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Westport CT Homes for Sale ($3MM - $5MM)

2-A Owenoke Park, Westport image
2-A Owenoke Park, Westport $4,999,999

The property consists of 17 waterfront acres including a 7 acre upland section.

  • 24215220 MLS
22 Dawn Dr, Westport image
22 Dawn Dr, Westport $4,995,700

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 t...

  • 4 Beds
  • 5 Baths
  • 24176377 MLS
238 Hillspoint Rd, Westport image
238 Hillspoint Rd, Westport $4,995,000

The dream of waterfront living is officially taking shape-construction is underway by renowned builder The O'Dell Group. This is your chance to secure a front-row seat to...

  • 3 Beds
  • 4 Baths
  • 24194201 MLS
1 Coastal Ct, Westport image
1 Coastal Ct, Westport $4,995,000

Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of ...

  • 5 Beds
  • 7 Baths
  • 24126503 MLS
22 Evergreen Ave, Westport image
22 Evergreen Ave, Westport $4,850,000

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 i...

  • 5 Beds
  • 5 Baths
  • 24172211 MLS
2 Windy Hill Rd, Westport image
2 Windy Hill Rd, Westport $4,600,000

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 Cypres...

  • 6 Beds
  • 8 Baths
  • 24204809 MLS
1 Twin Oaks Ln, Westport image
1 Twin Oaks Ln, Westport $4,550,000 ▼

A fresh take on Modern Luxury awaits at this new construction home set on stunning property in the Old Hill area of Westport. Now complete and ready for immediate enjoyme...

  • 5 Beds
  • 7 Baths
  • 24204438 MLS
159 Easton Rd, Westport image
159 Easton Rd, Westport $4,450,000

YES - we have the CO!! :) The home you've been waiting for is ready for sale and yes; you can close and move in in time to host Thanksgiving!! How much would you love a h...

  • 6 Beds
  • 8 Baths
  • 24215185 MLS
19 Roosevelt Rd, Westport image
19 Roosevelt Rd, Westport $4,250,000

Tucked along a tranquil lane, mere steps from the soft sands of Westport's coveted Compo Beach, 19 Roosevelt Road is coastal living at its most refined. This picture-perf...

  • 4 Beds
  • 4 Baths
  • 24213343 MLS
6 Janson Dr, Westport image
6 Janson Dr, Westport $4,250,000

Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. ...

  • 6 Beds
  • 9 Baths
  • 24165540 MLS
22 Fillow St, Westport image
22 Fillow St, Westport $4,050,000

NEW CONSTRUCTION BY RENOWNED WESTPORT LUXURY BUILDER WALTER MATTERA IN THE CHERISHED FLOWER ESTATES NEIGHBORHOOD! An exceptional opportunity to own a brand-new 5-bedroom,...

  • 5 Beds
  • 8 Baths
  • 24215100 MLS
11 Woodside Ln, Westport image
11 Woodside Ln, Westport $4,050,000

Privately set in Westport's coveted Old Hill neighborhood, this like-new sophisticated residence designed by famed architect Peter Wormser pairs striking architecture wit...

  • 5 Beds
  • 6 Baths
  • 24211806 MLS
9 Berkeley Rd, Westport image
9 Berkeley Rd, Westport $3,695,000

Exceptional new construction, 9 Berkeley Road presents a sophisticated interpretation of modern Westport living, blending timeless architecture with beautifully considere...

  • 5 Beds
  • 5 Baths
  • 24209539 MLS
17 Greenbrier Rd, Westport image
17 Greenbrier Rd, Westport $3,450,000

Welcome to 17 Greenbrier Rd- an irreplaceable masterpiece that perfectly balances elite, high-end refinement with effortless daily livability. Nestled high in a vibrant N...

  • 4 Beds
  • 4 Baths
  • 24216789 MLS
9 N Ridge Rd, Westport image
9 N Ridge Rd, Westport $3,400,000

In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can be...

  • 6 Beds
  • 7 Baths
  • 24208426 MLS
4 Turkey Hill Ln, Westport image
4 Turkey Hill Ln, Westport $3,295,000

Built in 2013 by Chris O'Dell, this 5-bedroom, 5.5-bathroom, 5,318 sq. ft. home sits on 1.07 acres in Westport's Long Lots neighborhood. Used exclusively as a summer retr...

  • 5 Beds
  • 5 Baths
  • 24212748 MLS

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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