Westport Real Estate

Welcome to Westport, Connecticut – a picturesque coastal town nestled in the heart of Fairfield County. Known for its stunning landscapes, vibrant culture, and rich history, Westport offers a unique blend of suburban charm and urban sophistication. With its prime location along the Long Island Sound, residents enjoy breathtaking waterfront views, sandy beaches, and a plethora of outdoor activities.

Westport boasts a thriving arts scene, with numerous galleries, theaters, and music venues that celebrate both local talent and renowned artists. The town is home to the Westport Country Playhouse, a historic theater that has been entertaining audiences since 1931. Additionally, the vibrant downtown area is filled with boutique shops, gourmet restaurants, and cozy cafes, making it a perfect spot for leisurely strolls and social gatherings.

For families, Westport is known for its exceptional school system, which consistently ranks among the best in Connecticut. The community is dedicated to education, providing students with a wealth of resources and opportunities to thrive. Parks and recreational facilities abound, offering everything from sports fields to serene walking trails, ensuring that residents of all ages can stay active and engaged.

Westport’s rich history is evident in its charming colonial architecture and historic landmarks, which tell the story of a town that has evolved while preserving its heritage. Whether you're looking for a peaceful retreat or a vibrant community, Westport is a place where you can truly feel at home. Come discover the magic of Westport – where coastal beauty meets a lively community spirit!

Newest Listings in Westport

$5,900,000

7 Beds ⋅ 8 Baths ⋅ 24194285 MLS

Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Thoughtfully conceived with elegant architecture, exceptional proportions, soaring 10-foot ceilings on the main level, 9-foot ceilings on the second floor and finished lower level, and light-filled interiors, the home blends sophisticated style with effortless everyday living. A stunning custom kitchen appointed with premium Thermador appliances anchors the home, flowing seamlessly into beautifully designed living and entertaining spaces. Superior materials, custom millwork, and bespoke finishes define every room, while 6 ensuite bedrooms in the main residence provide exceptional comfort. Outdoors, beautifully landscaped grounds create a private resort setting featuring a spectacular saltwater pool and spa. Elevator-ready! Walk-up attic offers added possibilities. A separate 550-square-foot guest/pool house/ADU offers ideal accommodations for guests, wellness, or entertaining, while the expansive property provides ample room for a future tennis or sport court. A rare offering in one of Westport's most coveted and prestigious locations, it's just minutes from Westport's bustling downtown, sunny beaches, and award-winning schools. This remarkable estate combines thoughtful design and an unparalleled lifestyle defined by privacy, bespoke design and high-end amenities. Still time to customize. Floor plans available

22 Cavalry Rd, Westport

$7,990,000

6 Beds ⋅ 8 Baths ⋅ 24194541 MLS

Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds, fine dining, and more. To be custom built by Coastal Luxury Homes, Fairfield County's foremost luxury builder, this distinguished residence will offer three beautifully finished levels defined by unrivaled quality and meticulous craftsmanship. Expansive walls of glass will bathe the interiors in natural light, showcase the magnificent grounds, and create a seamless connection to the outdoors. Exquisite millwork, natural stone, refined finishes, a curated selection of top-tier appliances, and generous allowances will elevate every space, while the sumptuous primary suite will serve as a private, resort-inspired retreat. Thoughtfully tailored to your every wish with room for a pool, this remarkable home will reflect your personal style and vision for sophisticated coastal living.

4a Compo Pkwy, Westport

$2,999,000

6 Beds ⋅ 6 Baths ⋅ 24192039 MLS

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.

36 E Main St, Westport

$4,995,000

3 Beds ⋅ 4 Baths ⋅ 24194201 MLS

The dream of waterfront living is officially taking shape-construction is underway by renowned builder The O'Dell Group. This is your chance to secure a front-row seat to the Long Island Sound on one of Westport's most prestigious stretches of coastline. This exceptional property offers direct water frontage + sweeping, uninterrupted views of the Sound + the iconic Old Mill Beach. Imagine waking up to the soft glow of a sunrise over the water, spending your afternoons enjoying the refreshing salt air, or relaxing to the rhythm of the tide. Every detail of this build is designed to maximize the connection to the sea, offering a lifestyle defined by beauty + tranquility. Nestled in a welcoming and picturesque community, you'll enjoy access to top-ranked schools + Westport's vibrant downtown, known for its exceptional dining, shopping, and cultural experiences. Plus, the location is ideal for commuters, with close proximity to Metro-North for a seamless trip to Grand Central Station in NYC. As the last available parcel of its kind for development in this coveted location, this project represents a rare opportunity to own a brand-new architectural masterpiece in an idyllic setting. With The O'Dell Group's signature craftsmanship now in motion, the vision for this ultimate beach house is becoming a reality. Seize the opportunity to claim this piece of paradise and personalize your finishing touches while there is still time. Reach out today to make this coastal sanctuary your own.

