Sold
Last Sold Price
5 beds7,391 sqft
369 Whippoorwill Rd, Chappaqua, NY 10514
Single FamilyProperty Type
2.21 acresLot Size
1994Year Built
$542/sq ftPrice per sq ft
3 carsParking Spaces

Description

Updated Farmhouse Colonial embraces country life with its warmth and character yet infuses sophisticated, modern vibes at every turn. Reclaimed beams and wood accents are abundant along with exquisite designer lighting, designer wall coverings and wide board white oak floors underfoot. The formal rooms segue to casual living spaces with a bright, open kitchen at the hub for effortless entertaining. Upstairs offers a private primary suite with dressing room and a spa bath. A Jack-and-Jill bedroom...Updated Farmhouse Colonial embraces country life with its warmth and character yet infuses sophisticated, modern vibes at every turn. Reclaimed beams and wood accents are abundant along with exquisite designer lighting, designer wall coverings and wide board white oak floors underfoot. The formal rooms segue to casual living spaces with a bright, open kitchen at the hub for effortless entertaining. Upstairs offers a private primary suite with dressing room and a spa bath. A Jack-and-Jill bedroom suite, bedroom with bath, and a large loft space with den, bedroom, bath and laundry, complete the upper level. An extraordinary, two-story cabana room with its barreled ceiling, abundant windows and summer kitchen flows seamlessly to the outdoors with a built-in grill, an extensive patio, heated pool with spa and a golf green. Top this off with lush specimen plantings on a level, 2-acre property, steps from the hiking trails at Glazier Preserve, close to towns and trains, and you have the perfect solution turning the everyday into extraordinary. Additional Information: Amenities:Soaking Tub,Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,

Listing Agent

  1. Brian Milton

    Brian Milton

    Listing Agent

    Compass Greater NY, LLC

    P: (914) 469-9889

    M: (914) 469-9889

Listing closed: 06/24/2024 12:00 AM • Source: ONEKEY as distributed by MLS GRID, MLS#: H6305280

