Whippoorwill Hills Agnew Farm Rd, Armonk, NY 10504
Community View
$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath | Listing by Julia B Fee Sothebys Int. Rlty
Beautiful curb appeal
$12,500 | 49 Miller Circle, North Castle, NY 10504 | 4 Bed, 5 Bath | Listing by William Raveis Real Estate
Gated Community
$8,500 | 7 Hopkins Lane, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by William Raveis Real Estate
Welcome home to 25 Hopkins Lane in Armonk!
$1,450,000 | 25 Hopkins Lane, North Castle, NY 10504 | 4 Bed, 4 Bath | Listing by William Raveis-New York, LLC
Welcome home!
$1,525,000 | 26 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by William Raveis Real Estate
Community View
$11,500 | 8 Caruso Place, North Castle, NY 10504 | 4 Bed, 4 Bath | Listing by Compass Greater NY, LLC
Traditional-style house with a garage, a front yard, and driveway
$1,479,000 | 7 Caruso Place, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by Coldwell Banker Realty
Traditional home with roof with shingles, driveway, an attached garage, and a front lawn
$10,500 | 42 Miller Circle, North Castle, NY 10504 | 5 Bed, 4 Bath | Listing by William Raveis Real Estate
Welcome Home!
$1,079,000 | 30 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath | Listing by William Raveis Real Estate
Community View
$9,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath | Listing by Julia B Fee Sothebys Int. Rlty
Front View
$1,795,000 | 8 Raven Court, North Castle, NY 10504 | 4 Bed, 4 Bath | Listing by Houlihan Lawrence Inc.
View of front of house
$1,395,000 | 9 Caruso Place, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by Houlihan Lawrence Inc.
Welcome to 9 Hopkins Lane!
$1,050,000 | 9 Hopkins Lane, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by Houlihan Lawrence Inc.
Townhome
$7,850 | 7 Hopkins Lane, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by William Raveis Real Estate
Beautiful Curb Appeal
$10,000 | 42 Miller Circle, North Castle, NY 10504 | 5 Bed, 4 Bath | Listing by William Raveis Real Estate
Welcome to 19 Miller Circle in Whippoorwill Hills
$1,595,000 | 19 Miller Circle, North Castle, NY 10504 | 4 Bed, 5 Bath | Listing by William Raveis Real Estate
Welcome to 4 Raven Court in Armonk.
$1,560,000 | 4 Raven Court, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by Keller Williams Realty Group
Welcome home to your serene and lush yard.
$1,100,000 | 29 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 4 Bath | Listing by Julia B Fee Sothebys Int. Rlty
Welcome to Whippoorwill Hills
$10,500 | 1 Caruso Place, North Castle, NY 10504 | 4 Bed, 4 Bath | Listing by William Raveis Real Estate
Community View
$1,575,000 | 27 Miller Circle, North Castle, NY 10504 | 4 Bed, 3 Bath | Listing by Compass Greater NY, LLC

Whippoorwill Hills Community

Agnew Farm Rd, Armonk, NY 10504 | Westchester, NY county

Whippoorwill Hills is a gated residential community in the heart of Armonk that offers a welcoming neighborhood atmosphere combined with everyday convenience. Open green spaces, quiet roads, and a sense of privacy create an environment where residents can unwind while staying connected to everything the village has to offer. The ability to walk to shops, restaurants, the library, and nearby parks adds to the ease of daily life, while nearby Metro-North service and I-684 make commuting simple and efficient. Whippoorwill Hills continues to attract homeowners who value a comfortable, low-maintenance lifestyle in a setting that feels established, friendly, and well cared for an ideal place to enjoy the best of life in Armonk.

0.24 acres Average Lot Size
2 Active Listings
126 Total Housing Units
3,387 Average Square Footage

Resident Amenities

sports_basketball Basketball Court
family_group Clubhouse
fitness_center Fitness Center
award_star Gated Community
award_star Grounds & Common Area Maintenance
pickleball Pickleball Court
pool Pool
sports_tennis Tennis Court

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Resident Amenities

expand_less
sports_basketball Basketball Court
family_group Clubhouse
fitness_center Fitness Center
award_star Gated Community
award_star Grounds & Common Area Maintenance
pickleball Pickleball Court
pool Pool
sports_tennis Tennis Court

Active Listings & Homes For Sale and For Rent

Photo Lot Price Beds Baths Square Feet HOA Fees
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Whippoorwill Hills Community (and nearby)
For Sale
For Rent
In Contract
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Whippoorwill Hills Residences

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Available Home Models

Bristol

The Bristol offers 3–4 bedrooms across approximately 2,924–4,283 square feet, with 2.5–3.5 baths and two to three stories. Homes feature an open layout, hardwood floors, generous windows, and a first-floor primary suite with walk-in closets. Many include a loft, while finished walk-out lower levels can provide recreation space, a bedroom, or guest quarters. A two-car attached garage is included. Residents can enjoy Whippoorwill Hills’ pools, clubhouse, tennis court, and playgrounds, with downtown Armonk nearby. Select homes also offer a private deck or patio.

