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5 Bedroom Homes in Westport, CT
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19 listings
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5 Bedroom Homes in Westport, CT

5 Bedroom Homes in Westport, CT

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19 Listings
Map

5 Bedroom Homes in Westport, CT

19 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 191 Bayberry Lane — photo38Active

    $4,299,000

    5 bd · 5 ba · — sqft

    191 Bayberry Lane, Westport, CT

    Douglas Bross · Coldwell Banker Realty

  2. 4 Turkey Hill Lane — photo37Active

    $3,295,000

    5 bd · 5 ba · — sqft

    4 Turkey Hill Lane, Westport, CT

    Arthur Richards · eRealty Advisors, Inc.

  3. 23 Punch Bowl Drive — photo20Active

    $2,500,000

    5 bd · 5 ba · — sqft

    23 Punch Bowl Drive, Westport, CT

    Sandy Petrino · William Pitt Sotheby's Int'l

  4. 11 Woodside Lane — photo39Active

    $4,050,000

    5 bd · 6 ba · — sqft

    11 Woodside Lane, Westport, CT

    Cyd Hamer · William Pitt Sotheby's Int'l

  5. 1 Melon Patch Lane — photo40Active

    $2,050,000

    5 bd · 5 ba · — sqft

    1 Melon Patch Lane, Westport, CT

    Linda Raymond · William Raveis Real Estate

  6. 9 Berkeley Road — photo26Active

    $3,695,000

    5 bd · 5 ba · — sqft

    9 Berkeley Road, Westport, CT

    Jonathan Makovsky · Compass Connecticut, LLC

  7. 7 Elizabeth Drive — photo40Active

    $3,395,000

    5 bd · 6 ba · — sqft

    7 Elizabeth Drive, Westport, CT

    Karen Scott · Compass Connecticut, LLC

  8. 4 Bradley Street — photo36Active

    $2,885,000

    5 bd · 4 ba · 3,255 sqft

    4 Bradley Street, Westport, CT

    Hyleri Katzenberg · Compass Connecticut, LLC

  9. 20 Turkey Hill Circle — photo35Active

    $7,250,000

    5 bd · 9 ba · 9,648 sqft

    20 Turkey Hill Circle, Westport, CT

    Meredith Cohen · Serhant Connecticut, LLC

  10. 14 Owenoke Park — photo40Active

    $10,985,000

    5 bd · 7 ba · 6,050 sqft

    14 Owenoke Park, Westport, CT

    Deirdre Andreoli · Compass Connecticut, LLC

  11. 1 Twin Oaks Lane — photo40Active

    $4,750,000

    5 bd · 7 ba · 8,521 sqft

    1 Twin Oaks Lane, Westport, CT

    Douglas Bross · Coldwell Banker Realty

  12. 4 Crawford Road — photo40Active

    $2,595,000

    5 bd · 4 ba · 4,471 sqft

    4 Crawford Road, Westport, CT

    Barbara Sweeney · Coldwell Banker Realty

  13. 31 Stonybrook Road — photo36Active

    $5,349,000

    5 bd · 8 ba · 6,503 sqft

    31 Stonybrook Road, Westport, CT

    Kristi Law · William Pitt Sotheby's Int'l

  14. 4 Lantern Hill Road — photo14Active

    $6,650,000

    5 bd · 7 ba · 11,000 sqft

    4 Lantern Hill Road, Westport, CT

    Ian Defronze · Serhant Connecticut, LLC

  15. 52 Compo Mill Cove — photo25Active

    $6,800,000

    5 bd · 4 ba · 3,967 sqft

    52 Compo Mill Cove, Westport, CT

    Carly Woodard · William Pitt Sotheby's Int'l

  16. 53 Clinton Avenue — photoPrice Reduced40Active

    $2,499,000

    5 bd · 6 ba · 5,319 sqft

    53 Clinton Avenue, Westport, CT

    Alexander Chingas · Coldwell Banker Realty

  17. 279 Saugatuck Avenue — photo43Active

    $14,900,000

    5 bd · 8 ba · 9,546 sqft

    279 Saugatuck Avenue, Westport, CT

    Joseph Barbieri · Sotheby's International Realty

  18. 22 Evergreen Avenue — photo40Active

    $4,850,000

    5 bd · 5 ba · 5,103 sqft

    22 Evergreen Avenue, Westport, CT

    Valerie Alvarez · Serhant Connecticut, LLC

  19. 1 Coastal Court — photo22Active

    $4,995,000

    5 bd · 7 ba · 5,550 sqft

    1 Coastal Court, Westport, CT

    Julie Vanderblue · Higgins Group Real Estate

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

Greenwich MLS (GMLS)
Listing data courtesy of Greenwich MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.
Listing information ©2026 Greenwich MLS, Inc®. All Rights Reserved. Last Updated: 2026-09-16 13:55:32 UTC
SmartMLS
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #REB.0790925

    Call Thomas

    Westport, CT community profile

    Area
    26 sq. mi.

    Source: HJN community data

    Westport housing market

    September 2026 · This period is still settling

    Selling at 100.5% of asking price

    Buyers here are paying above asking. MLS · 18 sales · as of Sep 30, 2026

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $4,995,000
    Homes for sale
    64
    Median days on market
    19 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    2,936 sq. ft.