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$1,999,000
5 Beds ⋅ 4 Baths ⋅ 24191704 MLS
Experience modern luxury in this beautifully reimagined home, set on 1.57 scenic, park-like acres. Thoughtfully renovated, this 2,864 sq ft residence offers open-concept living spaces filled with natural light and sophisticated finishes throughout. The designer kitchen features a stunning island and premium cabinetry, flowing seamlessly into the dining and living areas with a dramatic linear fireplace. The spacious family room opens to a sun-soaked bluestone patio overlooking an expansive backyard extending to the pond-an idyllic setting for entertaining and everyday enjoyment. The fabulous primary suite is a private retreat with a cozy fireplace, incredible walk-in closet, and beautifully appointed modern bath. Two additional bedrooms complete the second level, while a private 4th-bedroom ensuite is ideal for guests or flexible living space. A main-level office/5th bedroom, powder room, and mudroom with custom built-ins leading to the 2-car garage add versatility and convenience. Ideally located within walking distance of Staples High School and Bedford Middle School, and minutes from Westport's beaches, vibrant downtown, shopping, dining, and train station.

110 Cross Hwy, Westport
$8,450,000
6 Beds ⋅ 8 Baths ⋅ 24190641 MLS
Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling details & European windows that flood the interiors w/ natural light.The Chef's Kitchen is highlighted by natural stone countertops,a dramatic stone backsplash & custom stone hood, premium appliances with column refrigerator & freezer all set flush to the cabinets. Luxurious living and entertaining spaces flow seamlessly to the outdoor oasis featuring a sparkling pool, spa, & private 1.6 property w/an irrigation system Belgium block trimmed driveway The magnificent primary suite is a private retreat, complete w/ a custom rift oak cathedral ceiling & a covered balcony w/ glass & wood railings overlooking the property.The 2nd level features 5 BRs w/ensuite baths. The 6th BR Suite is privately in the LL where there is a large FR & Gym.Additional amenities include natural gas, city water, Visual Comfort luxury lighting throughout, integrated recessed lighting, & countless custom features that elevate every room.This is a rare opportunity to own a newly built, architecturally stunning estate where exceptional design and refined living come together beautifully. Ready for move in Summer 2026

10 Beltas Farm Ln, Westport
$798,000
2 Beds ⋅ 1 Baths ⋅ 24166309 MLS
Weekender, year-round retreat, or investment opportunity; this condo alternative charmer checks every box. Sun-filled and single-story, this happy home was cherished by its original family for over 50 years and the now second owner refreshed and revealed the original integrity of the home through thoughtful updates and upgrades. Award-winning builder/owner created a beautiful blend of whimsy and sophistication that brings character and craftsmanship to every corner of this Westport cottage great for short or long term tenant. Custom kitchen cabinetry and new appliances make for easy living with elevated style in a warm, welcoming space ready for today's discerning buyer. A cozy finished lower level adds extra square footage perfect for a playroom, office, or relaxed retreat with natural light. Adjacent garage, better utilized as storage, walks out to the side garden. Steps away, a babbling brook with a sweet little bridge winds along the property, beckoning the nature lover to wander out and enjoy the outdoor oasis with patio, garden, and mature trees in this natural setting. Thoughtfully maintained with a roof new in 2013, plus a new furnace and new hot water heater in 2022 and in 2026 brand new windows throughout the home leave nothing for the next steward to do except live here and love life. Centrally set on a quiet cul-de-sac, all of Westport's amenities are minutes away. Welcome to the Bridge House!

3 Keller Ln, Westport
$4,795,000
6 Beds ⋅ 8 Baths ⋅ 24182984 MLS
Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

2 Windy Hill Rd, Westport
$1,600,000
5 Beds ⋅ 3 Baths ⋅ 24170442 MLS
Tucked away down a private drive on two serene wooded acres, this exceptional mid-century modern deck house offers the perfect blend of architectural character, privacy, and natural beauty. Bathed in tremendous natural light, the home showcases the signature design elements that make deck houses so timeless and sought after, with expansive windows, soaring ceilings, and seamless indoor-outdoor living. The four-bedroom, two-and-a-half-bath layout provides comfortable and flexible living spaces designed to embrace the surrounding landscape. 2 car detached garage to hold all of your extra and outdo0r items! Warm wood tones, open gathering areas, and walls of glass create an inviting atmosphere throughout the home. A spacious deck overlooks the peaceful property, offering the ideal setting for entertaining or quiet relaxation immersed in nature. It feels worlds away while still being conveniently located near all that Westport has to offer. Sold As Is

4 Baywood Ln, Westport
$4,995,700
4 Beds ⋅ 5 Baths ⋅ 24176377 MLS
Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage and specs can vary, but the standard of excellence does not. Coastal Luxury Homes is the premier Fairfield County bespoke builder.

