luxury houses for sale Westport, United States

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.

An exceptional home in coveted Greens Farms, 124 Hillandale Road captures the essence of classic Connecticut living. Timeless, elegant, and impeccably maintained, this beautiful estate is surrounded by mature landscaping and a peaceful, private setting, while remaining just minutes from everything Westport has to offer. Spanning four finished levels connected by an elevator, the home seamlessly blends classic architecture with modern comfort. Sun-filled living spaces, beautiful millwork, and thoughtfully designed interiors create an atmosphere that is both sophisticated and welcoming. Whether hosting family and friends or enjoying a quiet evening at home, the layout is designed to accommodate every stage of life with ease. Every detail has been carefully considered, from the state-of-the-art movie theater and golf simulator to the fitness and recreation spaces that make everyday living feel a little more special. Outside, beautifully landscaped grounds and picture perfect pool with auto-cover provide the perfect backdrop for relaxing, entertaining, and making lasting memories, with an outdoor fireplace and multiple gathering spaces to enjoy throughout the seasons. Effortlessly elegant, 124 Hillandale Road embodies the very best of Greens Farms living-a home where timeless design and modern amenities come together to create something truly special. Hillandale between Morningside South and Turkey Hill South

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

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.

Just completed and ready for immediate occupancy, this beautifully crafted new construction home is set on a quiet cul-de-sac in the desirable Greens Farms area. Situated on a level one-acre property with a pool, the home is filled with abundant natural light and offers a thoughtful, well-balanced layout designed for both everyday living and entertaining. The stunning kitchen opens to a dramatic double-height family room, creating an inviting central gathering space. With five-plus bedrooms, including a first-floor primary suite featuring a spacious walk-in closet and a well-appointed bath, the home provides flexibility to suit a variety of living arrangements. Two laundry rooms add convenience, while high-end finishes and attention to detail are evident throughout. A fully finished lower level offers additional living space with a gym, recreation area, and more. Ideally located for commuting, with easy access to town, beaches, shopping, and transportation.

*Due to strong interest, sellers kindly request best and final offer submission by 5pm Tuesday June 30th. No escalation clauses please* RARE opportunity for single-level living! The Meadows is one of Fairfield's most coveted communities and this spacious, updated 2BR/2BA Ranch provides comfortable, easy living at its best. Nestled within a serene nature preserve setting and surrounded by mature trees, landscaped plantings + marsh views, The Meadows offers a bucolic lifestyle, yet just minutes from all of Fairfield's vibrant amenities! Nearby recreational activities include golf, tennis, beach and walking trails - just moments away. Downtown Fairfield, bustling with shops/restaurants galore, is a mere 5-minute drive. This ranch home has lovely, neutral wall tones throughout, attractive wool berber carpeting and is sited in a desirable, quiet section of the community featuring peaceful backyard vistas. The spacious Foyer is bright w/attractive flooring and flows nicely to the cozy Library w/gas fireplace + built-ins. The formal Living + Dining Rooms are generously sized as is the renovated Kitchen w/stainless steel appliances, Quartz counters and pretty backsplash tile. Sliders access a private, bluestone patio. Primary BR Suite has large walk-in closet, backyard views and a nicely renovated Bath. A second BR, hall Bath, storage Attic, latch door Basement, Laundry/Mud Room and 1-car Garage complete this spacious 1965 SF home

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**

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

1008 Fairfield Beach Road- A Masterpiece on Fairfield's Iconic Coastline. Where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one of the coast's most exclusive rooftop terraces, featuring a state-of-the-art outdoor kitchen, rejuvenating Jacuzzi, gas fireplace, & direct elevator access-perfect for entertaining guests year-round. Step inside & experience exceptional craftsmanship w/ an open, airy layout & views of the water throughout the home. The main level features an open-concept living room, w/ dining area, all bathed in natural light. This true Chef's Kitchen offers custom, handmade cabinetry, top-of-the-line appliances, & spacious deck offering the perfect setting for Al Fresco dining. This expansive home offers 4 generously sized Bedrooms, each with its own luxurious Bathroom, ensuring complete privacy & comfort. The Primary Suite serves as a relaxing sanctuary, complete w/ a spa-like Ensuite Bath, & a serene deck where you can enjoy the sunrise in peace w/ a beverage of your choosing. Buyers also have the unique opportunity to personalize the home's finishes, tailoring every detail to their individual tastes and needs, ensuring this remarkable property becomes a true reflection of their dream lifestyle. GPS Friendly.

This historic Greens Farms acreage was once part of the famed Winfromere Stables where Edward T. Bedford's world class trotters were kept in grand style. Offering over 220 feet of broad frontage on private Bedford Drive, this scenic 1.14 acre parcel features a gentle rise above the street level, providing an ideal setting for a light filled home. Mature, statuesque trees grace the open landscape, offering established character and picturesque summer shade. City water and electricity are already on the property. This is a prime canvas for you to bring your vision to life in one of Connecticut's most sought-after neighborhoods.

