Westport Homes for Sale

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Newest Westport Homes for Sale

$2,950,000

5 Beds ⋅ 6 Baths ⋅ 24212624 MLS

A rare opportunity to own a truly exceptional woodland estate, where space, serenity, and natural beauty come together. Set beyond a long, gracefully meandering driveway, this expansive residence is surrounded by mature trees, creating a remarkable sense of arrival and seclusion. The substantial scale of the home offers an exceptional setting for sophisticated entertaining and relaxed everyday living, with the surrounding landscape providing a tranquil backdrop in every season. At the heart of the outdoor experience is a stunning natural gunite pool, beautifully integrated into the wooded setting and offering a resort-like oasis for summer entertaining and relaxation. Immersed in nature and thoughtfully positioned within its surroundings, this distinctive property offers the rare combination of generous living space, an extraordinary setting, and a true retreat-like atmosphere. Pre-inspection items have been completed and repaired, providing added confidence for the next owner. A remarkable sanctuary for those seeking an elevated lifestyle surrounded by the beauty of the woods.

142 Easton Rd, Westport

$6,975,000

4 Beds ⋅ 5 Baths ⋅ 24212594 MLS

Experience waterfront living at 233 Hillspoint Road, a striking new construction home located directly on Old Mill Beach with panoramic water views. A private elevator is planned to serve all three floors, providing convenient access from the garage to the living areas and up to the private rooftop deck. The planned home combines clean architectural lines with an open floor plan, 9 and 10 foot ceilings and expansive walls of glass that capture natural light and showcase Long Island Sound throughout. The design includes four bedrooms, each with an en-suite bath, highlighted by a spectacular primary suite. The very private rooftop deck offers an exceptional setting for entertaining, enjoying sea breezes and watching sailboats and fireworks over the Sound. The lower level is designed to accommodate a hot tub spa and cold plunge pool, complemented by an outdoor shower. A beach-level covered terrace provides a seamless connection to the beach. A rare opportunity to bring your vision to an extraordinary Westport waterfront setting.

233 Hillspoint Rd, Westport

$3,295,000

5 Beds ⋅ 5 Baths ⋅ 24212748 MLS

Turnkey 2013 Contemporary Oasis | 5 Beds | Pool | Prime Westport Flawless execution meets ultimate convenience at 4 Turkey Hill Lane. Built in 2013 and meticulously maintained, this 5,318sqft. contemporary offers the ultimate turnkey experience in Westport's highly sought-after Long Lots neighborhood. The Interiors: An open-concept, light-filled layout designed for modern living. The centerpiece is a spectacular 2-story great room with a floor-to-ceiling stone fireplace. The seamless flow leads right into a high-end chef's kitchen featuring Sub-Zero appliances, double wall ovens, a wine chiller, and a massive walk-in pantry. Upstairs, the primary suite delivers with dual walk-in closets, a luxe en-suite, and a private balcony. Three additional upper-level bedrooms feature smart Jack-and-Jill setups, while a massive third-floor rec room handles everything from billiards to a home gym. The Grounds: 1.07 level acres of unparalleled outdoor living. The backyard is fully equipped for summer: a heated gunite pool and spa, a custom stone patio with a pergola, and a dramatic outdoor stone fireplace. Beyond the pool, the expansive flat lawn rolls gently down to a private, scenic brook. The Lifestyle: Active solar features, a 3-car attached garage, and city utilities ensure effortless homeownership. Enjoy privacy without sacrificing convenience-you are just minutes from Westport's downtown dining, high-end retail, beaches, and the Metro-North station for a streamlined ci

4 Turkey Hill Ln, Westport

$1,199,000

3 Beds ⋅ 3 Baths ⋅ 24211260 MLS

Ideally situated in a highly walkable in-town location, this charming 1928 home offers a rare opportunity to create something truly special in the heart of Westport. Set on a lovely private lot, the property combines classic character with a wonderfully convenient setting close to shops, restaurants, schools, and all that downtown Westport has to offer. Owned and cherished by the same family for approximately 40 years, the home retains the warmth and architectural details that give an older house its distinctive appeal. Oak floors, gracious proportions, and timeless character provide a wonderful foundation for its next chapter. A first-floor in-law/primary bedroom suite, thoughtfully added in the 1960s, offers convenient one-level living and adds flexibility to the original floor plan. Upstairs, two roomy bedrooms share a generously sized bathroom that presents an exciting renovation opportunity: the space could be reconfigured to create two en-suite bathrooms, one for each bedroom, adding modern functionality while preserving the home's charm and character. While the house is in need of renovation, its established setting, private grounds, classic details, and highly desirable in-town location make it an exceptional opportunity for those looking to restore, renovate, and make the home their own. For buyers seeking in-town convenience, privacy, and authentic Westport character, this is a special property with tremendous potential.

