2 Whippoorwill Close

Off Market

2 Whippoorwill Close

Chappaqua NY 10514

3022 sq. ft.

69260 sq. ft.

Single-Family

Last sold for $2,000,000

Cindy Glynn, last sold this property on 09 February 2026 after 38 days on market.

Overview

Exceptionally renovated and truly turnkey, this striking Whippoorwill cul-de-sac Contemporary is located in the highly acclaimed Chappaqua School District. Dramatic, airy, and light-filled, the 4-bedroom home is set in a serene and sought-after neighborhood, offering both privacy and convenience. A wall of windows, skylights, soaring ceilings, and an open floor plan flood the interiors with natural light. The living and family rooms—each featuring a fireplace—flow seamlessly for effortless everyday living and entertaining. Hardwood floors extend throughout, while outdoor spaces include a stone patio and wraparound deck overlooking lush, park-like grounds. Extensive upgrades include new above-ground oil tanks, new windows, a new roof, new mechanicals, and more. Enjoy lake rights to Whippoorwill Lake and easy walking access to the Whippoorwill trails. This exceptional home is a rare offering and sure to delight the most discerning buyer.

Features

4 bedrooms

4 bathrooms

3 carspaces

3 garage spaces

3022 sq. ft. floor area

69260 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Chappaqua over the last 12 months, the estimated median property value of 2 Whippoorwill Close is $1.65m.

Median value

$1.65m

Estimated value range

$700k - $3.5m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Chappaqua. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 2 Whippoorwill Close

2026

Sold

$2,000,000

09 Feb 2026 by Cindy Glynn, of Compass Greater NY, LLC

2020

Sold

$997,000

02 Jul 2020 by Alicja Bohmrich, of Houlihan Lawrence Inc.

Happy sellers in Chappaqua

94%

94% of sellers in Chappaqua reported that their sale price either exceeded or met their price expectations.

Chappaqua stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 3 reviews in Chappaqua over the last 12 months.

Local market activity for 4 bedroom single-family properties in Chappaqua

In the last 12 months, 53 four-bedroom single-family properties similar to 2 Whippoorwill Close, have been sold.

This represents a 18% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Chappaqua for a market analysis.

Yarden Ronen-Van Heerden

at Compass Greater NY, LLC

(93 reviews)

Get a market analysis

Sari Shaw

at Compass Greater NY, LLC

(1 review)

Get a market analysis

Edward Holmes

at William Raveis-New York, LLC

(9 reviews)

Get a market analysis

Francie Malina

at Compass Greater NY, LLC

(90 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Chappaqua

Yarden Ronen-Van Heerden

Yarden Ronen-Van Heerden is an award winning recommended agent for Chappaqua. They have 1 local sale and collected 2 local reviews across the last 12 months.