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.

Completely renovated from top to bottom, this stunning 4-bedroom, 2-bath home blends modern luxury with timeless charm in Fairfield's desirable University area. Offering 1,814 sq ft of beautifully finished living space plus an additional 884 sq ft unfinished basement, this move-in-ready home provides style, comfort, and future potential. The open-concept layout features a designer kitchen with custom cabinetry, an oversized waterfall island, quartz countertops, sleek vent hood, and brand-new stainless steel appliances. Sun-filled living spaces showcase recessed lighting, wide-plank flooring, and modern finishes throughout. The home includes a beautifully designed primary suite, fully updated spa-inspired bathrooms, generous-sized bedrooms, and thoughtfully redesigned interiors. Contemporary exterior updates and attractive architectural details create excellent curb appeal, while the oversized deck and spacious backyard provide the perfect setting for outdoor living and entertaining. Additional highlights include a 2-car attached garage, updated mechanicals, premium finishes throughout, and a large unfinished basement ideal for storage or future expansion. Conveniently located near Fairfield University, downtown Fairfield, Metro-North, shopping, dining, beaches, parks, and major commuting routes. A rare opportunity to own a fully renovated home in one of Fairfield's most sought-after neighborhoods.

Built in 2022, 40 Richmondville Avenue offers a sense of ease that's increasingly hard to find… generous in scale, thoughtfully laid out, and ready to be lived in from day one. The home opens into a bright, open-concept main level where kitchen, dining, and living spaces come together naturally. High ceilings and oversized windows bring in light throughout, while the layout remains structured and intentional. At the center, the kitchen is designed for both everyday living and entertaining, featuring a full Thermador appliance suite, extensive cabinetry, and a large island with integrated outlets. A walk-in pantry connects to a dedicated mudroom with built-ins and cubbies that add a level of practical storage and organization. Upstairs, the home offers a well-balanced bedroom layout, including a spacious primary suite with a walk-in closet and a spa-like bath with heated floors, a soaking tub, and a separate oversized shower. Two secondary bedrooms are connected by a Jack and Jill bath, each with its own lofted space-an added layer of flexibility for work, play, or storage. Additional bedrooms allow for guests, office space, or evolving needs over time. The third floor provides a private, multi-purpose level-ideal as a home office, media room, or guest retreat-while the finished lower level extends the living space even further, complete with polished concrete floors and a bar/kitchenette area for casual entertaining. With six bedrooms, five-and-a-half baths, and multiple flexible living areas across four levels, the home adapts easily to a variety of lifestyles. Located just minutes from downtown Westport, with convenient access to restaurants, shopping, and everyday essentials, the property also sits within an area experiencing continued growth and investment and includes access to award-winning beaches. A newer home that offers space, flexibility, and a location that continues to evolve.

Built in 2022, 40 Richmondville Avenue offers generous scale, a thoughtful layout, and true move-in-ready ease. Bright, open-concept main level connects kitchen, dining, and living spaces, with high ceilings and oversized windows throughout. The kitchen features a full Thermador appliance suite, large island with integrated outlets, extensive cabinetry, walk-in pantry, and mudroom with built-ins. Upstairs includes a spacious primary suite with walk-in closet and spa-like bath with heated floors, soaking tub, and oversized shower. Two bedrooms are connected by a Jack and Jill bath, each with lofted spaces for added flexibility. Additional bedrooms offer options for guests, office, or evolving needs. Third floor provides a private, multi-purpose level, while the finished lower level includes polished concrete floors and a bar/kitchenette area for casual entertaining. Six bedrooms, five-and-a-half baths, and four finished levels offer exceptional flexibility. Located just minutes from downtown Westport, with easy access to shopping, dining, and beaches, in an area experiencing continued growth. Main Street to Richmondville Avenue

Experience style, comfort, and convenience in Fairfield's coveted University neighborhood. This home offers a bright, airy flow that highlights its classic character and thoughtful updates. The main level features hardwood floors and a spacious living room with a cozy fireplace. The dining room flows into the kitchen, offering a wealth of cabinet space. You'll love the layout of this level, where large windows look out over the beautiful backyard, pulling the outdoors in. The family room is a favorite retreat, with high vaulted ceilings and natural light pouring in. The upper level features a primary sanctuary designed for privacy and relaxation. Anchored by a dedicated sitting area and a bay window seat this is a room that actually lets you recharge. The walk-in closet is a total dream, custom-built with a center island and professional shelving that will have you feeling like you're shopping in a boutique every morning. The primary suite is completed by a luxurious en-suite bathroom with a double vanity. Three additional ample-sized bedrooms and a second full bath provide plenty of room, offering flexible living space that easily adapts to your lifestyle. The finished lower level adds another layer of versatility with a large recreation room, two separate office spaces, and a third full bathroom. Outside, the lush, flat backyard is a private oasis. The outdoor kitchen and patio make this backyard the designated spot for friends and family.

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