This home's estimate is 16.7% higher than the average sale price ($2.32M) of 6 comparable homes.
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- Sale & tax history
- Property details
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371 Whippoorwill Rd, Chappaqua, NY 10514
About this home
This spectacular farm-house colonial with welcoming front porch designed by noted architect David Graham with Shoreline Pool, spa, custom pool house and waterfall is perfectly situated on 2.76 acres on a private road in the prestigious Whippoorwill area. This well-crafted 5 BR. 4.5 bath home is flooded with sunlight. A gracious entry foyer with vaulted ceilings opens to a formal dining room with Butler's Pantry and formal living room with fireplace. In addition, there is a tranquil, relaxing sunroom, an office with custom bookcases and powder room. The gourmet kitchen with a windowed breakfast area features Christopher Peacock Cabinetry, quartzite counters and backsplash, Wolf 6 burner range, Viking wall oven, Subzero refrigerator, Miele dishwasher. The kitchen opens to a sun filled family room with wood burning stone fireplace and French doors leading to an outdoor deck and pool. Second floor boasts the primary en-suite bedroom with marble bath and walk in closets; 4 additional bedrooms and 3 full baths, bonus gathering/playroom or nanny's suite, laundry room, and sundeck. A fully finished basement with over 2000 sq ft offers plenty of space for entertaining, recreation, exercise and woodworking. Multiple upgrades include new roof, new above ground oil tanks, full home generator, freshly painted exterior. Perfectly maintained and well suited for today's discerning buyer, conveniently located to train, shopping and schools. Additional Information: Amenities:Dressing Area,Marble Bath,Storage,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
0 days MoM
- COMING SOON$1,599,0008 beds7 baths5,798 sq ft600 Bedford Rd, Chappaqua, NY 10514Listing by Houlihan Lawrence Inc.
- COMING SOON$1,375,0003 beds2 baths2,254 sq ft88 Brevoort Rd, Chappaqua, NY 10514Listing by Compass Greater NY, LLC
- COMING SOON$2,299,0005 beds4.5 baths4,661 sq ft20 Hitching Post Ln, Chappaqua, NY 10514Listing by William Raveis-New York LLC
- $5,750,0006 beds7.5 baths9,247 sq ft24 Trails End, Chappaqua, NY 10514Listing by Compass Greater NY, LLC
- $1,399,0003 beds3 baths2,821 sq ft10 Deborah Ln, Chappaqua, NY 10514Listing by Houlihan Lawrence Inc.
- $749,0003 beds1.5 baths1,414 sq ft27 Mill River Rd, Chappaqua, NY 10514Listing by Houlihan Lawrence Inc.
- $1,725,0004 beds3.5 baths3,581 sq ft53 W Orchard Rd, Chappaqua, NY 10514Listing by Houlihan Lawrence Inc.
- $1,800,0004 beds3.5 baths2,913 sq ft406 Bedford Rd, Chappaqua, NY 10514Listing by Howard Hanna Rand Realty
See all
Provided by Redfin
Sale history for 371 Whippoorwill Rd
$351/sq ft
$351/sq ft
$367/sq ft
$390/sq ft
$328/sq ft
Tax history for 371 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, Heated Garage
Interior
- Fireplace Information
- Has Fireplace
- Fireplaces Total: 2
- Heating & Cooling
- Cooling: Central Air
- Heating: Forced Air, Oil
- Interior Features
- Interior Features: Built-in Features,Cathedral Ceiling(s),Central Vacuum,Chefs Kitchen,Eat-in Kitchen,Entrance Foyer,ENERGY STAR Qualified Door(s),Formal Dining,High Ceilings,High Speed Internet,Primary Bathroom,Open Kitchen,Pantry,Walk-In Closet(s),Wet Bar
- Window Features: Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Screens
- Appliances: Cooktop, Dishwasher, Dryer, ENERGY STAR Qualified Appliances, Microwave, Refrigerator, Stainless Steel Appliance(s), Oil Water Heater
- Flooring: Hardwood
- Patio And Porch Features: Deck
- Room Information
- Basement YN: Yes
- Attic: Full
- Rooms Total: 10
- Basement: Finished, Full, Walk-Out Access
- Additional Rooms: Dining Area,Library/Den,Office
- Bathroom Information
- Bathrooms Full: 4
- Bathrooms Half: 1
Exterior
- Exterior Features
- Exterior Features: Balcony, Mailbox
- Construction Materials: Clapboard, Frame, Stone
- Other Structures: Outbuilding
- Security Features: Fire Sprinkler System, Security System
- Waterfront YN: No
- Pool Information
- Pool Features: In Ground
- Lot Information
- Additional Parcels YN: No
- Lot Features: Level, Near Public Transit, Near School, Near Shops, Sprinklers In Front, Sprinklers In Rear
- Property Information
- Other Equipment: Generator, Pool Equip/Cover
- Living Area Source: Public Records
- Property Sub Type: Single Family Residence
Financial
- Tax Information
- Tax Year: 2022
- Tax Source: Municipality
- Tax Annual Amount: $55,665
- 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 #371, just past Haights Cross Rd.
- County Or Parish: Westchester County
- Community Information
- Community Features: Park
Public facts
- Beds: 5
- Baths: 4.0
- Sq. Ft.: 6,410
- Stories: —
- Lot Size: 2.65 acres
- Style: Single Family Residential
- Year Built: 1994
- Year Renovated: —
- County: Westchester County
- APN: 553600A10101000020020030000
Around this home
Schools
Public PreK-4 • 0.8mi
Public 5-8 • 1.5mi
Public 9-12 • 1.2mi
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
26% 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 371 Whippoorwill Rd
| Address | Redfin Estimate |
|---|---|
5 Beds | 5.5 Baths | 7391 Sq. Ft. | $4,126,280 |
4 Beds | 2.5 Baths | 3450 Sq. Ft. | $1,830,333 |
| Address | Redfin Estimate |
|---|---|
5 Beds | 6 Baths | 6074 Sq. Ft. | $3,484,792 |
5 Beds | 4 Baths | 3478 Sq. Ft. | $1,893,257 |
| Address | Redfin Estimate |
|---|---|
6 Beds | 3 Baths | 7505 Sq. Ft. | $3,963,746 |
4 Beds | 5.5 Baths | 5579 Sq. Ft. | $2,845,224 |
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