Browse All Westport CT 5 Bedroom Properties for Sale

Better than new, this 2025 build by AR Luxury Homes is situated on a sought-after cul-de-sac in Long Lots. This 5/6 bedroom, 6.5-bath residence combines thoughtful design...

5 Beds
7 Baths
24198123 MLS

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

14 High Point Rd, Westport $2,999,999

Classic Colonial 5 Bedroom 5 - 1/2 Bath set on over 1 acre with a Gunite Swimming Pool on Westport's longest and perhaps, most sought after Cul-De-Sac! Almost 4700 sq ft ...

5 Beds
6 Baths
24213615 MLS

4 Surrey Ln, Westport $2,795,000

Lovingly cherished by the same family for over 50 years, this 1965 five bedroom home presents a wonderful opportunity to create something truly special in one of Westport...

5 Beds
4 Baths
24213304 MLS

142 Easton Rd, Westport $2,950,000

A rare opportunity to own an exceptional woodland estate, where space, serenity, and natural beauty converge. Set beyond a long, gracefully winding driveway, this expansi...

5 Beds
6 Baths
24212624 MLS

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

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 $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

7 Elizabeth Dr, Westport $3,395,000

Located on a quiet cul-de-sac, this home offers a beautiful blend of thoughtful architecture + effortless everyday living. If you've been searching for a residence that b...

5 Beds
6 Baths
24209742 MLS

4 Bradley St, Westport $2,885,000

Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five...

5 Beds
4 Baths
24209324 MLS

20 Turkey Hill Cir, Westport $6,800,000 ▼

The home offers timeless and classic New England, the charm you have been seeking. Set up on a quiet hill in the heart of Green Farms, this picturesque shingle home check...

5 Beds
9 Baths
24206974 MLS

14 Owenoke Park, Westport $10,985,000

100% FEMA compliant & storm friendly AND 100% completed, this special new construction Bluewater Home is priced to SELL. Located steps from Compo Beach on prestigious Owe...

5 Beds
7 Baths
24207610 MLS

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

28 Bulkley Ave N, Westport $2,350,000

Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens F...

5 Beds
5 Baths
24203971 MLS

4 Crawford Rd, Westport $2,595,000

Privately nestled in Westport's coveted Old Hill neighborhood, this distinctive five-bedroom New England residence blends timeless character with thoughtful modern update...

5 Beds
4 Baths
24203288 MLS

31 Stonybrook Rd, Westport $5,199,000 ▼

From the moment you enter the gates of this Old Hill estate, you know you've arrived- a rare sanctuary built with a level of custom stonework and craftsmanship impossible...

5 Beds
8 Baths
24201547 MLS

52 Compo Mill Cv, Westport $6,800,000

The best vacations are the ones you never have to leave. Set on the shores of Compo Mill Cove in the heart of Westport's coveted Compo Beach neighborhood, this exceptio...

5 Beds
4 Baths
24193394 MLS

53 Clinton Ave, Westport $2,499,000 ▼

Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparkling home showcases pride of ownership. A new 2026 drivewa...

5 Beds
6 Baths
24079819 MLS

279 Saugatuck Ave, Westport $14,900,000

Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes...

5 Beds
9 Baths
24179641 MLS

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 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

5 Franklin Ave, Westport $4,299,000 ▲

Nestled in one of Westport's most desirable walk-to-town neighborhoods, this exceptional new construction home combines timeless charm with modern luxury. Designed by acc...

5 Beds
6 Baths
24115906 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.

5 Bedroom Westport Real Estate

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