Westport, CT Homes for Sale with Pool

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  $5,599,000

  • 6 Beds
  • 9 Baths
  • 9,394 Sq Ft

  5 W Branch Rd, Westport, CT 06880

  Carefully crafted Connecticut modern farmhouse by award-winning Heine Development, this exceptional 6-bedroom residence blends timeless architecture with refined contemporary living amongst 4 finished levels on 2 private, level acres in one of Westport's most convenient luxury locations. Designed with perfection in symmetry, detail, and craftsmanship, the home pairs classic farmhouse inspiration

  Linda Skolnick Coldwell Banker Realty

  5 W Branch Rd, Westport, CT 06880
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  $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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  $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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  $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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  $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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  $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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  $5,650,000

  New Construction Open Sat 1PM - 3PM

  • 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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  $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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  $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
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  $5,199,000

  New Construction Open Sat 12PM - 3PM

  • 6 Beds
  • 8 Baths
  • 8,935 Sq Ft

  4 Sycamore Dr, Westport, CT 06880

  Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is a new construction lux home from CCO Habitats. 3 levels of finished living space with 10 foot ceilings on the 1st floor give an amazing sense of openness, as well as better functionality than 4 level homes. Think about it. Who really wants to walk up to the third floor every day? That's right; no one.

  Maryann Levanti Higgins Group Bedford Square

  4 Sycamore Dr, Westport, CT 06880
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  $1,075,000

  Open Fri 11AM - 1PM Coming Soon

  • 4 Beds
  • 3 Baths
  • 3,024 Sq Ft

  211 Newtown Turnpike, Wilton, CT 06897

  Set along the banks of a peaceful river on a level, professionally landscaped 1.10-acre lot, this enchanting 1953 Cape Cod estate seamlessly blends timeless New England charm with modern comfort. From the moment you arrive, the in-ground concrete pool creates a private resort-like setting, while the tranquil riverfront backdrop offers a rare sense of serenity and connection to nature. Inside, the

  Ryan Sullivan Berkshire Hathaway NE Prop.

  211 Newtown Turnpike, Wilton, CT 06897
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  $1,899,000

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

  2177 Cross Hwy, Fairfield, CT 06824

  2177 Cross Hwy welcomes you home. This extensively renovated iconic contemporary awaits your personal touches. The blending of dramatic architecture with everyday comfort, offering nearly 4,000 sq ft of functional living space designed for gathering, relaxing and entertaining. Soaring 22' ceilings, oversized windows and park-like views fill the main living area with light, while a striking

  JaKeith Action Jackson ASJ Realty Partners

  2177 Cross Hwy, Fairfield, CT 06824

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