Westport, CT Homes for Sale with Pool

The most private and serene of the remaining multi-acre estates in central-most Westport... Just two minutes from the beach, town center, I-95, and the Saugatuck Hamlet rail station. Located Near several well-regarded school systems in Connecticut. This grand estate offers space for recreation, relaxation, and entertaining. A stone-gated, walled circular driveway marks the end of a private road

Lisa Bortz William Pitt Sotheby's Int'l

Nestled along Westport's prestigious 'Gold Coast,' this architecturally magnificent estate on 4+ acres of park-like grounds with a breathtaking pool and professional-grade Har-Tru tennis court is a haven for luxury living and distinguished entertaining. Surrounded by major estates in one of the most sought-after coastal regions in the Northeast, it boasts access to pristine beaches, sophisticated

Doug Bross Coldwell Banker Realty

Fresh from the pages of Architectural Digest Italia comes this must-see, extraordinary luxury residence inspired by the timeless essence of midcentury design. This custom-built home is unlike one you've ever experienced, with a sophisticated design and elegant and elevated finishes throughout. The unsurpassed quality of Italian-imported Poliform walnut cabinetry and wall fittings throughout,

Cyd Hamer William Pitt Sotheby's Int'l

Exceptional Gated Estate in Greens Farms! Welcome to 355 Greens Farms Rd, a spectacular 2.25 acres estate designed for luxurious living and ultimate entertaining. This stunning home is a dream for car enthusiasts, featuring a four-car garage with room for lifts, making it perfect for showcasing and maintaining your collection. Step inside to find a brand-new kitchen and a newly designed primary

Meredith Cohen Serhant Connecticut, LLC

Crafted by Tomas Brothers Builders, 27 Narrow Rocks is a modern masterpiece on 1.86 acres. This newly built estate offers 7 bedrooms, 8 full baths, and 2 half baths across four levels, including a walkout lower level. The home features 10-ft ceilings, oversized windows, and a grand foyer with triple glass doors and a two-story oak staircase. Everywhere you look, there's a captivating moment-this

Susan Tracy Higgins Group Bedford Square

Spectacular move-in ready construction w/ breathtaking water views, located in the heart of Westport's exclusive Compo Beach. This ultimate retreat, designed by renowned award-winning architect Peter Cadoux, is more than just a place to live; it is a spectacular sanctuary designed to enhance every aspect of coastal living. The commitment to luxury is apparent in every detail. Classic and

Carol Cutler Higgins Group Bedford Square

This remarkable stone mansion, built in 1929, stands as one of the most historically and culturally significant residences in Westport and Fairfield County, celebrated as an exceptional trophy property. Meticulously restored and in impeccable, move-in ready condition, this home is poised for immediate enjoyment. Crafted in the esteemed tradition of Europe's grand Manor Houses, it boasts

Alex Chingas Coldwell Banker Realty

Offered for the first time in over 50 years, this cherished, custom-built waterfront retreat on Bermuda Lagoon is an extraordinary find. Lovingly maintained and never flooded, 100 feet of private beach, a deepwater dock, and breathtaking views of Long Island Sound and Bermuda Lagoon. Designed for year-round enjoyment, the home's soaring ceilings and expansive windows perfectly frame the stunning

Inna Agujen Coldwell Banker Realty

MOST UNIQUE HOUSE IN WESTPORT LARGE LOG HOME ON THE RIVER THAT IS STOCKED WITH TROUT. INGROUND GUNITE POOL BEAUTIFUL GROUNDS VERY PRIVATE ONE FLOOR LIVING. 4 BEDROOMS 3.5 BATHS. 1 HOUR TO NYC BEACH ACCESS. WONDERFUL RARE OPPORTUNITY TO OWN THE HOME YOU HAVE ALWAYS WONDERED ABOUT. THE BEAUTIFUL TRANQUIL RIVERVIEW LODGE LOG HOME THAT SITS ON THE MAJESTIC SAUGATUCK RIVER. WITH OVER 500+ FEET OF

