land that enhances its sense of calm. A dramatic foyer with a woodaccented ceiling and millwork feature wall introduces interiors defined by creative decor, walls of glass, and exquisite lighting. The great room, anchored by a marble fireplace and French doors to the pool and patio, flows into the designer kitchen with a striking island, stone counters, custom cabinetry, Thermador appliances, and a beautiful and functional pantry. The dining room is a jewel, offering an elegant setting with illuminated shelving and views of the grounds. A quiet office and superb mudroom add daily convenience. A glasslined stair tower leads to sunfilled bedroom suites, beginning with the sublime primary suite set beyond double doors. An arched entry reveals a kingsized bedroom with balcony, two custom walkin closets, and a spalike bath with glass shower and distinctive vanity. The upper level also offers a laundry room with double washer and dryers and access to the finished thirdfloor bonus space. The lower level includes a fifth bedroom suite, recreation room, gym and media areas, and generous storage. Outside, the pool becomes the centerpiece for entertaining and relaxing at this designcentric showplace of style.

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!

A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate, thoughtfully reimagined with an array of stunning features and superior craftsmanship. Sited on 2 private acres, this extraordinary property offers priceless panoramic views of a 7-acre nature preserve, affording permanent tranquility and a sense of wonder. The meticulous renovations center around a gracious farmhouse-style Colonial and spectacular post-and-beam Party Barn. Main residence features a gourmet chef's Kitchen with a single-piece, 14' Calacatta marble island, professional appliances, and dual Family Room fireplaces. Upstairs, the Primary Suite is highlighted by a custom marble-inlay bath floor, large walk-in shower + soaking tub, while the Living Room offers enhanced acoustics w/its tray ceiling for a superior piano experience. The property's exceptional appeal is anchored by the new Country Carpenters barn, connected by a breezeway w/barn doors that create an inviting welcome to backyard entertaining. This luxury 1BR barn is complete w/20-foot ceilings, heated floors, a full kitchen, and hinge-free retractable doors that seamlessly blend indoor/outdoor living. Resort-style amenities await outdoors with a Pebble Tec pool, waterfall hot tub & blue granite patio that remains cool underfoot on hot summer days. The entertainment porch features built-in heaters, a see-through fireplace, and an outdoor television. This is more than just a home, it's a legacy waiting to be claimed!

Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn. Designed for both grand entertaining and everyday living, the home features an extraordinary backyard anchored by a stunning pool and attached pool house, creating the ultimate resort-style setting. Inside, the thoughtfully designed floor plan includes a sought-after first-floor bedroom, expansive sun-filled living spaces, and seamless flow throughout. The dramatic family room showcases soaring 20-foot ceilings with striking wood beams, while the modern renovated kitchen beautifully blends contemporary style with everyday functionality. The second floor offers five spacious bedrooms along with an oversized playroom/flex space. A partially finished basement provides additional recreation room and storage possibilities. Zoned for highly desirable Long Lots Elementary and Bedford Middle School, this exceptional property combines timeless architecture, incredible outdoor living, and an unbeatable cul-de-sac location in the heart of Westport. Sturges Hwy to Daniel Court

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.

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**

A rare blend of scale, privacy and value, this beautifully maintained Redding retreat offers over 6,000 square feet of flexible living space. From the gracious front entry, the home unfolds with purpose and ease. To the right, a private library/home office creates a quiet place to work. Straight ahead, the living room frames peaceful views of the pool and grounds, while the formal dining room leads toward the heart of the home: a large eat-in gourmet kitchen open to an impressive family room with soaring ceilings, walls of windows, and abundant natural light overlooking the property. The traditional second floor offers a spacious primary suite with walk-in closets and serene backyard views, along with three additional bedrooms. The finished lower level adds tremendous versatility, featuring a large suite and lounge area ideal for guests, au pair, or in-law living, with direct access to the mudroom, garages and a separate exterior entrance. A second exterior entrance leads to a fully private studio or workshop. Outdoor living is a standout, with an expansive deck surrounding the pool and generous space for entertaining, relaxing and enjoying the private setting. The detached pool house/guest house adds incredible flexibility with a living area, kitchenette, bedroom and loft space. With exceptional square footage, privacy, lifestyle amenities and tremendous value compared with pricing being achieved in surrounding Fairfield County towns, this is a must see property.

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.

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.

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.

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.

The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by noted architects Visscher and Burley, this Colonial Revival style home has undergone thoughtful renovations over the years to preserve and enhance its original character. High ceilings, oversized windows, detailed millwork and sun-filled rooms create a sense of warmth and sophistication. Recent renovations include a new cedar roof on both house and barn, a like-new pool, spa & mechanicals, refinished hardwood floors, updated HVAC and new appliances. A unique highlight of this estate is its location across from Nyala Farms, offering scenic views of 50 acres of open meadows and fields with a deed restriction preventing any further development. Enjoy the ultimate lifestyle, minutes to the train, beaches, schools, shops and fine dining.

Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning four levels, this six-bedroom home features an airy layout with refined finishes throughout. The open-concept kitchen flows seamlessly into the main living spaces, highlighted by a statement fireplace. A glass-enclosed office offers privacy, while additional living and dining areas, a stylish scullery, and an oversized mudroom add everyday functionality. A dramatic pivot door opens to a gallery-style entry. Upstairs, the primary suite is a serene retreat with its own fireplace, dual walk-in closets, a dressing area, and a spa-like bath. Four en-suite bedrooms and a laundry room complete the second floor, while the top level offers a private sixth suite, office, and flexible open spaces. The walk-out lower level expands the home with walls of glass, a terrace, gym, bar, wine cellar, media/playroom, and additional office. Outside, a 16'x32' pool, multiple terraces, and a grilling area create effortless summer living, complemented by a three-car garage with EV charging. Taxes to be finalized after CO issued.

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.

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

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