View 301 Whippoorwill Road Chappaqua, NY MLS# H6333127
$3,599,000
5

Beds

6.1

Baths

10,594

Sq.Ft.

301 Whippoorwill Road

Chappaqua, NY

Courtesy of COMPASS GREATER NY, LLC
View 46 Annandale Road Chappaqua, NY MLS# 1052644
$3,299,000
5

Beds

5.2

Baths

7,597

Sq.Ft.

46 Annandale Road

Chappaqua, NY

Courtesy of COMPASS GREATER NY, LLC
View 301 Roaring Brook Road Chappaqua, NY MLS# 1055737
$3,088,000
7

Beds

7.0

Baths

5,345

Sq.Ft.

301 Roaring Brook Road

Chappaqua, NY

Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 18 Ivy Hill Road Chappaqua, NY MLS# 923774
$2,799,000
5

Beds

4.1

Baths

4,323

Sq.Ft.

18 Ivy Hill Road

Chappaqua, NY

Courtesy of COMPASS GREATER NY, LLC
View 20 Bessel Lane Chappaqua, NY MLS# 1035591
$2,790,000
6

Beds

5.1

Baths

7,978

Sq.Ft.

20 Bessel Lane

Chappaqua, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 790 King Street Chappaqua, NY MLS# 993886
  • Virtual Tour
1 of 49
$2,350,000
4

Beds

3.2

Baths

4,385

Sq.Ft.

790 King Street

Chappaqua, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 20 Hitching Post Lane Chappaqua, NY MLS# 1036792
$2,299,000
5

Beds

4.1

Baths

4,661

Sq.Ft.

20 Hitching Post Lane

Chappaqua, NY

Courtesy of WILLIAM RAVEIS-NEW YORK LLC
View 33 Greenbriar Drive Chappaqua, NY MLS# 973551
$2,249,000
3

Beds

4.0

Baths

6,115

Sq.Ft.

33 Greenbriar Drive

Chappaqua, NY

Courtesy of HOULIHAN LAWRENCE INC.
View 57 Random Farms Circle Chappaqua, NY MLS# 1073051
    1 of 44
    OPEN HOUSE: Saturday 11/14 1:00 PM - 3:00 PM
    $2,150,000
    5

    Beds

    4.1

    Baths

    4,278

    Sq.Ft.

    57 Random Farms Circle

    Chappaqua, NY

    Courtesy of SERHANT LLC
    View 76 Random Farms Circle Chappaqua, NY MLS# 1053697
    $1,995,000
    4

    Beds

    4.1

    Baths

    4,796

    Sq.Ft.

    76 Random Farms Circle

    Chappaqua, NY

    Courtesy of COMPASS GREATER NY, LLC
    View 21 King Street Chappaqua, NY MLS# 1005784
    $1,849,000
    3,219

    Sq.Ft.

    21 King Street

    Chappaqua, NY

    Courtesy of HOULIHAN LAWRENCE INC.
    View 25 Helena Drive Chappaqua, NY MLS# 1071774
    $1,825,000
    4

    Beds

    3.1

    Baths

    3,164

    Sq.Ft.

    25 Helena Drive

    Chappaqua, NY

    Courtesy of WILLIAM RAVEIS-NEW YORK, LLC
    View 406 Bedford Road Chappaqua, NY MLS# 1044050
    $1,749,000
    4

    Beds

    3.1

    Baths

    2,913

    Sq.Ft.

    406 Bedford Road

    Chappaqua, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 767 King Street Chappaqua, NY MLS# 1038452
    $1,665,000
    0.0

    Baths

    562,795

    Sq.Ft.

    767 King Street

    Chappaqua, NY

    Courtesy of WILLIAM RAVEIS-NEW YORK, LLC
    View 600 Bedford Road Chappaqua, NY MLS# 1052500
    $1,599,000
    8

    Beds

    6.2

    Baths

    5,798

    Sq.Ft.

    600 Bedford Road

    Chappaqua, NY

    Courtesy of HOULIHAN LAWRENCE INC.
    View 17 Lila Lane Chappaqua, NY MLS# 984583
    $1,590,000
    3

    Beds

    2.2

    Baths

    2,576

    Sq.Ft.

    17 Lila Lane

    Chappaqua, NY

    Courtesy of COMPASS GREATER NY, LLC
    View 9 Lori Lane Chappaqua, NY MLS# 1047882
    $1,575,000
    4

    Beds

    2.1

    Baths

    2,376

    Sq.Ft.

    9 Lori Lane

    Chappaqua, NY

    Courtesy of JULIA B FEE SOTHEBYS INT. RLTY
    View 131 Douglas Road Chappaqua, NY MLS# 1017997
    $1,490,000
    3

    Beds

    3.1

    Baths

    2,690

    Sq.Ft.

    131 Douglas Road

    Chappaqua, NY

    Courtesy of HOULIHAN LAWRENCE INC.
    View 10 Deborah Lane Chappaqua, NY MLS# 1046960
    $1,399,000
    3

    Beds

    3.0

    Baths

    2,821

    Sq.Ft.

    10 Deborah Lane

    Chappaqua, NY

    Courtesy of HOULIHAN LAWRENCE INC.
    View 676 Hardscrabble Road Chappaqua, NY MLS# 1063202
    $1,396,000
    3

    Beds

    2.1

    Baths

    2,420

    Sq.Ft.

    676 Hardscrabble Road

    Chappaqua, NY

    Courtesy of CORCORAN LEGENDS REALTY

    About Chappaqua

    Chappaqua is the largest hamlet of New Castle.  Its center is located in the southeastern part of the town.  The name Chappaqua comes from the Native Americans word, "shah-pah-ka," which means "the rustling land" or "the rattling land," or a place where nothing is heard but the rustling of the wind in the leaves.  Chappaqua provides meticulously restored colonial homes or vintage properties set on winding roads that reflect the exceptionally high quality of life.  The schools are among the best in the country, in fact, Horace Greeley High School in Chappaqua is ranked as one of the finest in the nation.  Chappaqua is ranked 42nd among the 100 highest income places in the United States.  CNNMoney listed Chappaqua fifth in their list of "25 top-earning towns in 2008.

    Listings in Chappaqua, NY

    32

    Estimated median home price

    $1,695,000
    Chappaqua NY Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of Chappaqua, New York real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chappaqua, NY.

    Homes for Sale by Price in Chappaqua, NY

    PriceCount
    $0 - 100K0
    $100K - 200K0
    $200K - 300K0
    $300K - 400K0
    $400K - 500K0
    $500K - 600K0
    $600K - 700K2
    $700K - 800K3
    $800K - 900K3
    $900K - 1M0
    $1M - Max24

    Homes for Sale by Type in Chappaqua, NY

    Property TypeCount
    Single Family24
    Townhouse0
    Condo5
    Commercial1
    Rental11
    Lots and Land2
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 11/12/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

    The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

    Information Copyright 2021, OneKey® MLS. All Rights Reserved.