22 Dawn Dr, Westport
$5,000,000
6 Beds ⋅ 7 Baths ⋅ 24168601 MLS
Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a pool with spa, expansive lounging areas, full outdoor kitchen, and a rare post-tension concrete tennis court - the premier surface used at elite clubs and college facilities. A truly extraordinary amenity rarely found in residential homes. The home offers an open floor plan filled with natural light and thoughtfully designed spaces. The gourmet chef's kitchen features high-end appliances, abundant workspace, and two dishwashers. Main-level highlights include elegant entertaining spaces, a private meditation room, and seamless indoor-outdoor flow. The primary suite is a retreat with a spa-inspired bath, steam shower, and dressing room with abundant closets. Upstairs, an incredible playroom with six built-in beds creates the perfect sleepover space or playroom. The walk-out lower level offers versatility with a media room, gym, office, and guest suite ideal for extended family, au pair, or guests. Rarely does a Westport luxury home offer resort-style amenities, premier tennis facilities, flexible living space, and walk-to-school convenience in such a private setting.

6 Twin Circle Dr, Westport
$5,650,000
7 Beds ⋅ 9 Baths ⋅ 24172635 MLS
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**

8 Pleasant Valley Ln, Westport
$6,495,000
6 Beds ⋅ 8 Baths ⋅ 24172743 MLS
NEW CONSTRUCTION-READY FOR MOVE-IN! Privately set at the end of a quiet cul-de-sac in the coveted Long Lots neighborhood, this 2.3-acre, flat, tree-lined property offers a rare combination of privacy and endless possibilities for creating a luxury compound. Introducing a truly exceptional estate by award-winning Builder, Westport Family Homes. The residence spans 9,062 sq. ft. with 6 bedrooms and 8 bathrooms, showcasing exceptional craftsmanship, thoughtful design, and high-end finishes throughout. Elevator ready, which enhances both convenience and long-term livability. At the heart of the home, a designer kitchen is complemented by a fully equipped scullery, offering a discreet secondary workspace for catering, entertaining and daily organization-an increasingly sought after feature in today's luxury homes. Outdoor living is equally impressive, with a resort-style saltwater pool and integrated spa, automatic safety cover, expansive covered and open-air patios, and an outdoor kitchen, designed for sophisticated entertaining. The property also offers ample space for a tennis court and guest house, further elevating its estate-like appeal. Additional highlights include a full-house generator, EV charging outlet, and the signature craftsmanship and attention to detail that define a Westport Family Homes build. A masterfully built home - designed to impress, built to last, and created for an exceptional lifestyle.

5 Baldwin Pl, Westport
$2,400,000
5 Beds ⋅ 5 Baths ⋅ 24168651 MLS
Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens Farms train. This special home captures the soul of historic Westport while delivering the comfort of today's lifestyle. Thoughtfully renovated, it blends original character, architectural detail, warmth, and six fireplaces with the amenities today's buyers expect. Set on a flat property with room for a potential pool, the home offers inviting indoor and outdoor spaces ideal for entertaining and everyday living. At the center is a chef's kitchen with a Sub-Zero refrigerator, a Wolf range, custom cabinetry, and generous prep space, opening to a sun-filled family room. Formal rooms, antique details, and multiple fireplaces create a space that feels both elegant and welcoming. The primary suite offers an oversized dressing room with abundant closet space, and a spa-like bath with a soaking tub and steam shower. The finished lower level includes a game room, wine cellar, and flexible recreation space. Outside, the expansive lawn offers space for sports, gatherings, gardens, or a future pool. Ideally located with one light to Greens Farms train, and minutes to Long Lots Elementary, Post Road shopping, and Main Street dining. A rare blend of antique charm and modern living.

28 Bulkley Ave N, Westport
$5,990,000
6 Beds ⋅ 7 Baths ⋅ 24147970 MLS
New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with generous room sizes, flexible living areas, and seamless indoor-outdoor flow. Additional highlights include a three-car garage and thoughtful design throughout. Conveniently located close to Westport schools, train, beaches, and town amenities, this is a rare opportunity to own a custom home in a coveted setting.

10 Mary Jane Ln, Westport

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