69 Whippoorwill Rd

Armonk, NY 10504

$1,350,000
Price
3
Beds
3,095 Sq. Ft.
$436 / Sq. Ft.
3,095
Sq. Ft.
$436
per Sq. Ft.
Listed By CompassPending
Listed By CompassPending
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Description

Nestled in the heart of Armonk sits 69 Whippoorwill Rd, a timeless 1790 antique gem set on 1.4 lush green acres. Brimming with historic character and modern comforts, the main home is a beautifully preserved 3-bedroom abode that lives like a 5-bedroom with unmatched charm throughout - original doors, wide plank floors, and hand-hewn exposed wooden beams honor the home’s rich heritage. The first floor offers seamless transition between the kitchen, living area and dining room with an attached screened-in...Nestled in the heart of Armonk sits 69 Whippoorwill Rd, a timeless 1790 antique gem set on 1.4 lush green acres. Brimming with historic character and modern comforts, the main home is a beautifully preserved 3-bedroom abode that lives like a 5-bedroom with unmatched charm throughout - original doors, wide plank floors, and hand-hewn exposed wooden beams honor the home’s rich heritage. The first floor offers seamless transition between the kitchen, living area and dining room with an attached screened-in porch perfect for enjoying afternoon tea and a summer's breeze. A bedroom with full bath off the kitchen provides a bonus space perfect for a guest room and/or home office. Upstairs you'll find a primary suite with a fully renovated bath and access to the finished 3rd floor. Additionally, a generously sized 2nd bedroom, fully renovated hall bath and sunny sitting room complete this floor. The detached garage which encompasses the historic charm of what once was the chauffeur's quarters from its original build includes a fully finished guest cottage with its own full bath—perfect for visitors, a home office, or creative retreat. This gorgeously landscaped property dotted with specimen trees and curated plantings borders the Fordham University Louis Calder Center, offering panoramic tranquility and land that gently slopes toward Calder Lake. Whether sipping coffee on the porch, relaxing on the tree swing or exploring the nature trails just beyond your backyard, this is a property that invites serenity and inspiration. A must-see Whippoorwill classic.

Listing Agents

  1. Catherine Orsini

    Catherine Orsini

    Listing Agent

    Compass

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  2. Francie Malina

    Francie Malina

    Alternative Listing Agent

    Compass

    CallTextEmail

Property Details for 69 Whippoorwill Road

City/Township
North Castle
View
Lake, Water
Architectural Style
Farmhouse
Garage Spaces
2.00
Waterfront
No
LISTING UPDATED: 11/18/2025 02:02 AM

Property Details for 69 Whippoorwill Road

StatusPending
MLS #888820
Days on Market116
Taxes$16,471 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1790
Lot Size1.43 AC / 62,160 SF
CountyWestchester County
Buyer's Agent Compensation2%

Location

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Building Information for 69 Whippoorwill Road

Stories-Year Built1790Building Size-Lot Size1.43 AC / 62,160 SF

Payment Calculator

$8,043 per month

30 year fixed, 6.28% Interest

Principal and Interest

$6,671

Property Taxes

$1,373

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 69 Whippoorwill Road

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: false
  • Levels: Two
  • Property Condition: Actual
  • Country: US
  • State Or Province: NY
  • Water Access YN: No
School Information
  • School District: Byram Hills
  • Elementary School District: Byram Hills
  • Elementary School: Coman Hill
  • Middle Or Junior School District: Byram Hills
  • Middle Or Junior School: H C Crittenden Middle School
  • High School District: Byram Hills
  • High School: Byram Hills High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 3800-107-000-00002-000-0001-008-0000
  • Tax Assessed Value: $15,000.00
  • Additional Fees: No
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Built-in Features, Eat in Kitchen, Farmhouse, Formal Dining, Granite Counters, Hardwood Floors As Seen, Lake Views, Patio, Porch, Walk In Closet, Water View, Well
  • Interior Features: First Floor Bedroom, Built-in Features, Eat-in Kitchen, Formal Dining, Granite Counters, Walk-In Closet(s)
  • Appliances: Cooktop, Dishwasher, Dryer, Refrigerator, Washer
  • Total Rooms: 13
  • Basement: Unfinished, Walk-Out Access
  • Attic Description: Full,Walkup
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Location Amenities: Walk Out Basement, Hardwood Floors As Seen, 1st Fl Master Bedroom, Eat in Kitchen, Formal Dining Room, Granit Countertops, Walk In Closet, Privacy, Brownstone, Scenic View, Patio, Porch, Lake Views, Water View
  • Spa: No
  • Flooring: Hardwood
  • Living Area: 3,095.00
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Patio, Porch, Detached, Driveway, Garage, Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Private, Stone/Brick Wall, Views
  • Elevation Certificate: No
  • Patio And Porch Features: Patio,Porch
  • Construction Materials: Cedar, Frame, Stone
  • Road Frontage Type: Municipal
  • Road Responsibility: Public Maintained Road
  • Horse: No
  • Pool Private: No
Lot Information
  • Lot Features: Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Private, Stone/Brick Wall, Views
  • Additional Parcel: No
  • Site Features: Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Private, Stone/Brick Wall, Views
  • Building Area Units: Square Feet
Parking
  • Parking Features: Detached, Driveway, Garage
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Hot Water, Oil
  • Heat Fuel Type: Hot Water, Oil
  • Sewer: Cesspool
  • Water Source: Well
  • Utilities: Trash Collection Public
Green Features
  • Green Features: Cooktop, Dishwasher, Dryer, Refrigerator, Washer, Hot Water, Oil
Agent
Payment and Rate
  • Down Payment Resource: No

Public Records for 69 Whippoorwill Road

Taxable ValueLand$2,800Additions$12,200Total$15,000
Home Facts
Beds5Total Finished SqFt2,307 SqFtAbove Grade Finished SqFt2,307 SqFtStories2Lot Size61,420 SqFtStyleSingle Family ResidenceYear Built1900ZoningR-2ACountyWESTCHESTERAPN553800 107.02-1-8Fireplace TypeHas Fireplace

Schools near 69 Whippoorwill Road

This home is within Byram Hills Central School District.
Rating
School
Type
Grades
Distance
Coman Hill School
Public - K to 2
Wampus School
Public - 3 to 5
H C Crittenden Middle School
Public - 6 to 8
Byram Hills High School
Public - 9 to 12
Rating
School
Distance
Coman Hill School
PublicK to 2

Wampus School
Public3 to 5

H C Crittenden Middle School
Public6 to 8

Byram Hills High School
Public9 to 12

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.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/26/2025 07:44 AM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.