238 Hillspoint Rd, Westport

$1,495,000

1 Beds ⋅ 1 Baths ⋅ 24191062 MLS

An exceptional offering on 1.38 private acres in the heart of Westport. Ideally situated just moments from vibrant Main Street, this centrally located property offers convenient access to shopping, dining, parks, tennis courts, beaches, the train, and Westport's award-winning schools. It provides an outstanding foundation for creating a one-of-a-kind estate. At the heart of this property stands the Studio-a remarkable 1,551-square-foot stone building designed and built in 1932 by Lewis Welch of Manhattan for renowned sculptor Berthold Nebel. Nebel's Westport estate originally encompassed nine acres, and this offering represents the last remaining parcel of his original estate. Berthold Nebel's daughter, photographer Lucia Nebel White, made the Studio her home and lived there until her death. The property has remained in the Nebel family for three generations. Today, the Studio includes one bedroom, one full bath, a full kitchen, and a dramatic open living space featuring soaring ceilings, a striking stone fireplace, oversized handcrafted timber doors, and exceptional natural light. Rich in character and architectural detail, the Studio offers a rare opportunity for restoration, thoughtful renovation, or integration into a distinctive new estate in one of Westport's most sought-after neighborhoods.

11 Hitchcock Rd, Westport

$6,800,000

5 Beds ⋅ 4 Baths ⋅ 24193394 MLS

The best vacations are the ones you never have to leave. Set on the shores of Compo Mill Cove in the heart of Westport's coveted Compo Beach neighborhood, this exceptional FEMA compliant Michael Greenberg-designed waterfront home offers the ultimate coastal lifestyle. State-of-the-art systems, including geothermal heating and cooling and tankless hot water, provide exceptional efficiency and year-round comfort. Begin your mornings with a walk along Compo Beach, spend afternoons moving between your private beach and pool, and end the day dining on the waterfront terrace beneath the stars or strolling over to one of Westport's renowned restaurants. Designed to embrace the water from every angle, the home features exposed beams, wide-plank hardwood floors, and water views from nearly every room. The chef's kitchen opens seamlessly to spacious living and dining areas, creating an effortless flow for entertaining. Offering five bedrooms and three-and-a-half baths, there's plenty of room for family and guests to experience one of Westport's most coveted waterfront settings. Rarely does a home combine architectural pedigree, resort-style amenities, and an irreplaceable location so beautifully. This is waterfront living at its finest.

52 Compo Mill Cv, Westport

$4,599,000

6 Beds ⋅ 6 Baths ⋅ 24193530 MLS

At the top of Clapboard Hill, through the gate and over the brick drive, an iconic Westport Colonial welcomes with an immediate feeling of privacy and classic beauty. The main entrance reveals a double height foyer, sweeping staircase and historic charm. The formal living room spans front to back with multiple seating areas flanking the original fireplace. A smart, chic library lands just off the center hall, followed by the gorgeous dining room ready for family dinners and holiday entertaining. The white and bright kitchen is anchored by an island and includes a full butler's pantry, a prohibition era wine closet, and the sunniest breakfast room overlooking the patio. The family room is so spacious with room for lounging by the fire and piling in for movie nights. Upstairs holds a total of six bedrooms. The primary suite includes a beautiful bath, multiple walk-in closets and sweeping views. A sweet set of bedrooms share a Jack and Jill bath. There are three additional bedrooms, a full bath, and a laundry room. The third level is fully finished as a recration room. The two acre property is fully irrigated, professionally landscaped, and sectioned for pool, play, patio spaces and privacy. The stunning pool includes a lap lane and the pool house is cabana perfection with a main room, poolside necessities (including a secondary bbq!) and full bath. There is a three car garage and automatic gate to split driveway. So close to beaches, GF train stations, schools and town!

6 Clapboard Hill Rd, Westport

$2,997,000

5 Beds ⋅ 4 Baths ⋅ 24193283 MLS

Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four additional bedrooms are ample in scale - one en-suite, with a Jack-and-Jill bath connecting two others - while a full bath and a dedicated office complete the first level. Outdoors, an expansive terrace invites al fresco dining and entertaining above a manicured, secluded yard set on a coveted corner lot. Beyond the door: sunrise strolls to the water, sunsets over the boardwalk, Longshore Club, downtown shops, dining, and the library, plus a straightforward Manhattan commute via Saugatuck Metro-North. Homes in this enclave seldom surface.

