301 Whippoorwill Rd
Compass Coming Soon
Compass Coming Soon
Description
Timeless elegance meets exceptional craftsmanship in this spectacular brick and stone estate, privately set behind gates on 4+ acres in one of Chappaqua's prestigious Whippoorwill neighborhoods. Designed by acclaimed architect Carol Kurth and masterfully built in 2003 by renowned builder Robert Torre, this extraordinary 5-bedroom, 6 full, 1 half bath residence offers over 10,000 square feet of impeccably crafted living space, where timeless architecture, luxurious finishes, and modern comfort come...Timeless elegance meets exceptional craftsmanship in this spectacular brick and stone estate, privately set behind gates on 4+ acres in one of Chappaqua's prestigious Whippoorwill neighborhoods. Designed by acclaimed architect Carol Kurth and masterfully built in 2003 by renowned builder Robert Torre, this extraordinary 5-bedroom, 6 full, 1 half bath residence offers over 10,000 square feet of impeccably crafted living space, where timeless architecture, luxurious finishes, and modern comfort come together seamlessly. A long private drive leads to a grand arrival. Inside, a dramatic two-story foyer with a sweeping circular staircase sets the tone for the home's impressive scale and refined design. Every room features soaring 10-ft ceilings, while the entry foyer and formal living room rise to over 20 feet, filling the home with light and volume. Rich hardwood floors, exquisite custom millwork, recessed lighting, and four fireplaces enhance the warmth and sophistication throughout. Designed for both grand entertaining and comfortable everyday living, the main level flows effortlessly from room to room. A spectacular formal living room with walls of windows opens to a gracious dining room, while the designer chef's kitchen features custom cabinetry, honed natural limestone floors, an oversized island with seating, breakfast area, abundant prep space, and premium stainless appliances including a 48" Wolf range, 30" Wolf convection oven, Thermador microwave, separate 36" Sub-Zero refrigerator and freezer, and 2 Bosch dishwashers. A butler's pantry enhances entertaining, and French doors lead to an expansive stone terrace overlooking the pool and grounds. Adjacent to the kitchen, the family room is anchored by a striking stone fireplace. The 1st floor also includes a spacious guest suite with a private bath, a back hall with pool bath, and access to the heated epoxy-finished three-car garage with room for up to five vehicles using lifts—a dream for the automobile enthusiast. Between 1st and 2nd floors is a private office and below a wine tasting room. The luxurious primary suite offers a dressing room, two oversized walk-in closets, a private balcony overlooking the backyard, and a spa-inspired bath with radiant heated floors, whirlpool tub, and steam shower. Three additional en-suite bedrooms, an expansive recreation room, and a 2nd floor laundry complete the upper level, while an additional 1st floor laundry room adds convenience. An enormous unfinished lower level offers exceptional potential for a home theater, fitness center, wine cellar, golf simulator, or additional recreation space. The outdoor setting is equally impressive. Beautifully landscaped grounds designed by acclaimed landscape architect Louis Fusco feature sprawling level lawns, specimen plantings, curated gardens, classic stone walls, and a magnificent Cardillo saltwater pool with a new filtration system and electric safety cover. An expansive stone patio and charming gazebo provide exceptional spaces for entertaining and relaxation. Bordering the Glazier Arboretum and backing to forever protected land, the property enjoys extraordinary privacy, tranquility, and picturesque natural surroundings. Additional amenities include a whole-house generator, electric vehicle charger, Elan smart home system for lighting, thermostats, and security. Just minutes from downtown Chappaqua, award-winning schools, and Metro-North for an approximately 50- minute commute to Manhattan, this remarkable Whippoorwill estate represents a rare opportunity to own one of Chappaqua's premier luxury properties.
