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

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
1 Twin Oaks Ln, Westport image
1 Twin Oaks Ln, Westport $4,750,000

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
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
159 Easton Rd, Westport image
159 Easton Rd, Westport $4,450,000

Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views f...

  • 6 Beds
  • 8 Baths
  • 24145772 MLS
16 Rockyfield Rd, Westport image
16 Rockyfield Rd, Westport $4,250,000

Ready to enjoy from day 1, all of the work has been done to upgrade and update 16 Rockyfield Road.The residence has been completely retooled (ask for the upgrade list!). ...

  • 5 Beds
  • 7 Baths
  • 24200327 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
61 Clapboard Hill Rd, Westport image
61 Clapboard Hill Rd, Westport $3,795,000 ▼

Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private ...

  • 4 Beds
  • 4 Baths
  • 24171986 MLS
9 N Ridge Rd, Westport image
9 N Ridge Rd, Westport $3,550,000

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
  • 24191286 MLS
240 North Ave, Westport image
240 North Ave, Westport $3,499,000

"MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed...

  • 5 Beds
  • 5 Baths
  • 24181944 MLS
27 Woody Ln, Westport image
27 Woody Ln, Westport $3,400,000

This beautifully renovated Ward French custom home offers elegant formal spaces, a chef's kitchen, flexible guest and office accommodations, a luxury primary suite, fitne...

  • 5 Beds
  • 5 Baths
  • 24204780 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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