Southport, CT Homes for Sale with Pool

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  /18

  $4,000,000

  New Construction

  • 7 Beds
  • 9 Baths
  • 7,105 Sq Ft

  20 Fresenius Rd, Westport, CT 06880

  We've saved the best for last! Of the 4 homes built at the end of this quiet and centrally located Westport cul-de-sac, this is the most expansive, and it's loaded with top-tier amenities. Entertain or hang out in style in gracious rooms curated by Susan Tracy Designs featuring a warm color palate, and not often found finishes like Venetian plaster and built-in hallway millwork. The open

  Patricia Shea Coldwell Banker Realty

  20 Fresenius Rd, Westport, CT 06880
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  /40

  $7,500,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 9,576 Sq Ft

  8 Loretta Ct, Westport, CT 06880

  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

  Lianne Owen Coldwell Banker Realty

  8 Loretta Ct, Westport, CT 06880
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  /40

  $15,000,000

  • 7 Beds
  • 6.5 Baths
  • 6,215 Sq Ft

  4 Sherwood Island Ln, Westport, CT 06880

  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

  Andrew Whiteley Brown Harris Stevens

  4 Sherwood Island Ln, Westport, CT 06880
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  /16

  $6,785,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 7,888 Sq Ft

  14 Burr School Rd, Westport, CT 06880

  RARE OPPORTUNITY TO CUSTOMIZE NEW CONSTRUCTION BY COASTAL LUXURY HOMES. PLANS APPROVED & PERMITS IN PLACE. CONSTRUCTION CAN BEGIN IMMEDIATELY, SAVE 6+ MOS ON NEW BUILD TIMELINE. This ultra luxury modern cul-de-sac residence features stucco exterior, DaVinci Boral roof, and expansive windows up to 10ft high. Main level includes luxe chef's kitchen w/ breakfast room opening to the great room with

  Jennifer Tanner The Riverside Realty Group

  14 Burr School Rd, Westport, CT 06880
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  /40

  $2,950,000

  Coming Soon

  • 5 Beds
  • 7 Baths
  • 6,302 Sq Ft

  72 Compo Rd N, Westport, CT 06880

  Incredibly located moments from downtown, Winslow Park, commuting routes, schools, beaches & more, this grand home on an acre of landscaped property with a stunning gunite pool is ready to exceed your expectations. This sun-splashed home blends the best of a traditional Colonial with modern flair, including high ceilings, tall windows, generous room scale and features for maximum comfort

  Alex Chingas Coldwell Banker Realty

  72 Compo Rd N, Westport, CT 06880
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  /40

  $15,000,000

  • 7 Beds
  • 10 Baths
  • 9,129 Sq Ft

  4800 Congress St, Fairfield, CT 06824

  The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
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  /6

  $1,045,000

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,965 Sq Ft

  165 Salt Meadow Rd, Fairfield, CT 06824

  Discover "The Meadows", one of Fairfield Beach's best kept secrets. The homes are sprawled across wide, winding streets lined with mature oak and maple trees, and enveloped by protected salt marsh and bird sanctuaries. Enjoy direct access to Pine Creek Marsh Trails, walk to the Carl Dickman Golf Course, Tennis Courts/Bubble, Ball Fields, and enjoy sunsets across South Pine Creek Beach. The

  Denise Walsh William Raveis Real Estate

  165 Salt Meadow Rd, Fairfield, CT 06824
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  /40

  $6,995,000

  New Construction $500K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,260 Sq Ft

  16 Westport Ave, Westport, CT 06880

  Brand-new net-zero coastal smart home, steps from Compo Beach, built to run quietly through whatever Long Island Sound throws at it. 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

  Karen Scott Compass Connecticut, LLC

  16 Westport Ave, Westport, CT 06880
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  /40

  $5,925,000

  • 6 Beds
  • 9 Baths
  • 6,561 Sq Ft

  3 Stony Point W, Westport, CT 06880

  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

  Debra Shaughnessy Coldwell Banker Realty

  3 Stony Point W, Westport, CT 06880
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  /40

  $2,790,000

  • 5 Beds
  • 3 Baths
  • 3,072 Sq Ft

  56 Charcoal Hill Rd, Westport, CT 06880

  A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail,

  Doug Bross Coldwell Banker Realty

  56 Charcoal Hill Rd, Westport, CT 06880
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  /19

  $3,900,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  1008 Fairfield Beach Rd, Fairfield, CT 06824

  1008 Fairfield Beach Road- A Masterpiece on Fairfield's Iconic Coastline. Where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one of the

  Valerie Alvarez Serhant Connecticut, LLC

  1008 Fairfield Beach Rd, Fairfield, CT 06824
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  /36

  $5,750,000

  • 5 Beds
  • 8 Baths
  • 6,503 Sq Ft

  31 Stonybrook Rd, Westport, CT 06880

  Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an

  Kristi Law William Pitt Sotheby's Int'l

  31 Stonybrook Rd, Westport, CT 06880
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  /40

  $3,500,000

  Open Thu 11AM - 1PM $500K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 4,911 Sq Ft

