Chappaqua, NY Real Estate Guide

Westchester County, New York

VIEW 52 COMMUNITY LISTINGS

Chappaqua is a residential hamlet covering a 21.5 square-mile area in the scenic midpoint of Westchester County.

Chappaqua is noted for its wooded winding roads and privately situated Westchester County real estate offering. The area’s rich history is preserved in a pre-Revolutionary War-era Quaker settlement that includes a 1753 meeting house and many 18th-century buildings, 11 of which are listed on the National Register of Historic Places. Located in the town of New Castle, which has a population of 17,550.

Chappaqua is noted for its wooded winding roads and privately situated Westchester County real estate offering. The area’s rich history is preserved in a pre-Revolutionary War-era Quaker settlement that includes a 1753 meeting house and many 18th-century buildings, 11 of which are listed on the National Register of Historic Places. Located in the town of New Castle, which has a population of 17,550.

Chappaqua is noted for its wooded winding roads and privately situated Westchester County real estate offering. The area’s rich history is preserved in a pre-Revolutionary War-era Quaker settlement that includes a 1753 meeting house and many 18th-century buildings, 11 of which are listed on the National Register of Historic Places. Located in the town of New Castle, which has a population of 17,550.

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Featured Listings

52 Whippoorwill Lake Road
Chappaqua, NY $1,495,000

52 Whippoorwill Lake Road

Chappaqua, NY

$1,495,000
  • 4 Beds
  • 2/1 Baths
  • 3,347 Sqft
2 Turner Drive
Chappaqua, NY $1,100,000

2 Turner Drive

Chappaqua, NY

$1,100,000
  • 5 Beds
  • 3 Baths
  • 3,199 Sqft
24 Trails End
Chappaqua, NY $5,750,000

24 Trails End

Chappaqua, NY

$5,750,000
  • 6 Beds
  • 7/1 Baths
  • 9,247 Sqft
301 Whippoorwill Road
Chappaqua, NY $3,599,000

301 Whippoorwill Road

Chappaqua, NY

$3,599,000
  • 5 Beds
  • 6/1 Baths
  • 10,594 Sqft
40 Algonquin Drive
Chappaqua, NY $3,389,000

40 Algonquin Drive

Chappaqua, NY

$3,389,000
  • 4 Beds
  • 6/1 Baths
  • 6,697 Sqft
201 Bedford Road
Chappaqua, NY $3,350,000

201 Bedford Road

Chappaqua, NY

$3,350,000
  • 4 Beds
  • 4/3 Baths
  • 5,712 Sqft
46 Annandale Road
Chappaqua, NY $3,299,000

46 Annandale Road

Chappaqua, NY

$3,299,000
  • 5 Beds
  • 5/2 Baths
  • 7,597 Sqft
39 Barnes Lane
Chappaqua, NY $2,995,000

39 Barnes Lane

Chappaqua, NY

$2,995,000
  • 4 Beds
  • 5/1 Baths
  • 5,343 Sqft

Chappaqua

Area Map

Chappaqua is within Westchester County, New York and borders Armonk.

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Featured Communities Within

Westchester County

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Chappaqua

(Chappaqua School District)

Market Snapshot

Units Sold

September 2026

17 TOTAL UNITS

image description +6.3% image description +41.7% vs

Median Sales Price

September 2026 - Single Family Homes

$1.3M
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Percentage of Asking Price

September 2026 Single Family Homes

100%
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