4 Bradley St, Westport

$2,799,000

5 Beds ⋅ 4 Baths ⋅ 24189715 MLS

Privately nestled in Westport's coveted Old Hill neighborhood, this extraordinary five-bedroom New England residence offers a rare opportunity to own a home where timeless character & modern comfort come together beautifully. Thoughtfully updated while preserving its remarkable architectural details, the residence features sun-filled interiors, beautifully scaled rooms, & an inviting warmth throughout. Original elements reflect the home's storied past, while carefully integrated updates provide exceptional comfort for today's lifestyle. A standout feature is the distinctive pub room with its original wood bar - an unforgettable setting for intimate gatherings, celebrations, or quiet evenings at home. The versatile third level offers endless possibilities as a private guest retreat, second primary suite, or home office. Outside, mature specimen trees, flowering gardens, rolling lawns, and elegant stone terraces create a private retreat that evolves beautifully with the seasons. Completing the property is a charming barn with electricity, water, cable, & convenient parking, offering exceptional flexibility as a studio, workshop, recreation space, or a future vision uniquely tailored to the next owner. Just minutes from downtown Westport, award-winning schools, shopping, restaurants, beaches, & the train, this exceptional property presents a rare opportunity to become the next steward of one of Westport's most treasured homes. A truly special place to call home!

4 Crawford Rd, Westport

$1,795,000

4 Beds ⋅ 4 Baths ⋅ 24191980 MLS

Offers due by 5PM Monday, 7/27. Tucked into one of Westport's most treasured beach neighborhoods, this sun-filled Colonial is where people ride bikes until dinner, neighbors become lifelong friends, and an evening walk to Compo Beach can become part of your daily routine. From the moment you step inside, soaring ceilings, natural light, and beautifully connected living spaces create a home that feels larger, brighter, and happier than its square footage suggests. Designed for the way families actually live, the open floor plan flows effortlessly from the kitchen to the family room, while the unfinished lower level with soaring ceiling height offers potential for a home gym, golf simulator, media room, or recreation space-adding tremendous future value. Then there's something you won't find in most homes: an owned Tesla Solar Roof with integrated battery backup. Not panels mounted on top, but the roof itself generating power. Enjoy remarkably low electric costs, automatic backup power during outages, and annual income through Tesla's Virtual Power Plant-all without compromising the home's classic architecture. Outside, gather around the fire pit beneath the stars, tend the garden, and simply enjoy the feeling of belonging that makes this neighborhood so special. With beach rights, top-rated Westport schools, Longshore just around the corner, and one of the area's most welcoming communities, this is more than a beautiful home. It's the heart of Compo Beach living.

5 Drumlin Rd, Westport

$6,495,000

4 Beds ⋅ 5 Baths ⋅ 24192357 MLS

Experience the future of coastal living in this brand-new smart home located just steps from the sands of Compo Beach. This is the only just-completed residence on the Compo Beach side of Westport delivered as a fully integrated, self-monitoring home: rooftop solar power w/battery storage, intelligent load management, leak detection w/automatic water shutoff, energy-recovery ventilation, radiant heated floors, singular app-controlled lighting, shades, locks + HVAC. The house can be monitored + adjusted from anywhere in the world and stays powered on stored solar when the grid goes down. Designed by The O'Dell Group across three vertical levels + a panoramic rooftop deck w/gas fireplace, the home opens to Long Island Sound through full-height glazing & connects ground-floor living to a private loggia, heated gunite spa, + landscaped courtyard. Inside, the open kitchen pairs Subzero refrigeration + an integrated appliance package w/a generous island + pantry; the primary suite includes a private balcony + spa-style bath; a fully accessible shower is finished in stone, and a flexible main-level room w/full bath lives as an additional bedroom, home office, or guest suite. Iconic Compo Beach is just a short drive to the Metro-North station and about an hour to Grand Central/Midtown Manhattan. The Westport Project is in a category of its' own; a home engineered to take care of itself, and you, whether you're upstairs, in the city, or on the other side of the world.

16 Westport Ave, Westport

$899,000

2 Beds ⋅ 2 Baths ⋅ 24192304 MLS

The beach lifestyle, water views, natural light, and endless possibilities await at 3 Madeline Avenue. Freshly painted and furnished, this charming 2-3 bedroom cottage offers an open and inviting floor plan featuring refinished hardwood floors, expansive windows, and a sun-filled living space one house from the waterfront. The kitchen is equipped with granite countertops and ample cabinetry, providing abundant storage and functionality. The lower level includes a mudroom, full bath, and a versatile bonus room with a skylight and window-ideal for a home office, guest space, gym, or creative studio. Upstairs, soaring vaulted ceilings, skylights, and oversized windows create a bright and airy retreat. Recent improvements include new flooring and a beautifully updated bath with a new vanity and tub. Step outside to a spacious patio, perfect for outdoor dining, entertaining, or simply enjoying the coastal setting. Whether you're looking for a turnkey weekend escape, year-round residence, investment opportunity, or the perfect site to renovate, expand, or build new, this property offers exceptional flexibility in a sought-after location. A rare opportunity to secure water views and exceptional potential in one of the area's most desirable coastal neighborhoods.

3 Madeline Ave, Westport

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