Rebecca Ellsley Higgins Group Bedford Square

Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

Heather Fitzgerald YellowBrick Real Estate LLC

Design Your Dream Home with an Award-Winning Builder Step into a world of elegance and sophistication with a soon-to-be-built 6,600 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

Annie Klyver Higgins Group Real Estate

Welcome to 107 Old Road, an exceptional new development by Joe Feinleib founder of Coastal Luxury Homes. Soon to be the only gated community development in Westport, CT, this uniqiue four-lot enclave presents unparalleled luxury and privacy. Each custom home, to be designed in collaboration with your client, boasts approximately 6,500 to 7,500 square feet of living space, with an additional 1,100

Nickolaos Andronikidis Shelby's Realty Services

Introducing an exceptional new construction by Cypress Development, this luxurious home on a private acre in one of Westport's most sought-after locations seamlessly merges timeless design with modern luxury. Step into an impressive two-story foyer showcasing sun-soaked interiors, hardwood floors, tall ceilings, and meticulous custom millwork. A formal living room and formal dining room set the

Jacob Bivona Keller Williams Prestige Prop.

This 1 bed + den with 2-baths features floor-to-ceiling windows, an open kitchen with modern finishes, appliances by Wolf, Bosch, & SubZero, and a gas linear fireplace. The primary bedroom includes an en-suite bathroom with heated floors, a dual vanity, walk in shower, & a large dressing area. The 2nd sleeping area has flexible use and a wall of glass to add privacy when desired. Originally a

Ashlei De Souza Serhant Connecticut LLC

This impressive home has floor-to-ceiling windows, wood floors and a linear gas fireplace. The kitchen has an oversized island, high-end appliances, and is complete with custom cabinetry. The 2 bedrooms are on opposites sides of the home for maximum privacy. The primary suite has a generous walk-in closet and a luxurious windowed bathroom with rain shower, dual sinks, and heated floors. Stairs

Ashlei De Souza Serhant Connecticut LLC

Tucked away at the end of a peaceful cul-de-sac, this custom-built home offers comfortable living, an abundance of natural light throughout, & unmatched convenience, being 5 minutes from schools & Green's Farms train station. With 4 bedrooms, 4.5 bathrooms, & flexible living spaces, this home is designed for entertaining & everyday family living. A double-height foyer welcomes you with a feature

Karen Liss-uomoleale William Raveis Real Estate

Set on a picturesque cul-de-sac, this elegant Colonial offers timeless charm and modern amenities. Nestled on a level two-acre lot, the home boasts lovely curb appeal and a private, fully fenced backyard perfect for entertaining, play, and recreation. Inside, you'll find four spacious bedrooms with the option for a fifth bedroom or private home office on the main level, complete with a full bath.

Meredith Kamo Compass Connecticut, LLC

Discover Westport's Premier Coastal Gem. Immerse yourself in modern elegance with this stunning new beach house, located in the highly sought-after Saugatuck Shores neighborhood. Constructed in 2022, this five-bedroom, four-and-a-half-bathroom residence spans over 3,700 square feet of finished living space. Tucked away on a peaceful cul-de-sac, the home offers easy access to the vibrant energy

Doug Bross Coldwell Banker Realty

Prepare to experience the extraordinary and discover the future at this new residence by Skyview Builders. Now complete and ready for immediate enjoyment, this world-class estate elevates the standard against which all others are measured. Set on two spectacular, level acres in the heart of Westport's premier estate section, long considered a haven for celebrities & influential figures. The gated

Doug Bross Coldwell Banker Realty

Welcome to 27 Blue Ribbon Road - A Serene Retreat in the Heart of Westport. Tucked away on a quiet, tree-lined street where neighbors still greet each other by name, this expanded split-level home offers the perfect blend of comfort, style, and community. With 4 spacious bedrooms, a dedicated home office, and a thoughtfully updated layout, this property is ideal for both everyday living and

