5 Winthrop Drive, Rye Brook, NY 10573
OFF MARKET

$3,071,300

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 5,672 sqft (on 1.07 acres)

5 Winthrop Drive, Rye Brook, NY 10573

Est. Refi. Payment $19,607/mo*
Refinance Your Home
Currently Off Market - Sold Jun 7, 2024 for $2,570,000

Home Value

Trulia Estimate
$3.07M
Since last month
Decreased$11K (-0.4%)
Since last year
Increased$298K (+10.7%)
Since last sale
Increased$501K (+19.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +87% in the last 10 years
MonthEstimated value
2026
August 2026$3.07M
July 2026$3.08M
June 2026$3.03M
May 2026$2.99M
April 2026$2.9M
March 2026$2.86M
February 2026$2.86M
January 2026$2.82M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
345 Betsy Brown Road, Rye Brook, NY
0.39
Single-Family Home
$3,450,000
06/26/26
5
6
5,590
38 Lincoln Avenue, Pt Chester, NY
0.36
Single-Family Home
$1,190,000
06/15/26
4
4.5
5,823
23 Sylvan Road, Rye Brook, NY
0.53
Single-Family Home
$2,975,000
12/22/25
5
5.5
5,091
10 Carlton Lane, Rye Brook, NY
0.17
Single-Family Home
$2,170,000
04/09/26
4
3.5
3,185
4 Elm Hill Drive, Rye Brook, NY
0.35
Single-Family Home
$1,200,000
10/23/25
6
7
5,590
14 Eagles Bluff, Rye Brook, NY
0.35
Single-Family Home
$2,250,000
04/07/26
5
3.5
3,297
10 Oriole Place, Rye Brook, NY
0.63
Single-Family Home
$2,350,000
05/22/26
5
2.5
3,606

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
2 Winthrop Drive, Rye Brook, NY 10573
0.07
$1,761,500
3
2.5
3,054
Off Market
18 Berkley Drive, Rye Brook, NY 10573
0.14
$1,700,200
5
3
2,758
Off Market
9 Mohegan Lane, Rye Brook, NY 10573
0.13
$1,517,100
3
2
2,593
Off Market
7 Carlton Lane, Rye Brook, NY 10573
0.13
$1,615,000
5
3
2,213
Recently Sold
7 Red Roof Drive, Port Chester, NY 10573
0.17
$3,280,500
6
5.5
5,890
Off Market
5 Carlton Lane, Rye Brook, NY 10573
0.14
$1,075,000
4
3
2,619
Recently Sold
10 Mohegan Lane, Rye Brook, NY 10573
0.15
$1,888,000
4
3.5
3,126
Off Market
65 Windingwood Road S, Pt Chester, NY 10573
0.17
-
3
2
2,078
Off Market
3 Berkley Lane, Rye Brook, NY 10573
0.20
$1,365,000
4
2
1,934
Off Market
1 Mark Drive, Rye Brook, NY 10573
0.17
-
3
3.5
4,451
Off Market
29 Mohegan Lane, Rye Brook, NY 10573
0.17
$2,056,400
4
3.5
3,492
Off Market

Local Information

  • Map ViewExplore the area around 5 Winthrop Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Lot Size
1.07 acres
Living Area
5,672 sqft
Price/Sqft
$541
Parking
3 Parking Spaces

About this House

A rare & exceptional 6 bedroom, 5 bath colonial home nestled in the coveted Pine Ridge section of Rye Brook. This unique residence is situated on over a 1-acre lush flat property which provides an unparalleled level of luxury & privacy. Step inside this elegant home to discover a stunning array of modern features. The center of the home is the impressive custom kitchen w/ heated floors designed by Georgio with Quartzite countertops, custom cabinetry and high end appliances. The wall of glass doors from the kitchen leads to the blue stone patio for the ultimate entertaining flow. The show-stopping family room impresses with soaring ceilings & designer finishes. A first floor guest bedroom provides the comfort for various lifestyle needs. Don't miss the inviting office that actually makes you want to work! Upstairs you will find the primary bedroom which is a private sanctuary w/ high ceilings, large closets & an unparalleled new custom bathroom. 4 addl bedrooms & 2 full baths give you all the space you need. The beautiful gunite pool creates a resort-like atmosphere for outdoor entertaining. Featuring a rare three-car garage, large mudroom, formal living room, large dining room, PLUS bonus room for recreation, this home effortlessly combines elegance with modern functionality. Situated on a quiet street close to the park, this property offers a once-in-a-lifetime opportunity for refined living. Don't miss the chance to experience the epitome of luxury and style in this exclusive home. Additional Information: ParkingFeatures:3 Car Attached,
5 Winthrop Drive, Rye Brook, NY 10573 is a 6 bedroom, 5 bathroom, 5,672 sqft single-family home built in 1900. It last sold for $2,570,000 on Jun 7, 2024 (7% below the $2,775,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,071,300, with a rent estimate of $14,572/month.
Last check for updates: about 4 hours ago
Listed by Kori Sassower, (914) 727-0169
Compass Greater NY, LLC, (914) 223-7623
Bought with: Kori Sassower, (914) 727-0169, Compass Greater NY, LLC, (914) 223-7623
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6289442

