209 Whippoorwill Road

Sold 9/27/13

Sold

Last Sold Price

$1,410,000

4 beds4 baths6,993 sqft

209 Whippoorwill Rd, Chappaqua, NY 10514

Single FamilyProperty Type

5.88 acresLot Size

1974Year Built

$202/sq ftPrice per sq ft

Description

Crowning an expansive, private lot in prestigious Whippoorwill this classic gated contemporary is the epitome of peaceful seclusion! The exterior of this meticulously maintained home is timeless expression; a lush fusion of mature trees, & greenery overlooking WCC golf course. Inside, open floor plan flows with an easy, relaxed elegance. Home or country retreat, amenities include entertainers kitchen, luxury spa master and generous LL walk-out quarters for Au-pair and/or extended stay guests!Crowning an expansive, private lot in prestigious Whippoorwill this classic gated contemporary is the epitome of peaceful seclusion! The exterior of this meticulously maintained home is timeless expression; a lush fusion of mature trees, & greenery overlooking WCC golf course. Inside, open floor plan flows with an easy, relaxed elegance. Home or country retreat, amenities include entertainers kitchen, luxury spa master and generous LL walk-out quarters for Au-pair and/or extended stay guests!

Listed by: Beth S Silfen 914.234.9099 • Houlihan Lawrence Inc.
Listed by: Todd Goddard 914.328.8400 • Houlihan Lawrence Inc.

Listing closed: 09/27/2013 12:00 AM • Source: HGMLS, MLS#: 3307817

Recent comparable sales

Median sold price

$1,600,018

Avg days on market

Sale-to-list ratio

109.7%

$1,610,000

Sold 06/16/25

4
Bedrooms: 4
Bathrooms: 3,858
Square Feet: 1.62
Acres

52 Old Lyme Road, Chappaqua, NY 10514

$1,310,000

Sold 01/09/25

4
Bedrooms: 4
Bathrooms: 2,384
Square Feet: 1.07
Acres

10 Algonquin Drive, Chappaqua, NY 10514

$1,330,000

Sold 08/14/26

4
Bedrooms: 3.5
Bathrooms: 3,314
Square Feet: 0.5
Acres

35 Kings Court, Chappaqua, NY 10514

$1,720,000

Sold 02/04/26

4
Bedrooms: 4
Bathrooms: 3,244
Square Feet: 1.47
Acres

6 Whippoorwill Lake Road, Chappaqua, NY 10514

$1,731,000

Sold 08/06/26

4
Bedrooms: 4
Bathrooms: 3,138
Square Feet: 0.51
Acres

14 Crossways, Chappaqua, NY 10514

$1,501,000

Sold 07/21/25

4
Bedrooms: 4
Bathrooms: 3,525
Square Feet: 1.04
Acres

23 Cross Ridge Road, Chappaqua, NY 10514

a front view of a house with a yard and porch

$1,725,000

Sold 10/31/25

4
Bedrooms: 4
Bathrooms: 4,100
Square Feet: 0.48
Acres

9 Point Place, Chappaqua, NY 10514

$1,095,000

Sold 10/18/24

4
Bedrooms: 3
Bathrooms: 3,208
Square Feet: 0.54
Acres

5 Brevoort Road, Chappaqua, NY 10514

$1,600,018

Sold 12/04/24

4
Bedrooms: 4
Bathrooms: 3,689
Square Feet: 1.3
Acres

70 Cowdin Circle, Chappaqua, NY 10514

Amenities

Contemporary
Gym
Parking Included
Private Outdoor Space
Spa

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Location

Listing Courtesy of Houlihan Lawrence Inc.

Sold By Douglas Elliman Real Estate

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$10,958 per month

30 year fixed, 6.71% Interest

Principal and Interest

$7,286

Property Taxes

$3,672

HOA Dues

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Property Information for 209 Whippoorwill Road

Property Details

Taxes: $44,066 / year
MLS Type: Single Family / Detached
County: Westchester County

Building Information

Year Built: 1974
Lot Size: 5.88 AC / 256,133 SF

Property History for 209 Whippoorwill Road

Date	Event & Source	Price	Appreciation
Sep 25, 2013	Sold (Public Record) Public Record #634133423	$1,410,000	—
Sep 25, 2013	Sold (Public Record) Public Record #634133423	$1,410,000	-10.1% / yr
Dec 19, 2012	Sold (Public Record) Public Record #634367573	$1,530,000	—
Dec 19, 2012	Sold (Public Record) Public Record #634367573	$1,530,000	-1.1% / yr
Apr 18, 2006	Sold (Public Record) Public Record #203698685	$1,650,000	+1.0% / yr
Jun 17, 2004	Sold (Public Record) Public Record #276288643	$1,620,000	—

