Homes Recently Sold in Chappaqua, NY

price
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1-40 of 54 Homes
Sold, last 90 days
a front view of a house with a garden
Closed 11/10/25

$1,815,000

4
Bedrooms
3,457
Square Feet
2
Acres

58 Spring Lane, Chappaqua, NY 10514

a view of house with yard
Closed 10/23/25

$1,391,022

4
Bedrooms
3,776
Square Feet
1.36
Acres

6 Algonquin Drive, Chappaqua, NY 10514

a view of a house with a garden
Closed 10/16/25

$525,000

3
Bedrooms
880
Square Feet
2.29
Acres

380 Whippoorwill Road, Chappaqua, NY 10514

a front view of a house with a garden
Closed 11/4/25Virtual Tour

$2,700,000

4
Bedrooms
5,354
Square Feet
1.22
Acres

35 Overlook Drive, Chappaqua, NY 10514

a front view of a house with a yard and potted plants
Closed 12/26/25

$2,960,000

4
Bedrooms
6,542
Square Feet
3.66
Acres

93 Haights Cross Road, Chappaqua, NY 10514

a living room with furniture and a large window
Closed 12/12/25

$1,075,000

4
Bedrooms
3,240
Square Feet
2.24
Acres

70 Spring Valley Road, Ossining, NY 10562

$792,500 | 22 Daly Cross Road, Mount Kisco, NY 10549
Closed 12/23/25Virtual Tour

$792,500

3
Bedrooms
1,457
Square Feet
0.52
Acres

22 Daly Cross Road, Mount Kisco, NY 10549

a view of a brick house with potted plants
Closed 12/8/25

$670,000

2
Bedrooms
2,020
Square Feet

71 Pheasant Run, Millwood, NY 10546

a front view of a house with a garden

Listing Courtesy of William Raveis-New York, LLC

Closed 12/18/25

$1,298,000

4
Bedrooms
2,060
Square Feet
0.39
Acres

26 Kings Court, Chappaqua, NY 10514

a front view of a house with a garden

Listing Courtesy of William Raveis Real Estate

Closed 11/19/25

$799,000

4
Bedrooms
1,420
Square Feet
0.31
Acres

37 Hollow Oak Road, Chappaqua, NY 10514

$2,000,000 | 50 Overlook Drive, Chappaqua, NY 10514

Listing Courtesy of Houlihan Lawrence Inc.

Closed 10/29/25

$2,000,000

6
Bedrooms
5,234
Square Feet
1.2
Acres

50 Overlook Drive, Chappaqua, NY 10514

a aerial view of a house with a yard and potted plants

Listing Courtesy of Julia B Fee Sothebys Int. Rlty

Closed 12/5/25Virtual Tour

$2,060,000

5
Bedrooms
4,172
Square Feet
2.6
Acres

77 Haights Cross Road, Chappaqua, NY 10514

a front view of house with yard and green space

Listing Courtesy of Houlihan Lawrence Inc.

Closed 10/6/25

$1,275,000

3
Bedrooms
2,111
Square Feet
0.7
Acres

4 Southview Road, Chappaqua, NY 10514

a front view of a house with a yard

Listing Courtesy of Keller Williams Realty Partner

Closed 10/21/25

$1,646,500

4
Bedrooms
2,550
Square Feet
0.33
Acres

59 Crest Road, Chappaqua, NY 10514

a view of a big yard in front of a brick house with large windows

Listing Courtesy of Houlihan Lawrence Inc.

