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Off Market

21 Winding Brook Road

New Rochelle NY 10804

5
4
2
4228 sq. ft.
13939 sq. ft.
Single-Family
Last sold for $1,680,000
Lauren HurwitzLauren Hurwitz, last sold this property on 09 September 2025 after 64 days on market.

Overview

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.

Features

5 bedrooms
4 bathrooms
2 carspaces
2 garage spaces
4228 sq. ft. floor area
13939 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in New Rochelle over the last 12 months, the estimated median property value of 21 Winding Brook Road is $1.36m.

Median value
$1.36m
Estimated value range
$840k - $2.22m
Median days on market
16
Estimated value trend
-3%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in New Rochelle. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 21 Winding Brook Road

2025
Sold
$1,680,000
09 Sep 2025 by Lauren Hurwitz, of Compass Greater NY, LLC

Happy sellers in New Rochelle

87%
87% of sellers in New Rochelle reported that their sale price either exceeded or met their price expectations.

New Rochelle stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 3 reviews in New Rochelle over the last 12 months.

Local market activity for 5 bedroom single-family properties in New Rochelle

In the last 12 months, 28 five-bedroom single-family properties similar to 21 Winding Brook Road, have been sold.

This represents a 15% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in New Rochelle

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France Tucker

France Tucker is a recommended agent for New Rochelle.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (10 reviews)
  •  1 Review in New Rochelle
  •  1 Sale in New Rochelle
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Mary Stetson

Mary Stetson is a recommended agent for New Rochelle.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (6 reviews)
  •  1 Review in New Rochelle
  •  1 Sale in New Rochelle
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Joseph Cosentino

Joseph Cosentino is a recommended agent for New Rochelle.  They have collected 1 local review across the last 12 months.

  •   5   (16 reviews)
  •  1 Review in New Rochelle
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Elizabeth Winkler

Elizabeth Winkler is a recommended agent for New Rochelle.  They have 6 local sales across the last 12 months.

  •  6 Sales in New Rochelle
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