Date	Event & Source	Price
09/25/2013	Sold (Public Record) Public Record #634133423	$1,410,000
09/25/2013	Sold (Public Record) Public Record #634133423	$1,410,000 -10.1% / yr
12/19/2012	Sold (Public Record) Public Record #634367573	$1,530,000
12/19/2012	Sold (Public Record) Public Record #634367573	$1,530,000 -1.1% / yr
04/18/2006	Sold (Public Record) Public Record #203698685	$1,650,000 +1.0% / yr
06/17/2004	Sold (Public Record) Public Record #276288643	$1,620,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 209 Whippoorwill Road

Taxable ValueLand$200,000Additions$104,880Total$304,880

Tax Record2025$41,227 ($3,436 / month)

Home Facts

Beds4Baths3Total Finished SqFt6,993 SqFtAbove Grade Finished SqFt5,307 SqFtFinished Basement SqFt1,686 SqFtStories2Lot Size256,133 SqFtStyleSingle Family ResidenceYear Built1974ZoningR-2ACountyWESTCHESTERAPN553600 101.18-3-9Fireplace TypeHas Fireplace

Schools near 209 Whippoorwill Road

This home is within Chappaqua Central School District.


Rating	School	Type	Grades	Distance
10/10	Douglas G Grafflin School	Public - Nearby school	PK to 4	1.1 mi
9/10	Robert E Bell School	Public - Nearby school	5 to 8	1.8 mi
10/10	Horace Greeley High School	Public - Serves this home	9 to 12	2.0 mi
10/10	Roaring Brook School	Public - Nearby school	K to 4	3.1 mi
10/10	Westorchard School	Public - Nearby school	K to 4	4.0 mi
8/10	Seven Bridges Middle School	Public - Nearby school	5 to 8	4.5 mi


Rating	School	Distance
10/10	Douglas G Grafflin School PublicPK to 4 Nearby school	1.1 mi
9/10	Robert E Bell School Public5 to 8 Nearby school	1.8 mi
10/10	Horace Greeley High School Public9 to 12 Serves this home	2.0 mi
10/10	Roaring Brook School PublicK to 4 Nearby school	3.1 mi
10/10	Westorchard School PublicK to 4 Nearby school	4.0 mi
8/10	Seven Bridges Middle School Public5 to 8 Nearby school	4.5 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Chappaqua

A leafy hamlet that’s sleepy, but polished. 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...

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Nearby home values

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 209 Whippoorwill Road, Chappaqua, NY 10514	$1,410,000	4	4	6,993	256,133
201 Whippoorwill Road, Chappaqua, NY 10514	$350,000	4	2	3,318	102,366
211 Whippoorwill Road, Chappaqua, NY 10514	$1,470,000	6	4	3,916	99,752
67 Whippoorwill Crossing, Armonk, NY 10504	$1,850,000	3	5	4,400	243,065
34 Frog Rock Road, Armonk, NY 10504	$1,350,000	5	5	5,702	89,298
30 Frog Rock Road, Armonk, NY 10504	–	5	6	6,169	70,567
63 Whippoorwill Crossing, Armonk, NY 10504	$2,000,000	4	6	4,590	206,165
61 Whippoorwill Crossing, Armonk, NY 10504	$1,225,000	4	3	3,301	93,218
26 Frog Rock Road, Armonk, NY 10504	$1,590,000	3	4	4,650	87,991
35 Frog Rock Road, Armonk, NY 10504	$1,545,000	5	5	5,151	91,476
29 Frog Rock Road, Armonk, NY 10504	–	4	5	4,750	94,961
45 Carolyn Place, Chappaqua, NY 10514	$3,493,425	5	9	8,116	169,448
49 Carolyn Place, Chappaqua, NY 10514	–	6	7	8,147	91,040
51 Carolyn Place, Chappaqua, NY 10514	$3,400,000	5	8	9,679	119,533
59 Whippoorwill Crossing, Armonk, NY 10504	–	3	3	4,677	201,683
115 Whippoorwill Road, Armonk, NY 10504	–	–	3	1,923	140,699

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Listing Courtesy of Houlihan Lawrence Inc.

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