Recent comparable sales

Median sold price

$2,995,000

Avg days on market

98

Sale-to-list ratio

96.2%

Chappaqua, NY

9 comparable properties found

1

$3,975,000

Sold 06/01/26

5
Bedrooms
6
Bathrooms
6,935
Square Feet
2
Acres
2

$3,900,000

Sold 03/06/25

5
Bedrooms
6
Bathrooms
6,965
Square Feet
2.1
Acres
$2,995,000 | 724 King Street, Chappaqua, NY 10514
3

$2,995,000

Sold 12/27/24

5
Bedrooms
6,026
Square Feet
4.29
Acres
4

$2,950,000

Sold 05/30/25

5
Bedrooms
6
Bathrooms
6,824
Square Feet
4.67
Acres
$2,875,000 | 76 Valley Lane, Chappaqua, NY 10514
5

$2,875,000

Sold 03/21/25

5
Bedrooms
6,177
Square Feet
2.22
Acres
$2,500,000 | 61 Carolyn Place, Chappaqua, NY 10514
6

$2,500,000

Sold 12/18/25

5
Bedrooms
5,907
Square Feet
2.19
Acres
a front view of a house with a yard table and chairs
7

$3,400,000

Sold 09/09/25

4
Bedrooms
7,305
Square Feet
1.29
Acres
$2,875,000 | 26 Hemlock Hills, Chappaqua, NY 10514
8

$2,875,000

Sold 07/31/25

5
Bedrooms
7,038
Square Feet
4.79
Acres
$4,900,000 | 71 Carolyn Place, Chappaqua, NY 10514
9

$4,900,000

Sold 10/09/24

5
Bedrooms
8,204
Square Feet
6.78
Acres

Location

Sold By Compass Greater NY, LLC

Add your commute

Payment Calculator

$28,601 per month

30 year fixed, 7.03% Interest

Principal and Interest

$21,381

Property Taxes

$7,220

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 369 Whippoorwill Road

Property Details
  • Taxes: $86,644 / year
  • MLS Type: Single Family
  • City/Township: New Castle
  • Architectural Style: Colonial
  • Community Features: Park
  • Waterfront: No
Building Information
  • Stories: 2
  • Year Built: 1994
  • Lot Size: 2.21 AC / 96,268 SF
Summary
Location and General Information
  • Hamlet: Chappaqua
  • Senior Community YN: No
  • Year Built Effective: 2017
  • Property Attached: No
  • Structure Type: Detached
  • Levels: Two
  • Property Condition: Actual
  • State Or Province: NY
School Information
  • School District: Chappaqua
  • Elementary School: Douglas G Grafflin School
  • Middle Or Junior School: Robert E Bell School
  • High School District: Chappaqua
  • High School: Horace Greeley High School
Rental
Rental
  • Lease Considered: No
  • Seasonal Rental: No
  • RentSpree Y/N: false
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: First
  • RoomDescription 1: EF, LR/Fpl, DR, Office, FPwdrRm, Gourmet Kit/Island/BkfstRm, FamRm/Fpl, MudRm, BkStrs, Pool House w/SummerKit, Full Bth
Room 2 Information
  • Room Level: Second
  • Room Description: UL Loft, PrimaryBR/WIC/SpaBth, BR/Bth/BR, BR/Bth, Laundry, Loft, Den, BR/Bth/Sauna
Room 3 Information
  • Room Level: Lower
  • Room Description: Gym, Storage, Mechanicals
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 3600-101-010-00002-000-0002-2
  • Tax Assessed Value: $545,500.00
  • Additional Fees: No
  • Association Amenities: Park, Sauna
  • Tax Source: Municipality
  • Tax Year: 2023
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Cathedral/Vaulted/High Ceiling, Chefs Kitchen, Colonial, Eat in Kitchen, Entrance Foyer, First Floor Full Bath, Formal Dining, High Ceilings, In Ground, Inside, Kitchen Island, Park, Patio, Porch, Primary Bathroom, Public, Quartz/Quartzite Counters, Sauna
  • Interior Features: Cathedral Ceiling(s), Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, First Floor Full Bath, High Ceilings, Kitchen Island, Primary Bathroom, Quartz/Quartzite Counters
  • Appliances: Oil Water Heater
  • Total Rooms: 14
  • Basement: Full, Walk-Out Access
  • Attic Description: Pull Stairs
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Location Amenities: Walk Out Basement, Cathedral/Vaulted/High Ceiling, Chef's Kitchen, Eat in Kitchen, Entry Foyer, Foyer, Formal Dining Room, High Ceilings, Island Kitchen, Patio, Porch, In Ground Pool
  • Laundry Features: Inside
  • Living Area: 7391
  • Basement: Yes
Exterior Features
  • Exterior Property Features: In Ground, Patio, Porch, Attached, Park
  • Elevation Certificate: No
  • Patio And Porch Features: Patio, Porch
  • Construction Materials: Clapboard, Frame
  • Road Responsibility: Public Maintained Road
  • Pool Features: In Ground
  • Pool Details: In Ground
Lot Information
  • Site Features: Park
Parking
  • Parking Features: Attached
  • Parking Total: 3.00
Utilities
  • Cooling: Central Air
  • Heating: Hydro Air, Oil
  • Heat Fuel Type: Hydro Air, Oil
  • Sewer: Septic Tank
  • Water Source: Public
  • Utilities: Trash Collection Private
Green Features
  • Green Features: Oil Water Heater, Hydro Air, Oil, In Ground
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 369 Whippoorwill Road

DateEvent & SourcePriceAppreciation
Jun 24, 2024

Sold (Public Record)

Public Record #1535424197

$4,005,000

+5.8% / yr

Jun 24, 2024

Sold

ONEKEY #H6305280

$4,005,000—
May 24, 2024

Pending

ONEKEY #H6305280

—
DateEvent & SourcePrice
06/24/2024

Sold (Public Record)

Public Record #1535424197

$4,005,000

+5.8% / yr

06/24/2024

Sold

ONEKEY #H6305280

$4,005,000
05/24/2024

Pending

ONEKEY #H6305280

—

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

Public Records for 369 Whippoorwill Road

Taxable ValueLand$125,000Additions$420,500Total$545,500
Tax Record2025$30,730 ($2,561 / month)
Home Facts
Beds5Baths5Total Finished SqFt7,391 SqFtAbove Grade Finished SqFt7,391 SqFtStories2Lot Size96,268 SqFtStyleSingle Family ResidenceYear Built1994ZoningR-2ACountyWESTCHESTERAPN553600 101.10-2-2.2Fireplace TypeHas Fireplace

Schools near 369 Whippoorwill Road

This home is within Chappaqua Central School District.
Rating
School
Type
Grades
Distance
Public - PK to 4
Public - 5 to 8
Public - 9 to 12
Public - K to 4
Rating
School
Distance
Douglas G Grafflin School
PublicPK to 4

Robert E Bell School
Public5 to 8

Horace Greeley High School
Public9 to 12

Roaring Brook School
PublicK to 4

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
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...

Similar Homes

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 369 Whippoorwill Road, Chappaqua, NY 10514
$4,005,000
5
7,391
96,268
$2,200,000
5
6,074
174,780
$2,050,000
4
5
5,579
227,819
$890,000
4
3,450
52,272
–
4
4
4,325
44,431
$1,245,000
4
2,808
54,886

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Based on information submitted to the MLS GRID as of 12/07/2024 04:10 PM. 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. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.