Chappaqua, NY Homes for Sale & Real Estate

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1-35 of 35 Homes
$499,999 | 150 Bedford Road, Unit 12A, Chappaqua, NY 10514
1/17
Listed By Compass

$499,999

2
Bedrooms
924
Square Feet

150 Bedford Road, Unit 12A, Chappaqua, NY 10514

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$3,389,000 | 40 Algonquin Drive, Chappaqua, NY 10514
1/47
Listed By Compass

$3,389,000

4
Bedrooms
5,563
Square Feet
1.53
Acres

40 Algonquin Drive, 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

$2,895,000 | 39 Barnes Lane, Chappaqua, NY 10514
1/9
Listed By Compass

$2,895,000

4
Bedrooms
4,589
Square Feet
1.06
Acres

39 Barnes Lane, 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

$849,999 | 58 Maple Avenue, Chappaqua, NY 10514
1/35

Listing Courtesy of Howard Hanna Rand Realty

$849,999

2
Bedrooms
711
Square Feet
0.28
Acres

58 Maple Avenue, Chappaqua, NY 10514

$3,100,000 | 23 Inningwood Road, Ossining, NY 10562
1/50

Listing Courtesy of Woodfront Realty, Inc.

Virtual Tour

$3,100,000

3
Bedrooms
6,091
Square Feet
1.52
Acres

23 Inningwood Road, Ossining, NY 10562

$579,000 | 309 North Greeley Avenue, Chappaqua, NY 10514
1/27

Listing Courtesy of RE/MAX Prestige Properties

$579,000

2
Bedrooms
1,200
Square Feet

309 North Greeley Avenue, Chappaqua, NY 10514

$649,000 | 353 North Greeley Avenue, Unit 353, Chappaqua, NY 10514
1/17

Listing Courtesy of Houlihan Lawrence Inc.

$649,000

2
Bedrooms
1,478
Square Feet

353 North Greeley Avenue, Unit 353, Chappaqua, NY 10514

$1,199,000 | 4 Annes Wood Lane, Mount Kisco, NY 10549
1/36

Listing Courtesy of Houlihan Lawrence Inc.

$1,199,000

2
Bedrooms
1,903
Square Feet
0.01
Acres

4 Annes Wood Lane, Mount Kisco, NY 10549

a front view of a house with a garden
1/49

Listing Courtesy of Houlihan Lawrence Inc.

$1,100,000

5
Bedrooms
2,715
Square Feet
0.73
Acres

2 Turner Drive, Chappaqua, NY 10514

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 aerial view of a house with a yard table and chairs
1/50

Listing Courtesy of Corcoran Legends Realty

$1,695,000

3
Bedrooms
2,420
Square Feet
1.48
Acres

676 Hardscrabble Road, Chappaqua, NY 10514

$890,000 | 20 Waters Edge, Chappaqua, NY 10514
1/25

Listing Courtesy of William Raveis-New York, LLC

Virtual Tour

$890,000

3
Bedrooms
1,569
Square Feet

20 Waters Edge, Chappaqua, NY 10514

a front view of a house with a yard and garage
1/49

Listing Courtesy of Berkshire Hathaway HS NY Prop

$1,600,000

11
Bedrooms
Unavailable
Square Feet
18.14
Acres

120 Spring Valley 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

$1,750,000 | 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

$1,595,000 | 52-54 Orchard Ridge Road, Chappaqua, NY 10514
1/49

Listing Courtesy of Link NY Realty

$1,595,000

7
Bedrooms
5,200
Square Feet
0.46
Acres

52-54 Orchard Ridge Road, Chappaqua, NY 10514

a front view of a house with a yard
1/50

Listing Courtesy of Berkshire Hathaway HS NY Prop

$2,699,000

4
Bedrooms
5,918
Square Feet
2.26
Acres

40 Hamilton Drive, Chappaqua, NY 10514

$3,100,000 | 2 Heathcote Drive, Mount Kisco, NY 10549
1/50

Listing Courtesy of Howard Hanna Rand Realty

Virtual Tour

$3,100,000

5
Bedrooms
7,238
Square Feet
2.09
Acres

2 Heathcote Drive, Mount Kisco, NY 10549

$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

$1,050,000 | 568 Saw Mill River Road, Chappaqua, NY 10514
1/30

Listing Courtesy of William Raveis Real Estate

$1,050,000

3
Bedrooms
2,160
Square Feet
1.34
Acres

568 Saw Mill River Road, Chappaqua, NY 10514

$725,000 | 65 Laurelton Road, Mount Kisco, NY 10549
1/24

Listing Courtesy of Ginnel Real Estate

$725,000

4
Bedrooms
1,307
Square Feet
0.25
Acres

65 Laurelton Road, Mount Kisco, NY 10549

$899,000 | 2 Timberland Pass, Chappaqua, NY 10514
1/27

Listing Courtesy of Dorothy Jensen Realty, Inc.

$899,000

3
Bedrooms
1,586
Square Feet

2 Timberland Pass, 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

$895,000 | 249 Mill River Road, Chappaqua, NY 10514
1/33

Listing Courtesy of Town and Village Real Estate

Virtual Tour

$895,000

4
Bedrooms
2,100
Square Feet
0.45
Acres

249 Mill River Road, Chappaqua, NY 10514

a front view of a house with garden
1/27

Listing Courtesy of Greene Realty Group

$1,085,000

4
Bedrooms
2,606
Square Feet
2
Acres

54 Allapartus Road, Ossining, NY 10562

$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

$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

a front view of a house with garden
1/35

Listing Courtesy of Houlihan Lawrence Inc.

$2,990,000

6
Bedrooms
8,200
Square Feet
4.11
Acres

20 Bessel Lane, 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

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

$1,665,000 | 767 King Street, Chappaqua, NY 10504
1/20

Listing Courtesy of William Raveis-New York, LLC

$1,665,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
12.92
Acres

767 King Street, Chappaqua, NY 10504

a front view of a house with a yard
1/37

Listing Courtesy of Houlihan Lawrence Inc.

$3,900,000

4
Bedrooms
9,284
Square Feet
1.68
Acres

16 Taylor Road, Mount Kisco, NY 10549

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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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