This home's estimate is 25.3% higher than the average sale price ($2.74M) of 6 comparable homes.
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- Sale & tax history
- Property details
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365 Whippoorwill Rd, Chappaqua, NY 10514
About this home
Private, spectacular & superbly crafted Whippoorwill estate colonial beautifully sited on 4+ acres featuring expansive lawns, Gunite pool, rolling hills, & views of adjacent Glazier Arboretum. This sophisticated & inviting home, designed by renowned architect David Graham, features custom details & exceptional finishes - lavish millwork, hardwd flrs, elegant marble, extensive built-ins, 3 fireplaces. Gourmet modern kitchen - oversized granite island w/counter seating & top-of-the-line appliances. 5 bedrms including a luxurious master bdrm ste w/sitting rm, oversized his-&-hers walk-in closets & sumptuous bath, plus 4 addt'l bedrms, 2 w/en-suite bths & 2 w/Jack n' Jill bth. Spectacular lower level (1,400 sq ft additional) w/gym, screening rm, playrm & pool changing rm. Expansive mudrm w/built-ins. 3+ car garage w/lift. Balconies & patios around home create easy indoor outdoor living & entertainment ease. 6 bdrm septic, two 330 gallon above ground oil tanks. A truly special offering! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,
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Market trends in 10514, NY
Last updated August 2026
Buyer's Market
Seller's Market
Seller's market
- OPEN SAT, 12:30PM TO 3PM
53 W Orchard Rd, Chappaqua, NY 10514$1,725,0004 beds3.5 baths3,581 sq ft53 W Orchard Rd, Chappaqua, NY 10514Listing by Houlihan Lawrence Inc. - OPEN SUN, 12PM TO 2PM$1,800,0004 beds3.5 baths2,913 sq ft406 Bedford Rd, Chappaqua, NY 10514Listing by Howard Hanna Rand Realty
- $1,325,0003 beds3 baths2,238 sq ft35 Marcourt Dr, Chappaqua, NY 10514Listing by Houlihan Lawrence Inc.
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Provided by Redfin
Sale history for 365 Whippoorwill Rd
$362/sq ft
$375/sq ft
$411/sq ft
$432/sq ft
$453/sq ft
$453/sq ft
$432/sq ft
$453/sq ft
$493/sq ft
$453/sq ft
** Price available after signing in.
Tax history for 365 Whippoorwill Rd
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Property details
Parking
- Parking Information
- Parking Total: 3
- Parking Features: Attached, Garage Door Opener
Interior
- Fireplace Information
- Has Fireplace
- Fireplaces Total: 3
- Heating & Cooling
- Cooling: Central Air
- Heating: Hydro Air, Oil
- Interior Features
- Interior Features: Cathedral Ceiling(s),Chandelier,Eat-in Kitchen,Entrance Foyer,Formal Dining,Granite Counters,Marble Counters,Primary Bathroom,Pantry,Walk-In Closet(s)
- Window Features: Blinds, Screens
- Laundry Features: Inside
- Appliances: Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater
- Flooring: Hardwood
- Levels: Three Or More
- Patio And Porch Features: Deck, Patio
- Room Information
- Basement YN: Yes
- Attic: Pull Stairs
- Rooms Total: 14
- Basement: Finished, Full, Walk-Out Access
- Bathroom Information
- Bathrooms Full: 5
- Bathrooms Half: 2
Exterior
- Exterior Features
- Exterior Features: Speakers
- Construction Materials: Block, Cedar, Shake Siding
- Security Features: Fire Sprinkler System, Security System
- Waterfront YN: No
- Pool Information
- Pool Features: In Ground
- Lot Information
- Additional Parcels YN: No
- Lot Features: Near Public Transit, Near School, Near Shops, Sprinklers In Front, Sprinklers In Rear
- Property Information
- Stories: 3
- Other Equipment: Generator, Pool Equip/Cover
- Living Area Source: Public Records
- Property Sub Type: Single Family Residence
Financial
- Tax Information
- Tax Year: 2018
- Tax Source: Municipality
- Tax Annual Amount: $67,715
- Financial Information
- Buyer Financing: Conventional
Utilities
- Utility Information
- Electric Company: Con-Edison
- Sewer: Septic Tank
- Utilities: Trash Collection Public
Location
- HOA Information
- Association Amenities: Park
- School Information
- Elementary School: Douglas G Grafflin School
- Middle Or Junior School: Robert E Bell School
- High School: Horace Greeley High School
- High School District: Chappaqua
- Location Information
- Hamlet: Chappaqua
- Directions: Whippoorwill Rd to #365, shared drive way, bear left and proceed to white gate
- County Or Parish: Westchester County
- Community Information
- Community Features: Park
Public facts
- Beds: 5
- Baths: 5.0
- Sq. Ft.: 6,068
- Stories: —
- Lot Size: 4.01 acres
- Style: Single Family Residential
- Year Built: 1994
- Year Renovated: —
- County: Westchester County
- APN: 553600A10101000020020010000
Around this home
Schools
Public PreK-4 • 0.8mi
Public 5-8 • 1.5mi
Public 9-12 • 1.3mi
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
Minimal risk of a flood reaching the building in the next 30 years
Unlikely to be in a wildfire in next 30 years
7 days above 98° expected this year, 15 days in 30 years
27% chance of strong winds in next 30 years
4 unhealthy days expected this year, 6 days in 30 years
Sun exposure
In this area, properties receive around 8.7 hours in June and 4.3 hours in December, placing it below the U.S. average for solar exposure.
Nearby similar homes
New listings for sale in 10514
Home values near 365 Whippoorwill Rd
| Address | Redfin Estimate |
|---|---|
5 Beds | 4.5 Baths | 6410 Sq. Ft. | $2,757,324 |
6 Beds | 3 Baths | 7505 Sq. Ft. | $3,884,480 |
| Address | Redfin Estimate |
|---|---|
5 Beds | 5.5 Baths | 7391 Sq. Ft. | $4,133,059 |
4 Beds | 2.5 Baths | 3450 Sq. Ft. | $1,835,657 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 1 Baths | 2064 Sq. Ft. | $1,512,385 |
5 Beds | 4 Baths | 3478 Sq. Ft. | $1,896,637 |
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