Bristol
Bristol
Bristol
Bristol
Bristol
Bristol

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

Single Family Residence
Build Type
3–4
Beds
2.5–3.5
Baths
2,924–4,283
Sqft
—
Garages
3
Stories

Cornell

With 4–5 bedrooms, approximately 3,134–4,321 square feet, and 2.5–4.5 baths, the Cornell spans two to three stories and includes a two-car attached garage. Its open layout commonly brings the kitchen and family room together, with features such as a fireplace, oversized windows, and a deck. A primary suite with a sitting area and walk-in closet is complemented by additional bedrooms, including options with en-suite or Jack-and-Jill baths. Finished walk-out lower levels add flexible space for recreation, exercise, storage, or guests. Community amenities include pools, tennis, a clubhouse, and playgrounds.

Cornell
Cornell
Cornell

$1,795,000 | 8 Raven Court, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

$1,595,000 | 19 Miller Circle, North Castle, NY 10504 | 4 Bed, 5 Bath

Listing by William Raveis Real Estate

$1,299,000 | 6 Miller Circle, North Castle, NY 10504 | 5 Bed, 5 Bath

Listing by Houlihan Lawrence Inc.

Single Family Residence
Build Type
4–5
Beds
2.5–4.5
Baths
3,134–4,321
Sqft
2
Garages
2–3
Stories

Gloucester

The Gloucester is a distinctive option in Whippoorwill Hills, with just four models noted in the community. This two-story home offers 3 bedrooms, 3.5 baths, and 3,790 square feet, along with a two-car attached garage. Its two-story living room features a fireplace, while the dining room and gourmet eat-in kitchen provide space for gathering. The first-floor primary suite has two walk-in closets and a spacious bath. Upstairs, a bright loft with built-ins joins two bedrooms and a full bath. A walk-out lower level adds a family room, office or guest room, and full bath.

Gloucester

$1,095,000 | 49 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

Townhouse
Build Type
3
Beds
3.5
Baths
3,790
Sqft
—
Garages
—
Stories

Norfolk

The Norfolk is a two-story Colonial offering 4 bedrooms, 3.5 baths, and 3,495 square feet, with a two-car attached garage. Its features include built-ins and custom closets throughout, plus a whole-house sound system serving the first floor, primary bedroom, and backyard. The kitchen and primary bath were updated, and a washer and dryer were also noted among the home’s improvements. A finished walk-out basement provides additional private space and a full bath. The home is within walking distance of town and close to Whippoorwill Hills’ pool, tennis facilities, and clubhouse.

Norfolk

$1,250,000 | 21 Miller Circle, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

Single Family Residence
Build Type
4
Beds
3.5
Baths
3,495
Sqft
—
Garages
—
Stories

Princeton

The Princeton offers 3–4 bedrooms, approximately 2,940–4,122 square feet, and 3.5–4 baths across two to three stories. Homes feature an open floor plan and natural light, often with a first-floor primary suite and a two-story family room with tall windows. Kitchens open to family or breakfast areas, while upper levels may include a loft and additional bedrooms. Finished walk-out lower levels provide flexible recreation or guest space, and a two-car attached garage is included. Whippoorwill Hills residents have access to pools, tennis, a clubhouse, and playgrounds, with downtown Armonk within walking distance.

Princeton
Princeton
Princeton
Princeton

$1,369,000 | 47 Miller Circle, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by The Foxes Real Estate

$1,295,000 | 11 Miller Circle, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

$1,250,000 | 34 Miller Circle, North Castle, NY 10504 | 4 Bed, 5 Bath

Listing by Houlihan Lawrence Inc.

$1,265,000 | 47 Miller Circle, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

Single Family Residence
Build Type
3–4
Beds
3.5–4
Baths
2,940–4,122
Sqft
—
Garages
2
Stories

Rockland

Priced from $1,450,000

The Rockland offers 3–4 bedrooms, approximately 2,540–3,931 square feet, and 2.5–3.5 baths across three stories, with a two-car attached garage. Floor plans may include a primary suite on the first floor, while some homes have additional bedrooms and a full bath upstairs. Features described include an open, light-filled layout, a walk-in pantry, and a finished walk-out lower level suited to recreation or fitness. Select homes also offer a second primary suite or a bonus room. The gated community provides pools, tennis, a clubhouse, and playgrounds, with Armonk shops and dining nearby.

