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Luxury Homes in Fairfield, CT
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71 listings
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Luxury Homes in Fairfield, CT

Luxury Homes in Fairfield, CT

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24 of 71 Listings
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Luxury Homes in Fairfield, CT

24 of 71 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 67 Craig Court — photoNew40Active

    $2,300,000

    4 bd · 4 ba · — sqft

    67 Craig Court, Fairfield, CT

    Laurie Quatrella · Higgins Group Real Estate

  2. 204 Old Post Road Unit 1 — photoNew16Active

    $2,695,000

    3 bd · 4 ba · — sqft

    204 Old Post Road Unit 1, Fairfield, CT

    Jennifer McDade · BHHS Darien/New Canaan

  3. 443 Brambley Hedge Circle — photo40Active

    $2,695,000

    4 bd · 7 ba · — sqft

    443 Brambley Hedge Circle, Fairfield, CT

    Paul Triantafel · William Pitt Sotheby's Int'l

  4. 108 Colonial Drive — photo40Active

    $2,795,000

    5 bd · 4 ba · — sqft

    108 Colonial Drive, Fairfield, CT

    Nancy Freedman · William Pitt Sotheby's Int'l

  5. 590 Sturges Highway — photo27Active

    $5,975,000

    6 bd · 8 ba · — sqft

    590 Sturges Highway, Fairfield, CT

    Julie Vanderblue · Higgins Group Real Estate

  6. 195 Old South Road — photo40Active

    $4,950,000

    4 bd · 5 ba · — sqft

    195 Old South Road, Fairfield, CT

    Matt Lahey · Higgins Group Real Estate

  7. 28 Country Road Unit 28 — photo33Active

    $1,199,000

    4 bd · 4 ba · — sqft

    28 Country Road Unit 28, Fairfield, CT

    Denise Daniels-Biagi · Coldwell Banker Realty

  8. 1321 Brookside Drive — photo40Active

    $1,500,000

    2 bd · 2 ba · — sqft

    1321 Brookside Drive, Fairfield, CT

    Annie Klyver · Higgins Group Real Estate

  9. 285 Old Dam Road — photo28Active

    $2,100,000

    4 bd · 3 ba · — sqft

    285 Old Dam Road, Fairfield, CT

    Robin Righter · Houlihan Lawrence

  10. 41 Reynolds Drive — photo40Active

    $1,399,000

    4 bd · 3 ba · — sqft

    41 Reynolds Drive, Fairfield, CT

    Sarah Fair · William Raveis Real Estate

  11. 2177 Cross Highway — photo40Active

    $1,875,000

    4 bd · 5 ba · — sqft

    2177 Cross Highway, Fairfield, CT

    Derek Greene · Derek Greene

  12. 280 Tuckahoe Lane — photo12Active

    $2,199,999

    6 bd · 7 ba · — sqft

    280 Tuckahoe Lane, Fairfield, CT

    Elizabeth Casey · William Raveis Real Estate

  13. 73 Old Dam Road — photo36Active

    $1,875,000

    4 bd · 3 ba · — sqft

    73 Old Dam Road, Fairfield, CT

    Katie O'Grady · Compass Connecticut, LLC

  14. 228 Woodrow Avenue — photo28Active

    $1,180,000

    3 bd · 2 ba · — sqft

    228 Woodrow Avenue, Fairfield, CT

    Happy Wang · Keller Williams Realty

  15. 265 Autumn Ridge Road — photo39Active

    $1,495,000

    5 bd · 3 ba · — sqft

    265 Autumn Ridge Road, Fairfield, CT

    Lindsay Violette · Houlihan Lawrence

  16. 128 Linley Drive — photo40Active

    $1,195,000

    3 bd · 3 ba · — sqft

    128 Linley Drive, Fairfield, CT

    Victor Vitti · Higgins Group Real Estate

  17. 999 Bronson Road — photo39Active

    $1,949,000

    4 bd · 3 ba · — sqft

    999 Bronson Road, Fairfield, CT

    Jackie Davis · William Raveis Real Estate

  18. 211 Old Farm Road — photo40Active

    $1,050,000

    4 bd · 3 ba · — sqft

    211 Old Farm Road, Fairfield, CT

    Cedric Smith · ERA Insite Realty Services

  19. 97 Gorham Road — photoPrice Reduced25Active

    $1,049,000

    4 bd · 2 ba · 1,697 sqft

    97 Gorham Road, Fairfield, CT

    Erica Acheychek · Compass Connecticut, LLC

  20. 1859 Fairfield Beach Road — photo33Active

    $6,499,000

    4 bd · 5 ba · 3,511 sqft

    1859 Fairfield Beach Road, Fairfield, CT

    Mary Kate Klemish-Boehm · Brown Harris Stevens

  21. 11 Oldfield Drive — photo38Active

    $1,195,000

    4 bd · 2 ba · 2,124 sqft

    11 Oldfield Drive, Fairfield, CT

    Andrew Whiteley · Brown Harris Stevens

  22. 738 Rowland Road — photoPrice Reduced37Active

    $1,675,000

    3 bd · 3 ba · 2,360 sqft

    738 Rowland Road, Fairfield, CT

    Lynn Dolan · William Pitt Sotheby's Int'l

  23. 50 Southport Place 50 — photo40Active

    $1,350,000

    3 bd · 4 ba · 3,288 sqft

    50 Southport Place 50, Fairfield, CT

    Helene Daly · Compass Connecticut, LLC

  24. 2493 Redding Road — photo40Active

    $2,395,000

    5 bd · 5 ba · 5,415 sqft

    2493 Redding Road, Fairfield, CT

    John Foran · Compass Connecticut, LLC

123

About Luxury Homes in Fairfield, CT

Luxury Homes in Fairfield, CT: 71 active listings as of October 10, 2026, 03:26 UTC.

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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

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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

    Fairfield, CT community profile

    Area
    27.6 sq. mi.

    Source: HJN community data

    Fairfield housing market

    September 2026 · This period is still settling

    Fairfield 12-month median sale price trend

    Selling at 104.3% of asking price

    Buyers here are paying above asking. MLS · 39 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 11, 2026

    Median sale price
    $1,030,000$772,500–$1,382,500 typical range
    Price per sq. ft.
    $582
    Sales
    22
    Paid in cash
    27.3%

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

    Median list price
    $1,049,000
    Homes for sale
    117
    Median days on market
    25 days

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

    Year-over-year
    21.3%

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

    Median home size
    1,969 sq. ft.