Off market may 2025 for $1.1M

$1,118,029

Est. refi paymentEst. refi $1,938/mo

•

1,922

sq ft

44 Wynnewood Rd, Chappaqua, NY 10514

About this home

Discover your dream home in Chappaqua! Located less than 1 mile from town and train, yet a tranquil retreat surrounded by mature trees on a quiet road. This light filled cape offers the charm and warmth of the 30's with modern conveniences including a fabulous new kitchen with stainless Bosch appliances. The house features exposed white beamed ceilings and wood floors throughout. The floor plan offers a first floor bedroom and full bath, a gracious formal living room with cozy fireplace and French door to screened in porch, a family room (formerly used as a formal dining room) with a WIC/pantry, new kitchen with door to large patio for grilling and entertaining, and a breakfast room with bay window. The second floor features a large primary bedroom with high ceilings, bath, office/nursery and and walk in attic storage. Full lower level (finished storage) with 2 large windows offers potential for office, playroom and gym, laundry, utilities, above ground oil tanks, mudroom and door to 1 car garage. The total acreage, taxes, and assessment include an additional .08 parcel (separate tax lot) affording additional privacy. Low taxes!

Single-familyProperty Type

1937Year Built

0.36 acresLot Size

$582Est. Price/Sq.Ft.

1 car garageParking

Listing by Barbara Pagliuca • Houlihan Lawrence Inc.

Contact: 914-238-4766

Bought with Jessica Broomhead • Compass Greater NY, LLC

Redfin checked: a minute ago

•Source:OneKey® MLS as Distributed by MLS Grid #828028

Redfin Estimate

$1,118,029

$32K since sold in May 2025$3,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.6% higher than the average sale price ($1.06M) of 6 comparable homes.

SOLD OCT 5, 2026
$1,275,000
A
3 beds2 baths1,850 sq ft
1 Commodore Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
SOLD OCT 16, 2026
$915,000
B
3 beds2 baths1,825 sq ft
460 Washington Ave, Pleasantville, NY 10570
Listing by Compass Greater NY, LLC
SOLD SEP 15, 2026
$870,000
C
3 beds1.5 baths1,538 sq ft
220 Mill River Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD JUL 23, 2026
$1,376,000
D
3 beds2 baths1,702 sq ft
65 Douglas Rd, Chappaqua, NY 10514
Listing by North Country Sothebys Int Rlt
SOLD JUL 30, 2026
$1,200,000
E
3 beds2.5 baths2,048 sq ft
7 Hays Hill Rd, Pleasantville, NY 10570
Listing by Corcoran Baer & McIntosh
SOLD SEP 1, 2026
$715,000
F
3 beds2.5 baths1,299 sq ft
80 Bischoff Ave, Chappaqua, NY 10514
Listing by Keller Williams NY Realty

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Sell

$156,769

Est. take-home

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Refinance

Est. cash available

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Rent

$4,101/mo

Redfin rental estimate

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Market trends in 10514, NY

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

111.3%

2.1% MoM

Median sale price

$1.6M

$140K MoM

Avg. days on market

17d

0 days MoM

Recently sold homes

6 MoM

New listings for sale

OPEN TODAY, 12PM TO 2PM
$799,000
2 beds2.5 baths1,244 sq ft
13 Deer Run, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
See all

Provided by Redfin

Sale history for 44 Wynnewood Rd

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #828028

May 6, 2025

Sold

$1,150,000

$598/sq ft

Mar 13, 2025

Pending

—

Mar 5, 2025

Listed

$849,000

$442/sq ft

Public Records

Oct 23, 2020

Sold

$850,000

$442/sq ft

OneKey® MLS as Distributed by MLS Grid #H6055176

Oct 19, 2020

Sold

$650,000

$338/sq ft

Jul 31, 2020

Listed

$639,000

$332/sq ft

1930's Country Charmer with LOW taxes. This inviting home can live as a 3 bedroom; first-floor bedroom and a bedroom plus open loft on the second floor. Both floors have full baths. 'Get away from it all' and simplify. Work from home in this private, natural setting, with screened porch, bluestone patio, and usable yard. Special Features include exposed beams, wood-burning fireplace, breakfast room with bay window, 2nd floor high ceilings, hardwood floors, outdoor stone walls, flower gardens and a sunny vegetable garden location. Lower level offers finished storage spaces, laundry, mechanicals and door to single car garage. Tucked in the corner of a sought-after neighborhood this home has excellent proximity to town, Saw Mill Parkway, shops, train, schools and the new Whole Foods at Chappaqua Crossing. Those qualified receive an annual STAR reduction of $1,775. Additional Information: Amenities:Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:1 Car Attached,