Meredith Cohen Serhant Connecticut, LLC

Experience the charm of Residence 214 at The Mill Westport. This 2-bed, 2-bath home spans 1,400+ sq ft with a spacious living area, a modern gas fireplace, exposed brick, and a private covered balcony. The windowed kitchen boasts an oversized island, Poliform cabinetry, and top-tier appliances by Wolf, SubZero, and Bosch. The primary suite includes a walk-in closet, balcony access, and a luxe

Ashlei De Souza Serhant Connecticut LLC

Refined living awaits on Boxwood Lane, a prime Hunt Club cul-de-sac featuring tranquil private entrances to stately colonial style homes. From its cobblestone-lined, semi-circular driveway to the backyard pool and bluestone patio oasis, the grounds of 5 Boxwood Lane are simply spectacular. The home itself stands apart, meticulously designed with exquisite details and custom amenities. Four

Karen Scott Compass Connecticut, LLC

Calling all renovators, designers, and discerning buyers seeking an extraordinary Westport estate. Opportunity awaits at 342 Greens Farms Road, set on 2.02 lush acres just steps from Connecticut's Gold Coast. This 1861 Victorian home, complemented by a thoughtful, high-quality 2008 rear addition, features over 6600 square feet of living space with Audubon Society land bordering the rear and side.

Adrienne Durkin Compass Connecticut, LLC

Experience the unparalleled luxury of this exquisite Compo Beach seaside home,a masterpiece of design and craftsmanship, designed by renowned architect Peter Cadoux. Just steps from a private beach, this architectural gem is bathed in natural light and boasts breathtaking panoramic water views from nearly every room.The full chef's kitchen opens to a radiant sunroom with a glass ceiling, perfect

Elizabeth Steffen Higgins Group Bedford Square

1031 exchange or the perfect Airbnb income awaits you! 2 MIN. WALK TO BEACH! **Jennings House - A Timeless Treasure Awaits!** Step into an extraordinary opportunity to own a piece of Westport's vibrant history, just a leisurely stroll from the beach! This stunningly restored three-bedroom carpenter gothic-style masterpiece is a true gem, showcasing the exquisite craftsmanship of the Victorian

Mar Jennings Higgins Group Bedford Square

This 1 bed + den with 2-bths features floor-to-ceiling windows, an open kitchen with modern finishes, appliances by Wolf, Bosch, & SubZero, and a linear fireplace. The primary bedroom has an en-suite bath with heated floors & a large dressing area. The 2nd sleeping area has flexible use and a wall of glass. Originally a candlewick mill built in the 1800s and later a destination for artists to

Ashlei De Souza Serhant Connecticut LLC

Relaxed, entertaining luxury with all the bells and whistles....Privacy, serenity and convenience featuring Entertaining at it's finest - step into 249 Sturges Highway greeted by welcoming floor plan from living room, dining room, open concept kitchen which highlights gorgeous quartzite counters, a Subzero refrigerator, Bosch dishwasher, and a 60" Viking Dual Fuel range flowing into the great

Lainie Floyd William Pitt Sotheby's Int'l

A TRUE PIECE of ART. Tranquil Hamptons alternative at a great price point and views of Long Island Sound. A short walk across the Wooden Footbridge w/ Sherwood Mill Pond on your left and LI Sound on your right leads to the gated private Island of Compo Mill Cove & a handful of unique waterfront homes. The property itself has been customized from top to bottom w/ exceptional thought & detail. Only

Robert Perriello Century 21 AllPoints Realty

Ready for immediate occupancy and enjoyment - welcome home to Residence 203 at The Mill Westport. Offering high-end luxury living with all the amenities of a fine custom home in the heart of downtown Westport, CT - this unit offers original historic details combined with modern comfort. With a concierge on-site and spectacular interior and exterior amenity spaces such as The Great Room & Cafe,

Doug Bross Coldwell Banker Realty

The Mill Westport offers high-end luxury living with all the amenities of a fine custom home in the heart of downtown Westport. With a concierge on-site and approximately 10,000 square feet of spectacular interior and exterior amenity spaces such as The Great Room & Cafe, Pool, Health & Wellness Center, Patio & Rooftop Deck, residents will enjoy carefree, 5-star living. The 31 residences feature

