Recently Sold 2 Bedroom Homes in Chappaqua, NY

109 homes

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SOLD
FEB 27, 2026
$1,600,000
3 Beds
3.5 Baths
2,866 sqft
36 Pond Hill Road,
Chappaqua, NY 10514
William Raveis-New York, LLC
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SOLD
FEB 20, 2026
$1,775,000
4 Beds
3.5 Baths
3,732 sqft
35 Whitlaw Lane,
Chappaqua, NY 10514
Compass Greater NY, LLC
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SOLD
FEB 13, 2026
$925,000
4 Beds
3 Baths
2,745 sqft
12 Whitlaw Ln,
Chappaqua, NY 10514
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SOLD
FEB 9, 2026
$2,000,000
4 Beds
3.5 Baths
3,022 sqft
2 Whippoorwill Close,
Chappaqua, NY 10514
Compass Greater NY, LLC
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SOLD
FEB 5, 2026
$3,500,000
4 Beds
6 Baths
7,708 sqft
5 Sutton Farm Drive,
Chappaqua, NY 10514
Compass Greater NY, LLC
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SOLD
FEB 4, 2026
$1,720,000
4 Beds
3.5 Baths
3,244 sqft
6 Whippoorwill Lake Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
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SOLD
FEB 2, 2026
$1,375,000
4 Beds
2.5 Baths
2,541 sqft
341 Millwood Road,
Chappaqua, NY 10514
Houlihan Lawrence Inc.
SOLD
FEB 2, 2026
$2,275,000
2 Beds
3 Baths
2,613 sqft
22 Carriage Ln,
Chappaqua, NY 10514
SOLD
JAN 30, 2026
$1,725,000
5 Beds
5.5 Baths
4,616 sqft
675 Quaker Road,
Chappaqua, NY 10514
Douglas Elliman Real Estate
SOLD
JAN 23, 2026
$2,275,000
2 Beds
3.5 Baths
3,269 sqft
22 Carriage Lane,
Chappaqua, NY 10514
JLJ Realty
SOLD
JAN 21, 2026
$1,290,000
3 Beds
2 Baths
1,957 sqft
71 Commodore Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
JAN 20, 2026
$1,700,000
4 Beds
2 Baths
2,707 sqft
31 Whitlaw Ln,
Chappaqua, NY 10514
SOLD
JAN 20, 2026
$1,920,000
5 Beds
4.5 Baths
3,849 sqft
73 Whippoorwill Lake Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
JAN 13, 2026
$1,780,000
4 Beds
4.5 Baths
4,191 sqft
56 Annandale Rd,
Chappaqua, NY 10514
SOLD
JAN 12, 2026
$1,382,000
4 Beds
4.5 Baths
3,561 sqft
260 Mill River Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
JAN 8, 2026
$1,877,300
5 Beds
3.5 Baths
3,085 sqft
45 Deerfield Rd,
Chappaqua, NY 10514
SOLD
DEC 26, 2025
$2,960,000
4 Beds
4.5 Baths
6,542 sqft
93 Haights Cross Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
DEC 22, 2025
$805,000
2 Beds
3 Baths
1,536 sqft
149 King St,
Chappaqua, NY 10514
SOLD
DEC 22, 2025
$1,780,000
4 Beds
4.5 Baths
4,543 sqft
56 Annandale Drive,
Chappaqua, NY 10514
William Raveis-New York, LLC
SOLD
DEC 18, 2025
$1,298,000
4 Beds
2.5 Baths
2,060 sqft
26 Kings Court,
Chappaqua, NY 10514
William Raveis-New York, LLC
SOLD
DEC 18, 2025
$2,500,000
5 Beds
5.5 Baths
5,907 sqft
61 Carolyn Place,
Chappaqua, NY 10514
Julia B Fee Sothebys Int. Rlty
SOLD
DEC 15, 2025
$1,350,000
3 Beds
2 Baths
2,414 sqft
5 Rose Ln,
Chappaqua, NY 10514
SOLD
DEC 15, 2025
$732,500
2 Beds
2.5 Baths
1,244 sqft
30 Rambling Brook Road,
Chappaqua, NY 10514
Nestedge Realty
SOLD
DEC 15, 2025
$2,825,000
5 Beds
8 Baths
8,775 sqft
70 Haights Cross Road,
Chappaqua, NY 10514
Houlihan Lawrence Inc.
SOLD
DEC 15, 2025
$2,800,000
4 Beds
4 Baths
5,488 sqft
500 Hardscrabble Rd,
Briarcliff Manor, NY 10510
SOLD
DEC 12, 2025
$1,600,000
3 Beds
2.5 Baths
2,830 sqft
27 Deepwood Hill,
Chappaqua, NY 10514
Houlihan Lawrence Inc.
SOLD
DEC 12, 2025
$1,625,000
2 Beds
2.5 Baths
2,906 sqft
20 Wallace Way,
Chappaqua, NY 10514
Corcoran Legends Realty
SOLD
DEC 11, 2025
$1,320,000
3 Beds
2.5 Baths
2,034 sqft
41 Valley Lane,
Chappaqua, NY 10514
William Raveis-New York, LLC
SOLD
DEC 11, 2025
$1,679,000
2 Beds
3.5 Baths
3,269 sqft
10 Carriage Ln,
Chappaqua, NY 10514
SOLD
DEC 9, 2025
$1,100,000
4 Beds
2.5 Baths
3,264 sqft
569 Millwood Road,
Chappaqua, NY 10514
William Raveis-New York, LLC
SOLD
DEC 8, 2025
$2,800,000
4 Beds
6.5 Baths
5,488 sqft
500 Hardscrabble Road,
Briarcliff Manor, NY 10510
Houlihan Lawrence Inc.
SOLD
DEC 5, 2025
$2,060,000
5 Beds
4.5 Baths
4,172 sqft
77 Haights Cross Road,
Chappaqua, NY 10514
Julia B Fee Sothebys Int. Rlty
SOLD
DEC 4, 2025
$2,597,511
5 Beds
4.5 Baths
4,348 sqft
482 Armonk Road,
Mount Kisco, NY 10549
William Raveis-New York, LLC
SOLD
DEC 3, 2025
$2,300,000
3 Beds
3.5 Baths
3,638 sqft
24 North Way,
Chappaqua, NY 10514
SOLD
DEC 2, 2025
$3,000,000
5 Beds
5 Baths
5,285 sqft
3 Round Hill Place,
Chappaqua, NY 10514
Julia B Fee Sothebys Int. Rlty
SOLD
NOV 21, 2025
$700,000
4 Beds
5 Baths
2,875 sqft
136 Roaring Brook Road,
Chappaqua, NY 10514
Douglas Elliman Real Estate
SOLD
NOV 21, 2025
$805,000
2 Beds
2.5 Baths
1,767 sqft
149 King Street #4,
Chappaqua, NY 10514
Julia B Fee Sothebys Int. Rlty
SOLD
NOV 19, 2025
$799,000
4 Beds
2 Baths
1,420 sqft
37 Hollow Oak Road,
Chappaqua, NY 10514
William Raveis Real Estate
SOLD
NOV 14, 2025
$595,000
3 Beds
2 Baths
2,420 sqft
676 Hardscrabble Rd,
Chappaqua, NY 10570
SOLD
NOV 12, 2025
$799,000
3 Beds
1 Bath
1,660 sqft
816 Hardscrabble Rd,
Chappaqua, NY 10514

Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information