21 Winding Brook Rd

3,211 Sq. Ft.
$523 / Sq. Ft.
3,211
Sq. Ft.
$523
per Sq. Ft.

Description

Run, don’t walk to this exceptional center-hall-split perched atop a quiet hill in New Rochelle's coveted Pinebrook Estates! A true standout in the neighborhood, 21 Winding Brook Road is a stunning fusion of timeless elegance, comfort, and functionality. The main level boasts open-concept living and a dining area with an effortless flow into the gourmet kitchen, complete with stainless steel appliances, custom wood cabinetry, and a large peninsula—truly a chef’s dream. Just off the kitchen, an impeccably...Run, don’t walk to this exceptional center-hall-split perched atop a quiet hill in New Rochelle's coveted Pinebrook Estates! A true standout in the neighborhood, 21 Winding Brook Road is a stunning fusion of timeless elegance, comfort, and functionality. The main level boasts open-concept living and a dining area with an effortless flow into the gourmet kitchen, complete with stainless steel appliances, custom wood cabinetry, and a large peninsula—truly a chef’s dream. Just off the kitchen, an impeccably maintained mahogany deck leads to a flat backyard featuring a beautiful stone patio and generous lawn space, ideal for entertaining or relaxing. But the true crown jewel? The ~900 square foot primary suite—a private retreat with two walk-in closets, a luxurious hotel and spa-style bath, sauna, blackout curtains, sound- and heat-proof windows, and a serene balcony—perfect for enjoying your morning coffee or a peaceful evening breeze. This home offers five total bedrooms, including one on the main level that’s ideal as a home office or playroom, and three-and-a-half bathrooms with tasteful modern updates. Every inch of this exceptional property has been thoughtfully utilized, including a fully finished basement with custom built-ins, a gym area, ample storage, and a cedar closet. Even the garage is heated! Notable upgrades include new roof and siding (2016), whole-house gas generator (2018), updated full hall bathroom (2021), French drain system around the perimeter, and a custom upstairs laundry room. Located in one of New Rochelle’s most desirable neighborhoods—where residents enjoy outdoor movie nights, festive gatherings, and community events—this home delivers more than just a place to live... it offers an elevated lifestyle in the heart of Pinebrook Estates.

Listing Agents

  1. Lauren Hurwitz

    Lauren Hurwitz

    Listing Agent

    Compass

  2. Seth Keslow

    Seth Keslow

    Alternative Listing Agent

    Compass

    seth.keslow@compass.com

    P: (917)-626-9568

Property Details for 21 Winding Brook Road

City/Township
New Rochelle
Architectural Style
Split Level
Community Features
Other,Playground
Garage Spaces
2.00
Waterfront
No
LISTING UPDATED: 09/09/2025 01:54 PM

Property Details for 21 Winding Brook Road

StatusClosed
MLS #879263
Days on Market11
Taxes$26,424 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1958
Lot Size0.32 AC / 13,939 SF
CountyWestchester County
Buyer's Agent Compensation2%

Location

Sold By Houlihan Lawrence Inc.

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Building Information for 21 Winding Brook Road

Stories-Year Built1958Building Size-Lot Size0.32 AC / 13,939 SF

Payment Calculator

$10,390 per month

30 year fixed, 6.15% Interest

Principal and Interest

$8,188

Property Taxes

$2,202

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 21 Winding Brook Road

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: false
  • Levels: Three Or More
  • State Or Province: NY
School Information
  • School District: New Rochelle
  • Elementary School District: New Rochelle
  • Elementary School: William B Ward Elementary School
  • Middle Or Junior School District: New Rochelle
  • Middle Or Junior School: Albert Leonard Middle School
  • High School District: New Rochelle
  • High School: New Rochelle High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 1000-000-007-02657-000-0041
  • Tax Assessed Value: $19,600.00
  • Included In Taxes: Sewer,Trash
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Ceiling Fan(s), Chandelier, Deck, Double Vanity, Eat in Kitchen, Entrance Foyer, High Ceilings, His and Hers Closets, Laundry Room, Marble Counters, Open Floorplan, Open Kitchen, Other, Patio, Playground, Primary Bathroom, Public, Quartz/Quartzite Counters, Recessed Lighting, Sauna, Soaking Tub, Split Level, Walk In Closet, Washer/Dryer Hookup, Wet Bar
  • Interior Features: First Floor Bedroom, Ceiling Fan(s), Chandelier, Double Vanity, Eat-in Kitchen, Entrance Foyer, High Ceilings, His and Hers Closets, Marble Counters, Open Floorplan, Open Kitchen, Primary Bathroom, Quartz/Quartzite Counters, Recessed Lighting, Sauna, Soaking Tub, Walk-In Closet(s), Washer/Dryer Hookup, Wet Bar
  • Appliances: Dishwasher, Dryer, Freezer, Gas Range, Refrigerator, Stainless Steel Appliance(s), Washer
  • Total Rooms: 9
  • Basement: Finished
  • Attic Description: Crawl
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Location Amenities: Stainless Steel Appliances, Tot Lot, 1st Fl Master Bedroom, Dual Sinks, Eat in Kitchen, Entry Foyer, Foyer, High Ceilings, Marble Countertops, Open Kitchen, Soacking Tub, Walk In Closet, WD Hookup, Wetbar, Heated Parking, Deck, Patio
  • Laundry Features: Laundry Room
  • Spa: No
  • Living Area: 3,211.00
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Deck, Patio, Driveway, Garage, Heated Garage, Storage, Other, Playground
  • Elevation Certificate: No
  • Patio And Porch Features: Deck,Patio
  • Construction Materials: HardiPlank Type
  • Horse: No
  • Pool Private: No
Lot Information
  • Site Features: Other, Playground
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Garage, Heated Garage, Storage
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Forced Air
  • Heat Fuel Type: Forced Air
  • Sewer: Public Sewer
  • Water Source: Public
  • Utilities: Electricity Connected, Natural Gas Connected, Sewer Connected, Trash Collection Public, Water Connected
Green Features
  • Green Features: Dishwasher, Dryer, Freezer, Gas Range, Refrigerator, Stainless Steel Appliance(s), Washer, Forced Air
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 21 Winding Brook Road

