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95 Properties
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95 Properties Available

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  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
  • 50 Overlook DR, Chappaqua, NY 10514
    6 Beds6 Baths5,234 SqFt
    1/36 36
    Coming Soon

    $2,225,000

    50 Overlook DR, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 200 Millwood RD, Chappaqua, NY 10514
    4 Beds3 Baths3,009 SqFt
    1/32 32
    Open Sat 12PM-2PM

    $1,799,999

    200 Millwood RD, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

  • 34 Glenside PL, Chappaqua, NY 10514
    3 Beds2 Baths1,880 SqFt
    1/40 40
    Open Sat 11AM-3PM

    $1,199,000

    34 Glenside PL, Chappaqua, NY 10514

    Listed by Keller Williams NY Realty

  • 249 Mill River RD, Chappaqua, NY 10514
    4 Beds2 Baths2,100 SqFt
    1/48 48
    New

    $863,400

    249 Mill River RD, Chappaqua, NY 10514

    Listed by Town and Village Real Estate

  • 41 Rambling Brook RD, Chappaqua, NY 10514
    3 Beds3 Baths1,416 SqFt
    1/29 29
    New

    $5,900

    41 Rambling Brook RD, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

  • 4 Southview RD, Chappaqua, NY 10514
    3 Beds3 Baths2,111 SqFt
    1/41 41
    New

    $1,425,000

    4 Southview RD, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 29 Begg DR, Chappaqua, NY 10514
    3 Beds3 Baths2,000 SqFt
    1/31 31
    New

    $1,200,000

    29 Begg DR, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 352 N Greeley AVE, Chappaqua, NY 10514
    1 Bed2 Baths1,100 SqFt
    1/19 19
    New

    $3,500

    352 N Greeley AVE, Chappaqua, NY 10514

    Listed by ERA Insite Realty Services

  • 61 Carolyn PL, Chappaqua, NY 10514
    5 Beds6 Baths5,907 SqFt
    1/39 39
    New

    $2,800,000

    61 Carolyn PL, Chappaqua, NY 10514

    Listed by Julia B Fee Sothebys Int. Rlty

  • 24 Glen TER, Chappaqua, NY 10514
    4 Beds3 Baths2,539 SqFt
    1/42 42
    Active

    $1,475,000

    24 Glen TER, Chappaqua, NY 10514

    Listed by William Raveis-New York, LLC

  • 35 Overlook DR, Chappaqua, NY 10514
    4 Beds7 Baths5,354 SqFt
    1/45 45
    Active

    $2,699,000

    35 Overlook DR, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

  • 100 Castle RD, Chappaqua, NY 10514
    3 Beds4 Baths2,590 SqFt
    1/40 40
    Price Dropped by $76K

    $1,049,000

    100 Castle RD, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 50 Kerry LN, Chappaqua, NY 10514
    4 Beds5 Baths4,051 SqFt
    1/32 32
    Active

    $1,890,000

    50 Kerry LN, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 26 Mayberry RD, Chappaqua, NY 10514
    5 Beds3 Baths3,200 SqFt
    1/30 30
    Active

    $1,265,000

    26 Mayberry RD, Chappaqua, NY 10514

    Listed by William Raveis-New York, LLC

  • 33 High WAY, Chappaqua, NY 10514
    3 Beds4 Baths1,917 SqFt
    1/36 36
    Active

    $1,199,000

    33 High WAY, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

  • 93 Haights Cross RD, Chappaqua, NY 10514
    4 Beds5 Baths6,542 SqFt
    1/42 42
    Active

    $3,499,000

    93 Haights Cross RD, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

  • 149 King ST #15, Chappaqua, NY 10514
    2 Beds3 Baths1,925 SqFt
    1/23 23
    Pending

    $820,000

    149 King ST #15, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 5 Briarcliff RD, Chappaqua, NY 10514
    4 Beds7 Baths7,305 SqFt
    1/48 48
    Active

    $3,699,999

    5 Briarcliff RD, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

  • 57 Hamilton DR, Chappaqua, NY 10514
    3 Beds3 Baths3,728 SqFt
    1/38 38
    Price Dropped by $75K

    $1,275,000

    57 Hamilton DR, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 124 Seven Bridges RD, Chappaqua, NY 10514
    3 Beds2 Baths1,918 SqFt
    1/44 44
    Active

    $1,200,000

    124 Seven Bridges RD, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 91 Bedford RD #2E, Chappaqua, NY 10514
    1 Bed1 Bath670 SqFt
    1/8 8
    Active

    $3,500

    91 Bedford RD #2E, Chappaqua, NY 10514

    Listed by ERA Insite Realty Services

  • 2 Dewitt DR, Chappaqua, NY 10514
    3 Beds4 Baths3,353 SqFt
    1/26 26
    Active

    $12,500

    2 Dewitt DR, Chappaqua, NY 10514

    Listed by Houlihan Lawrence Inc.

  • 7 High Point CIR, Chappaqua, NY 10514
    4 Beds4 Baths4,099 SqFt
    1/33 33
    Pending

    $1,525,000

    7 High Point CIR, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

  • 122 Valley View RD, Chappaqua, NY 10514
    6 Beds4 Baths3,939 SqFt
    1/32 32
    Pending

    $1,699,999

    122 Valley View RD, Chappaqua, NY 10514

    Listed by Compass Greater NY, LLC

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HomeSmart Homes and Estates

Michael & Tara Holmes License ID: 10401274851

+1(914) 292-1415 mikeholmesrealestate@gmail.com

777 Westchester Ave, White Plains, NY, 10604, USA

Fair Housing Notice: Federal, State and Local Fair Housing Laws protect individuals from housing discrimination. It is unlawful to discriminate based on certain protected characteristics, which include, but are not limited to: race, creed, color, national origin, sexual orientation, gender identity or expression, military status, sex, age, disability, marital status, lawful source of income or familial status. Click here to read more. Click here to view the New York Standardized Operating Proced

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      Home
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      Buy
      1. Affordability Calculator
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HomeSmart Homes and Estates

Michael & Tara Holmes License ID: 10401274851

+1(914) 292-1415 mikeholmesrealestate@gmail.com

777 Westchester Ave, White Plains, NY, 10604, USA

Fair Housing Notice: Federal, State and Local Fair Housing Laws protect individuals from housing discrimination. It is unlawful to discriminate based on certain protected characteristics, which include, but are not limited to: race, creed, color, national origin, sexual orientation, gender identity or expression, military status, sex, age, disability, marital status, lawful source of income or familial status. Click here to read more. Click here to view the New York Standardized Operating Proced

Get My App

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.