Public Records

Jan 31, 2001

Sold

$475,000

$247/sq ft

Public Records

Oct 3, 1994

Sold

$233,500

$121/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$16,741 (−0.6%)

$17,300 + $77,700

$95,000

2025

$16,837 (+3.2%)

$17,300 + $77,700

$95,000

2024

$16,319 (+2.7%)

$17,300 + $77,700

$95,000

2023

$15,893 (+3.0%)

$17,300 + $77,700

$95,000

2022

$15,436 (+1.4%)

$17,300 + $77,700

$95,000

2021

$15,218 (+14.3%)

$17,300 + $77,700

$95,000

2020

$13,313 (+2.0%)

$17,300 + $77,700

$95,000

2019

$13,054

$17,300 + $77,700

$95,000

2018

$17,300 + $77,700

$95,000

2017

$17,300 + $77,700

$95,000

2016

$17,300 + $77,700

$95,000

2014

$17,300 + $77,700

$95,000

2013

$17,300 + $77,700

$95,000

2012

$17,300 + $77,700

$95,000

2011

$17,300 + $77,700

$95,000

2010

$17,300 + $77,700

$95,000

2009

$17,300 + $77,700

$95,000

2008

$17,300 + $77,700

$95,000

Tax history for 44 Wynnewood Rd

Year

Property tax

Land + Additions

Assessment*

2026

$16,741 (−0.6%)

$17,300 + $77,700

$95,000

2025

$16,837 (+3.2%)

$17,300 + $77,700

$95,000

2024

$16,319 (+2.7%)

$17,300 + $77,700

$95,000

2023

$15,893 (+3.0%)

$17,300 + $77,700

$95,000

2022

$15,436 (+1.4%)

$17,300 + $77,700

$95,000

2021

$15,218 (+14.3%)

$17,300 + $77,700

$95,000

2020

$13,313 (+2.0%)

$17,300 + $77,700

$95,000

2019

$13,054

$17,300 + $77,700

$95,000

2018

$17,300 + $77,700

$95,000

2017

$17,300 + $77,700

$95,000

2016

$17,300 + $77,700

$95,000

2014

$17,300 + $77,700

$95,000

2013

$17,300 + $77,700

$95,000

2012

$17,300 + $77,700

$95,000

2011

$17,300 + $77,700

$95,000

2010

$17,300 + $77,700

$95,000

2009

$17,300 + $77,700

$95,000

2008

$17,300 + $77,700

$95,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

0.26 Acres

Year renovated

—

Sq. Ft.

1,922

Year built

1937

Style

Single Family Residential

County

Westchester County

APN

553600A10001000010090000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking Information
Carport YN: No
Parking Total: 1
Parking Features: Attached

Garage Information
Garage Spaces: 1
Has Garage

Interior

Fireplace Information
Fireplaces Total: 1
Fireplace Features: Living Room

Heating & Cooling
Cooling: None
Heating: Hot Water, Oil

Interior Features
Interior Features: First Floor Bedroom,First Floor Full Bath,Beamed Ceilings,Entrance Foyer,Quartz/Quartzite Counters
Laundry Features: In Basement
Appliances: Dishwasher, Dryer, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
Flooring: Wood
Levels: Two

Room Information
Basement YN: Yes
Attic: Partial
Rooms Total: 7
Basement: Partially Finished
Additional Rooms: Dining Area,Home Office,Library/Den

Bathroom Information
Bathrooms Full: 2

Exterior

Exterior Features
Construction Materials: Brick, Wood Siding
Waterfront YN: No

Lot Information
Additional Parcels YN: Yes
Lot Features: Back Yard

Property Information
Living Area (Sq. Ft.): 1922.00
Building Area Total (Sq. Ft.): 1922.00
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2024
Tax Source: Municipality
Tax Annual Amount: $16,980

