380 Whippoorwill Rd

Off Market

380 Whippoorwill Rd

Chappaqua NY 10514

880 sq. ft.

99752 sq. ft.

Single-Family

Last sold for $525,000

Sari Shaw, last sold this property on 16 October 2025 after 188 days on market.

Overview

This charming cottage has been completely reimagined, seamlessly blending timeless character with modern luxury. Fully gut-renovated and thoughtfully redesigned from top to bottom, this inviting home offers the perfect retreat—whether you're seeking a serene weekend escape or a full-time residence. Ideally located just minutes from downtown Chappaqua and seconds from Chappaqua Crossing, Horace Greeley High School, and Whippoorwill Park, the convenience is unmatched. Inside, the sun-drenched interior features an open layout with high-end finishes throughout. The custom kitchen (2018) is outfitted with sleek appliances and tailored cabinetry, while the beautifully updated bathrooms exude style and sophistication. Cozy living spaces and gorgeous hardwood floors enhance the home’s warmth and character. Every detail has been carefully curated, including updated systems and new windows, all while preserving the home’s original charm.

Features

3 bedrooms

2 bathrooms

1 carspace

1 garage space

880 sq. ft. floor area

99752 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Chappaqua over the last 12 months, the estimated median property value of 380 Whippoorwill Rd is $1.33m.

Median value

$1.33m

Estimated value range

$525k - $2.3m

Median days on market

Estimated value trend

11%

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 380 Whippoorwill Rd

2025

Sold

$525,000

16 Oct 2025 by Sari Shaw, of Compass Greater NY, LLC

2023

Rented

Undisclosed

26 May 2023 by Compass Greater NY, LLC

2021

Rented

Undisclosed

13 Apr 2021 by Compass Greater NY, LLC

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 3 bedroom single-family properties in Chappaqua

In the last 12 months, 41 three-bedroom single-family properties similar to 380 Whippoorwill Rd, have been sold.

This represents a 8% decrease in three-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.