Listing Agent
![Cindy Glynn]()
P: (914)-523-6163
Property Details for 301 Whippoorwill Road
City/Township
New Castle
Architectural StyleEstate
Garage Spaces3.00
WaterfrontNo
LISTING UPDATED: 07/10/2026 05:01 AM
Property Details for 301 Whippoorwill Road
| Status | Coming Soon |
|---|---|
| MLS # | H6333127 |
| Days on Market | - |
| Taxes | $90,893 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Single Family |
| Year Built | 2003 |
| Lot Size | 4.39 AC / 191,228 SF |
| County | Westchester County |
Location
Add your commute
Building Information for 301 Whippoorwill Road
Stories-Year Built2003Building Size-Lot Size4.39 AC / 191,228 SF
Payment Calculator
$25,509 per month
30 year fixed, 6.36% Interest
Principal and Interest
$17,934
Property Taxes
$7,574
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 301 Whippoorwill Road
Summary
Location and General Information
- Senior Community YN: No
- Property Attached: No
- Structure Type: Detached
- Levels: Three Or More
- State Or Province: NY
School Information
- School District: Chappaqua
- Elementary School District: Chappaqua
- Elementary School: Douglas G Grafflin School
- Middle Or Junior School District: Chappaqua
- Middle Or Junior School: Robert E Bell School
- High School District: Chappaqua
- High School: Horace Greeley High School
Rental
Rental
- Lease Considered: No
- RentSpree Y/N: false
Unit Information
Unit Information
- Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
- Parcel Number: 3600-101-014-00001-000-0007
- Tax Assessed Value: $547,600.00
- Additional Fees: No
- Tax Source: Municipality
- Tax Year: 2026.0
- Association: No
Interior and Exterior Features
Interior Features
- Amenities: 1st Floor Bedrm, Balcony, Deck, Estate, Fenced, First Floor Full Bath, Garden, Gas Grill, Gazebo, Hardwood Floors As Seen, In Ground, Juliet Balcony, Laundry Room, Lighting, Mailbox, Multiple Locations, Patio, Pool Cover, Pool/Spa Combo, Public, Salt Water, Security Lights, Security System, Smoke Detector(s), Wood Burning
- Interior Features: First Floor Bedroom, First Floor Full Bath
- Appliances: Cooktop, Dishwasher, Dryer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater
- Number Of Kitchens: 1.0
- Total Rooms: 15
- Basement: Full, Unfinished, Walk-Out Access
- Attic Description: Full
- Fireplace: Yes
- Fireplaces Total: 5
- Fireplace Features: Wood Burning
- Location Amenities: Stainless Steel Appliances, Walk Out Basement, Balcony, Juliet Balcony, Fenced, Fenced Yard, Hardwood Floors As Seen, 1st Fl Master Bedroom, Heated Parking, Deck, Patio, In Ground Pool, Security System
- Laundry Features: Laundry Room, Multiple Locations
- Security Features: Security Lights, Security System, Smoke Detector(s)
- Spa: Yes
- Flooring: Hardwood
- Living Area: 10,594.00
- Basement: Yes
Exterior Features
- Exterior Features: Balcony, Garden, Gas Grill, Juliet Balcony, Lighting, Mailbox
- Exterior Property Features: Balcony, Garden, Gas Grill, Juliet Balcony, Lighting, Mailbox, In Ground, Pool Cover, Pool/Spa Combo, Salt Water, Deck, Patio, Driveway, Electric Vehicle Charging Station(s), Garage, Garage Door Opener, Heated Garage, Fenced
- Elevation Certificate: No
- Fencing: Fenced
- Patio And Porch Features: Deck, Patio
- Construction Materials: Brick, Stone
- Other Structures: Gazebo
- Pool Private: Yes
- Pool Features: In Ground, Pool Cover, Pool/Spa Combo, Salt Water
- Pool Details: In Ground,Pool Cover,Pool/Spa Combo,Salt Water
Lot Information
- Additional Parcel: No
- Building Area Units: Square Feet
Parking
- Parking Features: Driveway, Electric Vehicle Charging Station(s), Garage, Garage Door Opener, Heated Garage
- Parking Total: 5.00
- Garage: Yes
- Carport: No
Utilities
- Cooling: Central Air
- Heating: Hot Air, Oil
- Heat Fuel Type: Hot Air, Oil
- Number Of Heating Zones: 7
- Sewer: Septic Tank
- Water Source: Public
- Utilities: Cable Connected, Electricity Connected, Trash Collection Public, Water Connected
Green Features
- Green Features: Cooktop, Dishwasher, Dryer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater, Hot Air, Oil, Balcony, Garden, Gas Grill, Juliet Balcony, Lighting, Mailbox, In Ground, Pool Cover, Pool/Spa Combo, Salt Water
Agent
Payment and Rate
- Down Payment Resource: No
Property History for 301 Whippoorwill Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Apr 22, 2002 | Sold HGMLS #2112667 | $1,250,000 | — |
| Dec 19, 2001 | Contract HGMLS #2112667 | — | |
| Sep 5, 2001 | Listed (Active) HGMLS #2112667 | $1,250,000 | — |
| Jul 10, 2000 | Listed (Active) HGMLS #2010750 | $1,250,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 04/22/2002 | Sold HGMLS #2112667 | $1,250,000 |
| 12/19/2001 | Contract HGMLS #2112667 | — |
| 09/05/2001 | Listed (Active) HGMLS #2112667 | $1,250,000 |
| 07/10/2000 | Listed (Active) HGMLS #2010750 | $1,250,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 301 Whippoorwill Road
Taxable ValueLand$220,000Additions$327,600Total$547,600
Tax Record2025$35,138 ($2,928 / month)
Home Facts
Beds5Baths5Total Finished SqFt10,594 SqFtAbove Grade Finished SqFt10,594 SqFtStories2Lot Size191,228 SqFtStyleSingle Family ResidenceYear Built2003ZoningR-2ACountyWESTCHESTERAPN553600 101.14-1-7Fireplace TypeHas Fireplace
Schools near 301 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
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...
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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 07/10/2026 05:01 AM. 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.