280 Main St, Westport

$4,299,000

5 Beds ⋅ 5 Baths ⋅ 24212297 MLS

Welcome to BAYBERRY FARMS- a refined oasis of style, comfort and custom amenities begins to unfold upon arrival at this property in an area known for fine estates. A gated drive welcomes you home, first to an ample motor court and then you will pass through carefully landscaped gardens. Inside, the creative and energetic spirit of this home begins to reveal the array of quality features that define it. Sensitively blending the character of a country retreat w/bold modern vision, this 5-BR residence was completely reimagined in 2025. The large living room w/built-ins, bay window & fpl is ideal for grand entertaining. The large sunroom/office is lined w/windows & glass doors. The gourmet kitchen has custom exotic wood cabinetry, Viking appliances & a breakfast area with a folding glass wall that leads to the pool terrace. The DR has a wall of glass, unique corner fpl & original built-ins. The family rm has a modern fpl feature wall & large-scale space for any gathering. Flexible layout w/2nd sunny office. A bonus area over the garage has an incredible game room & gym. The primary ste is an incredible retreat- you will not find another like it. This five-star space has an amazing glass-lined bedroom, two custom walk-in dressing rms w/full glass-fronted built-ins, & a stunning bath w/massive glass shower, soaking tub & more. The rear property rivals boutique hotels w/very large stone terrace, full summer kitchen w/pizza oven, gunite pool w/auto cover, hot tub, porch, garden

191 Bayberry Ln, Westport

$5,995,000

6 Beds ⋅ 9 Baths ⋅ 24199970 MLS

Magnificent new construction by AR Luxury Homes on a flat, private acre at the end of a coveted cul-de-sac in Greens Farms. Thoughtfully designed finishes by Tara Benet Design of Greenwich, this 6-bedroom, 6 full/2 half bath residence offers 7,874 sq ft across the first and second floors, plus a finished 1,950+/- sq ft walk-out lower level. Soaring 10' first-floor ceilings anchor an open plan with a great room, custom kitchen, formal dining room, living room, office, wet bar, and mudroom. The primary suite offers a spa bath and walk-in closet, with four additional ensuite bedrooms. The walk-out lower level includes a bedroom, full bath, playroom, gym, and ample storage. Outside, enjoy a 20' x 40' heated pool with spa and automatic cover on a bucolic property. City water, septic, and propane service the home. There is space for an elevator to all floors that can be added, and 1,800 sq ft can be finished on the walk up third floor at additional cost. A rare opportunity, with time to customize select finishes. Home to be completed late spring 2027.

19 Harding Ln, Westport

$2,895,000

3 Beds ⋅ 4 Baths ⋅ 24211839 MLS

A masterclass in modern coastal architecture, this four-level waterfront retreat delivers a seamless connection to the Saugatuck River. Floor-to-ceiling glass anchors the open-concept main floor, filling it with natural light and showcasing broad river views. Recent high-end infrastructure and tech upgrades make the home as smart as it is stylish--featuring custom Lutron automated window shades throughout, a fully integrated audio/video system, custom window and retractable door screens, and EV charger pre-wiring. Outdoors, enjoy an automatic irrigation system, a conservation-approved custom wire and rail fence, and dock approvals nearing completion, clearing the path to launch your boat into Long Island Sound. An adjacent park further preserves the home's scenic setting and surrounding privacy. Spanning 1,841 intelligently planned square feet, the layout offers ideal space separation and turn-key, lock-and-go convenience: a private second-floor primary suite with walk-in closet and en suite bathroom with tub and steam shower, a third-floor guest suite with a private balcony, and a lower-level family room next to a third bedroom with ensuite bathroom and walk-in closet. Just outside, a water's edge terrace offers effortless riverfront entertaining--all in a prime Westport setting moments from downtown, offering immediate access to local dining, shops and parks.

79 Riverside Ave, Westport

$2,049,000

3 Beds ⋅ 3 Baths ⋅ 24212313 MLS

Welcome to Saugatuck Shores, where you're not simply purchasing a home, you're embracing a lifestyle. This exceptional beach house offers an inviting floor plan, luxurious modern finishes, custom millwork, incredible water views, and a spacious private backyard. Enjoy your favorite wine al fresco from the charming screened-in front porch, expansive rear deck, or your private balcony off the primary suite. Step inside to a spacious living room anchored by a beautiful stone fireplace, an elegant formal dining room, and a stunning kitchen featuring custom white cabinetry, professional-grade stainless steel appliances, a large center island, and Carrara marble countertops. Coffered ceilings and custom millwork add character throughout the main level, which is completed by a beautiful full bath with an elegant glass-enclosed shower. Upstairs, the impressive primary suite boasts panoramic water views, a luxurious en-suite bath, walk-in closet, and access to its own private balcony. Two additional generously sized bedrooms feature beautiful wood beams that add warmth and distinctive character, while a full hallway bath is finished with marble tile and a tub/shower combination. Perfectly positioned to enjoy everything this sought-after waterfront community has to offer, while remaining just minutes from exceptional restaurants, shopping, nightlife, major highways, and the train. A rare opportunity to enjoy coastal living in one of Saugatuck's most desirable settings.