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Electric Company: Con-Edison
Sewer: Septic Tank
Utilities: Electricity Connected

Location

School Information
Elementary School: Roaring Brook
Middle Or Junior School: Robert E Bell School
High School: Horace Greeley High School
High School District: Chappaqua

Location Information
County Or Parish: Westchester County

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 1,922
Stories: —
Lot Size: 0.26 acres
Style: Single Family Residential
Year Built: 1937
Year Renovated: —
County: Westchester County
APN: 553600A10001000010090000000

Home facts updated by county records on Sep 25, 2026

Around this home

Schools

K - 12
Preschool & daycare

Some nearby schools may not be within this home's attendance zone. Please check the Chappaqua Central School District website to verify.

Robert E Bell School

Public 5-8 • 0.7mi

9/10

Horace Greeley High School

Public 9-12 • 1.7mi

10/10

Douglas G Grafflin School

Public PreK-4 • 1.4mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 99° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 5 days in 30 years

Provided by First Street

Historical weather

Chappaqua, NY • 10514

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

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.

8.7 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.06M – $1.29M

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New listings for sale in 10514

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Home values near 44 Wynnewood Rd

Data from public records.

Address	Redfin Estimate
5 Wynnewood Rd, Chappaqua, NY 4 Beds \| 2 Baths \| 2208 Sq. Ft.	$1,151,462
21 Wynnewood Rd, Chappaqua, NY 2 Beds \| 3 Baths \| 1768 Sq. Ft.	$1,212,305
22 Wynnewood Rd, Chappaqua, NY 5 Beds \| 3 Baths \| 2524 Sq. Ft.	$1,261,433
40 Martha Pl, Chappaqua, NY 3 Beds \| 2 Baths \| 3042 Sq. Ft.	$1,533,346
39 Dunbow Dr, Chappaqua, NY 4 Beds \| 2.5 Baths \| 1890 Sq. Ft.	$1,258,588
63 Martha Pl, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3229 Sq. Ft.	$1,647,244
70 Park Dr, Chappaqua, NY 2 Beds \| 1 Baths \| 904 Sq. Ft.	$674,760

Address	Redfin Estimate
41 Wynnewood Rd, Chappaqua, NY 3 Beds \| 3 Baths \| 2747 Sq. Ft.	$1,357,525
31 Wynnewood Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 2420 Sq. Ft.	$1,602,949
5 Peck Pl, Chappaqua, NY 3 Beds \| 2 Baths \| 2041 Sq. Ft.	$1,361,199
84 Park Dr, Chappaqua, NY 3 Beds \| 1.5 Baths \| 1289 Sq. Ft.	$981,785
32 Martha Pl, Chappaqua, NY 4 Beds \| 2.5 Baths \| 1938 Sq. Ft.	$1,067,392
65 Park Dr, Chappaqua, NY 2 Beds \| 3 Baths \| 2618 Sq. Ft.	$1,168,526
25 Leroy Rd, Chappaqua, NY 3 Beds \| 3 Baths \| 4280 Sq. Ft.	$1,652,017

Address	Redfin Estimate
12 Wynnewood Rd, Chappaqua, NY 4 Beds \| 2 Baths \| 1904 Sq. Ft.	$1,288,425
34 Wynnewood Rd, Chappaqua, NY 2 Beds \| 2 Baths \| 2022 Sq. Ft.	$1,036,332
73 Park Dr, Chappaqua, NY 3 Beds \| 2 Baths \| 2709 Sq. Ft.	$1,277,578
46 Park Dr, Chappaqua, NY 4 Beds \| 2.5 Baths \| 2242 Sq. Ft.	$1,132,523
56 Martha Pl, Chappaqua, NY 3 Beds \| 2 Baths \| 2579 Sq. Ft.	$1,302,514
76 Park Dr, Chappaqua, NY 3 Beds \| 2 Baths \| 1524 Sq. Ft.	$1,052,564
9 Peck Pl, Chappaqua, NY 4 Beds \| 3.5 Baths \| 3884 Sq. Ft.	$2,040,477

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2025. This data may not match . Learn more.

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