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5 Bedroom Homes in Greenwich, CT
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38 listings
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3 bedsNew constructionWith a pool

5 Bedroom Homes in Greenwich, CT

5 Bedroom Homes in Greenwich, CT

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19 of 38 Listings
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5 Bedroom Homes in Greenwich, CT

19 of 38 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 58 Halsey Drive — photoNew19Active

    $4,674,000

    5 bd · 7 ba · 5,497 sqft

    58 Halsey Drive, Greenwich, CT

    Natalya Parker · William Raveis Real Estate

  2. 50 Zaccheus Mead Lane — photo36Active

    $8,000,000

    5 bd · 7 ba · 5,953 sqft

    50 Zaccheus Mead Lane, Greenwich, CT

    Sally Maloney · Houlihan Lawrence

  3. 21 Calhoun Drive — photo14Active

    $6,150,000

    5 bd · 8 ba · 6,143 sqft

    21 Calhoun Drive, Greenwich, CT

    Danielle Malloy · Serhant Connecticut LLC

  4. 58 Shore Road — photo40Active

    $19,995,000

    5 bd · 7 ba · 7,000 sqft

    58 Shore Road, Greenwich, CT

    Danielle Malloy · Serhant Connecticut, LLC

  5. 89 Indian Field Road — photo55Active

    $3,495,000

    5 bd · 5 ba · 5,354 sqft

    89 Indian Field Road, Greenwich, CT

    Danielle Malloy · Serhant Connecticut LLC

  6. 18 Shady Brook Lane — photo37Active

    $3,450,000

    5 bd · 5 ba · 4,274 sqft

    18 Shady Brook Lane, Greenwich, CT

    Gloria Gimenez Ferrer · Berkshire Hathaway NE Prop.

  7. 7 Bailiwick Road — photo33Active

    $4,250,000

    5 bd · 6 ba · 5,482 sqft

    7 Bailiwick Road, Greenwich, CT

    Jennifer Leahy · Compass Connecticut, LLC

  8. 61 Center Drive — photo29Active

    $1,549,000

    5 bd · 3 ba · 2,353 sqft

    61 Center Drive, Greenwich, CT

    Roberta Jurik · Berkshire Hathaway NE Prop.

  9. 739 Lake Avenue — photo40Active

    $4,500,000

    5 bd · 6 ba · 5,281 sqft

    739 Lake Avenue, Greenwich, CT

    Carissa Larriuz · Houlihan Lawrence

  10. 18 Sidney Lanier Lane — photo27Active

    $4,500,000

    5 bd · 6 ba · 6,134 sqft

    18 Sidney Lanier Lane, Greenwich, CT

    BK Bates · Houlihan Lawrence

  11. 37 Mary Lane — photo36Active

    $2,999,000

    5 bd · 4 ba · 3,176 sqft

    37 Mary Lane, Greenwich, CT

    Joy Kim Metalios · Houlihan Lawrence

  12. 14 Highview Avenue — photo23Active

    $3,495,000

    5 bd · 3 ba · 3,670 sqft

    14 Highview Avenue, Greenwich, CT

    Mark Pires · Coldwell Banker Realty

  13. 74 Glenville Road — photo28Active

    $4,500,000

    5 bd · 6 ba · 4,937 sqft

    74 Glenville Road, Greenwich, CT

    Chelsea Hammerschmidt · William Pitt Sotheby's Int'l

  14. 121 Round Hill Road — photo8Active

    $4,995,000

    5 bd · 5 ba · 3,573 sqft

    121 Round Hill Road, Greenwich, CT

    Sabine Schoenberg · PrimeSites, Inc.

  15. 1 Hendrie Dr Extension — photo8Active

    $3,300,000

    5 bd · 3 ba · 2,092 sqft

    1 Hendrie Dr Extension, Greenwich, CT

    Susan Connal · Coldwell Banker Realty

  16. 64 Hillside Road — photo12Active

    $7,495,000

    5 bd · 8 ba · 6,975 sqft

    64 Hillside Road, Greenwich, CT

    Amanda Bates · Houlihan Lawrence

  17. 203 Shore Road — photo40Active

    $9,875,000

    5 bd · 6 ba · 6,723 sqft

    203 Shore Road, Greenwich, CT

    Tracey Koorbusch · Sotheby's International Realty

  18. 65 Sherwood Place — photo31Active

    $2,490,000

    5 bd · 6 ba · 2,885 sqft

    65 Sherwood Place, Greenwich, CT

    Scott Kelland · CLS Group

  19. 65 Sherwood Place 65 — photo30Active

    $2,490,000

    5 bd · 6 ba · 2,885 sqft

    65 Sherwood Place 65, Greenwich, CT

    Scott Kelland · CLS Group

12

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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: 2026-09-11 20:44:04 UTC
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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.
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    Thomas O'Leary

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