DateEvent & SourcePriceAppreciation
Sep 9, 2025

Sold (Public Record)

Public Record #1913278997

$1,680,000

+5.5% / yr

Sep 9, 2025

Sold

ONEKEY #879263

$1,680,000
Jul 18, 2025

Temporarily Off Market

ONEKEY #879263

$1,450,000
Jul 18, 2025

Pending

ONEKEY #879263

Jul 7, 2025

Listed (Active)

ONEKEY #879263

$1,450,000
Jun 5, 2009

Sold

HGMLS #2904978

$700,000
May 21, 2009

Sold (Public Record)

Public Record #270922166

$700,000

-4.8% / yr

Apr 23, 2009

Contract

HGMLS #2904978

Feb 17, 2009

Listed (Active)

HGMLS #2904978

$799,000
Jan 20, 2006

Sold (Public Record)

Public Record #197129695

$825,000

+26.9% / yr

Jan 20, 2006

Sold

HGMLS #2526930

$825,000
Dec 12, 2005

Contract

HGMLS #2526930

Oct 30, 2005

Listed (Active)

HGMLS #2526930

$899,000
Feb 27, 2004

Sold (Public Record)

Public Record #136456168

$525,000
Aug 20, 2003

Sold

HGMLS #2308680

$525,000
Aug 3, 2003

Contract

HGMLS #2308680

May 15, 2003

Listed (Active)

HGMLS #2308680

$599,000
Feb 4, 2003

Listed (Active)

HGMLS #2301988

$649,900
DateEvent & SourcePrice
09/09/2025

Sold (Public Record)

Public Record #1913278997

$1,680,000

+5.5% / yr

09/09/2025

Sold

ONEKEY #879263

$1,680,000
07/18/2025

Temporarily Off Market

ONEKEY #879263

$1,450,000
07/18/2025

Pending

ONEKEY #879263

07/07/2025

Listed (Active)

ONEKEY #879263

$1,450,000
06/05/2009

Sold

HGMLS #2904978

$700,000
05/21/2009

Sold (Public Record)

Public Record #270922166

$700,000

-4.8% / yr

04/23/2009

Contract

HGMLS #2904978

02/17/2009

Listed (Active)

HGMLS #2904978

$799,000
01/20/2006

Sold (Public Record)

Public Record #197129695

$825,000

+26.9% / yr

01/20/2006

Sold

HGMLS #2526930

$825,000
12/12/2005

Contract

HGMLS #2526930

10/30/2005

Listed (Active)

HGMLS #2526930

$899,000
02/27/2004

Sold (Public Record)

Public Record #136456168

$525,000
08/20/2003

Sold

HGMLS #2308680

$525,000
08/03/2003

Contract

HGMLS #2308680

05/15/2003

Listed (Active)

HGMLS #2308680

$599,000
02/04/2003

Listed (Active)

HGMLS #2301988

$649,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 21 Winding Brook Road

Taxable ValueLand$6,600Additions$13,000Total$19,600
Home Facts
Beds5Baths2.5Total Finished SqFt4,228 SqFtAbove Grade Finished SqFt3,019 SqFtFinished Basement SqFt1,209 SqFtStories2Lot Size13,939 SqFtStyleSingle Family ResidenceYear Built1958CountyWESTCHESTERAPN551000 7-2657-0041Fireplace TypeHas Fireplace

Schools near 21 Winding Brook Road

This home is within New Rochelle City School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Private - PK to 8
Rating
School
Distance
William B Ward Elementary School
PublicK to 5

Albert Leonard Middle School
Public6 to 8

New Rochelle High School
Public9 to 12

Westchester Torah Academy
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Based on information submitted to the MLS GRID as of 09/09/2025 01:54 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.