Recently Sold 2 Bedroom Homes in Chappaqua, NY

133 homes

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SOLD
MAY 15, 2026
$2,551,201
4 Beds
2.5 Baths
4,500 sqft
00 Gray Rock Lane,
Chappaqua, NY 10514
Houlihan Lawrence Inc.
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SOLD
MAY 11, 2026
$1,600,000
4 Beds
2.5 Baths
2,892 sqft
56 Cross Ridge Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
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SOLD
MAY 7, 2026
$2,850,000
4 Beds
6 Baths
5,536 sqft
211 Bedford Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
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SOLD
APR 28, 2026
$2,000,000
4 Beds
2.5 Baths
2,658 sqft
40 Smith Street,
Chappaqua, NY 10514
Julia B Fee Sothebys Int. Rlty
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SOLD
APR 21, 2026
$1,655,800
4 Beds
2.5 Baths
2,932 sqft
9 Whitlaw Lane,
Chappaqua, NY 10514
William Raveis-New York, LLC
SOLD
APR 20, 2026
$1,375,000
4 Beds
2.5 Baths
2,069 sqft
111 Seven Bridges Road,
Chappaqua, NY 10514
William Raveis-New York, LLC
SOLD
APR 6, 2026
$1,780,444
4 Beds
4 Baths
3,029 sqft
636 Quaker Road,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
APR 6, 2026
$2,100,000
4 Beds
2 Baths
1,974 sqft
87 Campfire Rd,
Chappaqua, NY 10514
SOLD
APR 6, 2026
$2,775,000
4 Beds
4.5 Baths
5,087 sqft
32 North Way,
Chappaqua, NY 10514
SOLD
MAR 27, 2026
$1,300,033
4 Beds
2.5 Baths
2,445 sqft
29 Meadow Lane,
Chappaqua, NY 10514
Houlihan Lawrence Inc.
SOLD
MAR 25, 2026
$1,275,000
4 Beds
2 Baths
2,139 sqft
35 Hamilton Road,
Chappaqua, NY 10514
Houlihan Lawrence Inc.
SOLD
MAR 9, 2026
$1,240,000
4 Beds
4 Baths
2,900 sqft
9 Garey Dr,
Chappaqua, NY 10514
SOLD
MAR 6, 2026
$1,168,000
4 Beds
3 Baths
3,136 sqft
507 Millwood Rd,
Chappaqua, NY 10514
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
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
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
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
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
JAN 20, 2026
$1,700,000
4 Beds
2 Baths
2,707 sqft
31 Whitlaw Ln,
Chappaqua, NY 10514
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
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
$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 15, 2025
$2,800,000
4 Beds
4 Baths
5,488 sqft
500 Hardscrabble Rd,
Briarcliff Manor, NY 10510
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
AUG 25, 2026
$2,310,018
5 Beds
4.5 Baths
4,489 sqft
1 Hitching Post Lane,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
AUG 12, 2026
$2,555,000
5 Beds
3.5 Baths
4,166 sqft
111 Prospect Drive,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
AUG 11, 2026
$2,915,000
5 Beds
4.5 Baths
4,975 sqft
3 Pondfield Drive S,
Chappaqua, NY 10514
Houlihan Lawrence Inc.
SOLD
JUL 10, 2026
$2,621,000
5 Beds
3.5 Baths
5,247 sqft
33 Aldridge Road,
Chappaqua, NY 10514
Ginnel Real Estate
SOLD
JUL 8, 2026
$3,150,000
5 Beds
4.5 Baths
6,515 sqft
118 Hardscrabble Lake Dr,
Chappaqua, NY 10514
SOLD
JUL 6, 2026
$1,950,612
5 Beds
4 Baths
3,605 sqft
251 Millwood Rd,
Chappaqua, NY 10514
SOLD
JUL 6, 2026
$2,750,000
5 Beds
5.5 Baths
6,800 sqft
1 Brittany Ct,
Chappaqua, NY 10514
SOLD
JUN 26, 2026
$2,750,000
5 Beds
5.5 Baths
6,800 sqft
1 Brittany Ct,
Chappaqua, NY 10514
SOLD
JUN 23, 2026
$2,450,000
5 Beds
5 Baths
5,767 sqft
5 Morning View Ct,
Chappaqua, NY 10570
SOLD
JUN 11, 2026
$2,510,000
5 Beds
4.5 Baths
5,792 sqft
114 Random Farms Drive,
Chappaqua, NY 10514
Compass Greater NY, LLC
SOLD
JUN 10, 2026
$3,975,000
5 Beds
6 Baths
6,935 sqft
56 Algonquin Dr,
Chappaqua, NY 10514
SOLD
APR 27, 2026
$1,725,000
5 Beds
3 Baths
2,885 sqft
18 Hayrake Lane,
Chappaqua, NY 10514
William Raveis-New York, LLC
SOLD
APR 7, 2026
$2,496,500
5 Beds
3 Baths
5,475 sqft
289 Hamilton Rd,
Chappaqua, NY 10570

Based on information submitted to the MLS GRID as of 2026-09-04 15:18:21 PDT 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