Off Market May 2025 for $1.1M

$1,122,003

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

$584Est. 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: 3 minutes ago

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

Redfin Estimate

$1,122,003

$28K since sold in May 2025$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.1% lower than the average sale price ($1.22M) of 6 comparable homes.

SOLD AUG 18, 2026
$1,510,000
A
3 beds2.5 baths2,010 sq ft
100 Devoe Rd, Chappaqua, NY 10514
Listing by William Raveis-New York, LLC
SOLD JUL 23, 2026
$1,376,000
B
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
C
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
D
3 beds2.5 baths1,299 sq ft
80 Bischoff Ave, Chappaqua, NY 10514
Listing by Keller Williams NY Realty
SOLD SEP 1, 2026
$1,250,000
E
4 beds2.5 baths2,207 sq ft
21 Campfire Rd, Chappaqua, NY 10514
Listing by Compass Greater NY, LLC
SOLD AUG 26, 2026
$1,275,000
F
3 beds2.5 baths2,423 sq ft
10 Grandview Ave, Pleasantville, NY 10570
Listing by RE/MAX Ace Realty

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Earn from this home

Sell

$157,515

Est. take-home

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Refinance

Est. cash available

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Rent

$4,034/mo

Redfin rental estimate

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Market trends in 10514, NY

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

113.6%

0.2% MoM

Median sale price

$1.7M

$11K MoM

Avg. days on market

17d

0 days MoM

Recently sold homes

11 MoM

New listings for sale

NEW 32 HRS AGO
$1,399,000
3 beds3 baths2,821 sq ft
10 Deborah Ln, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
$749,000
3 beds1.5 baths1,414 sq ft
27 Mill River Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
$1,575,000
4 beds2.5 baths2,376 sq ft
9 Lori Ln, Chappaqua, NY 10514
Listing by Julia B Fee Sothebys Int. Rlty
$1,725,000
4 beds3.5 baths3,581 sq ft
53 W Orchard Rd, Chappaqua, NY 10514
Listing by Houlihan Lawrence Inc.
$1,800,000
4 beds3.5 baths2,913 sq ft
406 Bedford Rd, Chappaqua, NY 10514
Listing by Howard Hanna Rand Realty
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

HGMLS #2014174

Nov 7, 2000

Price Changed

$254/sq ft

Nov 7, 2000

Delisted

—

Sep 18, 2000

Listed

$247/sq ft

Public Records

Oct 3, 1994

Sold

$233,500

$121/sq ft

** Price available after signing in.

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 Jul 30, 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 Jul 30, 2026

Around this home

Schools

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

$1.07M – $1.29M

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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.	$1,206,168
21 Wynnewood Rd, Chappaqua, NY 2 Beds \| 3 Baths \| 1768 Sq. Ft.	$1,197,542

Address	Redfin Estimate
41 Wynnewood Rd, Chappaqua, NY 3 Beds \| 3 Baths \| 2747 Sq. Ft.	$1,272,013
31 Wynnewood Rd, Chappaqua, NY 4 Beds \| 3 Baths \| 2420 Sq. Ft.	$1,674,399

Address	Redfin Estimate
12 Wynnewood Rd, Chappaqua, NY 4 Beds \| 2 Baths \| 1904 Sq. Ft.	$1,210,262
34 Wynnewood Rd, Chappaqua, NY 2 Beds \| 2 Baths \| 2022 Sq. Ft.	$1,017,759

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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