luxury real estate for sale Westport, United States

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 in the heart of Westport, Connecticut, this stunning new construction residence redefines elegant suburban living with unparalleled sophistication, timeless grace and is complete and ready for immediate occupancy. Boasting six generous bedrooms and six luxurious bathrooms, the home features soaring nine-foot ceilings that bathe its expansive interiors in natural light and create an atmosphere of airy grandeur. Thoughtfully designed with premium finishes, custom millwork, and state-of-the-art systems. From the chef's kitchen with Thermador Appliances and a commanding kitchen island to the serene primary suite with a warming fireplace and a walk in closet fit for royalty; every detail invites effortless entertaining and refined daily living. Spanning three floors, this home offers exceptional versatility with a peaceful third floor sanctuary housing a private office and media room for entertainment or productivity. The finished lower lever further elevates the lifestyle with a spacious additional family room and an exercise studio, creating inviting spaces for relaxation, recreation, and personal wellness. Set against Westport's coveted landscape, located across from Winslow Park and upscale shopping, this exceptional property offers a rare opportunity to embrace modern luxury within one of Fairfield County's most distinguished communities.

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.

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. Perhaps you'll create a new residence that reflects some of elegance and distinction of Standard Oil's philanthropic tycoon...

Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a higher elevation, the home enjoys FEMA compliance with fewer stairs to the main living level than many neighboring properties. Sunlight pours through oversized windows, illuminating beautifully proportioned living spaces designed for both everyday comfort and effortless entertaining. The stunning chef's kitchen opens seamlessly to inviting gathering spaces and out to a private backyard featuring a spacious patio, outdoor fireplace, mature landscaping, and room for a pool. The flexible floor plan lives as four bedrooms, with a private third-floor suite and adjacent full bath offering an ideal extra bedroom, guest retreat, office or bonus space. Thoughtful features, including a full-house generator, provide an added layer of comfort and confidence, allowing the home to perform as beautifully as it lives. Adjacent to the coveted Sunnieholme neighborhood, this is a rare opportunity to own a beautifully crafted home in one of Fairfield's most desirable beachside locations, where coastal living, convenience, and enduring quality come together.

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.

Welcome to this beautiful home perfectly situated at the end of a quiet cul-de-sac in a prime university neighborhood off of Mill Plain Road. This pristine property features 3 bedrooms and 3.5 baths, offering an exceptional blend of comfort, style, and modern convenience. The main living areas feature gleaming hardwood floors that have just been redone throughout the house. The heart of the home is a renovated kitchen expertly designed by a chef, with custom cabinetry to maximize space, perfectly fitting all your gadgets while offering extra outlets and newer appliances. For quiet evenings, the home offers an additional cozy den complete with a classic fireplace and sliders leading directly out to the deck. The lower level provides an incredible bonus for flexible living, featuring its own full kitchen, full bath, and a private walk-out exit. This versatile setup is absolutely perfect for multi-generational living or an in-law suite. Additional premium features include a large 2-car garage, central air, and a laundry room located right on the main level for ultimate convenience. Location is everything, and this property is central to downtown, local beaches, and commuting routes, while being less than half a mile to Riverfield School. Do not miss the opportunity to make this completely updated home your own.

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, this 6-bedroom, 5.5-bath home offers four finished levels of flexible living just minutes from downtown Westport. Open-concept main level features high ceilings, oversized windows, and a Thermador kitchen with large island, walk-in pantry, and mudroom with built-ins. Upstairs includes a primary suite with heated floors, soaking tub, and oversized shower. Two bedrooms share a Jack and Jill bath with lofted spaces. Additional bedrooms provide options for guests or office. Finished third floor and lower level with bar/kitchenette add versatile living and entertaining space. Convenient to shopping, dining, and beaches, in an area experiencing continued growth. Main Street to Richmondville

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.