  22 Sturges Commons, Westport, CT 06880

  22 Sturges Commons offers the rare combination of timeless elegance, true neighborhood living, and unmatched convenience in one of Westport's most sought-after locations near the Hunt Club. Just one traffic light to the Greens Farms Station train station, this home makes commuting to New York City effortless while allowing you to return home to a peaceful walking neighborhood where charming

  Judy Michaelis Coldwell Banker Realty

  22 Sturges Commons, Westport, CT 06880
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  /40

  $5,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  69 Birch Rd, Fairfield, CT 06824

  Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with

  Jaclyn Picarillo Higgins Group Bedford Square

  69 Birch Rd, Fairfield, CT 06824
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  /40

  $4,850,000

  • 5 Beds
  • 5 Baths
  • 5,103 Sq Ft

  22 Evergreen Ave, Westport, CT 06880

  Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate

  Valerie Alvarez Serhant Connecticut, LLC

  22 Evergreen Ave, Westport, CT 06880
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  /14

  $8,696,000

  New Construction

  • 7 Beds
  • 8 Baths
  • 9,422 Sq Ft

  688 Hulls Farm Rd, Southport, CT 06890

  Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury

  Jaclyn Picarillo Higgins Group Bedford Square

  688 Hulls Farm Rd, Southport, CT 06890
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  /34

  $4,700,000

  • 6 Beds
  • 6.5 Baths
  • 7,575 Sq Ft

  21 Daniel Ct, Westport, CT 06880

  Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn.

  Meredith Cohen Serhant Connecticut, LLC

  21 Daniel Ct, Westport, CT 06880
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  /40

  $1,975,000

  • 4 Beds
  • 3 Baths
  • 3,253 Sq Ft

  5 Tanglewood Ln, Westport, CT 06880

  Set on a quiet, convenient street in Westport's coveted Old Hill, this charming home captures the essence of Fairfield County living. A picturesque acre with level lawns, a sparkling pool, and expansive patios creates an exceptional outdoor retreat ideal for relaxing or entertaining. A welcoming front porch leads into a thoughtfully renovated interior with beautifully proportioned spaces and

  Doug Bross Coldwell Banker Realty

  5 Tanglewood Ln, Westport, CT 06880
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  /39

  $2,995,000

  $355K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,789 Sq Ft

  221 Greens Farms Rd, Westport, CT 06880

  The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and

  Patricia Shea Coldwell Banker Realty

  221 Greens Farms Rd, Westport, CT 06880
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  /39

  $1,899,000

  • 4 Beds
  • 5 Baths
  • 3,921 Sq Ft

  2177 Cross Hwy, Fairfield, CT 06824

  Down a long private driveway on the Westport border, past a peaceful pond and into a setting that feels worlds away, 2177 Cross Hwy welcomes you home. This iconic contemporary blends dramatic architecture with everyday comfort, offering nearly 4,000 sq ft of functional living space designed for gathering, relaxing and entertaining. Soaring 22' ceilings and park-like views fill the main living

  JaKeith Action Jackson ASJ Realty Partners

  2177 Cross Hwy, Fairfield, CT 06824
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  /2

  $5,980,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 10,521 Sq Ft

  21 Sturges Commons, Westport, CT 06880

  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

  21 Sturges Commons, Westport, CT 06880
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  /2

  $6,999,999

  New Construction

  • 6 Beds
  • 9 Baths
  • 10,521 Sq Ft

  32 Narrow Rocks Rd, Westport, CT 06880

  NEW CONSTRUCTION BY RENOWNED LUXURY BUILDER MATTERA CONSTRUCTION - STEPS TO COMPO BEACH! A rare opportunity to own a brand-new, architecturally refined home in one of Westport's most coveted coastal locations-just steps to Compo Beach, Longshore Club, downtown Westport, the train, and schools. Currently under construction, this impeccably designed 6-bedroom residence spans four finished levels

  Judy Michaelis Coldwell Banker Realty

  32 Narrow Rocks Rd, Westport, CT 06880
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  /40

  $5,650,000

  New Construction

  • 7 Beds
  • 9 Baths
  • 8,762 Sq Ft

  8 Pleasant Valley Ln, Westport, CT 06880

  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

  Doug Bross Coldwell Banker Realty

  8 Pleasant Valley Ln, Westport, CT 06880
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  /15

  $6,995,826

  New Construction

  • 6 Beds
  • 10 Baths
  • 8,417 Sq Ft

  24 Edgemarth Hill Rd, Westport, CT 06880

  This Beauty will be ready Summer 2026! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted

  Jaclyn Picarillo Higgins Group Bedford Square

  24 Edgemarth Hill Rd, Westport, CT 06880
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  /7

  $10,650,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,100 Sq Ft

  11 Dogwood Ln, Westport, CT 06880

  Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

  Jen Kass Higgins Group Bedford Square

  11 Dogwood Ln, Westport, CT 06880

Showing Results 41 - 65, Page 2 of 2