Homes for Sale in Chappaqua, NY

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$2,250,000 | 82 Shingle House Road, Millwood, NY 10546
1/6

Listing Courtesy of Century 21 Elite Realty

$2,250,000

4
Bedrooms
4,340
Square Feet
6.97
Acres

82 Shingle House Road, Millwood, NY 10546

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a aerial view of a house next to a yard
1/50

Listing Courtesy of Berkshire Hathaway HS NY Prop

$1,150,000

4
Bedrooms
2,982
Square Feet
0.49
Acres

49 East Ridge Lane, Mount Kisco, NY 10549

a front view of a house with a yard and plants
1/36

Listing Courtesy of William Raveis-New York, LLC

Virtual Tour

$1,550,000

3
Bedrooms
2,451
Square Feet
0.48
Acres

312 Quaker Road, Chappaqua, NY 10514

$1,995,000 | 12 Brandon Drive, Mount Kisco, NY 10549
1/39
Listed By Compass

$1,995,000

4
Bedrooms
3,288
Square Feet
2.03
Acres

12 Brandon Drive, Mount Kisco, NY 10549

$1,590,000 | 131 Douglas Road, Chappaqua, NY 10514
1/30

Listing Courtesy of Houlihan Lawrence Inc.

$1,590,000

3
Bedrooms
2,690
Square Feet
0.77
Acres

131 Douglas Road, Chappaqua, NY 10514

$1,099,000 | 4 Annes Wood Lane, Mount Kisco, NY 10549
1/36

Listing Courtesy of Houlihan Lawrence Inc.

$1,099,000

2
Bedrooms
1,903
Square Feet
0.01
Acres

4 Annes Wood Lane, Mount Kisco, NY 10549

a front view of a house with garden
1/37

Listing Courtesy of Houlihan Lawrence Inc.

$929,000

3
Bedrooms
1,917
Square Feet
0.83
Acres

28 Inningwood Road, Ossining, NY 10562

a front view of a house with a yard
1/48

Listing Courtesy of Corcoran Legends Realty

$1,594,000

3
Bedrooms
2,420
Square Feet
1.48
Acres

676 Hardscrabble Road, Chappaqua, NY 10514

$1,998,999 | 4 Old House Lane, Chappaqua, NY 10514
1/48

Listing Courtesy of Houlihan Lawrence Inc.

$1,998,999

4
Bedrooms
3,124
Square Feet
1.32
Acres

4 Old House Lane, Chappaqua, NY 10514

$3,500,000 | 335 Croton Dam Road, Ossining, NY 10562
1/49
Listed By Compass

$3,500,000

10
Bedrooms
8,881
Square Feet
45.06
Acres

335 Croton Dam Road, Ossining, NY 10562

a view of a back yard
1/27

Listing Courtesy of William Raveis-New York LLC

Virtual Tour

$49,500,000

8
Bedrooms
26,079
Square Feet
101.6
Acres

Undisclosed Address, Bedford Corners, NY 10549

$1,025,000 | 568 Saw Mill River Road, Chappaqua, NY 10514
1/30

Listing Courtesy of William Raveis Real Estate

$1,025,000

3
Bedrooms
2,160
Square Feet
1.34
Acres

568 Saw Mill River Road, Chappaqua, NY 10514

$879,000 | 2 Timberland Pass, Chappaqua, NY 10514
1/27

Listing Courtesy of Dorothy Jensen Realty, Inc.

$879,000

3
Bedrooms
1,586
Square Feet

2 Timberland Pass, Chappaqua, NY 10514

$1,750,000 | 51 Pinesbridge Road, Ossining, NY 10562
1/50

Listing Courtesy of William Raveis Real Estate

$1,750,000

9
Bedrooms
5,337
Square Feet
3.95
Acres

51 Pinesbridge Road, Ossining, NY 10562

$2,649,000 | 40 Hamilton Drive, Chappaqua, NY 10514
1/50

Listing Courtesy of Berkshire Hathaway HS NY Prop

$2,649,000

4
Bedrooms
5,918
Square Feet
2.26
Acres

40 Hamilton Drive, Chappaqua, NY 10514

$989,000 | 10 Horseshoe Road, Mount Kisco, NY 10549
1/23
Listed By Compass

$989,000

3
Bedrooms
1,581
Square Feet
1
Acres

10 Horseshoe Road, Mount Kisco, NY 10549

$1,079,000 | 54 Allapartus Road, Ossining, NY 10562
1/27

Listing Courtesy of Greene Realty Group

$1,079,000

4
Bedrooms
2,606
Square Feet
2
Acres

54 Allapartus Road, Ossining, NY 10562

$875,000 | 249 Mill River Road, Chappaqua, NY 10514
1/33

Listing Courtesy of Town and Village Real Estate

Virtual Tour

$875,000

4
Bedrooms
2,100
Square Feet
0.45
Acres

249 Mill River Road, Chappaqua, NY 10514

a aerial view of a house with yard and green space
1/43

Listing Courtesy of Houlihan Lawrence Inc.

$2,499,000

3
Bedrooms
6,115
Square Feet
0.93
Acres

33 Greenbriar Drive, Chappaqua, NY 10514

a front view of a house with garden and porch
1/23
Listed By Compass

$1,590,000

3
Bedrooms
2,576
Square Feet

17 Lila Lane, Chappaqua, NY 10514

$809,000 | 73 South Bedford Road, Chappaqua, NY 10514
1/30

Listing Courtesy of Thomas S. Hennerty

$809,000

4
Bedrooms
1,584
Square Feet
0.26
Acres

73 South Bedford Road, Chappaqua, NY 10514

a front view of a house with garden
1/46

Listing Courtesy of Stetson Real Estate

$1,095,000

5
Bedrooms
3,867
Square Feet
3.06
Acres

27 Allapartus Circle, Ossining, NY 10562

$639,000 | 65 South Bedford Road, Chappaqua, NY 10514
1/6

Listing Courtesy of REO Edge LLC

$639,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.17
Acres

65 South Bedford Road, Chappaqua, NY 10514

$4,500,000 | 150 Old Farm Road North, Chappaqua, NY 10514
1/44

Listing Courtesy of Julia B Fee Sothebys Int. Rlty

$4,500,000

5
Bedrooms
7,608
Square Feet
4.45
Acres

150 Old Farm Road North, Chappaqua, NY 10514

$825,000 | 81 Glendale Road, Ossining, NY 10562
1/37

Listing Courtesy of North Country Sothebys Int Rlt

$825,000

3
Bedrooms
3,990
Square Feet
14.5
Acres

81 Glendale Road, Ossining, NY 10562

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Chappaqua

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The name of this picturesque wooded hamlet comes from tribes of the Mohegan Confederation, who called it “Shepequa” because of its plentiful water sources. Today, Chappaqua’s abundance of natural beauty—parks, trails, and nature preserves—continues to nourish its long-time residents and lure newcomers.

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