This home's estimate is 6.7% higher than the average sale price ($1.73M) of 6 comparable homes.
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398 Whippoorwill Rd, Chappaqua, NY 10514
About this home
Every day will feel like a vacation as you enjoy this charming colonial and it's breathtaking, sanctuary like property. Awaiting your updates and finishing touches, this home and it's convenient location is close to all that Chappaqua and Westchester County have to offer. Magnificent screened in porch brings the beauty of the exterior spaces indoors. The interior features a stately formal dining room and living room with fireplace. Master suite plus three additional bedrooms. Two car garage with breezeway. Hardwood flooring throughout. Full basement with fireplace is partially finished and offers 4 additional rooms and a full bath. Seller will include an additional subdivided lot directly behind the house which is 5.5919 acres Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,
Redfin Estimate
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Market trends in 10514, NY
Last updated October 2026
Buyer's Market
Seller's Market
Seller's market
- COMING SOON$1,825,0004 beds3.5 baths3,164 sq ft25 Helena Dr, Chappaqua, NY 10514Listing by William Raveis-New York, LLC
- $799,0002 beds2.5 baths1,244 sq ft13 Deer Run, Chappaqua, NY 10514Listing by Compass Greater NY, LLC
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Provided by Redfin
Sale history for 398 Whippoorwill Rd
$243/sq ft
$256/sq ft
$270/sq ft
Tax history for 398 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: 2
- Parking Features: Detached, Driveway
Interior
- Virtual Tour Information
- Fireplace Information
- Has Fireplace
- Fireplaces Total: 2
- Heating & Cooling
- Cooling: Central Air
- Heating: Baseboard, Oil
- Interior Features
- Interior Features: Eat-in Kitchen,Formal Dining,Primary Bathroom,Walk-In Closet(s)
- Laundry Features: Inside
- Appliances: Indirect Water Heater
- Levels: Two
- Patio And Porch Features: Porch
- Room Information
- Basement YN: Yes
- Attic: Pull Stairs
- Rooms Total: 11
- Basement: Full, Partially Finished
- Bathroom Information
- Bathrooms Full: 3
- Bathrooms Half: 1
Exterior
- Exterior Features
- Construction Materials: Frame
- Waterfront YN: No
- Property Information
- Stories: 2
- Living Area Source: Public Records
- Property Sub Type: Single Family Residence
Financial
- Tax Information
- Tax Year: 2018
- Tax Source: Municipality
- Tax Annual Amount: $30,367
- Financial Information
- Buyer Financing: Cash
Utilities
- Utility Information
- Sewer: Septic Tank
- Utilities: Trash Collection Public
Location
- 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
- County Or Parish: Westchester County
Public facts
- Beds: 4
- Baths: 3.0
- Sq. Ft.: 3,312
- Stories: —
- Lot Size: 1.97 acres
- Style: Single Family Residential
- Year Built: 1963
- Year Renovated: —
- County: Westchester County
- APN: 553600A09301800010040000000
Around this home
Schools
- K - 12
- Preschool & daycare
Public PreK-4 • 1.2mi
Public 5-8 • 1.6mi
Public 9-12 • 0.8mi
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
23% 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 4.2 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 398 Whippoorwill Rd
| Address | Redfin Estimate |
|---|---|
5 Beds | 3.5 Baths | 3556 Sq. Ft. | $2,033,310 |
5 Beds | 5 Baths | 4210 Sq. Ft. | $1,888,649 |
3 Beds | 3 Baths | 4267 Sq. Ft. | $2,022,503 |
4 Beds | 4.5 Baths | 4330 Sq. Ft. | $1,832,060 |
4 Beds | 3.5 Baths | 3750 Sq. Ft. | $1,861,883 |
4 Beds | 2.5 Baths | 3416 Sq. Ft. | $1,597,963 |
5 Beds | 3.5 Baths | 3145 Sq. Ft. | $1,931,505 |
| Address | Redfin Estimate |
|---|---|
6 Beds | 3.5 Baths | 4612 Sq. Ft. | $3,183,603 |
5 Beds | 5.5 Baths | 6600 Sq. Ft. | $3,495,618 |
3 Beds | 2.5 Baths | 2613 Sq. Ft. | $1,400,475 |
5 Beds | 4.5 Baths | 6367 Sq. Ft. | $2,275,409 |
4 Beds | 2.5 Baths | 3912 Sq. Ft. | $1,986,277 |
4 Beds | 2.5 Baths | 2443 Sq. Ft. | $1,701,479 |
4 Beds | 4.5 Baths | 4792 Sq. Ft. | $1,959,264 |
| Address | Redfin Estimate |
|---|---|
4 Beds | 4 Baths | 5188 Sq. Ft. | $3,106,567 |
5 Beds | 6 Baths | 6241 Sq. Ft. | $2,887,956 |
4 Beds | 2.5 Baths | 2566 Sq. Ft. | $1,416,836 |
3 Beds | 3 Baths | 2625 Sq. Ft. | $1,687,706 |
4 Beds | 4.5 Baths | 4305 Sq. Ft. | $1,913,775 |
3 Beds | 2 Baths | 1608 Sq. Ft. | $1,092,367 |
5 Beds | 5 Baths | 6340 Sq. Ft. | $3,193,818 |
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