Doug Bross Coldwell Banker Realty

The Mill Westport offers high-end luxury living with all the amenities of a fine custom home in the heart of downtown Westport. With a concierge on-site and approximately 10,000 square feet of spectacular interior and exterior amenity spaces such as The Great Room & Cafe, Pool, Health & Wellness Center, Patio & Rooftop Deck, residents will enjoy carefree, 5-star living. The 31 residences feature

Doug Bross Coldwell Banker Realty

Residence 306 is a beautiful 2 bedroom corner home with dual exposure, historic brick & beams, a gas fireplace, ceilings reaching 15 & a half feet, skylights & a huge storage loft! The primary bed has 2 walk through closets leading to the luxurious bathroom with soaking tub, dual sinks & rain shower. Originally a candlewick mill from the 1800s, The Mill has undergone a complete restoration into

Ashlei De Souza Serhant LLC

Strathmore ln is a sought-after complex, with a very convenient location to Westport and Norwalk amenities. Unit needs updating. The condo has a Westport address however the schools and amenities are Norwalk.

Georgia Wasserman Coldwell Banker Realty

Walk to downtown shops and restaurants from this stunning, reimagined, & rebuilt 1920 Dutch colonial home, situated on a spacious 1.17-acre in-town property.This is truly a work of art, as 2 properties have been seamlessly combined into one, creating a private oasis set way back from the road.Upon entering the home, you will be captivated by the meticulous attention to detail & the perfect blend

Hyleri Katzenberg Compass Connecticut, LLC

Introducing an exceptional new construction home by Redcoat Homes. Spanning over 8,000 square feet, this stunning property is situated on a flat, one-plus acre lot in the desirable Old Hill neighborhood of Westport. The location is private yet conveniently close to I-95 and the Merritt Parkway, just minutes from the beach and town. It also borders Earth Place, one of the top family-friendly

James Lanzaro Compass Connecticut, LLC

Skyview Builders presents a unique opportunity - unmatched for both the modern expression of luxurious living it embodies, as well as the captivating private setting over which the residence presides. Two acres of your own private park-like property, nestled against the Paul Newman-Poses Preserve, will create an unforgettable backdrop for this European-inspired home for all seasons. The long,

Doug Bross Coldwell Banker Realty

NEW CONSTRUCTION TO BE BUILT IN THE COVETED HUNT CLUB NEIGHBORHOOD - Renowned, luxury builder Mattera Construction is well-known for architecturally significant & stunning modern homes filled with elegance, timeless beauty, custom interiors with state-of-the-art amenities. Now offering a perfectly designed 6 bedroom home finished on 4 levels filled with elegant finishes, well sited on a quiet

Patricia Shea Coldwell Banker Realty

Compo Beach living, 2 short blocks from the beach on private road! Luxury construction, just completed. 5 bed, 4.5 bath modern home offers all of the lush amenities seen in the finest resorts both inside & out. Custom Italian cabinetry by L'Ottocento in kitchen, butler's pantry, bathrooms, and mudroom. 9ft.+ ceilings, open stairs with glass railings & oak floors. Open ceiling in entry hall w/

Deborah Aulfinger Goldan Home Realty, LLC.

Set on a pristine, level acre on one of Westport's most popular cul-de-sacs, this exquisite stone & shingle home combines timeless craftsmanship with modern luxury. Featuring 9' & 10' ceilings, extensive millwork, and five fireplaces with custom mantles, the home is built for elegant living and entertaining throughout nearly 9000sqft. The main level offers a chef's kitchen that flows into a warm

Amy Swanson William Raveis Real Estate

Welcome to Saugatuck Shores, an exceptional waterfront enclave offering unparalleled luxury and privacy.A boater's dream come true w/ a deep water dock and direct access to LI Sound.This hidden gem neighborhood has a labyrinth of quiet,walkable streets, culminating in a cul-de-sac.Private Covlee Assn membership w/ sandy beach & social gatherings.The 5 bedroom high-end masterpiece w/ elevator was

Julie Vanderblue Higgins Group Real Estate