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5 Bedroom Homes in New Canaan, CT
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5 Bedroom Homes in New Canaan, CT

5 Bedroom Homes in New Canaan, CT

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17 Listings
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5 Bedroom Homes in New Canaan, CT

17 Listings

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Thomas O'Leary

Realty.com

Lic. #REB.0790925

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  1. 68 Old Stamford Road — photoNew37Active

    $1,495,000

    5 bd · 3 ba · 2,788 sqft

    68 Old Stamford Road, New Canaan, CT

    Ted Sibilia · Keller Williams Prestige Props

  2. 102 Silver Ridge Road — photo40Active

    $5,475,000

    5 bd · 7 ba · 8,096 sqft

    102 Silver Ridge Road, New Canaan, CT

    Katie Nugent · Berkshire Hathaway NE Prop.

  3. 716 Cheese Spring Road — photo37Active

    $3,600,000

    5 bd · 6 ba · — sqft

    716 Cheese Spring Road, New Canaan, CT

    Melissa Engel · Douglas Elliman of Connecticut

  4. 284 Park Street — photo33Active

    $3,450,000

    5 bd · 5 ba · — sqft

    284 Park Street, New Canaan, CT

    John Dunn · Compass Connecticut, LLC

  5. 51 Briscoe Road — photo40Active

    $4,250,000

    5 bd · 7 ba · 8,243 sqft

    51 Briscoe Road, New Canaan, CT

    Michele Murray Sloan · Houlihan Lawrence

  6. 761 New Norwalk Road — photoPrice Reduced37Active

    $1,599,000

    5 bd · 4 ba · 2,904 sqft

    761 New Norwalk Road, New Canaan, CT

    Kelly Defrancesco · William Raveis Real Estate

  7. 16 Grace Street — photo38Active

    $2,995,000

    5 bd · 5 ba · 2,778 sqft

    16 Grace Street, New Canaan, CT

    Hannelore Kaplan · William Raveis Real Estate

  8. 78 & 92 Pastures Lane — photo110Active

    $8,995,000

    5 bd · 7 ba · 8,438 sqft

    78 & 92 Pastures Lane, New Canaan, CT

    Danielle Malloy · Serhant Connecticut LLC

  9. 248 Turtle Back Road — photo38Active

    $4,000,000

    5 bd · 6 ba · 5,291 sqft

    248 Turtle Back Road, New Canaan, CT

    John Dunn · Compass Connecticut, LLC

  10. 38 Gerrish Lane — photoPrice Reduced40Active

    $3,695,000

    5 bd · 6 ba · 5,374 sqft

    38 Gerrish Lane, New Canaan, CT

    Christine Saxe · Compass Connecticut, LLC

  11. 215 Cross Ridge Road — photoPrice Reduced37Active

    $2,950,000

    5 bd · 6 ba · 6,261 sqft

    215 Cross Ridge Road, New Canaan, CT

    Maxwell Erni · The Bridge Realty Inc.

  12. 48 Driftway Lane — photoPrice Reduced39Active

    $6,500,000

    5 bd · 7 ba · 10,655 sqft

    48 Driftway Lane, New Canaan, CT

    Danielle Spada · Coldwell Banker Realty

  13. 537 Oenoke Ridge — photoPrice Reduced38Active

    $4,700,000

    5 bd · 7 ba · 6,823 sqft

    537 Oenoke Ridge, New Canaan, CT

    Douglas Milne · Houlihan Lawrence

  14. 171 Proprietors Crossing — photoPrice Reduced32Active

    $2,495,000

    5 bd · 4 ba · 5,532 sqft

    171 Proprietors Crossing, New Canaan, CT

    Jaime Sneddon · William Pitt Sotheby's Int'l

  15. 145 River Street — photo37Active

    $2,695,000

    5 bd · 6 ba · 5,300 sqft

    145 River Street, New Canaan, CT

    Ruth Jones · Blue Anchor Realty Group

  16. 67 Carter Street — photo8Active

    $5,500,000

    5 bd · 8 ba · 9,300 sqft

    67 Carter Street, New Canaan, CT

    Richard Breglia · Coldwell Banker Realty

  17. 44 Benedict Hill Road — photo27Active

    $2,750,000

    5 bd · 4 ba · 3,200 sqft

    44 Benedict Hill Road, New Canaan, CT

    John-Michael Rachinsky-Wood · Harbor Bridge Realty

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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: 2026-10-07 15:41:52 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.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #REB.0790925

    Call Thomas

    New Canaan, CT community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    New Canaan housing market

    September 2026 · This period is still settling

    New Canaan 12-month median sale price trend

    Selling at 100.1% of asking price

    Sales here are closing essentially at asking. MLS · 23 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 4, 2026

    Median sale price
    $2,300,000$2,002,500–$2,525,000 typical range
    Price per sq. ft.
    $764
    Sales
    11
    Paid in cash
    18.2%

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

    Median list price
    $2,822,500
    Homes for sale
    62
    Median days on market
    18 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    39.4%

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

    Median home size
    3,355 sq. ft.