Sold
Last Sold Price
5 beds3,211 sqft$523/sqft
21 Winding Brook Rd, New Rochelle, NY 10804
Single FamilyProperty Type
0.32 acresLot Size
1958Year Built
$523/sq ftPrice per sq ft
2 carsParking Spaces

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 Greater NY, LLC

    P: (516) 729-3609

    M: (516) 729-3609

  2. Seth Keslow

    Seth Keslow

    Alternative Listing Agent

    Compass Greater NY, LLC

    P: (917) 626-9568

    M: (917) 626-9568

Listing closed: 09/09/2025 12:00 AM • Source: ONEKEY as distributed by MLS GRID, MLS#: 879263

Recent comparable sales

Median sold price

$1,450,000

Avg days on market

29

Sale-to-list ratio

104.3%

New Rochelle, NY

9 comparable properties found

$1,700,000 | 139 Fenimore Road, New Rochelle, NY 10804
1

$1,700,000

Sold 09/24/24

5
Bedrooms
3,436
Square Feet
0.27
Acres
$1,475,000 | 45 Wilmot Road, New Rochelle, NY 10804
2

$1,475,000

Sold 08/10/26

5
Bedrooms
3,374
Square Feet
0.34
Acres
$1,450,000 | 16 Broadfield Road, New Rochelle, NY 10804
3

$1,450,000

Sold 07/17/25

5
Bedrooms
3,455
Square Feet
0.35
Acres
a front view of a house with a garden and plants
4

$1,710,000

Sold 07/23/25

5
Bedrooms
3,391
Square Feet
0.38
Acres
front view of a house with a yard
5

$1,325,000

Sold 08/05/25

5
Bedrooms
2,753
Square Feet
0.48
Acres
$1,295,000 | 15 Van Meter Fenway, New Rochelle, NY 10804
6

$1,295,000

Sold 05/01/25

5
Bedrooms
2,986
Square Feet
0.39
Acres
a front view of a house with a garden
7

$1,450,000

Sold 12/17/25

5
Bedrooms
3,420
Square Feet
0.24
Acres
front view of a house with a yard
8

$1,900,000

Sold 06/30/25

5
Bedrooms
2,679
Square Feet
0.21
Acres
$1,300,000 | 41 Paine Avenue, New Rochelle, NY 10804
9

$1,300,000

Sold 12/02/24

5
Bedrooms
3,323
Square Feet
0.43
Acres

Location

Sold By Houlihan Lawrence Inc.

Add your commute

Payment Calculator

$10,741 per month

30 year fixed, 6.55% Interest

Principal and Interest

$8,539

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

Property Details
  • Taxes: $26,424 / year
  • MLS Type: Single Family
  • Buyer's Agent Compensation: 2%
  • City/Township: New Rochelle
  • Architectural Style: Split Level
  • Community Features: Other, Playground
  • Garage Spaces: 2
  • Waterfront: No
Building Information
  • Year Built: 1958
  • Lot Size: 0.32 AC / 13,939 SF
Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: Detached
  • 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
  • Tax Source: Municipality
  • Tax Year: 2025
  • 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: 3211
  • 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
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

For completeness, we 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
Tax Record2025$26,551 ($2,213 / month)
Home Facts
Beds5Baths2.5Total Finished SqFt3,567 SqFtAbove Grade Finished SqFt3,211 SqFtFinished Basement SqFt356 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 7
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 7

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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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 21 Winding Brook Road, New Rochelle, NY 10804
$1,680,000
5
3,211
13,939
$975,000
3
2,047
20,909
$685,000
4
2,471
33,106
$655,000
3
3,215
3,920
$920,000
4
1,941
14,283
$555,000
2
2,340
4,356

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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.