luxury real estate for sale Westport, United States

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.

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...

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.

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

COMPO BEACH WATER VIEWS at this picture-perfect beach house. Edgewater Hillside is the best-kept secret at Compo Beach, a private Hamptons-style cul de sac where each home is prettier than the next and water views abound. This exceptional residence combines timeless design with high-end amenities and so much space to live and entertain, walking distance to Compo Beach and Old Mill Beach, and moments to Longshore Club Park's golf, tennis, swimming and boating, and downtown. The four beautifully-finished levels are highlighted by so much attention to detail: soaring coffered ceilings, built-ins, and oversized windows taking in the views of the Sound, the Mill Pond and walls of blooming hydrangea. A chef's dream kitchen is equipped with Viking and Subzero appliances, and a fully-equipped outdoor kitchen and stunning stone fireplace make entertaining a breeze in all seasons. The generously-sized primary suite offers a sumptuous bath with soaking tub, walk-in closet and gas fireplace. The versatile floor plan includes a third floor retreat also with jaw-dropping views, balcony and full bath. The fully finished lower level also includes a full bath. The home and road access are not in a flood zone, and city water, sewer and natural gas plus a whole-house generator make life easy. Enjoy privacy, water views and the lifestyle only Compo Beach offers. Even room for a small pool! Also available fully furnished for a turnkey beach residence!

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.

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.

Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases you best. The welcoming living room with its broad bay window and formal fireplace provides ample room for your guests and the Baby Grand piano! The custom country kitchen is both practical and beautiful with wide plank wood floors, cherry and glass cabinetry, granite counters and a walk-in pantry. The adjoining family room with it's cathedral ceiling is filled with natural light and includes a fireplace, wet bar and French doors that open to a wraparound deck. The most recent addition is an impressive library with long, tall windows set amid tailored built-ins. An additional exterior entry makes it ideal for home office use while the adjacent full bathroom and closet offers the possibility of a first floor bedroom suite. The informal rear foyer includes access to a laundry area, powder room and extra closets. Just beyond is a 2nd private office or den. Upstairs you'll discover the primary suite with full bathroom and walk-in closet, as well as 4 very spacious additional bedrooms. Unseen value found in the new roof, updated mechanicals and whole house generator!

Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The front to back living room with marble fireplace offers peaceful views through expansive windows. The formal dining room with picture window is adjacent to a generous country kitchen featuring a bay window, granite countertops, a gas cooktop and double ovens. The oversized family room boasts a vaulted ceiling and access to main level laundry area. The rear of the house features a 58 ft long deck overlooking private acreage. The home contains 5 bedrooms and 4 full bathrooms. The primary suite includes a full bathroom, dressing area, linen closet and a walk in closet with built-in armoire. This home has fabulous closet space with each bedroom offering a minimum of 2 closets. The walk out lower level hosts a private den / office with wet bar and sliders to a stone patio. There is an additional laundry area and storage space that leads to an oversized 2 bay garage. Central air conditioning will keep you comfortable during summer months while five zone heating, Thermopane windows and extra insulation keep this home energy efficient all year long. Westport's luxury shops, fine restaurants, relaxing beaches and award winning school system combine to make this an irresistible value!

Tucked behind a gated entry in prime Old Hill, this stunning 5-bedroom, 6 & 2 half bathroom home offers a rare blend of elegance, privacy, and natural beauty. The property is surrounded by multiple serene water features—including a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain, and a picturesque brook that winds along the edge of the property. Whether you're relaxing poolside or enjoying the sound of flowing water from the rear stone patio, the setting is nothing short of magical. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an expansive, light-filled layout is ideal both for grand entertaining and quiet retreat. A dramatic wall of windows captures sweeping views of the brook, creating a seamless connection between indoor comfort and the surrounding landscape. The ground floor consists of a gourmet kitchen, large family room with fireplace, dining room with built-in wet bar, living room with fireplace + lounge area with water views, a large entry foyer with stone floors and two powder rooms. Upstairs, there is a large primary bedroom suite with two balconies overlooking the pond and brook, two walk in closets + a beautifully appointed bathroom, 4 additional bedrooms each with its own bathroom, and a large home office (or optional 6th bedroom) with fireplace and brook + pond views. Additionally, there is a large tv/playroom with full bathroom on the second floor, a home gym, and another tv/family room on the 3rd floor, offering multiple options for relaxation and entertainment. The house has a Crestron lighting system, heated 3 car garage attached to the house by a stately porte cochere, a full house generator, automated driveway gates, fencing around entire property, mature landscaping, and a gas grill seamlessly built into the stonework by the pool. This is a rare opportunity to own a true sanctuary—where thoughtful design, natural beauty, and resort-style amenities converge to create an extraordinary living experience.

Panoramic vistas of Long Island Sound extend from this gated, resort-style estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawn, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Secluded outdoor shower with exterior access powder room. Separate 2-bedroom guest cottage with kitchen, laundry and one-car attached garage. Full house generator.

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.