Closed 12/12/25

$1,600,000

3
Bedrooms
2,830
Square Feet
1.79
Acres

27 Deepwood Hill Street, Chappaqua, NY 10514

a front view of a house with a yard

Listing Courtesy of William Raveis-New York, LLC

Closed 10/27/25

$1,175,000

3
Bedrooms
2,695
Square Feet
1.16
Acres

495 Quaker Road, Chappaqua, NY 10514

a view of a house with backyard and sitting area

Listing Courtesy of Julia B Fee Sothebys Int. Rlty

Closed 12/2/25

$3,000,000

5
Bedrooms
5,285
Square Feet
2.5
Acres

3 Round Hill Place, Chappaqua, NY 10514

a front view of a house with a garden

Listing Courtesy of William Raveis-New York, LLC

Closed 12/11/25

$1,320,000

3
Bedrooms
2,034
Square Feet
1.19
Acres

41 Valley Lane, Chappaqua, NY 10514

$1,075,000 | 21 Kipp Street, Chappaqua, NY 10514

Listing Courtesy of Julia B Fee Sothebys Int. Rlty

Closed 10/10/25

$1,075,000

4
Bedrooms
2,447
Square Feet
0.66
Acres

21 Kipp Street, Chappaqua, NY 10514

a view of residential house with outdoor space and lake

Listing Courtesy of McGrath Realty Inc

Closed 10/22/25Virtual Tour

$775,000

2
Bedrooms
1,549
Square Feet
0.01
Acres

77 Further Lane, Chappaqua, NY 10514

an aerial view of a house

Listing Courtesy of Douglas Elliman Real Estate

Closed 11/20/25

$2,300,000

3
Bedrooms
3,960
Square Feet
1
Acres

24 North Way, Chappaqua, NY 10514

a aerial view of a house with yard and green space

Listing Courtesy of William Raveis-New York, LLC

Closed 12/9/25Virtual Tour

$1,100,000

4
Bedrooms
3,264
Square Feet
1.26
Acres

569 Millwood Road, Chappaqua, NY 10514

a view of a big yard with plants and large trees

Listing Courtesy of RE/MAX Prestige Properties

Closed 11/3/25

$799,000

3
Bedrooms
1,660
Square Feet
0.58
Acres

816 Hardscrabble Road, Chappaqua, NY 10514

$805,000 | 149 King Street, Unit 4, Chappaqua, NY 10514

Listing Courtesy of Julia B Fee Sothebys Int. Rlty

Closed 11/21/25

$805,000

2
Bedrooms
1,767
Square Feet
0.03
Acres

149 King Street, Unit 4, Chappaqua, NY 10514

a front view of a house with a garden and plants

Listing Courtesy of Houlihan Lawrence Inc.

Closed 10/9/25

$1,800,000

5
Bedrooms
5,089
Square Feet
0.73
Acres

73 Random Farms Drive, Chappaqua, NY 10514

a aerial view of a house with swimming pool

Listing Courtesy of William Raveis-New York, LLC

Closed 12/22/25

$1,780,000

4
Bedrooms
4,543
Square Feet
1.4
Acres

56 Annandale Road, Chappaqua, NY 10514

$2,500,000 | 61 Carolyn Place, Chappaqua, NY 10514

Listing Courtesy of Julia B Fee Sothebys Int. Rlty

Closed 12/18/25

$2,500,000

5
Bedrooms
5,907
Square Feet
2.19
Acres

61 Carolyn Place, Chappaqua, NY 10514

$2,825,000 | 70 Haights Cross Road, Chappaqua, NY 10514

Listing Courtesy of Houlihan Lawrence Inc.

Closed 12/15/25

$2,825,000

5
Bedrooms
8,775
Square Feet
2.17
Acres

70 Haights Cross Road, Chappaqua, NY 10514

$700,000 | 136 Roaring Brook Road, Chappaqua, NY 10514

Listing Courtesy of Douglas Elliman Real Estate

Closed 11/21/25

$700,000

4
Bedrooms
2,875
Square Feet
1.02
Acres

136 Roaring Brook Road, Chappaqua, NY 10514

$706,499 | 52 Red Oak Lane, Mount Kisco, NY 10549

Listing Courtesy of Houlihan Lawrence Inc.

Closed 10/30/25

$706,499

2
Bedrooms
1,775
Square Feet
0.29
Acres

52 Red Oak Lane, Mount Kisco, NY 10549

Sold 11/12/25

$530,000

1
Bedrooms
Unavailable
Square Feet
0.99
Acres

1008 King Street, Chappaqua, NY 10514

Sold 11/13/25

$595,000

3
Bedrooms
2
Bathrooms
2,420
Square Feet
1.5
Acres

676 Hardscrabble Road, Chappaqua, NY 10514

a front view of a house with a yard and porch

Listing Courtesy of Keller Williams Realty Partner

Closed 10/31/25

$1,725,000

4
Bedrooms
4,100
Square Feet
0.48
Acres

9 Point Place, Chappaqua, NY 10514

a front view of a house with a yard

Listing Courtesy of Douglas Elliman Real Estate

Closed 10/8/25

$2,300,000

5
Bedrooms
5,183
Square Feet
1.11
Acres

3 Boulder Trail, Chappaqua, NY 10514

Sold 10/30/25

$2,175,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
Unavailable
Acres

25 South Bedford Road, Chappaqua, NY 10514

a front view of a house with garden

Listing Courtesy of Houlihan Lawrence Inc.

Closed 10/27/25

$1,250,000

4
Bedrooms
3,300
Square Feet
0.48
Acres

7 Kisco Park Drive, Mount Kisco, NY 10549

$1,625,000 | 20 Wallace Way, Chappaqua, NY 10514

Listing Courtesy of Corcoran Legends Realty

Closed 12/12/25

$1,625,000

2
Bedrooms
2,906
Square Feet

20 Wallace Way, Chappaqua, NY 10514

a front view of a house with a garden

Listing Courtesy of William Raveis-New York, LLC

Closed 12/4/25

$2,597,511

5
Bedrooms
4,348
Square Feet
13.71
Acres

482 Armonk Road, Mount Kisco, NY 10549

a front view of a house with garden

Listing Courtesy of Nestedge Realty

Closed 12/15/25

$732,500

2
Bedrooms
1,244
Square Feet

30 Rambling Brook Road, Chappaqua, NY 10514

$5,900,000 | 402 Sarles Street, Bedford Corners, NY 10549

Listing Courtesy of Julia B Fee Sothebys Int. Rlty

Closed 10/9/25

$5,900,000

5
Bedrooms
7,645
Square Feet
15.03
Acres

402 Sarles Street, Bedford Corners, 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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