7 Marsh Rd, Westport

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 24212307 MLS

Tucked away on 1.25 serene acres in Westport's sought-after Coleytown neighborhood, this timeless 5-bedroom Georgian Colonial seamlessly blends grand architectural elegance with comfortable everyday living. Welcomed by an inviting, large front porch this impressive home offers exceptional space both inside and out. Inside, the grand main level flows effortlessly between a large formal living room, a gracious formal dining room, and a designated home office. At the heart of the home, a spacious, sunny kitchen connects directly to a casual den/TV room, while double doors lead from both the kitchen and dining room onto a lovely patio ideal for outdoor dining and entertaining. One of the home's most show-stopping features is the massive bonus room,expertly crafted from real barn wood and complete with exposed timber beams, wide plank wood floors, and a dedicated fireplace, perfect for cozy evenings or hosting large gatherings. Throughout the main house, you will find a total of 3 fireplaces creating a warm, inviting atmosphere. Upstairs, the expansive primary suite serves as a peaceful retreat featuring a massive walk-in closet and a remarkably large primary bathroom. A second spacious bedroom functions as its own suite, featuring a private bathroom and an exclusive balcony overlooking the grounds. The resort-style backyard oasis centers around an inground pool and a fun, fully equipped pool house featuring a private bathroom and its own fireplace for chilly evening gathering.

23 Punch Bowl Dr, Westport

$1,990,000

7 Beds ⋅ 5 Baths ⋅ 24197538 MLS

Tucked away in Westport's coveted Greens Farms neighborhood, this beautifully updated home is set on over 2 acres and offers the perfect balance of comfort, flexibility, and modern living. Beloved by its owners for many years, it has been the setting for countless family gatherings, celebrations, and cherished memories and is now ready for its next chapter. The renovated kitchen features an induction cooktop, abundant pantry space, and a bright eat-in area with sliders to a newly built deck, creating an effortless connection to the beautifully landscaped backyard. The adjoining family room, with its soaring cathedral ceiling and inviting fireplace, is the perfect place to gather. The spacious primary suite offers a renovated ensuite bath, while four additional bedrooms, including one ideal for a home office, provide ample space for family and guests. A renovated hall bath features a double vanity. A private wing with its own full kitchen and separate entrance provides flexibility for an in-law or au pair suite. The walk-out lower level adds a bedroom, full bath, and generous storage for guests, recreation, or extended living. Major improvements include the roof, replacement windows and doors, exterior repainting, high-efficiency furnace, hot water heater, and oil tank. Lovingly cared for and thoughtfully updated, this special home offers space, privacy, and versatility. Just minutes from schools, beaches, train, shopping, and all that Westport has to offer

11 Turkey Hill Cir, Westport

$4,050,000

5 Beds ⋅ 6 Baths ⋅ 24211806 MLS

Privately set in Westport's coveted Old Hill neighborhood, this like-new sophisticated residence designed by famed architect Peter Wormser pairs striking architecture with timeless, understated elegance. Soaring ceilings, beautifully curated spaces and abundant natural light define the stylish interiors, creating a home that is at once impressive and inviting. 4 finished levels provide exceptional space for everyday living, entertaining, work and guests. The primary suite stuns with its 20-foot ceilings, fireplace, 2 walk-in closets and spa bath. 4 additional bedrooms each feature walk-in closets, while 2 private offices offer dedicated work-from-home space. A 3rd-floor recreation room with full bath adds more flexibility, while the beautifully finished lower level has a home theater, gym, space for play, plus storage. Outdoors, the magical setting unfolds through multiple entertaining spaces, from inviting covered porches to an expansive stone patio with a fully-equipped outdoor kitchen, built-in grill and Big Green Egg, offering an exceptional backdrop for gatherings large and small. Lush, established landscaping creates a remarkable sense of privacy, yet the home is just over a mile to Westport's vibrant downtown. Whole-house generator, solar and level 2 EV charger! The NYC-bound train is just 9 minutes away. Distinctive, sophisticated and effortlessly livable, this exceptional Old Hill residence is a rare offering of inspired architecture, privacy and a prime location.

11 Woodside Ln, Westport

$1,699,000

4 Beds ⋅ 4 Baths ⋅ 24204801 MLS

Set on a stunning, meticulously manicured, lush, one-acre property in the heart of Greens Farms and approx. 1 mile to the beach. This inviting 4 bedroom, 3.5 bath home is a jewel box with endless potential to personalize, expand and create your ideal retreat or simply enjoy it's current curated beauty. The property's expansive grounds, mature landscaping and beautiful garden create a peaceful backdrop for everyday living. Conveniently located in the heart of Westport, just minutes from beaches, train, shopping, dining, schools, and everyday amenities. 4 Lookout Lane offers an exceptional opportunity to enjoy the beauty, convenience, and a coastal community lifestyle that that is the essence of Westport. **Please see addendum for a full list of upgrades, including new roof in 2021, new oil tank 2025, newer windows and furnace and full house generator among multiple other improvements.**

4 Lookout Ln, Westport

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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