Rockland
Rockland
Rockland
Rockland
Rockland
Rockland

$1,450,000 | 25 Hopkins Lane, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by William Raveis-New York, LLC

$11,500 | 8 Caruso Place, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Compass Greater NY, LLC

$1,395,000 | 9 Caruso Place, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

$9,500 | 8 Caruso Place, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Compass Greater NY, LLC

$970,000 | 9 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$899,000 | 28 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

Single Family Residence
Build Type
3–4
Beds
2.5–3.5
Baths
2,540–3,931
Sqft
—
Garages
3
Stories

Available Home Models

Bristol
Bristol
Bristol
Bristol
Bristol
Bristol

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$10,000 | 16 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

Bristol

Single Family Residence
Build Type
3–4
Beds
2.5–3.5
Baths
2,924–4,283
Sqft
—
Garages
3
Stories

The Bristol offers 3–4 bedrooms across approximately 2,924–4,283 square feet, with 2.5–3.5 baths and two to three stories. Homes feature an open layout, hardwood floors, generous windows, and a first-floor primary suite with walk-in closets. Many include a loft, while finished walk-out lower levels can provide recreation space, a bedroom, or guest quarters. A two-car attached garage is included. Residents can enjoy Whippoorwill Hills’ pools, clubhouse, tennis court, and playgrounds, with downtown Armonk nearby. Select homes also offer a private deck or patio.

Cornell
Cornell
Cornell

$1,795,000 | 8 Raven Court, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

$1,595,000 | 19 Miller Circle, North Castle, NY 10504 | 4 Bed, 5 Bath

Listing by William Raveis Real Estate

$1,299,000 | 6 Miller Circle, North Castle, NY 10504 | 5 Bed, 5 Bath

Listing by Houlihan Lawrence Inc.

Cornell

Single Family Residence
Build Type
4–5
Beds
2.5–4.5
Baths
3,134–4,321
Sqft
2
Garages
2–3
Stories

With 4–5 bedrooms, approximately 3,134–4,321 square feet, and 2.5–4.5 baths, the Cornell spans two to three stories and includes a two-car attached garage. Its open layout commonly brings the kitchen and family room together, with features such as a fireplace, oversized windows, and a deck. A primary suite with a sitting area and walk-in closet is complemented by additional bedrooms, including options with en-suite or Jack-and-Jill baths. Finished walk-out lower levels add flexible space for recreation, exercise, storage, or guests. Community amenities include pools, tennis, a clubhouse, and playgrounds.

Gloucester

$1,095,000 | 49 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

Gloucester

Townhouse
Build Type
3
Beds
3.5
Baths
3,790
Sqft
—
Garages
—
Stories

The Gloucester is a distinctive option in Whippoorwill Hills, with just four models noted in the community. This two-story home offers 3 bedrooms, 3.5 baths, and 3,790 square feet, along with a two-car attached garage. Its two-story living room features a fireplace, while the dining room and gourmet eat-in kitchen provide space for gathering. The first-floor primary suite has two walk-in closets and a spacious bath. Upstairs, a bright loft with built-ins joins two bedrooms and a full bath. A walk-out lower level adds a family room, office or guest room, and full bath.

Norfolk

$1,250,000 | 21 Miller Circle, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

Norfolk

Single Family Residence
Build Type
4
Beds
3.5
Baths
3,495
Sqft
—
Garages
—
Stories

The Norfolk is a two-story Colonial offering 4 bedrooms, 3.5 baths, and 3,495 square feet, with a two-car attached garage. Its features include built-ins and custom closets throughout, plus a whole-house sound system serving the first floor, primary bedroom, and backyard. The kitchen and primary bath were updated, and a washer and dryer were also noted among the home’s improvements. A finished walk-out basement provides additional private space and a full bath. The home is within walking distance of town and close to Whippoorwill Hills’ pool, tennis facilities, and clubhouse.

Princeton
Princeton
Princeton
Princeton

$1,369,000 | 47 Miller Circle, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by The Foxes Real Estate

$1,295,000 | 11 Miller Circle, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

$1,250,000 | 34 Miller Circle, North Castle, NY 10504 | 4 Bed, 5 Bath

Listing by Houlihan Lawrence Inc.