Home Details for 5 Winthrop Drive

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 15
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 5672 Square Feet
Appliances & Utilities
Utilities: Trash Collection PublicAppliances: Gas Water Heater
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: Two

Exterior Features

Parking & Garage
No CarportParking Spaces: 3Parking: Attached
Pool
Pool: In GroundPool
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1900Year Renovated: 2022
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: Brick, ClapboardNot Attached Property
Property Information
Condition: ActualParcel Number: 48051350000004200100470000000

Price & Status

Price
List Price: $2,775,000
Status Change & Dates
Off Market Date: Fri Mar 29 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: Rye Brook
School Information
Elementary School: Bruno M Ponterio Ridge Street SchooJr High / Middle School: Blind Brook-Rye Middle SchoolHigh School: Blind Brook High SchoolHigh School District: Blind Brook-Rye

Building

Building Area
Building Area: 5672 Square Feet

Community

Community Features: ParkNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.0722 Acres

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash

Miscellaneous

BasementMls Number: H6289442Attic: WalkupAttribution Contact: (914) 727-0169Showing AttendedShowing Requirements: Lockbox

Additional Information

HOA Amenities: Park

Price and Tax history

DateEventPrice
Jun 7, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6289442
Sold
$2,570,000
Mar 29, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6289442
Pending
$2,775,000
Feb 26, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6289442
Listed For Sale
$2,775,000
Jun 28, 2013
Source: OneKey® MLS as distributed by MLS GRID #H3305355
Sold
$1,800,000
Mar 19, 2013
Source: Agent Provided
ListingRemoved
$1,675,000

Market trends in Rye Brook

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
18

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Rye Brook

At least 100 Trulia users voted on each feature.

  • 84 % Say it's dog friendly

  • 80 % Say people would walk alone at night

  • 78 % Say yards are well-kept

  • 76 % Say car is needed

  • 75 % Say parking is easy

  • 72 % Say there's holiday spirit

  • 70 % Say there are sidewalks

  • 68 % Say it's quiet

  • 67 % Say it's walkable to restaurants

  • 65 % Say they plan to stay for at least 5 years

  • 65 % Say streets are well-lit

  • 61 % Say it's walkable to grocery stores

  • 57 % Say kids play outside

  • 53 % Say neighbors are friendly

  • 46 % Say there's wildlife

  • 37 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Michael Hirsch
    "Lots of green grass for dogs to run around. Lots of parks to take dogs to as well. Pretty much the ideal suburban neighborhood for any dog. "
    0
    Flag
  • Dawn W
    "Lots of dogs being walked. Friendly neighbors. Dog parks nearby. People pick up mostly after their dogs "
    0
    Flag
  • Lorraine olivieri
    "It’s 25 mins not a bad commute at all. I think I would like to live closer to my job eventually. I don’t think this part is necessary "
    0
    Flag
  • Gsprague914
    "It’s a safe place to live and the schools are very good. There are many shops and clean parks for children and families to visit. "
    1
    Flag
  • Carlie F.
    "Great community & great people. Safe neighborhood with great schools. Very lucky to be living in such a great town in Westchester. "
    2
    Flag
  • Fredbediaga
    "It has easy access to Hutchison highway so you can go anywhere very quickly. For the train you will need to go to port Chester "
    0
    Flag
  • Laurensullivan122
    "Very good & quiet neighborhood. Safe to raise families, schools are good. No bars no nightlife. It’s pricey but nonetheless worth it. "
    1
    Flag
  • Neubauer1811
    "Great area and neighborhood for families! Schools are well regarded and it is so safe! Great for cycling, Cranberry Lakes around.... Enjoy!"
    2
    Flag
  • Marisol S.
    "Its a suburban area but it doesn’t feel like it, in a good way. You still see people walking to the nearest stores or restaurant. People don’t depend on a car to get to and from. "
    0
    Flag
  • Trulia User
    "Special education programs are limited within the Blind Brook District are very limited. Most children are moved out of the schools. "
    0
    Flag
  • Ccruz
    "Auto is best way to travel but local taxi service is acceptable to get around. Do not expect luxury cab service. "
    0
    Flag
  • davidnjones
    "Beautiful Historic Rye village, only 10 min drive away. Schools very good. Some bus services but car needed for convenience. Some beautiful homes in this well maintained area."
    0
    Flag

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-08-26 11:53:00 PDT 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. Some IDX listings have been excluded from this website. Click here for more information

Frequently asked questions about 5 Winthrop Drive

  • What is 5 Winthrop Drive estimated to be worth?
    Trulia's estimated value for 5 Winthrop Drive in Rye Brook, NY is $3,071,300.
  • What is the price history for 5 Winthrop Drive?
    5 Winthrop Drive in Rye Brook, NY last sold for $2,570,000 in June 2024.
  • Is Rye Brook a buyer's or seller's market?
    Rye Brook is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Rye Brook?
    Residents describe Rye Brook, NY as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Rye Brook, NY.
  • Does 5 Winthrop Drive have air conditioning?
    Yes, 5 Winthrop Drive in Rye Brook, NY has air conditioning.
  • Does 5 Winthrop Drive have a pool?
    Yes, 5 Winthrop Drive in Rye Brook, NY has a pool.

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