$1,265,000 | 47 Miller Circle, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

Princeton

Single Family Residence
Build Type
3–4
Beds
3.5–4
Baths
2,940–4,122
Sqft
—
Garages
2
Stories

The Princeton offers 3–4 bedrooms, approximately 2,940–4,122 square feet, and 3.5–4 baths across two to three stories. Homes feature an open floor plan and natural light, often with a first-floor primary suite and a two-story family room with tall windows. Kitchens open to family or breakfast areas, while upper levels may include a loft and additional bedrooms. Finished walk-out lower levels provide flexible recreation or guest space, and a two-car attached garage is included. Whippoorwill Hills residents have access to pools, tennis, a clubhouse, and playgrounds, with downtown Armonk within walking distance.

Rockland
Rockland
Rockland
Rockland
Rockland
Rockland

$1,450,000 | 25 Hopkins Lane, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by William Raveis-New York, LLC

$11,500 | 8 Caruso Place, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Compass Greater NY, LLC

$1,395,000 | 9 Caruso Place, North Castle, NY 10504 | 3 Bed, 4 Bath

Listing by Houlihan Lawrence Inc.

$9,500 | 8 Caruso Place, North Castle, NY 10504 | 4 Bed, 4 Bath

Listing by Compass Greater NY, LLC

$970,000 | 9 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

$899,000 | 28 Agnew Farm Road, North Castle, NY 10504 | 3 Bed, 3 Bath

Listing by Julia B Fee Sothebys Int. Rlty

Rockland

Priced from $1,450,000

Single Family Residence
Build Type
3–4
Beds
2.5–3.5
Baths
2,540–3,931
Sqft
—
Garages
3
Stories

The Rockland offers 3–4 bedrooms, approximately 2,540–3,931 square feet, and 2.5–3.5 baths across three stories, with a two-car attached garage. Floor plans may include a primary suite on the first floor, while some homes have additional bedrooms and a full bath upstairs. Features described include an open, light-filled layout, a walk-in pantry, and a finished walk-out lower level suited to recreation or fitness. Select homes also offer a second primary suite or a bonus room. The gated community provides pools, tennis, a clubhouse, and playgrounds, with Armonk shops and dining nearby.

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Community Facts

  • Community Name: Whippoorwill Hills
  • Neighborhood: Armonk
  • Year Established: 2002
  • Total Homes: 126 residences
  • Property Type: Houses, Townhomes
  • County: Westchester, NY county
  • Available Sales Listings: 0
  • Available Rental Listings: 2
  • Lifestyle & HOA: Life at Whippoorwill Hills is designed to be easy, active, and maintenance free. Residents enjoy a range of private community amenities that enhance daily living, including two swimming pools, a clubhouse, tennis courts, and a children’s playground. These shared spaces provide opportunities for recreation, relaxation, and social connection throughout the seasons. The Homeowners Association supports a low-maintenance lifestyle by overseeing exterior upkeep, landscaping, and common areas, allowing homeowners to spend more time enjoying their surroundings rather than managing chores. Gated access with 24-hour security adds an extra layer of comfort and peace of mind. Beyond the gates, residents benefit from proximity to Armonk’s library, shops, restaurants, and parks, as well as convenient access to major roadways and nearby Metro-North stations. Whippoorwill Hills offers a lifestyle that feels balanced and effortless - where community, convenience, and comfort come together in one of Westchester’s most desirable villages.

Frequently Asked Questions

Learn more about the Whippoorwill Hills community and available homes for sale and rent here in Armonk.

When was Whippoorwill Hills built?
Whippoorwill Hills was built in 2002.
Where is Whippoorwill Hills located?
Whippoorwill Hills is located at Agnew Farm Rd in Armonk in NY.
What amenities does the Whippoorwill Hills community provide?
Whippoorwill Hills provides the following resident amenities: Basketball Court, Clubhouse, Fitness Center, Gated Community, Grounds & Common Area Maintenance, Pickleball Court, Pool, Tennis Court.
What county is Whippoorwill Hills located in?
Whippoorwill Hills is located in Westchester, NY county.
How many homes are currently available in Whippoorwill Hills for sale or for rent?
Out of 126 homes in Whippoorwill Hills, there are currently 0 sales listings and 2 rental listings available.
What is the average square footage in the Whippoorwill Hills community?
The average square footage of homes in Whippoorwill Hills is 3387 sq.ft.
How big is the Whippoorwill Hills community?
The Whippoorwill Hills community is made up of 126 homes with an average lot size of 10271 sq.ft.

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